Chicago is a city that every traveler should visit at least a few times to experience its diverse neighborhoods and world-class attractions. With bikeable streets and an excellent public transportation system in place, it’s possible to see and do a lot in this city with just 48 hours of time. If you’ve never been to the city before and only have a weekend to spend, here are the 10 things you should check out before you leave!


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Run or Walk the Lakefront Trail Chicago Lakefront trail on a cloudy day
Chicago Lakefront trail on a cloudy day

Run or Walk the Lakefront Trail

Chicago might not have an ocean to call its own, but it has Lake Michigan, and that’s pretty awesome too. Start your 48 hours in Chicago off by getting a little exercise so you’ll have energy throughout the weekend and avoid guilt after eating all of the delicious Chicago specialties! The Lakefront path is a paved path that extends about 18 miles and is perfect for walking, rollerblading, biking, or running. It offers incredibly scenic views and passes by many neighborhoods that you can hop off at to check out along the way.

Snap a Photo by the Bean The famous
The famous "bean" at Millennium Park in downtown Chicago

Snap a Photo by the Bean

The Bean, which is officially known as Cloud Gate, is an outdoor work of art in Chicago’s Millennium Park. The Indian/British artist Anish Kapoor created this public art sculpture that has become one of the most iconic landmarks in the city. Its surface is mirrored so you can see the city from many different angles at once. It’s a must-stop spot to take a photo and share with your loved ones. While you’re in Millennium Park to see it, take some time to walk through the park to admire the architecture and see if there are any free events going on at that time.

Check Out a Local Festival Chicago Blues Festival
Chicago Blues Festival

Check Out a Local Festival

Chicago is also a city that loves festivals, and you can find one going on pretty much throughout the summer. There are lots of music festivals here, such as Lollapalooza, the Grant Park Music Festival, the Chicago Jazz Festival, and the Pitchfork Music Festival. Festivals are also a great opportunity to learn about the city’s various neighborhoods and get a sense of how unique they all are. For your 48 hours in Chicago, do a quick search online to see what festivals are going on during those couple days. However, Chicago festivals aren’t just for summertime. Some fun winter festivals to check out here include the Chicago Ale Fest, the Randolph Street Market Festival, the Chicago Flamenco Festival, and Christkindlemarket Chicago.

Try Some Deep-Dish Pizza Chicago pizza
Chicago pizza

Try Some Deep-Dish Pizza

There are few iconic Chicago foods that are must-tries when you visit Chicago – even for a short amount of time. Giordano’s has served the city’s famous deep-dish pizza since 1974 and is still a popular place to come to try this local specialty. Other recommended restaurants to visit if you’re having a pizza craving is Pequod’s Pizza in Lincoln Park, the Art of Pizza in Lakeview, the Pizzeria Uno in River North, and Lou Malnati’s in dozens of city and suburban locations. Sausage is always one of the most popular pizza toppings throughout the city to try if you’re feeling overwhelmed by choices.

Listen to Blues at Kingston Mines Live performance at Kingston Mines
Live performance at Kingston Mines

Listen to Blues at Kingston Mines

Chicago and blues music go hand-in-hand, and there are still some great blues venues around town to experience it. One of the best clubs to check out is Kingston Mines, which has been playing the blues since 1968. This venue has blues music every night of the week, and you can find a schedule of performers on the Kingston Mines website. Shows often run between 6pm and 2am. It’s located in the Lincoln Park neighborhood of the city and near lots of great restaurants and bars to check out before the shows too.

Chicago Architecture Boat Tour Chicago

Chicago Architecture Boat Tour

Chicago’s architecture is nothing short of impressive, and one of the best ways to really see it is from the water. The Chicago Architecture Foundation offers river cruises that last about 1.5 hours and leave from the southeast corner of the Michigan Avenue Bridge at Wacker Drive. These tours are narrated by tour guides who will tell you the story of how the city grew to become what it is today and the history of these towering skyscrapers. It’s also fun to take a twilight river cruise to experience the skyline at sunset.

Grab a Chicago-Style Hot Dog Chicago Style Hot Dog Ingredients with Mustard Pickles Relish Tomato and Peppers
Chicago Style Hot Dog Ingredients with Mustard Pickles Relish Tomato and Peppers

Grab a Chicago-Style Hot Dog

In addition to deep-dish pizza, it’s also crucial that you try a Chicago-style hot dog when you’re in town for a couple days. Chicago hot dogs are topped with mustard, but never ketchup, as well as chopped onions, pickle relish, tomato slices, pickled sport peppers, and celery salt. Top hot dog spots include Hot Doug’s on North California, Redhot Ranch on Western Avenue, and Byron’s Hot Dogs on Lawrence. If you don’t eat meat, you can find vegetarian-friendly hot dogs in Chicago at Kim & Carlo’s Hot Dog Stand at the Museum Campus or America’s Dog on Randolph Street.

Cubs Game at Wrigley Field Wrigley Field, Chicago
Wrigley Field, Chicago

Cubs Game at Wrigley Field

Wrigley Field is the home of Major League Baseball’s Chicago Cubs, a team that has certainly experienced its fair share of highs and lows in past years. This baseball field was built in 1914, and you can take a tour of the ballpark to learn more about its history. Going to a Cubs game here isn’t all about baseball either; it’s a cultural experience and an epic party. Even if you don’t get tickets, there are so many fun bars nearby to watch the plays on big TV screens with old and new friends.

Comedy Show at Second City Second City
Second City

Comedy Show at Second City

If you can squeeze in a show at Second City during your two days in Chicago, definitely do it. This venue plays live shows pretty much every night and has launched the careers of so many famous comedians. You can watch up-and-coming student performers for discounted rates or improv masters here.

See the Animals at Lincoln Park Zoo Lincoln Park Zoo
Lincoln Park Zoo

See the Animals at Lincoln Park Zoo

This is a wonderful zoo that is totally free to visit and close to lots of other things that you’ll likely be filling your time with on a weekend trip to Chicago. Here you can see mammals, reptiles, birds, and amphibians in beautiful outdoor and indoor exhibits. Stop by between 10am and 4:30pm to 6:30pm, depending on the season.

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