4 Days In Chicago: Itinerary For An Epic Long Weekend

Some may know Chicago, Illinois as the Windy City, home of the deep-dish pizza, land of some of the best restaurants in all of North America, or simply the city where Wrigley Field is.

And unless you visit for yourself, that’s all that Chicago may ever be to you, just another city with some notable foods and landmarks.

That’s what I thought too, which is why it’s taken me years upon years to muster up the energy to even want to visit Chicago. But wow was I mistaken.

Having returned from a trip to Chicago for the first time in my life, I now realize I was completely missing out on life. Chicago is amazing!

If you get the chance to visit Chicago for yourself, you’ll discover a world of magic–a vibrant energy unlike any other city in the Western Hemisphere. It’s truly a city that you need to experience firsthand!

Today, I’ve compiled a 4-day itinerary of Chicago based on the exact Chicago itinerary I used for my recent trip. This itinerary is based on many recommendations from Chicago locals, foodies, and even a famous smash burger chef — so you know there’s going to be some good, hidden gems on here.

Get ready for 4 epic days of deep-dish pizza, meaty sandwiches, eclectic neighborhoods, iconic sights, and uniquely Chicago experiences!

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Here’s a quick overview of all the useful info you need to plan an awesome trip!

  • When To Go: During the late spring, early summer, and early fall months: April, May, June, September, and October. Summers can be very hot and humid, but you’ll find plenty of outdoor events and festivals during this time.
  • Where To Stay: Near the center of all the action is best! I recommend The Westin Chicago River North or Pendry Chicago for more luxe vibes; Virgin Hotels Chicago for hip boutique hotel vibes at an affordable price!
  • Nearest Airport: O’Hare International Airport (ORD)
  • How to Get Around: Chicago is well-known for its convenient public transit system. It’s also a very walkable city! For longer distances, opt for rideshare before choosing to rent a car. Parking in downtown Chicago can be difficult and expensive — many hotels charge a daily fee for parking, and street parking can be limited and expensive.
  • Must-Do’s: See The Bean (Cloud Gate) at Millennium Park, take an architecture boat tour, visit Navy Pier, try a Chicago-style hotdog, and get a deep-dish pizza at Pequod’s (I recommend the spinach and garlic). And if you have the time to wait, get the iconic burger at Au Cheval.
  • Before You Go: Pick up Go City’s Chicago All-Inclusive Pass if you plan on sightseeing and going into museums. It’ll save you so much money on attraction tickets!


Prior to visiting Chicago myself, I knew nothing about the city of Chicago. Having finally visited, I now understand that there is a lot to love about Chicago. The city is completely brimming in history and culture and it’s totally worth visiting, even if you’re not a fan of urban cities!

If you know nothing about Chicago, let’s start with the basics. Chicago is the third most populated city in the United States. It is a Midwest city that sits adjacent to Lake Michigan and is famed for its architecture.

Chicago is best known for the following:

  • The Bean, which is officially known as Cloud Gate at Millenium Park
  • Impressive architecture and skyscrapers
  • Chicago deep-dish pizza
  • Chicago-style hot dogs
  • Navy Pier, one of Chicago’s most famous landmarks and a popular tourist destination
  • Wrigley Field, home to the Chicago Cubs
  • The Chicago Riverwalk, a pedestrian area lining the Chicago River that features plenty of restaurants and resting spots to enjoy the river


The best time to visit Chicago is between the months of April to June and between September to October. During these months, you’re going to have the best of everything–pleasantly warm temperatures, manageable crowds, more affordable flights and hotel prices, and many popular festivals/events to attend.

While there are many events happening in the summertime (which could be a plus), summers can be hot, humid, and muggy. And because of the summer influx of tourists, flights and hotels also tend to cost more during the months.

Winters in Chicago are notoriously and chillingly cold, with frequent snowfall and temperatures in January dipping below freezing. So unless you are able to brave the cold, I would avoid visiting in the winter season.

Pro Tip: No matter the season you choose, always come prepared! The weather can be unpredictable, so pack a light rain jacket and a wind-proof umbrella just in case.

When we visited in mid-October of this year, we experienced a few hours of sporadic rainfall here and there followed by warm sunshine with no clouds in sight.

Luckily we had checked the forecast earlier on and had packed rain jackets and umbrellas with us!


For first-timers, I would recommend a total of 4-5 days in Chicago. Even more ideal is 5-7 days! Trust me, you won’t need to be worried about being bored. With all the different and unique neighborhoods, museums, and free attractions dotted throughout this world-class city, it’s very easy to fill your days with fun things to do.

If you plan to visit Chicago again at a future point in your life, then you can get away with a shorter trip this time around, keeping in mind that you’ll be back to explore the rest of the city later!

Since this is a 4-day Chicago itinerary post, I will say that it is very possible to get a taste of the city, past its main highlights, in 4 days’ time. Not only will you have enough time to check out a few iconic attractions, but you’ll also have time to explore some of the eclectic neighborhoods that make so many travelers fall in love with the city.

Without further ado, let’s get to the good stuff! Here is my exact 4-day Chicago itinerary.


