15 Best Things to Do in Chicago (Local Favorites & Tourist Attractions)

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Chicago is one of my favorite cities to visit in the United States. Between the incredible food, iconic skyline, professional sports, museums, and neighborhoods, there’s always something new to experience.

Whether you’re visiting for a weekend getaway, a Cubs game, or simply crossing another city off your travel bucket list, you can accomplish a lot in 48 hours. Here are some of my favorite things to do in Chicago based on my own visits.

Need a hotel in Chicago? Before booking, compare prices on Priceline, Booking.com, and Expedia. I’ve found that rates can vary quite a bit depending on the site.

Magnificent Mile

If shopping is your thing, you’ll want to spend some time on the Magnificent Mile.

Located along North Michigan Avenue, this famous shopping district features hundreds of stores, restaurants, hotels, and attractions. You’ll find everything from Nike and Levi’s to luxury retailers, along with malls like Water Tower Place and The Shops at North Bridge.

Even if you aren’t planning to shop, it’s a great area to walk around and admire some of Chicago’s historic architecture.

Three Dots and a Dash

One of my friends recommended Three Dots and a Dash, and I’m glad they did.

This tiki bar is tucked away in an alley, so don’t be surprised if you walk past it the first time. Once you get inside, the atmosphere completely changes.

Their food menu isn’t huge, but the cocktails are the main attraction. If you enjoy rum drinks and unique tropical cocktails, add this place to your itinerary.

Batter & Berries

If you’re looking for breakfast or brunch, Batter & Berries is one of my favorite spots in Chicago.

They’re famous for their French toast, and it absolutely lives up to the hype. Just be prepared to wait because they don’t take reservations.

They also allow BYOB, so you can enjoy a mimosa or your favorite drink while waiting for your meal.

If you only have 48 hours in Chicago, I’d make time for this restaurant.

Giordano’s

You can’t visit Chicago without trying deep-dish pizza.

Every trip I make to the city includes a stop at Giordano’s. Their pizza is easily one of my favorites, and one small pie is usually enough for leftovers.

There are multiple locations throughout the city, so it’s easy to fit into your schedule.

If you’re trying to stretch your travel budget, learning how to save money before your trip can help you spend more on experiences like this.

North Avenue Beach

Most people don’t associate Chicago with beaches, but they should.

North Avenue Beach offers one of the best skyline views in the city. During the summer, it’s packed with people relaxing, playing volleyball, jogging, and enjoying Lake Michigan.

One tip: leave your alcohol at home. The city enforces the rules, and it’s not worth the risk.

Chinatown

Chicago’s Chinatown is another neighborhood worth exploring.

There are plenty of authentic restaurants, bakeries, tea shops, and specialty stores throughout the area. Even if you aren’t shopping, it’s a fun place to walk around for an hour or two.

If you’re a foodie, you’ll probably find something you’ve never tried before.

SafeHouse Chicago

SafeHouse is one of the more unique bars I’ve visited.

It’s designed around a spy theme, and getting inside is part of the experience. If you don’t know the password, the employees will usually have you complete a funny challenge before letting you enter.

Once inside, the entire place feels like a secret spy headquarters. It’s definitely worth checking out if you’re looking for something different.

Wrigleyville

If you’re a baseball fan, spend some time in Wrigleyville.

Home to Wrigley Field and the Chicago Cubs, this neighborhood is filled with bars, restaurants, and sports fans throughout the baseball season.

One of my favorite memories was relaxing on the balcony at Hotel Zachary while overlooking Wrigley Field before the game.

If you’re planning to catch a game, don’t wait until the last minute.

Going to a Cubs game? I always compare ticket prices on StubHub & TickPick before buying.

If you enjoy visiting stadiums around the country, check out my Sports Events Travel Hub for more sports travel inspiration.

River & Lake Cruises

One of the best ways to experience Chicago is from the water.

Whether you choose an architecture cruise on the Chicago River or a sightseeing cruise on Lake Michigan, you’ll get incredible views of the skyline while learning about the city’s history and famous buildings.

