3 Days in Chicago – What to See, Do, and Eat in The Windy City

Are you considering a trip to the Windy City? Read on my 3 days in Chicago including what to see, do, eat and drink.

Chicago is one of my favourite cities in the States. Think New York only clean and with arguably friendlier people. Its skyscraper past is fascinating and its food certainly won me over. There’s no shortage of arts and culture with its blues scene, renowned museums, and comedy clubs. There truly is so much to see and do. With just 3 days in Chicago, we better get started.

Note: This trip was taken pre-pandemic. Please use this info for future trip planning and adhere to local pandemic guidelines and travel restrictions.

Getting In

I have both flown and driven into Chicago. O’Hare Airport, one of the world’s busiest, is well connected and serviced by every major airline. Getting to the city is easy (follow the signs for Trains to the City) and affordable via the Blue Line metro train. It costs $5 to reach the Loop, Chicago is downtown core, and takes roughly an hour.

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Driving is not as daunting as New York but traffic can still be a crawl. Street parking can be upwards of $6.50 an hour in the Loop so driving can add up. That said, paired with a trip to Milwaukee, driving to Chicago or renting a car once there makes for a great road trip.

What to See in Chicago?

Chicago’s downtown core is very walkable and much of its sights can be covered on foot. Here are some of my favourites with 3 days in Chicago:

Cloud Gate

Often referred to as the “Silver Bean,“ Cloud Gate is the most interesting piece of public art in Chicago, if not the country. Inspired by liquid mercury, it was designed to reflect the city skyline and its surroundings. A must-visit on any trip to Chicago.

Crown Fountain

Steps from Cloud Gate you will find another uniquely Chicago public art piece, the Crown Fountain. Half video sculpture, half outdoor waterpark, the Crown Fountain is unique for its ever-changing faces on two giant glass brick towers. The fountain runs between May and October so be sure to stop bye if visiting then. Also, be sure to stick around long enough for the blast of water spotting from the mouth in the video displays.

Art Institute of Chicago

Sticking in the same area as Cloud Gate and the Crown Fountain, you’ll find arguably Chicago‘s most famous museum, the Art Institute of Chicago. Founded in 1879, it’s both one of the countries oldest and largest museums. With over 300,000 pieces in its collection, you can spend hours wandering its many exhibits.

Ranging from American Art to European, modern and contemporary, and textiles to sculptures, the museum is highlighted by Picasso’s “The Old Guitarist” and Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte.“ Also, being Chicago and all, there is an excellent architectural exhibit!


What to Do in Chicago?

From Blues to baseball, there is no shortage of activities to tackle with 3 days in Chicago.

Baseball Game at Wrigley Field

One of major-league baseball‘s most storied franchises is the Chicago Cubs and their home field of Wrigley. Going to a game here instantly takes you back to the peanuts and Cracker Jack days of America’s pass time. Opened in 1914, much of us it’s historic charm remains. Hallways are small, seats are cramped, and its ivy-covered brick in the outfield highlights the park. Even the scoreboard is the same and is still hand-turned!

Even if there is no game scheduled while you’re visiting Chicago, you can take a walking tour of the park. This gets you behind the scenes with a peek into the clubhouse and dugouts. Also don’t miss the statue of iconic cubs announcer Harry Carey, out front.

Go to a Blues Bar

Chicago’s blues roots run deep. The city has produced notable artists such as Muddy Waters and Buddy Guy. What makes Chicago a hotbed for blues music? Sadly, racism.

With racial divides and segregation in the southern States came a migration of black Americans north. With that came culture. Today, this culture is alive and well and can be experienced at many clubs around town. None better, than Kingston Mines in “Blues Alley.” Shows run nightly, 365, and features two stages. It’s also known as the “oldest continuously running Blues club in Chicago.“

Go to a Show at The Chicago Theatre or Second City

Along with baseball and the blues, Chicago is well known for its theatre and comedy. The Chicago Theatre and its landmark sign have been welcoming and entertaining locals and visitors since 1921.

The Second City, on the other hand, has been making people laugh since 1959. This iconic improv comedy club has been a launching pad for an endless list of comedians and actors including Bill Murray, Steve Carell, Tina Fey, Amy Poehler, and Mike Myers. Shows run daily and tickets can be purchased online.

Climb Willis Tower

Once the tallest tower in the world, the Willis Tower is a true testament to Chicago’s skyscraper traditions. Today it features a sky deck where daring guests can walk on a protruding glass floor 1353 feet in the air and see up to 80 km in the distance on a clear day.