Depending on what time you get in, you’ll either need breakfast/lunch or go straight to checking into your hotel. Our itinerary starts with a meal at one of the best spots for Mexican food in Downtown Chicago.


When you’re ready to eat, head to XOCO, a quick-service cafe that we can’t stop thinking about. Open early and closing late, this restaurant by Rick and Deann Bayless offers contemporary versions of Mexico’s most beloved street food and snacks.

You can expect hot-from-the-fryer churros, delicious tacos, frothy Mexican hot chocolate, crusty tortas, and the most creative fried chicken sandwiches I’ve ever tasted.

For lunch or dinner, the must-order dish here is the spicy churro chicken sandwich. We also loved the queso fundido from the happy hour menu (melted cheese with tortillas on the side). Order both, you’ll thank me later.


Navy Pier - 1 Day Chicago Itinerary For First Timers - TravelsWithElle

Your first attraction to check out in Chicago will be the Navy Pier, also known as the People’s Pier. This is Chicago’s lakefront treasure and a must-see while you’re in Chicago.

No matter how old you are, there’s something for you here. It’s where people go in Chicago for fun attractions, dining, shopping, local events, free public programs, and more.

Navy Pier stretches more than six city blocks and offers incredible views of the Chicago skyline, parks and Lake Michigan. One of the best things to do at Navy Pier is just to take a stroll through the whole thing!

While there is no admission fee to enter Navy Pier, some of the rides and attractions within Navy Pier do cost extra. For example, the Ferris wheel costs $15 for adults. There are also other ride passes for sale.

Fun Fact: The first Ferris wheel (ever) was showcased in Chicago during the World’s Columbian Exposition of 1893.

If you happen to be traveling in the summertime, it may be best to visit Navy Pier in the evening. There is a fireworks show that takes place on Wednesday and Saturday nights from Memorial Day weekend through Labor Day weekend. There were no fireworks when we visited in October, but Navy Pier was worth the stroll around nonetheless!

Lastly, if you’re visiting Chicago during the holiday season, don’t miss Navy Pier’s holiday event, Light Up the Lake. This holiday event runs from late November to early January.

At the event, you can expect massive light sculptures, an ice rink, an authentic holiday beer garden, kiddie train rides, a gift market, and other family-friendly and date-night activities!

Not visiting during either of these seasons? Check their event calendar for the latest happenings.

Navy Pier hours: Varies depending on the season, but generally 10am to 10pm
Cost: FREE


The Bean Chicago- 1 Day Chicago Itinerary For First Timers - TravelsWithElle

Since you’re still in the downtown area, head to Millenium Park so you can just get all the touristy stuff done and out of the way.

When in Chicago, of course, you have to see Cloud Gate, better known to most as “The Bean”. I mean, did you really go to Chicago if you didn’t see The Bean in person?

This is one of the city’s most iconic attractions, and rightfully so because it’s one of the largest sculptures of its kind in the world! This sculpture dates back to 2005 and was created by British artist Anish Kapoor.

Pro Tip: For optimal photos without hoards of other people in them, visit early! Before 9 am would be ideal. You can always come back later.

Once you’re done taking pictures of it and with it, it’s time to move on to the rest of Millennium Park!

Cost: FREE


Alright now that you’ve gotten your main selfie photo op out of the way, let’s explore the rest of Millennium Park!

While the park is best known as home to the iconic bean you just took a picture with, it also features ample green spaces, interactive fountains, tranquil gardens, public art, rock climbing, and a whole bunch of free events.

Millennium Park offers a jam-packed calendar of public events all year round. The summertime is popping with fun outdoor events such as Summer Music Series and Summer Film Series. Check for the latest events on their event calendar before visiting!

Your next stop will be Crown Fountain, also known as the fountain where faces are spitting water at you. This massive video sculpture is made of a black granite reflecting pool positioned between a pair of glass brick towers that display digital videos.

Crown Fountain - 1 Day Chicago Itinerary For First Timers - TravelsWithElle

Fancy a stroll in an award-winning garden? Head to Lurie Garden. Traveling with kids? Definitely don’t miss Maggie Daley Park (it’s a kid’s fantasyland).

If you’re looking to catch a film, music festival, or concert, check out Jay Pritzker Pavilion & The Great Lawn. Now there won’t be much here if there is no show going on, but when there is, the space transforms into something amazing! The Grant Park Music Festival, the Chicago Blues Festival, the Chicago Jazz Festival, and the World Music Festival all take place here.

Cost: FREE


Alright, you’ve done a good amount of walking at this point. It’s time to stop by one of Chicago’s all-local dining concepts for some fuel–Revival Food Hall. This food hall is essentially a stylish food court that spotlights the best of Chicago’s acclaimed culinary scene under one roof.

Choose from Danke, Bianca’s Bodega, Lito’s Empanadas, Smoque BBQ, The Budlong Hot Chicken, Bonnie Foods, Lashuk Street Food, and much more.

No matter who you’re traveling with, there will likely be something here that’ll appeal to each and every one of their tastebuds.


