20 Fun Things to Do in Chicago This Weekend

After busy weekdays, let’s have fun things to do in Chicago this weekend. Chicago provides thrilling offerings to fill your exciting weekends. Whether you are willing to enjoy the live music performances, attend summer workouts, or relish the food festivals, feel free to take joy in the Windy City. 

Keep an eye on the calendar of fascinating events in Chicago. You can choose the fun things to do based on your preference. There are exceptional art exhibits, spectacular live sports, major street fairs, aerial firework shows, and more. All are always available to attendees. Discover the fun things to do in Chicago this weekend. No worry! We have put together the list of fun things to do this weekend. Check this out.

1. Get a kick out of Pitchfork Music Festival

fun things to do in chicago this weekend
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Get a charge out of the best live music festival in Chicago, Pitchfork Music Festival. It is one of the fabulous and fun things to do to spend your weekend with a delightful experience. Located in Union Park, the lineups of various music genres are ready to present unrivaled performances. Whether you revel in electronic music, hip-hop, indie, rock alternative, or pop, the music festival welcomes you to enjoy your day.

More than 60,000 attendees have experienced the rewarding music weekend. Feel the welcoming atmosphere at the music festival. You are free to discover the upcoming music performances from around the world. Many local businesses are also available to promote Chicago’s food and arts. The tickets also come at affordable prices. Just exhaust your summer weekend at the Pitchfork Music Festival.

2. Feast at Silver Room Sound System Block Party

fun things to do in chicago this weekend
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Get involved in one of the fun things to do in Chicago this weekend, the Silver Room Sound System Block Party. It is a two-day Chicago festival that offers an enjoyable weekend experience. Come to see extended performances, including DJ music, rap, hip-hop, and other music genres from notable musicians. Top-notch Chicago musicians like Joey Purp, Enhu Tune, and DJ Ron are on hand.

Enjoy the luxurious experience by taking Afro Karaoke. You have the opportunity to perform karaoke on stage. If you are into a specific sport, come and join the capoeira demonstration. All you need to spend your weekend is in place.

3. Go to Tacos y Tamales Festival

fun things to do in chicago this weekend
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Tacos y Tamales is part of an annual food festival held in Pilsen. Visiting the festival brings you more sophistication to the next level. Feel free to savor the authentic tacos and tamales like no other. The excellent local eateries serve the best pan-Latin menus. Whether you cruise the vendor stalls, taste the tacos and tamales, or take an art tour, the festival delivers a memorable weekend. 

Don’t miss reveling in the live Latin music performance. You will be pleased to dance and weave through the lively music. The festival is free, but we suggest that you donate at the entrance. Get fun things from the signature traditional Mexican market by attending the Tacos y Tamales Festival. 

4. Head to Volleywood Festival

fun things to do in chicago this weekend
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One of the fun things to do in Chicago this weekend is taking part in the Volleywood Festival. It is the most-wanted party held in two days. Get an experience of dancing on the sands of North Avenue Beach. You are unfettered to gain an interactive experience with your peers. Invite them to enjoy the great live music. 

The excellent musicians and artists present unpredictable performances to captivate the attendees. Be a part of the attendees to have charming chances on your weekend. Don’t miss having a fun weekend by attending Chicago’s most fabulous beachfront music fest.

5. Attend Millennium Art Festival

fun things to do in chicago this weekend
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If you are crazy about art, let’s go to the Millennium Art Festival. Stretched along Lake Street, the festival should be on your weekend itinerary. Discover a wide range of unique furniture, sophisticated photography, classic jewelry, antique ceramics, and fantastic paintings. You are allowed to browse all the collections.

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More than 120 artists are feasible to expose their artworks. Whether you are willing to purchase the best art collections or go sightseeing, the place is perfect to lose your weekend. It is a free-admission festival. Feel free to have extraordinary things in Chicago by attending the Millennium Art Festival.

6. Spot Navy Pier Fireworks

fun things to do in chicago this weekend
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Are you getting bored on the weekend? You are encouraged to spot the Navy Pier fireworks. It is a well-known aerial display offering incomparable attractions on a summer night. Keep an eye on the seasonal firework schedules. The host runs a twice-weekly show on Wednesdays and Saturdays from the weekends of Memorial Day through the weekends of Labor Day.

