Last updated on February 28th, 2023
Here is the best Chicago 3 day Itinerary that you didn’t even know you needed. If you follow this itinerary, you’ll get to see the best Chicago has to offer!
Chicago is one of the most popular destinations in the States. Despite the brutal winters, thousands of people flock to the city yearly. And with it being the third largest city in America, it’s easy to get overwhelmed with all there is to do.
So, I’m giving the best itinerary for your Chicago weekend trip to allow for smoother travels.
You’ll learn all about what to do in Chicago, what to see, and the best places to eat.
After reading this Chicago travel guide, you’ll be well prepared for your adventure in the Windy City.
This post is all about a Chicago 3 day itinerary.
This post may contain affiliate links, which means I’ll receive a commission if you purchase through my links, at no extra cost to you. Please read the full disclosure for more information.
Chicago 3 Day Itinerary
Day 1 of The Best Chicago 3 Day Itinerary
Bus Tour
While bus tours are a super touristy activity, they are an excellent way to learn & see more about the area you’re visiting. So, I highly recommend booking a bus tour on your first day in Chicago. They’re an excellent introduction to the city, and you can hop on and off throughout the day.
Chicago Bus Tours offers different tickets depending on the length of the ride and the overall experience.
360 Chicago
Another great way to view the city is to visit 360 Chicago. 360 Chicago is an observatory located on the 94th floor of the John Hancock Building that has the best panoramic view of the Chicago skyline.
And not to mention, the glass tilts! 1,000 ft above Chicago – talk about a thrill.
You can also grab food and some drinks during happy hour while you enjoy the view. This is definitely an experience you don’t want to miss during your weekend in Chicago.
The Museum of Science & Industry
Spend the afternoon exploring one of the many museums in the city, the Museum of Science & Industry (MSI). The MSI is the largest science museum in the Western Hemisphere, with over 20 exhibits to check out.
Food Options for the Day
- Mi Tocaya Antojería: a delicious Mexican spot that serves authentic Mexican food that makes you feel all warm inside. They also have an excellent selection of cocktails.
- Luella’s Southern Kitchen: If you’re looking for a taste of Southern cooking, this black-owned restaurant is the spot! At Luella’s, you find classics like shrimp & grits, chicken & waffles, and yummy gumbo.
- Pat’s Pizza and Ristorante: Known to have some of the best thin-crust pizza in Chicago, Pat’s is not a spot you want to miss.
Remember to subscribe to the newsletter to keep up-to-date on the latest travel tips and inspiration!
Day 2 of What to do in Chicago
The Bean
Did you even go to Chicago if you didn’t visit the Bean?! And I know what you’re thinking, another touristy spot. But this is an iconic landmark you can’t miss.
The mirrored sculpture also makes an excellent backdrop for a photo op. So, make sure you get your picture taken!
Note: The Bean is usually busy during summer and on the weekends, so to beat the crowds, try to visit early in the morning.
The Skydeck
Chicago might not be the first place that comes to mind when you think about heights. But I can assure you, with all the skyscrapers, you will likely experience them. And there is no better spot to do so than the Skydeck at Willis Tower.
Experience the Ledge’s glass boxes that tower over 1300 feet in the air. These clear boxes also make another excellent opportunity for a photo op.
I happen to be scared of heights & I was absolutely terrified when I visited the Skydeck. Like my knees were shaking – scared. But it’s definitely worth the experience!
Buckingham Fountain
If you have extra time between activities or before dinner, check out the beautiful Buckingham Fountain in Grant Park. With the fountain being settled right in the middle of the park, it’s a great opportunity to grab a coffee and go for a walk.
Plus, you get to see another angle of the city’s beautiful skyline (and it’s free).
Magnificent Mile
Next, on day 2, is to spend time wandering on the Magnificent Mile, Chicago’s hottest commercial district. This neighborhood is full of shopping opportunities, from local boutiques to more high-end options. So, go get your shop on, or do some window shopping!
The Magnificent Mile also has several dining options, which is the perfect way for hungry shoppers to end the day.
Remember to subscribe to the newsletter to keep up-to-date on the latest travel tips and inspiration!
Day 3 in Chicago City
The Art Institute of Chicago
While Chicago is known as the Windy City, it’s also known for its huge art scene. In fact, Chicago is home to one of the world’s oldest & largest art museums, the Art Institute of Chicago.
The museum has several yearly exhibits that not only leave you in awe but leave you inspired as well. Just a few minutes inside, you’ll feel like you can create something amazing, even if you aren’t an artist.
Adler Planetarium
Another fabulous museum to explore is the Adler Planetarium, especially if you’re into planets & the solar system. Also, this museum is a fantastic, family-friendly option.
But if you’re an adult like me and you like learning more about our world, you’ll undoubtedly enjoy your time here.
Shedd Aquarium
And, of course, I had to add the Shedd Aquarium because who doesn’t love aquariums? One of Chicago’s most popular attractions, the Shedd Aquarium, sees roughly 2 million visitors annually.
As one of the top aquariums in the world, Shedd prides itself on protecting endangered species & their habitats. With so much sea-life swimming around, this aquarium is a delight to adults and children alike.
More Great Restaurants to Eat at in Chicago
Chicago is well-known for its abundance of delicious food spots. You could simply visit just for the food and still feel like you had a great experience. Calling all foodies!
Here are some of the best restaurants to add to your Chicago 3 day itinerary:
- Lou Malnati’s: You can’t leave Chicago without trying the famous Chicago deep dish pizza. And Lou Malnati’s is one of the best pizza places in town!
- Superdawg Drive-In: an old-fashioned drive-in serving delicious all-beef sausage hot dogs.
- Daises: freshly made pasta served with a homey feel.
- Taqueria Chingon: delicious tacos & churros.
- Smoque BBQ: phenomenal BBQ with tasty sides.
Bonus Tip: Saving $$$ on Attractions
The last tip on this Chicago travel guide is to save money by purchasing a Chicago CityPass. This pass allows you to save up to 50% off 5 attractions! (Many of the activities on this itinerary are included in the CityPass).
So, save money & see the best of Chicago all in one purchase!
Wishing you safe & happy travels.
This post is all about a Chicago 3 day itinerary.
Remember to subscribe to the newsletter to keep up-to-date on the latest travel tips and inspiration!
LIKE THIS POST?! PIN IT FOR LATER!
This website is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to amazon.com.
