The Second City, the City of Big Shoulders, Chi-Town, the Windy City—however you refer to it—Chicago has a long, storied history. Even though there’s a lot to digest in this city, there are many great experiences to be had in a short timeframe. 

Whether you’re looking for touristy daycation activities, food and drink staples or more off-the-cuff ideas of how to spend a day in Chicago, we have you covered below. 

Touristy Things to Do in Chicago

Sometimes, there’s a reason why a lot of people are doing something. This is certainly the case with the following things to do around Chicago, which (deservedly) attract some of the most tourists.

Stand Out on the Willis Tower Skydeck

Formerly known as the Sears Tower, Willis Tower is the tallest building in Chicago, and was for many years the tallest in the world. What makes this attraction a Chicago must-see is its unique Skydeck on the 103rd floor. Glass boxes built onto the side of the tower allow visitors to step out over the side of the building and look straight down. You can also get incredible views of the city and surrounding area.

Waist-down view from Willis Tower sky deck looking straight over other Chicago high rises.

Catch a Game at Wrigley Field

The Chicago Cubs were long known as the “lovable losers.” They went for 108 years without winning a World Series—an incredible streak that ended in 2016. Wrigley Field is one of the most storied sports venues in the world. Even though it has been updated to modern times, it still has an old-time feel with its ivy outfield wall, vintage scoreboard, and intimate setting. Day games are a blast at the stadium. You can also get a special package to view the game from one of the rooftops across the street.

There's nothing quite like seeing a day game at Chicago's Wrigley Field

Get Cultured at The Art Institute

Whether or not art is “your thing,” you’ll have a great day at the Art Institute of Chicago, which isn’t just one of the best museums in Chicago. It’s one of the top museums in the world. Walking through, you’ll see instantly recognizable works such as “A Sunday on La Grand Jatte” by Georges Seurat, “Nighthawks” by Edward Hopper, “The Bedroom” by Vincent van Gogh, “American Gothic” by Grant Wood, “The Old Guitarist” by Pablo Picasso, and many more. The collection comes from across the world, and ranges from thousands of years old, to the most contemporary works. 

Learn While Sight-Seeing on an Architectural Boat Tour

Chicago is known for being an architectural gem of a city. The downtown is full of skyscrapers—some of which are over a century old. It’s essential to take some time to appreciate the diverse array of buildings in the city. Taking a guided boat tour down the Chicago River is one of the best ways to do this. It only takes about 75 minutes, and you’ll learn a lot of interesting tidbits while seeing incredible structures. 

View of the Chicago River, Canal Street bridge, lined with beautiful buildings.

Have Family Fun at Lincoln Park Zoo

The Lincoln Park Zoo is a free attraction for the whole family. Located in the near-northside neighborhood of Lincoln Park, you can see animals from all over the world right in the heart of Chicago. This is open 365 days a year, so you can visit no matter when you take your Chicago day trip. 

Food Worth Checking Out in Chicago

When you go somewhere, it’s always worth checking out some of the local cuisine. Chicago certainly has a few staple dishes that have made it famous. 

Stuff Yourself with Deep Dish Pizza

There’s an endless debate about whether Chicago or New York City has the best pizza in the U.S. A deep-dish pizza is no light undertaking. Thick crust in a pan is topped with cheese, toppings, and tomato sauce. It’s certainly not for those with a small appetite. 

Some of the best places to go for this Chicago specialty are Pequod’s, Pizzeria Uno (only original location, or second location Pizzeria Due down the street), Lou Malnati’s, and Gino’s East. 

A big-crusted, nimble-cheesed deep dish pizza, the definition of bliss.

Stuff Yourself Even More with Italian Beef

Another hearty meal, the Italian beef is a sandwich not often seen outside the Chicagoland area. Thinly sliced roast beef is put on an Italian roll and doused in au jus. It’s commonly served with cheese and giardiniera, which is a mixture of pickled vegetables. It can often be quite hot when it comes with peppers, so be careful. Al’s Beef and Portillo’s are two of the more popular locations for Italian beef.

Nothing like a juicy italian beef with sport peppers from Portillo's.

Get Your Hot Dogs  

It’s possible you’re in the know about what goes into a Chicago-style hot dog: beef hot dog, poppyseed bun, mustard, white onion, sweet relish, tomato, pickle spear, celery salt and sport peppers. No ketchup. 

While you don’t need to adhere to this precise recipe to have a great hot dog, it can be fun to give this traditional recipe a try. The Vienna Beef factory store is a great place to go for a dog. You can also check out Maxwell Street for Polish Sausages, which are traditionally served with mustard and grilled onions. But as far as we’re concerned, Jim’s Original is the place to go.  

Two juicy chicago-style hot dogs with obligatory tator tots.