You can find the best spot to expend the dazzling free displays. The firework show also features a famous and dramatic music soundtrack. On any occasion, the unique soundtracks are attainable. Don’t miss getting high on the Ferris wheel that offers more exposure. Whether you relish the show from cruising the boat or on nearby beaches, Invite your friends to have an unrivaled night at the Navy Pier.

7. Visit Grant Park Music Festival

fun things to do in chicago this weekend
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The Grand Park Music festival welcomes classical music lovers to live it up. It would be best if you place this summer festival on your weekend schedule. An exciting range of classical music is available. Whether you enjoy world-class classical music performances or classic Broadway music, get a taste of the premiere concerts. Listen to an array of the best classical arrangements by Mozart, Beethoven, Shostakovich, Hayd, and more.

The professional musicians bring extraordinary music. You will hear famous classic songs, including the Eroica by Beethoven, Piano Concerto No. 2 by Rachmaninov, Sleeping Beauty by Tchaikovsky, and other symphonies. The music festival always delivers an excellent orchestra and chorus and musical sensation. Call your friends to take joy in the Grant Park Music Festival.

8. Taste Roscoe Village Burger Fest

fun things to do in chicago this weekend
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Find a fun way to extend your weekend by visiting Roscoe Village Burger Fest. Who doesn’t like eating burgers? Everyone loves savoring the best patty. The fest offers an excellent opportunity to taste a selection of signature burgers, from spicy flavors to unique toppings. Invite your family to allocate time for the fascinating weekend.

The event offers spectacular offerings, whether you prefer flavored food, unique art, or incredible crafts. Discover other thrilling lineups of activities like kid’s zones, live music shows, and more. The city’s top artists are also ready to present outstanding performances. Let’s have a fun weekend with the exceptional culinary experiences of the Roscoe Village Burger Fest. With a $10 donation, you can benefit from incomparable services and programs.

9. Let’s Rock at Parkway Bank Park

fun things to do in chicago this weekend
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Are you finding the fun things in Chicago this weekend? Head to the Rosemont’s Parkway Bank Park. Discover a parade of notable rock bands like the Tribute Project, Electric light orchestra, and classic rocks. The powerful music and skillful musicians deliver the most outstanding performances like no other. Whether you check out the show or gather with your peers, it is a perfect venue. 

Beverage tents are also up for grabs. You are free to bring your appetites. The park is dedicated to all attendees looking for remarkable events. Just get your seat and enjoy the whole performance. Don’t miss a firework display set up at the show’s conclusion.

10. Take Architectural Brunch on the Chicago River

fun things to do in chicago this weekend
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The weekend is the perfect time to relish having exceptional dining sophistication. Taking an architectural brunch is one of the fun things to do in Chicago this week. Thrill to the fantastic, unparalleled riverfront displays during the trip. You can also explore the spectacular river walk when cruising on the vessels. Savor irresistible cuisine and sip a glass of cocktail while admiring the impressive skyscrapers as well as architecture. All the foods are freshly served on the board. 

For more dining experience, get a taste of the live onboard DJ. Of course, it will enhance your enjoyment during the trip. The interactive tour leaders are also pleased to deliver informative explanations about the architectural icons along the river. Spot the seasonal Navy Pier fireworks from the boat. It is incredible to get a kick out of the long summer weekend.



11. Join Bronzeville Architecture Tour

fun things to do in chicago this weekend
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Adore Chicago’s attractive architecture by joining the Bronzeville architecture tour. If you are into architectural worlds, take the tour to explore the architecture and history of Bronzeville’s Grand Boulevard. The area is dotted with former mansions owned by some of the city’s wealthiest residents. Known as the center of a famous migration in the early 20th century, you will gain historical experience like no other.

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The tour guide will invite you to explore the highlights of Bronzeville, like old churches, mid-century schools, modern apartments, historic mansions, and more. Come and join the excellent architecture tour to reveal the history of the Bronzeville neighborhood.

12. Come Together at 5 Point Film Festival

fun things to do in chicago this weekend
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Get inspired and motivated by joining the 5 Point Film Festival. The free-admission fest offers unforgettable nights of entertainment that feature some favorite films. It is curated outdoor art, performance, and movies in one package. Feel free to freak out on the films, bringing positive vibes. 