If you still have energy left in your legs, take a 15-minute post-dinner stroll over to Buckingham Fountain, a real treat for all Europe lovers, public art enthusiasts, and architecture fanatics! If you can’t take any more walking, hop on a bus for a quick ride over to Grant Park.

Located right along the lake in the heart of Grant Park, the massive and enchanting Buckingham Fountain is one sight you really shouldn’t miss.

The design of the fountain was inspired by one of the opulent fountains located at the Palace of Versailles in France. Chicago’s version is double the size, making it one of the largest fountains in the entire world!

There is even a free water display, accompanied by lights and music, that happens every hour on the hour from May to mid-October. The best time to see this magical fountain is any time after sunset!

Cost: FREE



Shedd Aquarium - Chicago Itinerary For First Timers - Travels With Elle

It’s the morning of your second day in Chicago! The perfect way to start out the day? Visiting a world-class aquarium.

Having heard nothing but wonderfully positive things about Shedd Aquarium (and being a sucker for adorable marine animals), I needed to pay a visit to this aquarium. After visiting for myself, I’m recommending this to everyone!

In a nutshell, Shedd Aquarium is a state-of-the-art indoor aquarium, famous for its massive variety of habitats. It’s also one of the oldest aquariums in the United States and is often considered one of the best aquariums in the US.

Inside, you can expect a whole range of marine life including belugas whales (my personal favorite), penguins, dolphins, alligators, stingrays, sturgeons, sea turtles, sea otters, and even arapaimas!

I was absolutely blown away by all the different habitats showcased within the aquarium–there are around 80 of them within the aquarium. If you’re remotely interested in marine life or are looking for a kid-friendly activity to do in Chicago, Shedd Aquarium is definitely worth a visit.

Plus, it’s included with the Go City Chicago All-Inclusive Pass!

Cost: $39.95 for adults, $29.95 for children ages 3-11
Cost with Go City Chicago All-Inclusive Pass: FREE


Save with Go City’s Chicago All-Inclusive Pass

Save up to 51% on tickets to Chicago’s most popular attractions, including Shedd Aquarium, CHICAGO 360, Skydeck Chicago, Shoreline Architecture River Cruise, Museum of Science and Industry, and more. You can choose from 25+ different attractions in total.

We explored Chicago with this pass and got to see a lot more than we usually do in big cities — while saving a ton of money!


Chicago-style hot dog - 4 Day Chicago Itinerary - TravelsWithElle

Steps away from the Shedd Aquarium sits Kim and Carlo’s Hotdog Stand. Chicago-style hot dogs are a Chicago staple, and this food cart does it right. Not only are you getting a true poppyseed bun, but you’re also getting a bunch of delicious fixings on top!

They’re super easy to eat, which is why I’m calling them a snack. If you love hot dogs and can scarf them down like nothing, I recommend ordering 2 for yourself.


For lunch, head back towards downtown and the Chicago River. You’ll want to be close to your next activity, which is hopping aboard the architecture river cruise, arguably the one truly must-do activity in Chicago!

For lunch downtown, we recommend The Dearborn, or Joe’s Seafood, Prime Steak & Stone Crab. If you’ve never been inside an Eataly before, Eataly Chicago is a great place to visit and dine for lunch.


Architecture River Cruise - Chicago Itinerary - Travels With Elle - 12

After lunch, walk over to the Shoreline Sightseeing ticket booth and get your tickets for the Architecture River Cruise! This iconic Chicago cruise will take you on a tranquil boat ride along the Chicago River, through the history of the city, revealing hidden architectural gems and the city’s renowned landmarks.

You’ll sail down all three branches of the Chicago River–the Main Branch, North Branch, and South Branch–giving you an insight into how architecture and landmarks have changed over the years.

Along the way, you’ll learn all about the history of Chicago, from the Great Fire of 1871 to the thriving metropolis it is today. Don’t forget to bring a camera–you can’t miss the photo op at Wolf Point!

After our river cruise, we had learned so much about why Chicago was so unique (especially in the city’s architectural design). Additionally, we all became “pros” at identifying the architectural styles of buildings!

Architecture River Cruise - Chicago Itinerary - Travels With Elle

All in all, I would 100% recommend this activity to anyone who visits Chicago for the first time!

Cost: $40-50 for adults
Cost with Go City Chicago All-Inclusive Pass: FREE

Or, you can book this must-do activity by itself here:


360 Chicago - 1 Day Chicago Itinerary For First Timers - Travels With Elle

Time to enjoy some quintessential cityscape views at a staple Chicago landmark! Off to 360 Chicago we go. The easiest and quickest way to get here from the river cruise is by the CTA bus.

When you arrive at 360 CHICAGO, you’ll get to enjoy views of Chicago’s skyline through the all-glass panoramic windows in the 17,000 square-foot 360 CHICAGO Observation Deck. From the top, you’ll be able to see Lake Michigan, Navy Pier, Soldier Field, and the Magnificent Mile.

For an even more breathtaking view, visit at twilight when the lights of the city begin to turn on for the night!

360 CHICAGO also offers a palm sweat-inducing attraction for an extra cost. For $8, you can do the TILT! ride, offering visitors a downward facing view from 1,030 feet.