If Meats Aren’t Your Thing

Chicago is best known for its substantial meat-based dishes. But it’s also become a place with lots of quality vegetarian and vegan options. Upton’s Naturals, a producer of vegan meat substitutes, is based in Chicago. You can try some of their food at their Upton’s Breakroom restaurant. Some other great locations in the city include the Chicago Diner, Handlebar, Dimo’s (for vegan pizza), Kitchen 17, Loving Heart, and a wide selection of Indian and Ethiopian food on the north side. 

Places to Get a Drink in Chicago

It’s possible you’ll want to squeeze in a drink at some point during your Chicago day stay. Fortunately, there are many worthy options, even before the sun falls. 

Have a Few at Lagunitas Taproom

Lagunitas creates beer beloved by many people across the U.S. The Chicago taproom is open at noon Wednesday-Saturday, and features all the classics as well as recent experimental brews on tap. You can also take a tasting tour of the whole facility any day of the week. This is perfect for people who have a deep love of beer and brewery culture. 

Artsy octopus with bird on Half Acre Brewery Beer Truck.

Try a Chicago Brew at Half Acre

Half Acre is a Chicago-born beer company that prides itself on pushing the limits of brewing, while also delivering delicious results. They offer a wide variety of high-quality beers at their two physical locations in the city. In addition to the taprooms, you can also get some delicious food, or sit out in their beer garden at their newer location. 

Bar Hop Logan Square

If you’re wanting to check out a variety of places, Logan Square might be a good bet for you. There are tons of great bars along Milwaukee avenue and the surrounding area. This can be a really fun way to spend a day—especially on the weekend.

Have a Classy Drink at Z Bar at The Peninsula 

If you prefer something a bit fancier, consider grabbing a cocktail at Z Bar at The Peninsula. This lounge opens early in the day and offers a fantastic rooftop deck. The Peninsula is one of the premier hotels in the city, so you’ll get to enjoy top-quality beverages in an impeccable atmosphere. 

Other Cool Things to Do in Chicago

In a city so large, there’s never a shortage of things to do and see. You should consider checking whether there are any special events happening during your visit. During the summer, street festivals or other events are a weekly occurrence. Taste of Chicago and Wicker Park Fest are both great summer options. There are also fantastic farmers markets throughout the city on weekends during the warmer months. 

People looking for another cool way to spend a day in Chicago can consider one of the following options: 

Smell the Flowers at Garfield Park Conservatory

The Garfield Park Conservatory is one of the most impressive greenhouse gardens in the U.S. It has two acres of indoor plant displays, with an additional 10 outside the main building. Visitors always dazzle over the wide variety of plant species. It’s only a five-dollar suggested donation to enter, which makes it affordable for all budgets. 

Visitor looks on at all the greenery in the greenhouse of the Garfield Park Conservatory.

See Cultural Gems at the National Museum of Mexican Art

The National Museum of Mexican Art showcases a fantastic body of works. There are currently about 10,000 in its permanent collection. This is an institution of Mexican art and culture where you can be introduced to 3,000 years of history. The museum is free for visitors and located in the historic Pilsen neighborhood. 

Bring the Pack to Montrose Beach Dog Park

Whether you have a pup who likes to play and swim or just like to dog watch, Montrose Dog Beach is the place for you. This gated area on the shore of Lake Michigan allows dogs and their owners to frolic in a serene environment. It regularly tops lists of the best dog parks in America.  

Walkers, joggers and bicyclists line the Chicago lakefront path.

Bike down the Lakeshore Path and the 606

Chicago is blessed with some scenic bike paths. You can ride up and down the shore of Lake Michigan on the Lakeshore Path. Or you can go up on the 606, which is a multi-use path converted from an old train line. Both offer exceptional views and immersion in the city. 

There are plenty of choices out there for deciding how to spend a day in Chicago. While this list is by no means complete, it gives you a good entry point for your visit to the city. 

Get away for the day wherever with a day use room.

Image Credits (by order of appearance):

Featured Image: “Chicago” by Roman Boed via (CC BY 2.0)

“Sears Tower Skydeck” by Tania Liu via (CC BY-ND 2.0)

“Wrigley Field” by Mrs. Gemstone via (CC BY-SA 2.0)

“Chicago River” by Rachel Kramer via (CC BY 2.0)

“The Best Pizza I Have Ever Had” by Shaan Hurley via (CC BY 2.0)

“Portillo’s Italian Beef Sandwich” by Krista via (CC BY 2.0)

“Mmm… Chicago style hot dogs” by Jeffreyw via (CC BY 2.0)

“Half Acre Beer Company Truck” by Marco Verch via (CC BY 2.0)

“Dinosaurs live here” by Ryo Chijiiwa via (CC BY 2.0)

“Chicago Lakefront Trail” by Bernt Rostad via (CC BY 2.0)

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Andy Holsteen

Andy Holsteen writes all sorts of things—both for work and pleasure. He loves traveling to new places, and hopes to see Berlin and Santiago in the not-so-distant future.