Planning a quick trip to the Windy City? Chicago is packed with must-see attractions, iconic views and incredible food. Here’s the perfect Chicago 2 day itinerary to help you experience the best of this vibrant city!
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After visiting this great city a handful of times over the years, I’ve decided to finally create a travel guide to help you make the most of your time if you’ve got a short trip (like a long weekend).
From famous architecture and museums to deep-dish pizza and Lake Michigan views, this Chicago 2 day itinerary will help you squeeze the most out of your short trip, without feeling rushed or overwhelmed.
Let’s dive in!
👉Don’t have time to read the whole article? Here’s the best Chicago River Tour you’ll love!
2 day Chicago itinerary: what to do on day 1
Two days in Chicago is the sweet spot. It gives you enough time to see the city’s highlights without really rushing. Chicago is a large city, so this itinerary is set up to make the most of your time.
Morning: Millennium Park
Start your Chicago itinerary at one of the city’s most popular spots: Millennium Park. It’s a huge public space in the heart of downtown and is packed with free attractions. The star of the show? Cloud Gate, better known as “The Bean.”
The first time my son visited Chicago, this was #1 on his list! It’s fun for all ages to see your reflection a bazillion times in its shiny surface!
This is a great spot to visit in Chicago any time of the year, although it’s certainly less busy in the winter.
Wander through the park and soak up the skyline views, or check out Crown Fountain with its digital faces that spit water in the summer. And f you’re visiting in the summer, check out what’s happening at the Jay Pritzker Pavilion. You might catch a free concert or movie screening!
My last trip to Millennium Park, we stumbled upon a music festival rehearsal, which was cool.
Afternoon: Riverwalk & boat tour
Grab lunch near the park or head over to the Chicago Riverwalk. This wide pedestrian pathway along the Chicago River is full of public art, cool restaurants, and unbeatable views of the city’s famous architecture.
If you want to stay on foot, don’t miss the Vietnam Veterans Memorial Plaza, a peaceful spot decorated with flowers, fountains, and street art.
Chicago is world-famous for its architecture, so the best way to learn more (and take in the incredible buildings) is on an architecture boat tour, like this one. Boat tours are super informative and perfect for first-timers to the city.
You’ll cruise down the Chicago River while guides point out famous buildings by Frank Lloyd Wright, Jeanne Gang, and Ludwig Mies van der Rohe. It’s relaxing, educational, and the photo ops are endless.
👉Pro tip: I highly recommend booking this tour as far in advance as possible, as they do sell out!
Evening: Navy Pier
For dinner, you can try an iconic food: a Chicago-style hot dog. Head to Portillo’s, where you can grab a classic dragged through the garden hot dog, topped with mustard, relish, onion, tomato, celery salt, and a pickle spear. No ketchup allowed!
From there, head to Navy Pier. This lakeside attraction is perfect for nighttime sightseeing. Go for a walk along the water, grab ice cream or popcorn, or ride the Centennial Wheel for 360-degree views of the skyline.
It’s fun for all ages, too. With plenty of shopping, restaurants, and activities for kids too. One trip to Chicago, my group with tweens enjoyed the funhouse on the pier, which was a perfect nighttime activity.
And if you’re still feeling energized, hit up a rooftop bar in River North or the Loop to see the city sparkle at night.
Chicago 2 day itinerary – what to do your 2nd day
With an action-packed first day, there’s even more to see on your second full day in this vibrant city! Let’s keep going…
Morning: The Skydeck Chicago
Start your second day with a bucket-list experience: standing on The Ledge at The Skydeck Chicago! Head to the iconic Willis Tower (formerly Sears Tower), one of the tallest buildings in the Western Hemisphere. The Skydeck is on the 103rd floor, and the elevator ride alone is a thrill – our ears popped!
The Ledge is a glass box that extends out from the building, letting you look straight down onto the city streets below. You’ll only get a short time on the ledge, but can go through the line again if you want more photos. It’s a must for first-timers and one of the most exciting ways to kick off your Chicago 2 day itinerary!
👉Pro tip: book your tickets in advance because they do sell out.