Pro Tip: Personally, I think the price for this excursion is too steep for what you get. If you are not getting any version of the Go City Chicago pass, I would skip 360 Chicago and opt for similar views at The Signature Room at the 95th. This restaurant/lounge offers guests a dining experience with sweeping 360-degree views. All you have to do is pay for your meal or drinks!

Having said that, we actually didn’t have to pay out of pocket since we had the Go City Chicago All-Inclusive Pass. Nonetheless, the views up top are pretty cool.

360 Chicago Hours: Monday – Thursday: 9 AM – 9 PM / Friday and Saturday: 9 AM – 11 PM

Cost: Adult (12 and over): $30.00 / Youth (3 to 11): $20.00 / Children Under 3: Free
Cost with Go City Chicago All-Inclusive Pass: FREE


Just like The Bean, you can’t visit Chicago and not try deep-dish pizza! And this is coming from someone who was born in New York and grew up scarfing down pizza on the daily (aka a NY pizza snob).

Since you’re in the downtown area, the closest, most popular options are Giordano’s or Lou Malnati’s.

Pro Tip: While these pizza joints will give you a good sample of deep-dish pizza, my favorite is Pequod’s–but that comes later on the itinerary!


Cute, crafty, and delicious tiki drinks? Yes please.

This is a must-visit institution if you’re looking for post-dinner drinks in Chicago. Three Dots And A Dash is Chicago’s premier tropical tiki bar and craft cocktail destination hidden below the bustling streets of River North. It was even named one of The World’s 50 Best Bars by Drinks International!

If you’re looking to get the most value for your money, order a large group drink to share with friends!

They also have island-themed food to pair with your drinks such as coconut shrimp, pupu platters, loco moco, kalua pork sliders.


Today is all about exploring the unique neighborhoods of Chicago. Each neighborhood has its own distinct charm and personality, so I assure you that you won’t be bored at all during your Chicago exploration today.

I hope you brought your good walking shoes because Lincoln Park, Bucktown, Wicker Park, and others are best explored on foot!


Lincoln Park is a postcard-perfect upscale neighborhood in Chicago that is home to the largest park in the city, the Chicago History Museum, and a zoo that you can visit without spending a single dollar. While you’re here, expect to stroll through a lot of green spaces.

Lincoln Park really is a wonderful place for nature lovers and greenery lovers. First, start at the Lincoln Park Conservatory, the home of tens of thousands of plants under a glass dome and in a variety of greenhouse rooms.

Follow that up with a quick trip to the Alfred Caldwell Lilly Pool, a hidden gem of a spot just north of the Lincoln Park Zoo. This is the perfect hideaway (if only just for a brief moment) from the hustle and bustle of the city.

Cost: FREE


While you’re in Lincoln Park, be sure to make a stop at the Lincoln Park Zoo because this zoo is absolutely free to enjoy! In fact, the zoo has been free admission since its gates first opened in 1868, making it one of the most established zoos worth visiting in the United States.

Cost: FREE


Chicago Mural - Bucktown Chicago - 4 Day Chicago Itinerary

From Lincoln Park, take the bus or train to the Logan Square or Bucktown neighborhood. Just like Wicker Park, these artsy neighborhoods always have something cool and vibing going on.

In my opinion, one of Bucktown and Logan Square’s biggest draws is the fact that there are so many shops selling the most unique finds (it’s especially fun if you want to go thrifting). Oh, did we mention the ample street art these neighborhoods hold?

Logan Square Robin Williams Mural - 4 Day Chicago Itinerary

Foodies will also love these neighborhoods, as they’re home to some of the trendiest restaurants, cafes, breweries, and bars.

I’d recommend hopping off the train at Logan Square station and walking down N Milwaukee Ave. On that street alone, you’ll find so many cute shops and eateries to stop in! If you have more time, walk through the side streets and enjoy the local ambiance.

Pro Tip: You’ll need to make your way to Pequod’s for lunch at some point. If starting at Logan Square is too much walking for you, start your exploration at the Six Corners area where North, Milwaukee, and Damen Avenues intersect. This area is the heart of the neighborhood, where you’ll find endless vintage stores, record shops, trendy eateries, coffee shops, art galleries, and more.

Cost: FREE


Many lists out there have tourists thinking that the two pizza establishments that reign supreme are Lou Malnati’s and Giordano’s, but the real deep dish magic is at Pequod’s!

Yes, it is a bit further out and does take some work to get to, but trust me when I tell you that Pequod’s is the deep-dish champion. They’re so good that they even ship their pizza nationwide!

We ordered the pan pizza with sausage, spinach, and fresh garlic and boy was this thing delicious! I’m from New York, so I would consider myself a pizza connoisseur and even with my NY pizza loyalty, I still really enjoyed this meal.

Pro Tip: You’re going to need to make reservations ahead of time. Do NOT just show up because the wait can be 4 hours long for dinner, especially on weekends. Yes, it is that good. Good news though, lunch reservations are not too hard to snag.


Nightlife in Chicago - 1 Day Chicago Itinerary For First Timers - Travels With Elle

Wicker Park is another one of Chicago’s hippest and most eclectic neighborhoods, filled with restaurants, coffee shops, cocktail bars, record stores, and lots of shops!

