How to Spend 1 Day in Chicago Downtown for First Timers
Is 1 day in Chicago enough? Of course not, but as a local, I’ll freely admit to being biased. If you can’t spare much time, even a single day in the Windy City is so much better than nothing. When you plan carefully, you really can max out a one-day stay.
This suggested one day Chicago itinerary includes where to eat breakfast, lunch and dinner, as well as what to do while you’re in the city.
From mega-popular Millenium Park to modern art, an architecture cruise, the Lakefront Trail, and the best comedy shows in town – this is how to spend 24 hours in Chicago.
What to do in 1 day in Chicago Downtown
Chicago is made up of many different neighborhoods, and an area known as The Loop is what constitutes downtown Chicago. It’s home to the Riverwalk, Millennium Park, historic architecture, cultural venues, theaters, restaurants, shops and more.
Whether you’re in town for work or touristing, you can make the most of a day in Chicago by concentrating your time in the downtown area. Here is my local’s guide on what to do while you’re there.
Coffee and light breakfast at Sawada
You’re in for a hefty lunch today if you follow my advice, so consider a lighter breakfast. With rustic decor and a laid-back vibe, a visit to Sawada Coffee in the West Loop is a cozy way to start the day.
My sister and I both enjoy the lattes here, including the signature Military Latte, which contains espresso, matcha, cocoa and vanilla. You’ll also find pastries on offer.
If you do feel like you want something more filling, head to nearby Beatrix or Waffles for a full-on breakfast.
You can also visit Levain, Milk Bar and Voodoo Donuts in this area, which is handy if you’ve set your heart on sampling any of these east or west coast staples. Personally, though, I recommend Dorite or Stan’s for the best donuts in Chicago.
Millennium Park & Cindy’s Rooftop
Next, take a walk, bus or rideshare over to Millenium Park to check out: The Bean (aka Cloud Gate), tranquil Lurie Garden, Crown Fountain, the Jay Pritzker Pavilion music venue, and the adjoining Maggie Daley Park.
I also recommend heading up to Cindy’s Rooftop at the Chicago Athletic Association Hotel across the street. You’ll see panoramic views over the park, you don’t need a reservation, and it’s usually open from 11am.
Grab a drink and take in those views from the balcony. If it’s too early in the day for one of their specialty cocktails, they also serve coffee, soft drinks and mocktails. I love bringing friends up here when they’re visiting me from out of town.
Modern wing at the Art Institute of Chicago
Since touring the entire museum might take too long, you could limit your visit to the Modern Wing while you’re already near the Art Institute of Chicago.
There’s an impressive collection of contemporary art housed here including sculpture, photography, architecture and paintings. The building itself is 264,000 square feet, and was designed by a Pritzker prize-winning architect.
If you have time before your next activity, make your way to the Palmer House Hilton which is a 5-minute walk away. There, you can taste the original brownie! That’s right, it was invented right here in Chicago.
Architecture boat cruise & riverwalk
This is a favorite activity of locals and tourists alike. The architecture boat cruise includes commentary, so you can learn about the architectural history behind all the beautiful sights you’ll pass.
Time allowing, you may be able to stroll along the riverwalk before or after your boat ride as well.
In addition to some restaurants and shops along the riverwalk, there are plenty of areas to sit for a moment of tranquility amidst the bustling downtown surroundings.
Deep dish pizza at Uno’s
As you might expect in Chicago, there are plenty of deep dish pizza places to choose from, and we locals tend to have our own go-to spots. One of my favorites, Pizzeria Uno, is said to be the original.
Be prepared – it takes about 40 minutes to make a deep dish pizza, and it’s worth it! My personal favorite is spinach stuffed, but there are so many toppings (or rather, stuffings) to choose from.
Lakefront trail + Lincoln Park OR Chicago History Museum
Now, normally I like to sit around and rest after eating a heavy slice of deep dish. But with only 1 day in Chicago you’ve got more to explore. So, why not keep it moving by taking a walk along the lakefront trail?