Take an Architecture River Cruise

The number one thing to do in Chicago is taking an architecture river cruise. With Chicago being the home of the skyscraper, there is no better way to experience them than by boat. With its partnership with the Chicago Architecture Centre, the historic Chicago’s First Lady offers the best experience with knowledgeable guides. The 90-minute tour gets you up close and personal with the cities most notable buildings and is highlighted by a stunning view of the city from Lake Michigan. If you only do one thing on your 3 days in Chicago, do this!

Stroll Grant Park

Chicago’s Grant Park is one of the finest urban parks in the country. It covers 319 acres and was built on reclaimed marshland largely filled with debris from the Great Chicago Fire.

Today it is the perfect place to stroll with the city skyline in the background. It’s highlighted by Buckingham Fountain, Millennium Park, and the Art Institute of Chicago.

Riverwalk Stroll

Another notable stroll in downtown Chicago is the Riverwalk. Along the banks of the Chicago River you will find pedestrian walkways with parks, bars, and restaurants mixed in. Don’t miss DuSable Bridge one of 52 movable bridges on the river, and the iconic Chicago Tribune Tower.

Take a Street Art Stroll

If your legs aren’t dead just yet, the Loop features some great street art. Notable highlights include Agora, Flamingo, and Untilited by Picasso. Also, nearby is the starting off point for Route 66, the famous highway connecting Chicago to Los Angeles.

What to Eat in Chicago?

Be prepared to add a notch or two to your belt after your 3 days in Chicago as their well-known dishes are anything but light. Here are my must-eat items in Chicago and where to find them.

Deep Dish Pizza

Foodies (and Jon Stewert) will argue that Chicago Deep Dish is not pizza. That said, there’s no arguing about the taste. This sloppy pie is loaded with cheese, sauce, and toppings and is a feast, to say the least.

Although you can find it throughout town, head to Pizzeria Uno for the original. If you would prefer to skip the lines and nostalgia, Giordano’s, Pequod’s, and Bartoli’s are all great options.

Chicago Style Hotdog

Another staple that can be found around town is the Chicago Style Hotdog. This version is all about the toppings. So what’s on a Chicago hotdog exactly? White onions, mustard, a dill pickle spear, tomatoes, hot peppers, and celery salt all served on a poppyseed bun.

Head to Portillo’s for the best “Chicago Red” with a side of sports nostalgia. If you have room (and no heart conditions) order up a chocolate cake shake! And yes, it’s exactly what it sounds like it is.

Chicago Italian Beef Sandwhich

Is your belly-busting yet? If not, order up an Italian Beef. This gut-busting sandwich of shaved beef simmered in au jus sauce is seared is served on a roll and topped with peppers. I tried this local favourite at a couple of spots and recommend Exchequer Restaurant & Pub for its mob-style and ambience and Al’s Beef for overall taste.


Do-Rite Donuts & Chicken has been doing it right in Chicago for years now. This local chain is known for its tasty creations however the buttermilk old-fashioned takes the cake.


Chicago’s popcorn past runs deep with it being the home of flavoured popcorn and Cracker Jacks. Then there is Chicago Style which is a mix of salty cheese and sweet caramel popcorn. Head to one of the areas Garrett Popcorn shops and sample these favourites and more.

Take a Food Tour

If ticking off all these dishes seems like a demanding task, or if you are interested in more behind the scenes eateries consider taking a food tour. I took Secret Food Tours Chicago and can highly recommend it. It’s a great way to see the city with a local and get behind the scenes with some not so known locations.

Where Should I Stay in Chicago?

Looking for recommendations on where to stay for your 3 days in Chicago? Check out my picks from my visits to Chicago over the years!

Baller – Hyatt Regency

This massive complex is located in the Loop and close to all highlights listed above. Rooms are modern and makes for a comfortable stay. There’s also a massive two-level bar/restaurant in the lobby, a perfect place for a nightcap.


Value – Best Western River North Hotel

Located just north of the Loop, this Best Western wins points for its location next to both the Riverwalk and Portillo’s. Hello late night Chicago Reds!

Rooms are a touch dated but surprisingly large. Also, it’s within walking distance to the magnificent mile as well as touristy Navy Pier.


Budget – Hotel Chicago West Loop

Those visiting Chicago on a budget should consider the Hotel Chicago West Loop. This no-frills hotel is clean, comfortable, and located next to a great Mexican eatery!

Is 3 Days in Chicago Enough?

There you have it, my highlights on what to see, do, and eat with 3 days in Chicago. As you can tell, there is much to love about the Second City, and this is just scratching the surface. You could easily spend a week touring its many museums, wandering the shops of the Magnificent Mile, and playing tourist or Navy Pier. Still, if you only have 3 days, the highlights above are a must and cover off the very best the city has to offer.

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