If you’re not sick of walking yet and would rather get some fresh air, walk The 606 (formerly an abandoned railway turned greenspace) for a laidback afternoon stroll.

And when night falls, Wicker Park’s energy does not end. It’s home to some of the city’s best indie music venues, late-night clubs, pubs, speakeasies, and neighborhood dive bars. If you’re looking for cool spots to grab a drink or two, check out The Violet Hour, Debonair Social Club, or the rooftop bar in The Robey Hotel.

Cost: FREE


A pioneer in Chicago’s craft cocktail community, The Violet Hour serves seasonally-driven, pre-prohibition style libations to cocktail enthusiasts.

I am by no means a cocktail enthusiast, but my travel partner totally is! While he absolutely loved the drinks at the Violet Hour, I absolutely loved the decor of the place. We’re talking dim, romantic lighting, long floor-to-ceiling curtains, and an almost-enchanting, mystical vibe.

Due to its popularity, The Violet Hour does usually require reservations. You’re going to need to put down a deposit to secure your reservation, but that deposit will go right towards the drinks you order when you arrive!


You can choose to have dinner in Wicker Park or at any of the neighborhoods that you’ll pass on the way back to your hotel. If you’re looking for pointers, try Etta Bucktown.

Farther away in the ritzy Near North Side neighborhood is Le Colonial, which we really enjoyed (both their food and drinks were spot on).

For something more casual, the following local institutions will definitely hit the spot: Harold’s Chicken Shack, Al’s #1 Italian Beef or Portillo’s. When at Portillo’s you can’t miss their iconic chocolate cake!



Museum of Science And Industry - 1 Day Chicago Itinerary

Good morning! Wake up that brain of yours by getting your creative juices flowing. You absolutely need to work the Museum of Science and Industry into your 4-day Chicago itinerary. This museum is so worth your time!

The MSI is the largest science museum in the Western Hemisphere, boasting more than 400,000 square feet of hands-on, interactive exhibits designed to spark creativity and thinking. No matter if you’re traveling solo, with a group of only adults, or with children, each and every one of you will have a blast in this hands-on interactive museum.

From chasing tornados to milking farm cows, playing with funhouse mirrors at the circus exhibit to exploring futuristic ideas, the variety of topics covered at MSI was mindblowing.

On our last visit, we were lucky enough to catch the tail end of the Marvel: Universe of Super Heroes exhibit where we ogled at over 300 artifacts celebrating the past 80+ years of Marvel history. Where else could you find such a cool and detailed exhibit about such a fun topic?

Wondering how much there is to see at the MSI? Well depending on how hands-on you get with the exhibits, you can expect to spend about 3-5 hours at the museum.

Cost: $21.95 for adults, $12.95 for children ages 3-11
Cost with Go City Chicago All-Inclusive Pass: FREE


Head to the heart of Chinatown on Cermak Road and Wentworth Avenue. Here, you’ll find an extensive selection of shops, cafes, dim sum spots, and teahouses. Stroll around and snack on a few small buns/plates of dim sum.

Next, check out the outdoor Chinatown Square Mall, located just north of the main Wentworth Avenue District. Here, you’ll find lots of cafes and boutiques in a pedestrian-friendly setting.

If you’re looking for a dose of history, the Chinese-American Museum showcases the history of the neighborhood.

And of course, you can’t miss the Nine-Dragon Wall, which is an impressive reproduction of the 15th-century Nine-Dragon Wall in Beijing.

If you need pointers on where to eat, try Ken Kee Restaurant! But don’t eat too much while you’re here, you’ve got a long day of good eats ahead of you!


West Loop Chicago - 4 Day Chicago Itinerary

From the museum, hop back on the bus or train to the more central part of town. Next up: the trendy hotspot neighborhood of West Loop. Get ready, because your tastebuds might burst and explode from all the goodness it’s about to taste.

A former meat-packing district, the West Loop has become one of the most happening dining destinations in the city. Simply said, it’s a foodie mecca.

Restaurant Row (Randolph Street) is where you’ll find many of the neighborhood’s most celebrated spots, including Au Cheval, Trivoli Tavern, and Green Street Smoked Meats.

The West Loop is also home to Greektown, the second oldest American institution dedicated to Greek culture. Fulton Market is also nearby, featuring an energetic, industrial vibe, thanks to tons of trendy restaurants and bars that have taken over the old warehouse spaces.

Between meals, simply stroll around the neighborhood to discover the West Loops’s many art galleries and shops.

If you plan on eating at Au Cheval, we recommend putting your name down on the waitlist as early as possible before exploring West Loop area on foot. More on that below.


If you’re a burger fanatic, Au Cheval needs no introduction. It’s quite literally the best burger in the world. And I’m not just saying that–a lot of world-renowned, acclaimed chefs have called it that!

When attempting to work in Au Cheval into your Chicago itinerary, you’re going to need to be flexible. Show up on a nice weekend afternoon and the wait might be 4.5 hours! That’s why we recommend adding your name to the waitlist ASAP.

