Top Things To Do In Chicago!

Last Updated on Mar 11th, 2026 by Neha Sharma, Leave a Comment

There’s something special about the “Windy City” of Chicago. Maybe it is the stunning skyline, friendly people, signature dishes, or unique architecture. There’s no denying that there is a myriad of things to do in Chicago. From shopping to eating & exploring to partying! And with so many different neighborhoods to choose from, you’re sure to find the perfect place to stay during your visit.

Chicago also has a history of mural art, with many iconic murals located throughout the city. And, getting a picture clicked in one of them is definitely a vibe. The city is beautifully situated on the shores of Lake Michigan. Its downtown area is linked by a network of rivers & canals, which just look magical. 

Meanwhile, for the extra feature, the city’s architecture is also shaped by its unique geographical location. If you are looking for things to do in Chicago this weekend or for the next month, the city always has something to amaze you.

Interesting Things To Do In Chicago This Weekend

1. Getting Clicked In Front Of “The Bean.”

When it comes to free activities to do in Chicago, a tour of the Cloud Gate should always be on the top of your list. “The Bean” or the Cloud Gate is an iconic structure that is built using 168 stainless steel plates. The unique design of this sculpture features a 33-foot-high archway that visitors can walk through. The sculpture’s concave surface reflects the sky and the building.

This creates a beautiful optical illusion. And, what is even more interesting is that there’s no fee to get clicked in front of it or visit the structure. It’s open and free for all. Just head over to Millennium Park and spot the bean!

2. Go To The Cubs Game

The Cubs are one of the most storied franchises in baseball history. The reason their fans are some of the most passionate in all of sports. A trip to Wrigley Field to see a Cubs game is best for any baseball fan. It’s an experience you won’t forget anytime soon. Whether you’re cheering on the Cubs from the bleachers or enjoying a beer in the friendly confines of the ballpark. A Cubs game is always a good time. And, with so many great restaurants and bars in Chicago, you can make a day or night of it. If you’re looking to catch a Cubs game while in town, check out the schedule and get your tickets in advance. You won’t regret it!

3. See A Show At The Second City

The Second City is Chicago’s popular comedy theatre that is known for its live shows every night. Getting tickets to the Second City is one of the most fun things to do in Chicago with kids. It mostly produces shows in Chicago and Toronto. It has a training center where you can learn the art of improvisation. The company has launched the careers of many celebrities.

These are Tina Fey, Stephen Colbert, Steve Carell, Gilda Radner, Bill Murray & many more. Visitors can stroll around several theatres in the Second City complex. They can enjoy a mix of comedy, pop culture, songs, or whatever else is on the cast’s mind at the moment. You are guaranteed to laugh yourself silly at the Second City!

4. Take Chicago’s Architecture Tour

If you are new to the Windy City and looking for some free things to do in Chicago this weekend. Heading over to tour Chicago’s Architecture is the best thing to do. Chicago has long been known for its unique architecture. The city is home to buildings designed by some of the world’s most famous architects. These include Frank Lloyd Wright, Mies van der Rohe, Helmut Jahn, and Daniel Burnham.

Chicago is also home to the world’s largest collection of early 20th-century architecture. Moreover, Windy City has four of the five tallest buildings in the United States. Literally, more high-rises than in any other city in North America.

5. Try The Scrumptious Deep-Dish Pizza

A trip to Chicago is definitely incomplete without trying the Chicago-style deep-dish pizza. It is a signature dish of Chicago, & to try the same, there’s no better place to go than Pizzeria Uno. This iconic spot has been serving up its signature dish since 1943, and it’s still as popular as ever. The secret to Uno’s success is in the thick crust, which is made from a secret recipe and baked in a special deep-dish pan. The result is a pizza that’s crispy on the outside and soft and fluffy on the inside. Moreover, the toppings of deep-dish pizza are classic. These include pepperoni, sausage, mushrooms, onions, & green peppers. So yum – feeling hungry already!

6. Drip Into Chicago’s Vibe At The Millennium Park

If you are in the city and not really sure what to do, then Millennium Park is something every traveler should check out. This public space is perfect for a day of exploring. It has many gardens, sculptures, & views of the city skyline. You can also catch a free concert or movie in the park during the summer months. The place was originally intended to celebrate the second millennium. Today, it is a prominent civic center near the city’s Lake Michigan shoreline. Visitors can find plenty of free things to do in Chicago here, & can still do more than expected.

7. Get On A Sunset Cruise 

When searching for things for couples to do in Chicago, there’s nothing better than hopping on a sunset cruise with your partner. Watch the sun slowly hiding behind the buildings while sitting with your loved one on a romantic cruise. And, wrap up the end of the day with a chilled beer, a light snack, or a glass of wine. This can definitely be the best thing to do in Chicago if you are traveling with your partner. Also, the cruise tour is the perfect way to see all of Chicago’s most popular attractions in one day. Overall, it is an ideal way to relax and see the city from a different perspective.

8. Hop On A Double-Decker Bus

Tour Chicago’s most popular attractions on a double-decker bus. It is something that every traveler must experience at least once. This is the perfect way to see the city, learn about its history, and get great views. You’ll probably start by boarding a double-decker bus for a panoramic tour of the city. As you ride, you will see popular landmarks like the Willis Tower, Navy Pier, Millennium Park, & more. Your guide will provide commentary along the way, so you can learn about the city’s history and culture. After the bus tour, you’ll be guided to various other options. These include a cruise on Lake Michigan for unbeatable views.

