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Chicago 3 Day Itinerary

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Sharing all the best things to do during a Chicago 3 day itinerary!

Chicago is one of the United States’ most iconic cities. We had so much fun visiting and can’t wait to go back someday soon! It kinda reminded me of a smaller, cleaner version of New York, but with a river running through it. 😉

With history, awesome architecture, and some amazing food (deep dish pizza, anyone?), there’s so much to do in Chicago that it can be tricky to narrow it down.

That’s why I’ve listed a few of my favorite things about the city—enough so that you can create a three day Chicago itinerary. It’s the perfect amount of time to really take in what this cool city has to offer!

And if you’re looking for ideas on Where to Stay in Chicago, be sure to check out my Top Chicago Airbnbs post.

Pssst, heading to Chicago? Don’t miss these travel guides to help you plan your trip!

Chicago Travel Guide
Where to Stay in Chicago
Day Trips From Chicago
Famous Chicago Food You Have To Try

So let’s get into it—the top things you need to put on your Chicago 3 day itinerary!

Chicago 3 Day Itinerary

Chicago 3 Day Itinerary, by Travel Blogger What The Fab

John Hancock Building

Officially called 875 North Michigan Avenue—which, let’s face it, isn’t that catchy—the John Hancock building is a super-tall skyscraper on Magnificent Mile that you can travel all the way up to the 94th floor of.

If you’re a fan of views, then the 360 Chicago Observation Deck should be pretty awesome for you—you’ll be able to take in the grandeur of the surrounding skyscrapers.

From here, you can see up to 80 miles on a good day (that’s 4 states), or you could just try and spot which one of the hotels below is the one you’re staying in.

If you’re really up for an immersive experience, then you should check out TILT. This moving platform with floor-to-ceiling windows actually tilts out OVER the streets below (yes, that’s 94 floors down). Scary!!

It may not be as busy as the observation deck over at the Willis Tower where the famous Skydeck Chicago is, but that means there are fewer crowds and less of a wait to get up!

Chicago 3 day itinerary, by travel blogger What The Fab

Chicago Architecture Center

Formerly known as the Chicago Architecture Foundation, all architecture-lovers should make a beeline to this cultural hotspot.

Here, you’ll learn all about Chicago’s iconic buildings—from the historic Chicago Cultural Center to the modern Willis—and how it’s developed as a city throughout the years.

But for me, the coolest thing about this place is the model of the city of Chicago they have here—complete with 4,200 individual model buildings. You can really get a feel for the layout of the city from here.

Bonus: There are also walking tours on offer that start from the Chicago Architecture Center, which will take you around the city. Art Deco skyscrapers? Food and architecture? Historic gems? I’m all about it.

And you don’t even have to walk—there are double-decker bus and boat tours that take in the architecture of the Windy City, too!

Chicago 3 Day Itinerary, by Travel Blogger What The Fab

Navy Pier

Visiting Navy Pier is definitely one of the top things to do in Chicago!

Spanning a length of 3,300 feet, Navy Pier juts out into Lake Michigan and has been a popular attraction in the city for over a century! In fact, it’s one of the most popular tourist attractions in the city.

Take your pick of things to do here: ride on the Ferris wheel, catch a movie at the Imax, hang on the beach, see some Shakespeare, stroll in the park—it’s endless! Afterwards, head over to Goose Island Brewhouse for a beer.

If you’re in town during sunny summer days, then you’ll be in luck. That’s when Navy Pier really comes to life!

Chicago 3 Day Itinerary, by Travel Blogger What The Fab

Millennium Park

You may not have heard of Millennium Park, but it should 100% be high on your three days in Chicago itinerary checklist.

Located in the Loop, with Michigan Avenue on one side and connected to Maggie Daley Park, Millennium Park is where you will find such landmarks as Crown Fountain, “the Bean” and “the Picasso” (nobody knows what it’s called), to name just a few.

It’s free as well—no admission price! That’s why I love public art.

The Bean is actually a crazy sculpture by Anish Kapoor called “Cloud Gate.” It’s a MUST if you are looking for a prime selfie or Insta spot in Chicago.

Join in the crowds on a perfect sunny day, kicking back, meeting friends, or splashing around in the fountain. Have a coffee and simply watch the world go by!

Or if you’re there during the holidays, Millennium Park is where it’s at for Christmas lights!

Chicago 3 Day Itinerary, by Travel Blogger What The Fab

The Field Museum

The Field Museum is actually one of the largest natural history museums in the entire world, which is pretty cool.

It’s been open to the public since 1921, making it almost 100 years old, and has around 40 million artifacts and specimens to check out and learn about.

Head towards the South Loop to check out this incredible museum—you can literally spend a whole day here.

Cultural halls, underground adventures where you can learn about bugs, the largest and most complete T-rex skeleton (named “Sue,” apparently) that’s ever been discovered.

If you’re looking for a different type of museum, the Adler Planetarium is also a great choice!

If you’re thinking of going, you should grab yourself a Citypass, because this (and other attractions, like the aquarium) are covered by it.

River Cruise

Definitely a thing to do in Chicago—aside from eating Chicago deep-dish pizza, obviously—is heading out on the Chicago River (or Lake Michigan) for a cruise.

There are a bunch of different cruises you can embark on—a firework cruise, an architecture cruise, or even a jazz and cocktail cruise.

If you haven’t got a lot of time in the city, then a cruise is actually a good way to take in a good chunk of Chicago’s highlights without having to hit the streets.

Chicago 3 Day Itinerary, by Travel Blogger What The Fab

The Art Institute of Chicago

Founded in 1879, the Art Institute of Chicago is one of the largest and oldest art museums in the country.

It’s home to some super famous pieces that I bet you’d love to see in person! They’ve got “American Gothic” by Grant Wood, “Nighthawks” by Edward Hopper, Vincent van Gogh’s “The Bedroom” and “Self Portrait,” and a whole load of others.

The list goes on, with names like Hockney, Cezanne, Pollock, Monet, and Warhol, to name just a few.

Shedd Aquarium

Along Chicago’s museum campus, you’ll find the Shedd Aquarium.

Set on the shores of Lake Michigan, this is another one of those historic institutions of Chicago that make this city such a cultural powerhouse. It first opened its doors in 1930 and plays host to tens and thousands of marine creatures.

Here, you can learn about life in a coral reef and marvel at the beautiful jellyfish as they glide through the water.

And if you have a Chicago Citypass, this place is included and free to enter!

Those are all the places you have to hit up during a three day Chicago, Illinois trip! It’s the perfect amount of time to really experience Chicago.

Visiting Chicago means great food like the deep dish pizza, places to admire art and learn about history, and some cool places to visit.

Let me know what places you hit up on your trip—don’t forget to tag me (@wtfab) in your Insta stories and pics!

Love this Chicago 3 Day Itinerary? Be sure to check out my other Chicago travel content here.

Chicago Travel Guide
Where to Stay in Chicago
Gwen Hotel, Chicago
Day Trips From Chicago
Famous Chicago Food You Have To Try
Top 11 Chicago Black-Owned Restaurants
22 Best Indoor Activities Chicago Has to Offer
20 Fun Things to Do in Chicago at Night
18 Most Instagrammable Places in Chicago


What is the best month to visit Chicago?

The best month to travel to Chicago is from April to May or September to October.

Is downtown Chicago safe for tourists?

Yes, downtown Chicago is safe! Always be aware of your surroundings and avoid areas that make you feel uncomfortable.

What is the best way to travel in Chicago?

The best way to travel in Chicago is via public transportation. The public transportation is fast and cost efficient.

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