If you can’t get a seat at Au Cheval (sadly, they don’t take reservations), head to Small Cheval in Bucktown, North Riverside, or near Old Town to get your burger fix.

Small Cheval Bucktown - 4 Day Chicago Itinerary

You really shouldn’t leave Chicago without having this burger.


Sawada Coffee West Loop - 4 Day Chicago Itinerary

You just ate a really, really decadent burger. You’re probably going to need an afternoon pick-me-up! Steps away from Au Cheval is one of our personal favorite coffee shops in all of Chicago–Sawada Coffee.

What’s great about Sawada Coffee is that it’s always busy. This coffee shop was established by world-renowned barista and latte art expert Hiroshi Sawada.

If you’re looking for one iconic drink to order, it’ll be their signature Military Latte–espresso, matcha, vanilla, milk & cocoa powder all mixed up into one high octane drink!


There are so many cool spots in Chicago to grab drinks after dark. From comedy clubs to nightclubs to magic lounges, we recommend checking out the following:

  • The Violet Hour (speakeasy-style lounge in Wicker Park)
  • Debonair Social Club (nightclub/lounge in Wicker Park)
  • Three Dots and a Dash (tiki bar in River North/Downtown)
  • Joy District (nightclub in River North/Downtown)
  • Sparrow (bar in Near North Side)
  • Beauty Bar (kitschy bar/club in West Town)
  • Second City (comedy club in Lincoln Park)
  • Chicago Magic Lounge (magic bar and theater in Andersonville)

And that’s a wrap! Your 4-day Chicago itinerary has come to a close! Check out the next section for alternative things to do if you want to swap attractions in/out of this itinerary.


Trip map courtesy of Wanderlog, a vacation planner


  • Chicago Pizza Tour: Chicago’s only bus guided neighborhood pizza tour, includes 4 stops in different neighborhoods.
  • Bikes, Bites, and Brews – Chicago’s Signature Dishes Bike Tour: Half-day bike tour featuring classic eats like Chicago dogs, deep-dish pizza, cupcakes and craft beer!
  • Chicago Crime and Mob Bus Tour: Explore Chicago while hearing stories about Chicago’s most notorious criminals and mobsters including Al Capone and John Dillinger.
  • Chicago Architecture River Cruise: A must-do for first timers! We did this tour and loved every minute of the cityscape views and the storytelling our guide used to teach us the history of Chicago.
  • Prince: The Immersive Experience: Lose yourself on an interactive trip through the music and life of Prince. Journey through 10 multidimensional spaces
  • Harry Potter: Magic at Play: A unique, hands-on experience that will bring out the young witch or wizard in all of us. Explore, climb, and play your way through three floors of fun packed with playful celebrations of your favorite places and moments!


  • Free walking tour of Chicago – Usually a 2-hour pay-what-you-wish walking tour
  • Skydeck Chicago – a good alternative to 360 Chicago, located in the Willis Tower (formerly known as Sears Tower); you’ll get city views, but no lake views though
  • Field Museum Of Natural History – state-of-the-art natural history museum
  • Alder Planetarium – learn everything there is to know about the solar system
  • Skyline Lake Tour – a good alternative to the architecture river cruise
  • American Writers Museum – discover five centuries of literary history with interactive exhibits
  • Catch a show at Downtown Chicago’s Theater District – a hub for world-class productions and premieres
  • Art Institute of Chicago – a world-class art museum
  • See Wrigley Field with your own eyes – explore Wrigleyville afterward
  • Montrose Beach – beach and picnic in the summertime
  • North Avenue Beach – beach and do watersports
  • Garfield Park Conservatory – especially fun if you’re traveling with kids
  • Skokie Northshore Sculpture Park
  • Take a day trip to Lake Geneva (1.5 hours from Chicago)
  • Take a day trip to Milwuakee (1.5 hours from Chicago)


On my last trip to Chicago, I used Go City’s Chicago All-Inclusive Pass. This easy-to-use mobile attraction pass really helped us see a lot of Chicago in a really short amount of time, and it helped us save a ton of money!

The Go City Chicago Pass is a digital attraction pass that provides easy access and admission to some of Chicago’s most popular museums and excursions. With certain excursions, you’re even able to skip the line, saving you both money and time.

There are two types of passes–the All-Inclusive Pass and the Explorer Pass.

The Go City All-Inclusive Pass is really great for travelers who want to see as much as possible while they’re in Chicago. With the All-Inclusive Pass, you can choose between a 1, 2, 3, 5, 6 or 7-day pass that will give you free admission to 25+ museums and attractions throughout Chicago.

Prices start at $140 for the All-Inclusive Pass and you can visit literally as many attractions as you can fit into each day!

The pass includes admission to the following heavy-hitters:

  • Architecture River Cruise
  • Skydeck Chicago
  • 360 Chicago
  • Shedd Aquarium
  • Field Museum
  • Museum Of Science And Industry
  • Alder Planetarium
  • Skyline Lake Tour

If you don’t plan on visiting a ton of different attractions, Go City also has an Explorer Pass which will still save you a lot of money. With the Explorer Pass, you’ll pay one flat fee for a 2, 3, 4, 5, 6, or 7-choice pass.