Afternoon: Art Institute of Chicago
After you’ve soaked up the skyline, make your way to the world-famous Art Institute of Chicago! It’s seriously one of the best things to do for any Chicago weekend itinerary. It’s only about a 15-minute walk (or a short train or Uber ride) from Willis Tower.
The Art Institute is home to thousands of iconic works, including “American Gothic”, Monet’s “Water Lilies”, and Georgia O’Keeffe’s beautiful “Sky Above Clouds IV.”
My daughter had just learned about American Gothic in art at school so that was her favorite! My favorite collection was Pablo Picasso!
Even if you don’t consider yourself an art person, there’s something here for everyone, like armor collections, photography galleries, and modern art installations like the Thorne Miniature Rooms.
Plan to spend at least 2 to 3 hours here. It’s also a great spot to rest your feet and get some indoor time during a summer heatwave or a rainy afternoon.
It’s recommended to buy tickets in advance, especially if you have a specific window of time you’re planning to go.
Evening: escape room
Chicago has tons of highly-rated options that range from spooky mysteries to bank heists to time-travel puzzles. Whether you’re exploring the city with friends, a partner, or even a group of teens, an escape room is a great way to break up the usual sightseeing and test your teamwork.
During one of my trips to the Windy City, our group did an escape room and it was a highlight for the kids!
Optional alternatives for your Chicago itinerary
And if you’d like a little more variety (don’t we all??), here are a few other options you can include in your perfect Chicago 2 day itinerary:
- Shedd Aquarium: it’s one of the largest and most impressive indoor aquariums in the world, and the perfect activity for all ages! Be sure to book tickets in advance, especially a weekend visit.
- Maggie Daley Park: located just behind Millennium Park. It’s one of Chicago’s best green spaces, with a large playground, rollerblading ribbon, climbing walls, and tons of space to relax. It’s great for kids and adults alike, and offers a nice break from museums and city streets.
- Shop the Magnificent Mile: this famous stretch of Michigan Avenue is where you’ll find everything from luxury brands to classic department stores.
Where to eat in Chicago
Chicago is certainly a foodie’s paradise, and there’s no shortage of good restaurants. Every time I’ve been to Chicago, I’ve had such delightful food.
I’d highly recommend trying deep dish pizza while you’re in town. My favorite spot is Giordano’s Pizza, and with over a dozen locations, you’ll likely find a convenient spot!
And of course, no vacation getaway is complete without ice cream. Our family loves a cool treat, too. Our favorites are Amorino Gelato and Ghirardelli Chocolate! (Not gonna lie, I love visiting Ghirardelli Chocolate other places too, like San Francisco, San Diego, Vegas and even Monterey.
Tips for your 2 days in Chicago Illinois
Before we wrap up, here are a few tips to make your time in this city go smoothly…
- The city is very walkable and this 2 day in Chicago itinerary will have you walking a lot! One of the best tips for visiting Chicago is to have the right shoes for comfort. I loved my Vessi’s during my time in Chicago!
- Do not rent a car for Chicago. You can walk most places on this itinerary, and the public transportation is excellent. There’s very little parking in the city and you just don’t need a car.
- Consider layers and carry a small shoulder bag or backpack. Take along things like an umbrella, water bottle, sunblock, etc. so you’re prepared for the day!
2 days in Chicago itinerary – a recap!
Can you believe this fun city?! With so much to do in Chicago, there’s truly something for everyone. With a plethora of indoor activities and outdoor options, you’ll surely be able to create your perfect little getaway with this Chicago 2 day itinerary.
Whether you’re visiting with a partner, your kids, a girls’ trip or even solo, you’re bound to have a great time in Chicago!
More of the midwest:
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27 Awesome Things to Do in Sandusky Ohio You Can’t Miss
Most Instagrammable Spots in Omaha (with photos)
More fun cities to visit:
A Day in Seattle: What You Can’t Miss (Perfect Itinerary for a Single Day)
2 Days in San Diego: Your Perfect San Diego Itinerary
Phoenix Itinerary: Top Things You Absolutely Must Do
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