One day in Chicago

One day in Chicago day trip

Whether it’s a long layover or a quick trip – there are about a million things to do in Chicago, from the Bean to Chicago dogs. Here’s what to do, see and taste with just one day in Chicago. Chicago holds a special place in How Dare She’s heart, as the founder’s birthplace, but this guide is put together for you by Empty Nesters.

Everything in this guide can be done on your own, but if you prefer to book in advance or book a guide, links are provided and Chicago is so diverse, you can do tours with special interests (like this mob tour, this prohibition tour or this nighttime helicopter tour).

To make things easy for you, everywhere mentioned in this post is ALREADY PINNED in the embedded Google Map below!

One day in Chicago day trip

One day in Chicago

Chicago is an action-packed city, so narrowing down the sites to see and places to eat in just 24 hours will be tough, but by concentrating your efforts its possible. In order to hit some of the top sites and keep travel time to a minimum, I’m going to recommend focusing on downtown and Michigan Avenue. Hopefully, like me, you’ll fall in love with the city and come back many times to explore further.

Getting into Chicago

Arriving at either airport–Midway or O’Hare–will require about 30 minutes to get to downtown. My preference is Midway since its smaller and easier to navigate. It’s also a hub for Southwest which is my favorite domestic carrier. From the airport, I recommend taking an Uber or Lyft to your hotel or AirBnB.

First time using Uber? Sign up with this link for a discount on your first ride.

However, if you are on a tight budget, Chicago does have good public transportation and the elevated train or ‘L’ has lines from both airports to the downtown area.

one day in chicago day trip getting around

What to do in Chicago in a day

To make things easy for you, everywhere mentioned in this post is ALREADY PINNED in this Google Map, with a few bonus spots to see and eat.

Walking Chicago

Many cities around the world offer free walking tours and Chicago is no exception. We selected the Loop Tour offered through Free Tours By Foot. This is a great way to get an overview of a city. This particular tour starts at the Chicago Theater and ends at Millennium Park. Other highlights along the way include The Palmer House, the first bar in the city, and artworks by Chagall and Picasso. The total tour time is less than two hours, but the result is plenty of great information about the past and present of Chicago. If you want to stretch your legs further, here are some options for hiking near Chicago.

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Chicago theater

Millennium and Maggie Daley Parks

Since the free walking tour ends in Millennium Park, this is a great time to explore the area. When I was a kid the area that now is home to Millennium and Maggie Daley Parks was ugly rail yards. Former Mayor Richard M. Daley’s vision of two parks to replace those yards was a gift to the city of Chicago.

From almost anywhere you are staying in The Loop, these two parks are within walking distance. If you are staying a bit further out then simply find the nearest ‘L’ station. In combination, this space now offers something for everyone–fountains, an entertainment venue, outdoor art exhibits, secluded gardens, large lawns for picnics, and unique playgrounds for children.

parks in chicago

The Bean

And I would be remiss if I didn’t mention that Millennium Park is home to one of the most Instagrammed sites in the US: Cloudgate, or better known, “the bean.” If time permits I recommend exploring the park both during daylight and again after sunset. We especially enjoyed viewing Crown Fountain at night.

the bean chicago millennium park

Grant Park

Further down Michigan Ave. is the older Grant Park that is home to the spectacular Buckingham Fountain. You’ll likely find Grant Park less crowded but also a lovely outdoor space to explore. If you are here during the summer and have the time to come at night you’ll enjoy seeing the fountain’s light show.

buckingham fountain grant park chicago

The Art Institute

In between these parks is one of the top museums in the world, The Art Institute. This museum offers some of the most classic paintings in the world including Van Gogh’s self-portrait, Seurat’s A Sunday Afternoon, Wood’s American Gothic, and many more. A modern wing was added in 2009 and ever since the museum has been adding to this collection through acquisitions of Warhols, Koons, Lichtensteins, and others. Now if art isn’t your thing, then you might enjoy taking pictures of the famous Lions flanking the front entrance and moving on. However, if you are like me and adore art museums, then I definitely recommend setting aside two hours for this place.

The Art Institute Chicago

Chagall artwork in The Art Institute; image credit Empty Nesters

See Chicago by boat

This city was made famous by its architecture and the best way to experience it is on the river. I highly recommend booking an architectural boat tour which lasts about 90 minutes. As a kid, I saw these boats all the time and thought to myself, “how boring.” I was so wrong! We booked a tour around sunset and enjoyed every minute of the professionally narrated tour. And as an amateur photographer, this is a great vantage point for photos. Here’s more about Chicago river cruises.

chicago by boat

What to eat in Chicago

Chicago is a world-class foodie city. Options for amazing food are endless, but since you have just 24 hours, let’s get down to the three food items you must try; deep dish pizza, Italian beef and a Chicago dog. Having said that, there are endless opinions who does all of them the best.