You’ll then have 60 days to use the Explorer Pass on whichever attractions you’d like. There is also no need to pick attractions ahead of time, so you’ll have the flexibility to choose attractions as you go. Passes start at $69 for 2 choices.

You can buy the pass online here.

DEAL ALERT: For a limited time, use the above link + the promo code AFFGOALL for an additional 5% off your Go City pass. This code is valid for any Go City pass in any destination!


  • Chicago-style hot dog – Superdawg, Red Hot Ranch, Fatso’s Last Stand or Kim and Carlo’s Hotdog Cart
  • Deep-dish pizza – Pequod’s is superior to the rest! Get the spinach with garlic deep-dish!
  • Best burger in all of the world – Au Cheval
  • Italian beef sandwich – Al’s #1 Italian Beef (or Johnnie’s Beef or Portillo’s)
  • The most gluttonous chocolate cake shake you’ll ever see in your life – Portillo’s
  • Fried chicken churro sandwich – Xoco
  • Caramel and cheese popcorn – Garrett’s
  • Fried chicken – Harold’s Chicken Shack, Honey Butter Fried Chicken, and The Budlong


Staying in West Loop or the River North areas for this 4-day Chicago itinerary is going to be your best option. Both of these locations will put you within walking distance of some of Chicago’s best attractions. This means you’ll be able to save money on taking public transportation or taking Uber/Lyft everywhere.

What I also found was that sometimes, it was actually faster to walk myself to a nearby attraction than take the subway (especially when you account for all the train wait times and all).

On our last trip, we stayed at The Westin Chicago River North. I have nothing but wonderful things to say about this hotel. The location was perfect and the amenities were unbeatable. I mean, have you ever laid in Westin linens/bedding and not melted? Life-changing.

The gym was also one of the most impressive fitness centers I’ve ever experienced while traveling. The huge gym came equipped with lots of fitness equipment including multiple Peloton bikes, 2 Hypervolt percussion massage guns, as well as locker rooms, showers, and even a sauna!

Waking up with a solid morning workout at the hotel was an absolute dream! And upon stepping outside and realizing you’re in the middle of it all, right along the riverfront–magical.

Chicago Riverwalk - 4 Day Chicago Itinerary - TravelsWithElle

Other great hotels you can consider staying at in Downtown Chicago:

Budget-friendly hotels in Downtown Chicago ($)

  • Freehand Chicago – stylish boutique hostel located in River North in the city center (they have both private rooms and shared rooms)

Moderately-priced hotels in Downtown Chicago ($$)

  • Virgin Hotels Chicago – modern hotel featuring 2 restaurants, a nightclub, rooftop terrace, gym, and 2 bars/lounges

Luxury/higher-end hotels in Downtown Chicago ($$$)


If your travel dates fall within the dates of a festival or event, try to work it into your 4-day Chicago itinerary! Some of our favorite memories of travel destinations are from special local events that we happened to just stumble upon.

  • SoxFest (Jan) – celebrating all things baseball
  • Winter Brew (Jan) – beer festival
  • Chicago Ale Fest (Feb) – beer festival
  • Chicago Auto Show (Feb)
  • Chicago Theatre Week (Feb)
  • St. Patrick’s Day (March) – includes an annual dyeing of the Chicago River and huge parade
  • Windy City BREWHAHA (March) – beer festival
  • Chicago Restaurant Week (March)
  • Chicago Comic and Entertainment Expo (April) – largest pop culture convention in the Midwest
  • Chicago Memorial Day Parade (May)
  • Maifest Chicago (May) – honors German heritage and the start of spring
  • Gay Pride Chicago (June)
  • Chicago Blues Festival (June)
  • Taste of Chicago (July) – the world’s largest free-admission food festival
  • Pitchfork Music Festival (July)
  • Air and Water Show (August)
  • Lollapalooza (August)
  • Chicago Jazz Festival (September)
  • Hyde Park Jazz Festival (September)
  • Oktoberfest Chicago (September) – beer festival
  • Chicago International Film Festival (October)
  • Chicago Marathon (October)
  • The Magnificent Mile Lights Festival (November)
  • McDonald’s Thanksgiving Parade (November) – free parade featuring large marching bands, inflatable floats, and performance acts
  • Christkindlmarket (December) – inspired by the epic German market in Nuremberg
  • Fifth Third Bank Winter Wonderfest (December)


Everyone knows that Chicago during the winter is unbearably cold — especially if you don’t come from a state/country that sees snow and wet-cold!

So the question is… is the cold worth bearing in order to experience Chicago during the most festive time of the year?

The weeks leading up to Christmas are indeed a magical time to visit, especially if you enjoy festive holiday events and a snowy urban landscape! The city comes alive with holiday lights, winter markets, and other holiday-themed seasonal attractions.

Here are some notable events that can make a winter trip to Chicago #worthit:

Magnificent Mile Lights Festival:

  • Dates: Mid-November
  • Details: The Magnificent Mile Lights Festival marks the start of the holiday season with a grand parade, tree-lighting ceremony, and fireworks along Chicago’s iconic Magnificent Mile.

