Chicago In A Day: Best Things To Do + Itinerary
Wondering how to make the most of a day in Chicago?
Ah, Chicago. How I love this city! I’ve visited for girls’ trips, weekend getaways with my husband, and family trips as a young girl, and I even took the Amtrak train from Kansas City once.
Chicago remains a “Mecca of the Midwest” and the third-most populous city in the U.S. With an abundance of things to do and see, exploring everything the city has to offer could easily fill weeks. So planning to pack all that into a single day might seem daunting.
If you’re figuring out how to spend a day in the city or even wondering if Chicago is worth visiting in the first place, I’ve put together a guide to help you do just that.
This 24-hour itinerary will cover must-see attractions, top dining spots, and recommendations for where to stay so you can explore Chicago like a pro.
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Chicago In A Day Overview
There’s a lot to fit into a day when visiting Chicago. Here’s a brief overview of my suggested itinerary, with more details provided below.
- Morning: Visit some of the city’s biggest tourist attractions, like Cloud Gate and Willis Tower (Skydeck)
- Lunch: Sample some of Chicago’s “staples” such as deep-dish pizza
- Afternoon: Explore one of Chicago’s many incredible museums
- Early Evening: Enjoy an architectural boat tour on the Chicago River
- Evening: Wind down the day with drinks on a rooftop and tasty dinner
Chicago In A Day: 24-Hour Itinerary
Here’s a sample itinerary for how to spend a day in Chicago that covers all the major landmarks and attractions suited for first or second-time visitors. For return visitors, check out the Alternative Activities section at the end of this post.
Morning: The Bean & Skydeck
Breakfast
8:30 – 9:30 am
There’s no shortage of breakfast spots in Chicago (to say the least), but you can’t go wrong with Wildberry Pancakes and Cafe. Bonus: it’s located right next to the first stop on the itinerary, The Bean. Get their Blueberry Danish Pancakes (YUM!).
Alternatives: If you’re a foodie and don’t mind venturing outside the downtown area, I would also highly recommend Lula Cafe which recently won a James Beard award, Batter n Berries, or Kasma (expect a long wait, but you can also get takeout).
Cloud Gate (The Bean)
9:45 – 10:30 am
Start your day by visiting The Cloud Gate or “The Bean”, Chicago’s second-largest tourist attraction that’s estimated to get over 25 million visitors each year. This bean-shaped sculpture is made of 168 large stainless steel plates and reflects the city’s beautiful skyline. (a.k.a. it makes for a great photo spot)
The sculpture is located in Millennium Park and is completely free to visit!
TIP: As you can imagine, The Bean can get quite crowded. To beat the crowds and get that perfect photo, visit on a weekday or early in the morning. Millenium Park is open every day from 6 am to 11 pm.
Willis Tower | Skydeck
10:50 am – 12:20 pm
About an 18-minute walk from The Bean is Willis Tower, previously called Sears Tower. Here, it’s all about the incredible views! You’ve probably seen photos of people standing on a glass floor balcony (The Ledge) 1,353 feet high, looking straight down at the city below.
Rumor has it you can even see four states from the top!
TIP: Be prepared: you only get to spend 90 seconds on The Ledge (they will time you), but you can get back in line as many times as you want.
There’s also a museum worth spending some time at inside that includes exhibits about Chicago’s history, neighborhoods, and key landmarks. Open 365 days a year, it’s a great place to get that picture of Chicago’s skyline.
Afternoon: Deep-Dish, Museums, & Boat Tour
Sample Chicago’s Iconic Dishes
12:40 – 2:00 pm
Chicago takes its pizza pretty seriously! There’s an ongoing debate about the best deep-dish pizza in Chicago, but since you’re only here for a day, I recommend sticking with a “mainstream” option that’s conveniently located downtown—Lou Malnati’s.
Or if you are a lover of all things pizza, go on this highly-rated Chicago pizza tour that will take you off the beaten path to pizzerias in four different neighborhoods.
Alternatives: Of course, you hear alllll about Chicago deep-dish pizza. For something different, visit Chicago Pizza and Oven Grinder in Lincoln Park and get the pizza pot pie. Or, if pizza isn’t your thing, pick a spot along the Riverwalk instead (like Beatnik on the River).
Visit A Museum
2:30 – 4:30 pm
There are so many incredible museums in the city! Chicago even has a “Museum Campus” home to the Shedd Aquarium, Field Museum, and Adler Planetarium. I’ve visited all three and loved the Field Museum the most (it has the largest and most complete T. rex skeleton), but the Shedd Aquarium is also fantastic and very popular with kids.
This area is about a 30-minute walk from downtown (The Loop), but you can also take public transportation for under $5 to reduce the walking time:
- CTA Orange, Red, and Green Lines (Roosevelt Stop) and walk for 12 to 15 minutes (0.6 miles)
- CTA Bus #146 (Museum Campus Stop)
- Metra Electric Line and South Shore Line (Museum Campus/ 11th Street Station) and walk for 8 to 10 minutes (0.4 miles)
There’s also The Art Institute of Chicago which is the most convenient option located right next to The Bean on Michigan Avenue. It also happens to be my favorite!
The museum features so many well-known pieces like A Sunday on La Grande Jatte by Georges Seurat, Water Lilies by Claude Monet, and American Gothic by Grant Wood. As someone who loved art history class in my school days, it was pure heaven for me.