If it’s your first visit, I’d recommend making time for one of these cruises. It’s a relaxing break from walking around downtown all day.

Book your cruise before your trip to guarantee your preferred departure time.

Skydeck Chicago

No trip to Chicago feels complete without visiting Skydeck Chicago at Willis Tower.

The observation deck offers some of the best views in the city, and on a clear day, you can see for miles across Illinois and neighboring states. According to Skydeck Chicago, the biggest attraction is The Ledge, a series of glass boxes that extend outside the building, giving you the feeling of standing more than 100 stories above the ground.

If you’re afraid of heights, this might test your nerves. If not, it’s one of the coolest photo opportunities in Chicago.

Art Institute of Chicago

The Art Institute of Chicago is consistently ranked as one of the best art museums in the world.

Even if you’re not a huge art fan, it’s worth visiting to see famous works like American Gothic, Nighthawks, and The Old Guitarist. The museum also features an impressive collection of Impressionist, Modern, and Contemporary art.

Plan to spend at least a couple of hours here if you enjoy museums.

Grant Park

Grant Park is one of Chicago’s largest public parks and a great place to relax while exploring downtown.

It’s within walking distance of several major attractions, including Buckingham Fountain, Millennium Park, Soldier Field, and the Museum Campus. Depending on when you visit, you may also catch a festival, concert, or other public event.

If you’re visiting during the warmer months, it’s a nice place to take a break from the busy streets.

Millennium Park

Millennium Park is one of Chicago’s most recognizable attractions.

Most visitors come to see Cloud Gate, better known as “The Bean.” It’s one of the city’s most photographed landmarks and a great place to grab a few pictures before continuing your day.

The park is free to visit and frequently hosts concerts, festivals, and other public events throughout the year.

No matter how many times I visit Chicago, I always stop by Millennium Park.

Lincoln Park Zoo

If you’re traveling with kids, or just enjoy animals, Lincoln Park Zoo is worth adding to your itinerary.

Admission is free, making it one of the best values in the city. The zoo is home to hundreds of animals and is located inside beautiful Lincoln Park, making it easy to combine with a walk through the surrounding neighborhood.

Buckingham Fountain

Located in Grant Park, Buckingham Fountain is one of Chicago’s most famous landmarks.

During the day, the fountain performs water shows every hour, and at night it lights up for an even more impressive display.

If you’re already exploring Millennium Park or the lakefront, it’s an easy stop that doesn’t require much extra time.

Bonus: Drive Part of Route 66

If you’re extending your trip, consider driving part of historic Route 66.

Chicago marks the beginning of America’s most famous highway, and there are several interesting Route 66 museums and roadside attractions just outside the city. It’s a fun way to add another adventure to your visit if you have an extra day.

Getting Around Chicago

One thing I appreciated about Chicago was how easy it was to get around without renting a car.

I relied on Uber and Lyft for most of my transportation, and it ended up being cheaper than paying for a rental car, gas, and downtown parking.

Need a ride while you’re in Chicago?

Use Uber or Lyft to get around the city quickly without worrying about parking.

Save Money on Your Trip

Before booking your hotel, check Rakuten to see if your booking site offers cash back.

I’ve earned cash back simply by clicking through Rakuten before completing hotel reservations. It’s an easy way to save a little extra money on your trip.

If you’re flying into Chicago, comparing budget airlines before booking can also help lower your travel costs.

Chicago is one of those cities that offers something for everyone. Whether you’re into sports, great food, museums, architecture, or simply exploring different neighborhoods, it’s easy to fill an entire weekend.

My personal favorites are grabbing deep-dish pizza at Giordano’s, enjoying brunch at Batter & Berries, relaxing in Wrigleyville, and taking in the skyline from North Avenue Beach.

If it’s your first visit, mix the famous attractions with a few local favorites. You’ll leave with a much better appreciation for the city than if you only visited the tourist hotspots.