Christkindlmarket Chicago:

  • Dates: Late November to Christmas Eve
  • Details: Inspired by the traditional German holiday markets, Christkindlmarket in Chicago features festive stalls with handmade ornaments, crafts, and delicious European treats.

ZooLights at Lincoln Park Zoo:

  • Dates: Late November to early January
  • Details: Lincoln Park Zoo transforms into a winter wonderland with millions of twinkling lights, holiday displays, and seasonal activities for visitors of all ages.

Ice Skating in Millennium Park:

  • Dates: November to March (weather-dependent)
  • Details: The McCormick Tribune Ice Rink in Millennium Park opens in November, offering a picturesque setting for ice skating against the backdrop of the city skyline.

Winter WonderFest at Navy Pier:

  • Dates: December to early January
  • Details: Navy Pier hosts Winter WonderFest, featuring an indoor winter playground with ice skating, carnival rides, and holiday-themed attractions.

Holiday-Themed Theatre Shows:

  • Dates: Throughout December
  • Details: Catch a holiday-themed performance at one of Chicago’s iconic theaters, featuring holiday classics and seasonal favorites like The Nutcracker, A Christmas Carol, Christmas performances by Chicago Symphony Orchestra, and more.

New Year’s Eve Celebrations:

  • Dates: December 31st
  • Details: Join the city’s lively New Year’s Eve celebrations, including fireworks at Navy Pier, parties at various venues, and special events to ring in the new year.

While Chicago winters can be extremely bone-chillingly cold, the city’s holiday spirit and festive seasonal activities CAN make a winter trip worth the cold!


  • Comfortable walking shoes | You’re going to be doing a lot of hill climbing, so bring comfortable walking shoes. My all-time favorite travel shoes these days are the tried and true Ecco Soft 7‘s (they’re stylish, comfortable, and have been raved about for decades since they were first created)! Lucky for us, they have them for both men and women.
  • Portable Umbrella | Chicago can be quite wet during certain seasons. If you’re going to bring an umbrella, make it a compact umbrella like this one!
  • Light Rain Jacket | A lightweight waterproof rain jacket is critical for any destination with unpredictable weather. Since these weigh virtually nothing and are so easily packable, I recommend you carry one with you whenever you head outdoors. Depending on the weather forecast and chance of precipitation, I’ll either go with a rain shell or a puffier windbreaker. I’m never without some sort of outer layer! My top recommendations are Marmot Men’s PreCip (for men) and The North Face Women’s Venture 2 Jacket (for women).
  • Puffy Jacket | If you’re traveling in the fall or wintertime, you’re going to need layers. You have a lot of options here, but I personally have the North Face Thermoball, and it’s kept me warm throughout my many years of adventuring!
  • Travel Daypack | I’m a huge fan of the Fjallraven Kanken Mini Backpack. It stylish and has ample room for all the snacks and water you’ll need, as well as for your camera and the safety essentials for a hike or just a regular day out.
  • Sunhat | Sun protection is key for any destination, anytime.
  • Sunscreen | Sunscreen is absolutely necessary. Even if it’s overcast or cloudy, the UV index can be very high, so be sure to apply whenever you’re outdoors. No matter where we go, we like a coral reef-safe brand, as traditional sunscreens contain chemicals that damage our environment. For the face, we are absolutely obsessed with the magical Supergoop! Unseen Sunscreen.
  • Hand Sanitizer Hand sanitizer gel or wipes are a must any time you’re going to be in contact with surfaces many other people have touched. Never leave your hotel room without it! And if you do happen to forget it, remember to wash your hands often, especially before eating or touching your face.
  • Portable Power Bank | You’re probably going to be out all day, snapping away taking pictures… the last thing you want is to be driving along with no phone battery! A portable power bank is a must-have, and Anker’s ultra-light, ultra-portable power bank is tried and true by so many travelers! I never embark on a day of exploration without it.
  • Soft Hydration Flask | Stay hydrated throughout the day with a water bottle that can go anywhere with you—and fold up when not in use. I love the packability of these bottles!
  • Emergen-C packets or Liquid I.V. Hydration Packets | These are a great way to support your immune system and overall health on a trip. They are light, take up no space, and are very easy to pack!

And that concludes this 4-day Chicago itinerary! We hope that this post has inspired you to try something new! If you have any questions about the destinations or have your own travel tips to share, please don’t hesitate to leave them in the comments below.

More travel tips/resources:

CityPASS vs Go City Chicago: Which Is Better?

1 Day Chicago Itinerary For First Timers: The Must-Do Highlights

25 Best Things To Do In Chicago At Night

The Ultimate Lollapalooza Packing List: 21 Festival Essentials To Bring

45+ Genius Travel Hacks: Your Guide To Saving Money While Traveling

The Minimalist Traveler’s Guide to Packing

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Elle Leung

My name is Elle and I'm a travel blogger and adventurer based in California. I love helping people plan trips and create unique itineraries based on their interests and their budgets. I'm a huge fan of outdoor adventures and doing off-the-beaten-path things in my state (and all around the world too)!

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