Note: The art museum is closed on Tuesdays and Wednesdays.
If you are not a museum person, skip to the next item on this itinerary.
Chicago River Architecture Tour
5:00 – 6:30 pm
This is one of the top things everyone tells you to do in Chicago–and for good reason. You get to learn about Chicago’s rich architectural history and discover the “world’s first skyscraper” and the third tallest building in the United States.
Even if you are not an admirer of architecture, this tour is absolutely worth it! I book this nearly every time I’m in Chicago. P.S. There’s a full-service bar and bathrooms on board.
Boarding begins 15 minutes prior to departure time.
TIP: If you visit during the summer months, make sure to wear sunscreen. Learn from my (burnt) mistake: it gets warm on the top deck and there’s no shade.
Evening: Rooftop & Dinner
Pre-Dinner Drinks on a Rooftop (Optional)
6:45 – 7:30 pm
One of my favorite things to do in Chicago is enjoy a drink on a rooftop while taking in the views!
Two of the most popular spots are Cindy’s Rooftop, located across from Millennium Park, and LH Rooftop at London House, which provides amazing views of the river and surrounding architecture. Personally, I think London House has more of that “wow” factor, but you can’t go wrong with either. Note: Reservations require a food and beverage purchase per guest.
I recommend making reservations in advance for either place, as they are quite popular. However, if there are only two of you, you can sometimes do a “walk-in” at London House and still snag a table.
Dinner
7:40 – 9:40 pm
For dinner in Chicago, you have plenty of fantastic options. If you prefer to stay centrally located and walk to dinner, check out The Dearborn, The Purple Pig, RPM Italian, Quartino Ristorante, or Maple and Ash. Note: Reservations are recommended at all of these places.
If you’re up for a short Uber ride and want to explore the surrounding neighborhoods, there are so many great restaurants worth the trip. In the West Loop, try Trivoli Tavern, Rose Mary, avec, Girl and the Goat, or Au Cheval. Or, try Chicago’s original tapas bar, Cafe Ba-Ba-Reeba!, in Lincoln Park. AH-MAZING!
Nightcap (optional)
Chicago has so much to offer at night! Before you head to bed, squeeze in one final activity to complete your Chicago experience:
- Broadway in Chicago – see a Broadway play or musical in Chicago’s theatre district
- The Second City – a must for comedy lovers, known for its famous alumni such as Bill Murray, Stephen Colbert, and Tina Fey
- Chicago Cubs Baseball Game – the atmosphere at Wrigley Field is unmatched!
- Drunk Shakespeare – professional actors take shots of whiskey before attempting to perform a Shakespeare play (ages 21+)
- ART on THE MART – one of the largest permanent digital art projections in the world
Alternative Activities
If you’re reviewing this itinerary and thinking “been there, done that” and are seeking fresh ideas for your next visit, this list is for you!
- Sunbathe on the beach – There are 29 beaches in Chicago to choose from, with Oak Street Beach being my favorite (rent chairs and an umbrella)
- Enjoy a guided tour of Frank Lloyd Wright’s first home and studio in Oak Park
- Afternoon tea experience at The Drake Hotel
- Take the Chicago water taxi to Chinatown for some dim-sum
- Millennium Park Summer Music Series (completely free)
- Go shopping on Michigan Avenue – includes the Starbucks Reserve Roastery Chicago (the world’s largest Starbucks) and multi-level American Girl Place
Where to Stay
I recommend staying in the downtown area (The Loop) or the River North neighborhood for convenience and the best views of Chicago.
I’ve stayed in my fair share of hotels in these areas and have noted which ones I recommend…and others not so much.
Looking for more options? Use the interactive map below to input your desired dates and verify availability for hotels and vacation home rentals.
FAQs
Is one day enough for Chicago?
As you can see from this itinerary, you can actually pack a lot in a single day. While one day in Chicago isn’t enough to fully explore the city, it does allow you to visit the most popular attractions and try a few local staples. You’ll get a good taste of what Chicago has to offer and see some of its key highlights.
Is downtown Chicago walkable?
Downtown Chicago, also known as The Loop, is super walkable. So much so, that I even researched and bought top-rated walking shoes for my last visit because I knew I’d be walking everywhere.
Fun fact: Chicago was recently ranked the most walkable city in the U.S. for tourists by Travel + Leisure. Especially if you stay downtown or in the adjacent River North neighborhood, you can walk to most of the key attractions. It’s one of the top appeals of visiting Chicago, as many of the city’s highlights are within 30 minutes from each other.
What food is Chicago known for?
Chicago is known for deep-dish pizza, Chicago-style hot dogs (toppings: yellow mustard, onions, tomatoes, sport peppers, neon relish, celery salt, a pickle, and absolutely NO ketchup), Italian beef sandwiches, and Chicago-style Garrett Mix popcorn.
Conclusion
Exploring Chicago in a day is an adventure filled with iconic sights, delicious food, and unforgettable experiences. From marveling at architectural wonders to savoring deep-dish pizza, you’ll get a true taste of what makes this city special. It’s amazing how much you can pack into just 24 hours!
Remember, this guide is just a starting point. Chicago has so much to offer, and every visit can be a new adventure. Whether it’s your first time or you’re a returning visitor, there’s always something new to discover. So put on your walking shoes and get ready to make the most of your day in the Windy City!