9. Shop The America-Style At The Water Tower Place

A huge mall with amazing stores, Water Tower Place is one of the best things to do in Chicago with kids. You will be amazed by the number of floors it has. Your kids are going to love the wonderful shopping experience at the American Doll Store. Visitors can find a great balance of clothing for every age group. 

And what impresses everybody is their selection of stores. Even if you don’t want to shop, make your way to the food court, which has a great selection of restaurants. But the glass elevators are different & fun to ride on. So, head yourself to a different experience with your friends & family at Water Tower Place.

Popular Routes To Chicago

• Indianapolis to Chicago: With an aerial distance of 177 miles, Indianapolis to Chicago flights see a rise in popularity. Also making ensuring the route remains one of the busiest in Chicago. A nonstop flight on this route can take no more than 1 hour & 15 minutes.
• Pittsburgh to Chicago: It seems like most travelers prefer taking Pittsburgh to Chicago flights. The aerial distance between the two cities is 412 miles. One can find more than 60 flights on a daily basis on this route.
• Portland to Chicago: More than 100 Portland to Chicago flights by 11 airlines take off in a day. This is among the popular routes to Chicago. The total time taken by the PDX to ORD flight is around 4 hours in a nonstop flight. However, it is around 10 hours in a flight with 1 or 2 stops.
• Charlotte to Chicago: Around 12 airlines operate more than 95 Charlotte to Chicago flights on a daily basis. This route by air will take around 2 hours and 5 minutes on a nonstop flight and up to 10 hours with 1 or 2 stops.
• Miami to Chicago: Another popular route to the Windy City that is preferred by both business and leisure travelers. Miami to Chicago flights are operated by 18 airlines. One can easily find more than 100 nonstop and connecting flights daily.
• San Francisco to Chicago: This is one of the most popular routes that covers an aerial distance of 1854 miles. Around 16 airlines operate San Francisco to Chicago flights. More than 90 flights fly to this route a week. It can take you around 4 hours on a nonstop flight and around 10 hours with 1 or 2 stops.
• Dallas to Chicago: When it comes to the list of popular routes tothe  Windy City, the frequency of Dallas to Chicago flights is no exception. Many popular US airlines are serving the route. These are United Airlines, Frontier Airlines, and American Airlines.
• LA to Chicago:  Another popular city linking, Los Angeles to Chicago flights are served by several airlines. These include Southwest, Frontier, and Spirit Airlines. The air distance between the routes is 1741 miles, with more than 100 flights operating in a week.
• New York to Chicago: The total aerial distance covered by New York to Chicago flights is 709 miles, with all the famous US airlines serving the route. However, the number of flights available might be lower compared to others. But it is definitely among the busiest routes to Chicago.
• Atlanta to Chicago: There are several airlines that serve Atlanta to Chicago flight routes with an aerial distance of 593 miles. Flyers can easily find more than 100 flights per week on the ATL to ORD route.

Frequently Asked Questions

Q: What are the best things to do in downtown Chicago?

A: There are plenty of things to do in Downtown Chicago. Such as catching gorgeous views of Chicago from the sky-observation deck. Get fresh air at the Lakefront Trail and admire the beautiful fountain and skyline at Grant Park.

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Q: What are the interesting activities to do in Chicago today?

A: If you are done with the architectural tour, you can join the summer music festival at Ravenwood. You can also visit the Garfield Park Conservatory and find peace and calm away from the city hustle.

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Q: Which is the best place to enjoy the nightlife in Chicago?

A: There are several breweries and dance clubs to enjoy the thrilling nightlife in Chicago. Some of the popular ones include The Violet Hour, East Room, Smart Bar, Studio Paris Nightclub, Blue Chicago, and many more.

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Q: Where can I find vegetarian or vegan food in Chicago?

A: If you are craving a plant-based burger, vegetarian dumplings, or soy meat, you can reserve a table. These are Alice & Friends Vegan Kitchen, Urban Vegan Thai Cuisine, ALTHEA, IM Vegan Restaurant, Chicago Raw, & Native Foods.

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Q: How can I book cheap flights to Chicago?

A: Bag exclusive discounts and deals on flights to Chicago. Get in touch with the travel professionals at FareMaze. We are a licensed tour & travel agency. We strive to make flight booking easier and cheaper for travelers around the world.

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Q: Are you excited enough to explore Chicago?

A:   We hope you will add the above-mentioned things to do in Chicago to your bucket list & enjoy the best of the Windy City.

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Chicago is a beautiful & historic city located in the Midwest region of the United States. If you are interested in exploring the city’s history or checking out its modern architecture. There’s plenty to see & do in Chicago. The Windy City offers world-class museums & award-winning restaurants. It also has a variety of activities that will keep you busy from morning until night.

If you are ready to start planning your trip, reach out to our team of travel professionals at FareMaze. Save yourself the best discount on flights to Chicago in no time. Whether you are searching for airfares on Indianapolis to Chicago flights or on Pittsburgh to Chicago flights. We have a huge selection of cheap flight deals that are surely going to amaze you.