Inside: Spending 1 Day in Chicago what to see, eat and do for a quick trip to the windy city.

I spent a fun day in Chicago solo this month and I’m so happy to have had the time to explore such a great city. The food was amazing, and I’m just going to be honest if you only have 1 day to try out the food in Chi-town you’ll have to eat quick and make room for more! Ha.

You could easily use this itinerary and spread out the fun over a weekend, but if you only have one day just go for it I say.

Here’s what I’d recommend if you have 1 day to spend in Chicago and want to see as much as possible.

How to spend 1 day in chicago

Chicago 1 Day Itinerary

Here’s the quick recap of my itinerary for 1 quick and fast passed day in the windy city. Below you’ll find the step by step places, links and ideas to recreate my 1 day in Chicago quick (but amazing) trip.

  • First, I had some fun with the SkyDeck and Color Factory
  • Then, I saw The Bean and had a mimosa at Cindy’s
  • After that, it’s a quick walk to The Art Institute
  • I then headed to Lincoln Park area for Lunch and Shopping
  • Next, I meet friends for drinks, dinner & more late night fun with a pretty rooftop view to end the night.

Best Activities to do in Chicago

What To Do In Chicago For One Day

Sky Deck and Color Factory

Start your day early with a 9 am ticket to the Color Factory. This was easily one of my favorite things that I did in Chicago and I had so much fun here even by myself. 🙂

Going with a group, or making it a fun activity to do with your teens would be even better!

Think kids play land, mixed with gorgeous design, all done over a sensory explosion! Plus, they have cameras set up all throughout it so you leave with the most fun photos to treasure and share.

Color Factory Chicago

The Color Factory is located in the basement of the Willis Tower right next to the entrance to the Sky Deck.

Grab an 8:30/9am slot for the Sky Deck (hours change depending on the season) if you plan to do trust your luck high in the sky. Take your crazy glass-over-Chicago-photo and then head straight to The Color Factory.

This allows you to kick off 2 HUGE Chicago attractions before most of the city is even awake. I am not a huge fan of heights so I skipped the Sky Deck, but I’ve heard it is a great way to say hello to the city and take a fun epic photo while your at it.

Doing these two popular events first before the crowds arrive will allow your day to be off to a great start.

See The Bean

Grab an Uber and head straight from here to Millennium Park to see the bean!

Another activity you want to do before crowds are up and it gets too crazy is a visit to the famous Bean. Depending on where you are staying, you might even get up extra early and hit this first if it’s on the way, so that you’ll have the space to yourself.

I popped over here around 10:15am after my Color Factory fun and it was busy, but thankfully not totally packed out yet.

Seeing the bean is one of those things you feel like you’ve gotta do once when in Chicago… I was actually surprised how much I enjoyed seeing this, walking under it and getting a fun mirrored view of the city by looking in it.

Best things to do in Chicago see the bean Fun Bean photos to take

Make sure to spend a couple minutes strolling through the park after seeing the bean.

The artist Anish Kapoor also designed the huge metal pavilion behind the Bean that seems to frame the waterline just perfectly and Laurie Garden also in the park which is most beautiful if you visit in the spring/summer months – but even in the winter it was a pretty spot to wander.

Chicago Athletic club

View from rooftop of Cindys chicago

When you’re done with The Bean, cross the street to go into the Chicago Athletic club and hit up Cindy’s for Mimosas, morning snacks and the prettiest view of the waterline that you’ll find. I thought the view of the bean from up here was so great, loved watching all the people below.

Art Institute Of Chicago

After brunch I walked over to the Art Institute Of Chicago, which was one of my favorite museums of all time. They have the biggest collection of impressionist paintings outside of Paris and I had the chance to see works by Van Gogh, Monet and plenty of other favorite artists.

What to see in 1 day in Chicago - The Institute of Art

They have a full wing of contemporary art, architecture and ancient art as well. Don’t miss this!

Pink Balcony Chicago skyline

Also be sure to visit the outside deck before you leave. It’s not part of the main exhibits, to find it: head to the bag/coat drop area and head up the escalator.

Its pink glass obviously drew me into the space and it had pretty views of the city and water – all with a bright pink hue to them. My kind of stop for certain!

Best food and drinks Chicago

What To Eat & Drink In Chicago

Cindy’s Rooftop

Obviously, I’ve already talked about how much I loved Cindy’s – Depending on the season and day that you go, I’d suggest making a reservation to ensure you get a table here. Or just show up as part of your what to see in 1 day in Chicago plan and cross your fingers there’s an open seat at the bar.

They serve a full yummy brunch & I’d suggest the mimosas 100%! Also be sure that whatever you get comes with their hommies – AKA yummy crispy breakfast potatoes. So good!

Best Chicago Pizza Pequods


Call a taxi or Uber to take you to Lincoln Park area and have lunch at Pequod’s Pizza! They have a great lunch special and it gives you the traditional Chicago deep dish experience. It was one of my favorite pizzas I’ve ever eaten, with rich tomato sauce and just the right deep pizza crust that was also crispy at the ends.

After eating my lunch pizza I went shopping (mostly to make room for dinner ;). Then I freed up just enough room for these places…

Bar Sotano

Once you are all shopped out it’s time to relax and get a drink, head to the fun Bar Sotano by Rick Bayless to enjoy a fresh take on cocktails, some which may even come your way in a bag. This place was so fun to enjoy!

Girl & The Goat

Leave in time to catch your dinner reservations at Girl & The Goat. My meal here was incredibly good & fresh. Definitely worth the effort to make sure I got a table (reservations required).

The Alderman

Post dinner, cocktails at the Alderman for a luxe speakeasy style lounge with an amazing selection of hand crafted drinks.

Skyline at the VU rooftop bar Chicago skyline to end your 1 day trip

VU Rooftop

If you still have energy left in you after exploring everything in my what to see in 1 day in Chicago list, then head to VU rooftop bar for a lively and fun atmosphere with a pretty skyline view. You can always save this for another trip when you have more time as well.

Best shopping in Chicago Lincoln Park Area

Where To Shop In Chicago (Besides the Miracle Mile)

Between all this eating you’ll need to make more room. After my pizza lunch, I walked around the Lincoln park area and within a short few blocks stopped at some of my favorite stores in Chicago.

Within about 1/2 a mile you can hit up these great spots… I have never been to Jayson Home before and the entire store was beautiful! I only wish I wasn’t flying home so I could have taken more with me. Lucky for me, like many of the other stores they offer online shopping!

I also found the most fun local clothing store a little further away called Mrs. Catwalk, which had a fun selection of colorful options for wearing out on the town. I bought the pink tulle top, obviously!

Whatever you decide to fit in to see in 1 day in Chicago, I can assure you this city is one you’ll enjoy. Now, I’m aching to get back there for a longer visit and bring my kids along for the fun.