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Chicago pizza

Let’s start with pizza. I was fortunate enough to grow-up eating deep dish pizza and had the opportunity to do so at a number of different restaurants. Probably the most popular place for this classic dish is Lou Malnati’s and fortunately, they have 50 locations throughout the city. If you are visiting one of the downtown locations be prepared for a wait. However, they have a great system of pre-ordering your pie so the wait at your table won’t be too long.

Italian beef

Italian beef fans usually name two places, Al’s and Portillo’s. In the name of research, we tried both during our last trip to Chicago. I liked both, but if forced to choose it would be Portillo’s. Do not eat this sandwich dry, but instead order it dipped.

Chicago dogs

Finally, find any place you can for a Chicago dog. This is an all-beef hotdog covered with mustard, onions, relish, a dill pickle spear, tomato slices, pickled peppers and a celery salt (absolutely no ketchup!) We found a small hotdog stand in Millennium Park, purchased two Chicago dogs, and enjoyed them sitting in the sun with the ‘bean’ as a backdrop. I love this city!


Chicago hot dog

Finer dining in Chicago

For fine dining, head over to the West Loop section of town. You could spend months sampling all the food in this area, but you are only here for 24 hours. If you want to splurge, and have made reservations far in advance, then consider trying Girl & The Goat. We did not do this during our last trip, so instead, we made a visit to sister restaurant, Little Goat Diner, for breakfast. I highly recommend the Elvis waffle which is covered in bananas, peanut butter and maple syrup. Chicago is clearly not the city to visit while on a diet.

Elvis waffle at Little Goat Diner

Little Goat Diner; image credit Empty Nesters

Where to stay in Chicago

I love the Kimpton chain, so for our recent trip to Chicago we stayed at their Monaco Hotel which is in the Loop and very close to the river. This location was ideal for walking to everything in the area we wanted to see. Each evening they offer a wine hour and free coffee is available every morning in the lobby. The staff here were great!

Next door to the Kimpton Monaco Hotel is the Virgin Hotel, which has all the same benefits of a great location plus a cool vibe.

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About a block away from these two hotels is the LondonHouse Chicago, a Hilton property. This location overlooks the river and is well known for its rooftop bar offering a terrific view of the city.

Monaco Hotel

Virgin Hotel

LondonHouse Chicago

Budget accommodation in Chicago

If you’re looking for something more budget, you can go with HI Chicago Hostel in the Loop, Wrigley Hostel in Wrigleyville or Fieldhouse Jones near River North.

HI Chicago Hostel

Wrigley Hostel

Fieldhouse Jones

Other options to stay in Chicago:

  • AirBnb: Chicago has a ton of AirBnb options, even getting you in downtown lofts, or photo tours. Save $40 on your first booking with this link.
  • Booking: There are literal thousands of options on Booking; save $20 on your first booking with this link.

one day in Chicago day tripChicago day tours

If you prefer to do any of the above with guides, or book in advance, here are some great options.

If you’re looking for something slower paced than Chicago, here’s a list of the Best Small Towns to Visit in America to choose from (and Oak Park is nearby!).

Want to see secret Chicago?

Looking for hidden Chicago or secrets other visitors miss? I recommend checking out the book Secret Chicago: A Guide to the Weird, Wonderful, and Obscure.

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Whether it's a long layover or a quick trip - there are about a million things to do in Chicago, from the Bean to Chicago dogs. Here's what to do, see and taste with just one day in Chicago.

Whether it's a long layover or a quick trip - there are about a million things to do in Chicago, from the Bean to Chicago dogs. Here's what to do, see and taste with just one day in Chicago. Whether it's a long layover or a quick trip - there are about a million things to do in Chicago, from the Bean to Chicago dogs. Here's what to do, see and taste with just one day in Chicago.


Note: This post contains affiliate links and features sponsors. My opinions and advice remain my own. For more information on affiliates and sponsors of How Dare She, click here.

Wendy and Jason Lee
Wendy and Jason Lee

We’re Wendy and Jason Lee and we are Empty Nesters who love to travel. We both work full-time, but do our best to carve out plenty of time to explore locally, nationally and around the world.  Most of the time we travel as a couple, but when schedules permit, we also enjoy traveling as a family with our two grown children. At this point in our lives we have more control of our schedules and the resources to see the world, so we want to make the most of every minute.  Camping, backpacking and staying in hostels aren’t really our style. We prefer nice hotels or AirBnBs and certainly enjoy unique tours, good drinks, and eating well. When traveling farther afield isn’t possible, we instead opt to explore our own backyard, Southern California.

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