You can enter via the nearby (20-min walk) Oak Street Beach entrance. Once through to the lakefront trail, stroll for another 20 minutes or so and you’ll come across the 43rd Street pedestrian bridge.
This goes over Lake Shore Drive for lovely views over the downtown area. On the other side, you’ll be in sprawling Lincoln Park.
If you’re not up for an outdoor walk, you could head to the Chicago History Museum instead. Do note, though, that this closes at 4.30pm daily, except for Sundays when it’s open till 5pm and Mondays, when it’s closed.
Comedy show at The Second City
With live shows nightly, The Second City specializes in comedy sketch shows and theater, and is also home to an improv school.
Some comedic greats got their start here, so it’s definitely a cool experience to add to your itinerary. As a local, I’ve been several times myself.
Though schedules vary, a typical show will begin at 8pm and last for around two hours. Catching a show here is a must while you’re visiting Chicago.
Dinner in West Loop
West Loop is central to Chicago’s foodie scene, so it’s the place to go for dinner. You can find everything from laid-back eateries to fine dining restaurants with one or more Michelin stars.
I recommend trying Italian at Monteverde, Mediterranean at Aba, or the ever-popular Girl and the Goat. You’ll need to reserve a table in advance at any of these.
If you’re not that hungry, on a budget, or prefer something simpler, you could grab a burger at Small Cheval.
Seasonal ideas for your day in Chicago
If you’re looking for other ideas for things to do in Chicago, check out what’s on at the time of year you’ll be visiting.
In summer, you could take a look at what farmers markets or festivals are going on, or maybe catch a movie night at Millennium Park.
If you’re planning a winter visit, you’ll probably want to spend more time indoors at spots like local museums, going from shop to shop along the Magnificent Mile, or within the Block 37 mall.
For festive shopping, there’s also the Christkindlmarket if your trip will be between late November and late December.
Additional tips for a day in Chicago
Here are a few additional things to keep in mind as you plan your visit:
- How to get around Chicago: while this itinerary focuses a lot on walking you can also rely on rideshares and public transportation to get around the city. I don’t recommend renting a car, as driving and parking in the city can be chaotic
- Is 1 day in Chicago enough? Well, more would be better but work with what you can! You can still get a good feel for the city with 1 day, and use it to inspire a longer return trip later.
- Is Chicago safe? Employ your street smarts and consult my guide about solo traveling in Chicago for safety tips that are applicable for all.
Where to stay when spending 1 day in Chicago
Staying overnight? The best places to stay in Chicago are West Loop, River North and Lincoln Park. Here are my top picks in each of these areas.
🏨 Hampton Inn in West Loop
Max out a one night stay by picking the Hampton Inn Chicago West Loop. It’s close to the restaurants of the area and has a bar serving craft beers for post-dinner drinks. There’s also an indoor pool.
👉 Check prices and availability
🏨 Kinzie Hotel in River North
Kinzie Hotel offers boutique-style accommodations in the popular River North district. The front desk and gym are open 24/7, and the staff are very welcoming. Guest receptions are held here nightly in the lounge bar.
👉 Check prices and availability
🏨 Hotel Lincoln in Lincoln Park
This four-star hotel opposite Lincoln Park offers restaurants, a rooftop cocktail bar, and rooms with park or lake views. A 10-minute walk will take you from the front door to the Lakefront Trail.
👉 Check prices and availability
So, how will you spend your 1 day in Chicago?
I hope this guide to what to do during one day in Chicago has inspired your trip to my home city. Whether it’s your first or your fifth visit, there’s always plenty going on.
But if you prefer a more relaxed vibe, it’s also easy to find peace within the city parks, on the river or along the lake.
Tailor this itinerary based on your own interests, and you can even draw additional inspiration from this longer Chicago itinerary.
