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

World-class city views. A thriving food scene. Vibrant and eclectic neighborhoods. There’s a lot to love about Chicago. This city is as unique as it is diverse and should be on every traveler’s bucket list.

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!

If you’re looking for a 1-day Chicago itinerary, we’re glad you’re here. While I don’t recommend spending just one day in Chicago, sometimes you might not be able to help it.

Maybe Chicago is only a pit stop for a longer drive through the country. Maybe you have a long layover and wanted to spend your time in the city as opposed to sitting at the airport for 10 hours.

No matter the reason, I’ve got you on your 1-day Chicago itinerary! You won’t see it all, but I’ll show you how to maximize your time in Chicago and save money with an optimized sightseeing route using the Go City Chicago All-Inclusive Pass.

Get ready for 24 hours of deep-dish pizza, iconic sights, and uniquely Chicago experiences!

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WHAT IS CHICAGO KNOWN FOR?

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
  • Being a very windy city, hence the nickname, “The Windy City”
  • 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

WHEN IS THE BEST TIME TO VISIT CHICAGO?

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!


HOW MANY DAYS TO SPEND IN CHICAGO?

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!

Having said that, since this is a 1-day Chicago itinerary post, I will say that it is possible to catch a few of the main highlights in just one day. I personally think the easiest and most cost-efficient way of doing this is with the help of a Chicago attraction pass.

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!


WHAT IS THE GO CITY CHICAGO ATTRACTION PASS?

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 $95 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 $59 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!


1 DAY CHICAGO ITINERARY: MUST SEE HIGHLIGHTS

Without further ado, let’s get to the good stuff! Here is my exact 1-day Chicago highlights itinerary. With this itinerary, you’ll be hitting up some free-to-visit spots throughout the city as well as making use of the Go City Chicago All-Inclusive Pass!

1. NAVY PIER

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

Navy Pier, also known as the People’s Pier, 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.

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

The second best thing to do here is to catch the fireworks show in the summertime. The fireworks show 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

2. THE BEAN AT MILLENNIUM PARK

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

When in Chicago, 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.

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

3. MILLENNIUM PARK

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

4. SHEDD AQUARIUM

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

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. A huge plus? Admission was included with my Go City Chicago All-Inclusive Pass!

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!

I, for one, could not pass up the opportunity to visit such a world-class attraction and it completely exceeded my expectations.

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

5. MUSEUM OF SCIENCE AND INDUSTRY

Museum of Science And Industry - 1 Day Chicago Itinerary

Calling literally anyone who is a fan of science, curiosities, and learning! You absolutely need to work the Museum of Science and Industry into your 1-day Chicago itinerary. I know you won’t have much time in just one day, but 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 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

6. LUNCH

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 XOCO, 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.

7. ARCHITECTURE RIVER CRUISE

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: $46.87 for adults
Cost with Go City Chicago All-Inclusive Pass: FREE

8. 360 CHICAGO

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

Time to enjoy some quintessential cityscape views! 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!

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

9. DINNER: DEEP-DISH PIZZA AT PEQUOD’S

The true deep-dish pizza MVP is not Lou Malnati’s or Giordano’s, but rather Pequod’s. Yes, it is a bit further out, but trust me when I tell you that Pequod’s is the deep-dish champion. 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, especially on weekends. Yes, it is that good.

10. BUCKINGHAM FOUNTAIN / GRANT PARK

Calling all Europe lovers, public art enthusiasts, and architecture fanatics! You’ve gotta see Buckingham Fountain. 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

11. NIGHTLIFE

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

There are so many cool spots in Chicago to grab drinks after dark. We recommend checking out the following:

  • The Violet Hour (Wicker Park)
  • Three Dots and a Dash (Downtown Chicago)
  • Sparrow (Near North Side)

And that’s a wrap! Your 1-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.


OTHER POPULAR THINGS TO DO IN CHICAGO (IF YOU HAVE MORE TIME)

  • Skydeck Chicago – a good alternative to 360 Chicago, no lake views though
  • Field Museum – 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
  • Catch a show at Downtown Chicago’s Theater District – a hub for world-class productions and premieres
  • Lincoln Park Zoo – this zoo is absolutely free to enjoy
  • Walk the Chicago Riverwalk
  • Art Institute of Chicago – a world-class art museum
  • See Wrigley Field with your own eyes – explore Wrigleyville afterward
  • Explore Wicker Park – one of Chicago’s hippest neighborhoods filled with restaurants, coffee shops, cocktail bars, and shops

WHAT TO EAT IN CHICAGO

  • Chicago-style hot dog – Superdawg, Red Hot Ranch, Fatso’s Last Stand or Kim and Carlo’s Hotdog Cart
  • Deep-dish pizza – Pequod’s
  • Best burger in all of the world – Au Cheval
  • Italian beef sandwich – Al’s #1 Italian Beef
  • Gluttonous chocolate cake / shake – Portillo’s
  • Fried chicken churro sandwich – Xoco

WHERE TO STAY IN CHICAGO: 1-DAY ITINERARY

For such a short trip, you’re going to want to be as close to all the action as possible. I’d recommend staying in Downtown Chicago for this 1-day Chicago itinerary.

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 ($$)

  • Sonder at Grant Park – bright and spacious hotel located in The Loop, super close to everything
  • Virgin Hotels Chicago – modern hotel featuring 2 restaurants, a nightclub, rooftop terrace, gym, and 2 bars/lounges

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


ANNUAL EVENTS IN CHICAGO

  • 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)

ESSENTIAL PACKING LIST: CHICAGO, ILLINOIS

  • 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.
  • Smartphone UV Sanitizer and Charger | Our phones gather all the grime and bacteria we touch throughout the day, and then they are stored in warm, dark places like purses and pockets, which make for great breeding grounds for bacteria to grow. They are the third hand we never wash, but should! Using a UV sanitizer such as PhoneSoap on a regular basis will help keep germs and illness at bay.
  • First Aid Kit | It’s always good to carry a first aid kit around with you when traveling. If you need to pack light, simply make one of your own (pain medications, bandaids, motion sickness pills, etc.)
  • Portable Umbrella | You’re going to be in The Windy City. If you’re going to bring an umbrella, make it a compact, wind-proof 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.
  • Body Wipes / Feminine Wipes | Feeling a bit gross after a hike or bike ride but don’t have the time to shower right in that instant? Just whip out one of these body wipes for a quick refresher. The feminine wipes I like are infused with cucumber and aloe. Trust me, you will feel and smell so much better. Always good to have a few handy in your travel bag.
  • 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 post! 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:

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

The Minimalist Traveler’s Guide to Packing

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