Make the most of your day in Chicago with the best things to do and see!
If you’re planning a whirlwind adventure to the Windy City, get ready, because one day in Chicago is all you need to fall in love with this vibrant town! Whether you’re here for the food, the art, or just those breathtaking views, Chicago’s got a little bit of everything for everyone. I’m talking deep-dish pizza, epic rooftop scenes, and, yes, that famous “Bean” you’ve probably seen all over Instagram.
I heart Chicago because it’s such an approachable city. I’m typically a road trip, national park kind of girl. But Chicago is easy to visit and fun when you’re craving a metropolitan adventure. Because it’s only a four-hour drive from my home, I’ve been to Chicago many times—for weekend getaways with my husband, a family spring break, and most recently, a meetup with friends from across the country. Every time I go, there’s plenty of new things to see and do. Chicago is multifaceted, baby!
As a professional travel writer with over 10 years of experience writing for magazines, I’ve explored incredible destinations across the United States. My mission is to help people plan unforgettable vacations. For fun, offbeat trips, check out my guides. They make going on an awesome adventure easy!
So, lace up your walking shoes and bring your appetite, because I created a one-day itinerary for you with lots of sights to see and mouth-watering eats. From cozy breakfast bites at a local café to an artsy afternoon at a renowned museum, and finally a dazzling rooftop nightcap with a killer view of the skyline, this itinerary gives you a sample of what Chicago has to offer—even if you only have 24 hours to spare.
One Day in Chicago Itinerary
Follow this travel plan to make the most of your day in Chicago! It’s taken from my Chicago Weekend Itinerary Guide, a four-day travel plan for people who want to spend a long weekend in the city.
Grab a Quick Breakfast
Have a leisurely morning in your hotel room before walking to Dollop Coffee Co. for a cup of joe and a breakfast sandwich or pastry. Trust me, you’ll still be dreaming about their pistachio raspberry donut long after you leave Chicago. (345 E. Ohio St.)
Go on a Tour of The Loop at 11:30 a.m.
Check-in at the front desk of the Chicago Cultural Center for a free, one-hour walking tour to see iconic sights like “The Bean” sculpture and to see hidden gems most people miss. The tour starts at 11:30 a.m. (although you can catch another one at 1:30 p.m.). The tours are only offered on Fridays, Saturdays, and Sundays—no reservations are needed. (77 E. Randolph St.)
Have Lunch With a View
Enjoy lunch with panoramic views of the city and Lake Michigan at Cindy’s Rooftop Restaurant on top of the Chicago Athletic Association building. The menu is great, but the photo ops are even better! (12 S. Michigan Ave.)
Enjoy An Artsy Afternoon
Spend your afternoon exploring one of the best art museums in the world, the Art Institute of Chicago. From impressionist masterpieces to contemporary surprises, there’s something for everyone. Don’t miss Seurat’s Sunday on La Grande Jatte. (111 S. Michigan Ave.)
Nosh Deep-Dish Pizza for Dinner
Time to experience a Chicago food classic—deep-dish pizza! Choose between Lou Malnati’s Pizzeria (410 N. Michigan Ave.) or Giordano’s (130 E. Randolph St.), both just a short walk from the Art Institute of Chicago and known for their legendary pies.
Get a Nightcap
End your night at Sky Bar of the Riu Plaza Chicago Hotel, where you can sip cocktails and take in city views. It’s free to step out onto their thrilling glass balcony 27 stories up if you dare. (150 E. Ontario St.)
Optional Add-On Activities
If you like an action-packed day, you can add these fun activities to your one day in Chicago itinerary.
- Lake Michigan Boat Tour: If you’re visiting in the warmer months, a quick boat tour offers spectacular views of Chicago’s skyline and it’s a great way to learn some of the city’s history.
- Willis Tower Skydeck: For thrill-seekers, step out onto “The Ledge” at Willis Tower—1,353 feet above the city—and look down. Yikes!
- Chicago Riverwalk: Take a stroll along the Chicago River. There are many cafes along the way for you to stop and sip a drink overlooking the riverbank.
Can’t-Miss Chicago Photo Ops
These are the photos you’ll post to social or frame later. Take your time to get the just-right snap.
- Cloud Gate (“The Bean”): This reflective sculpture in Millennium Park is a must for your Chicago photo album. Stand near the side of the sculpture that faces buildings, not the park, so that you get a shot of the skyline reflected in The Bean.
- Cindy’s Rooftop: Capture panoramic views of Lake Michigan and Millennium Park from Cindy’s.
- The Art Institute: Snap a shot by the iconic bronze lions guarding the museum entrance.
Your Chicago Trip Is All Set
Why waste time trying to piece together a trip yourself? Grab my Chicago Weekend Itinerary Guide and know exactly what to do, see, and eat and where to stay, just like that! Click here.
Getting Around Chicago
This is a walkable itinerary focused on the popular area of the city known as The Loop. So bring comfortable shoes. To cover distance quickly, you can also opt for an Uber or Lyft ride.
Weather and What to Wear
Chicago is known for its wind, so be prepared for a breeze, especially near Lake Michigan and on rooftops like Cindy’s! Pack layers for fall or spring, a warm coat, gloves, and hat for winter, and don’t forget sunscreen in the summer.
Wrapping Up Your One Day in Chicago
Spending one day in Chicago may seem like a whirlwind, but with this well-planned itinerary, you’ll experience the best the city has to offer in just 24 hours. From grabbing a delicious breakfast at a local café to marveling at the city’s famous art, architecture, and food, this guide ensures you get a good feel for the Windy City.
But there’s only so much you can see in a day! Make a mental list of what to return for, like Navy Pier’s attractions, the Field Museum and Chinatown, and plan a future trip for a long weekend.
✅ Grab my Chicago Weekend Itinerary Guide and have an amazing long weekend in the city!