Invite your family to watch the films with you and get full of inspiration, perspective, and creativity. You will gain new insight after enjoying the movie. Take an opportunity to broaden your network with other attendees. Grab your snack and sip the cocktail before and during the film. It’s one of the fun things to do in Chicago. 

13. Get involved at Twilight Tunes

fun things to do in chicago this weekend
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Get ready to explore the Brookfield Zoo and enjoy the excellent summer concert, Twilight Tunes. It is a perfect chance to revel in the live show on the outdoor stage. Surrounded by natural settings and wildlife, let’s relax and feel the fresh air in the spectacular park. An array of 10 live music sessions are ready to take joy. 

One of them is an American English session. It is the most significant Beatles tribute, offering the top songs of the living-legend band. Head to the Sixteen Candles session, which offers amazing 1980s songs. Of course, it will bring nostalgia to the attendees. Make sure to prepare your appetite, lawn chairs, and blankets. Call your family and friends to come together to the festival.

14. See Trickery Chicago Magic Show

fun things to do in chicago this weekend
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Getting pleasure at the Chicago Magic Show is one of the fun things to do in Chicago this weekend. It is a hilarious and outrageous show, bringing you more surprises. With its lively venue, illuminating lighting, and inviting atmosphere, appreciate the show with lots of personalities! The musical backdrops also elevate the performance. 

Give applause to the very talented magicians offering up-close magic like no other. They are also pleased to present an excellent sense of humor and entertaining jokes. While rejoicing in the magic performance, get ready to purchase signature beverages and snacks. Of course, it creates fun things. Devote your weekend to exploring magic tricks and acts the Trickery Chicago.

15. Relax at Laugh Factory

fun things to do in chicago this weekend

Go to the center of Chicago’s stand-up comedy offering exceptional laughter. The hour and a half comedy show delivers funny scenes. Please stand up for the talented comedians, bringing you more laughter with their spontaneous and unscripted jokes. The city’s top-notch stand-up comedians like Tim Allen, Alonzo Bodden, Kevin Nealon, Jo Koy, Tiffany Haddish, and other comics are at beck and call to present the funniest comedy.

The attraction never fails to make the attendees laugh freely, from family to political jokes. It is an excellent place to release your boredom and upset. After being thrilled by the marks, return to your home full of motivation, happiness, and inspiration. The signature food and beverages are up for grabs.

16. Follow Chicago Greeter Tour

fun things to do in chicago this weekend
Source: choosechicago

Meet with the friendly locals to guide you in exploring the signature Chicago. You are encouraged to explore the city’s highlights, including iconic landmarks, great cultural traditions, and diverse histories. Get experience to explore an array of fascinating destinations like Chinatown, Rogers Park, Lakeview, Ravenswood, and more. The locals are pleased to guide the participants, so they can have a flexible and fast tour. Don’t hesitate to take the self-guided walking tour across the city. You can visit the preferred destination as you please. 

The free-admission neighborhood tour is available to the public. Get ready to invite your friends, family, or groups. You can see the great Chicago highlights throughout the neighborhood walking tour.

17. Get a kick out of the Energy Revolution exhibit

fun things to do in chicago this weekend
Source: architecture.org

The Chicago Architecture Center always provides fun things to do for all ages. One is the Energy Revolution exhibit. Get inspired at the most outstanding exhibition presenting the theme of climate change. The contemporary style utilizes eco-friendly and creative approaches to build the future environment. Feel free to gain experience with how the urban planners, engineers, and architects show their first-rate skills. 

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They work to create eco-friendly buildings with leading technologies, including high-performance facades and kinetic energy. Adore the greener future appliances that contribute to the net-zero carbon world. Elevate your awareness of climate change challenges by getting a kick out of the Energy Revolution exhibit.

18. See Prince: The Immersive Experience

fun things to do in chicago this weekend
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Allocate your summer weekend by following the Prince: the Immersive Experience. It is one of the fun things that you should do during your summertime. The event is dedicated to all music lovers looking for a next-level music experience. Get a taste of the interactive music tour. You are free to appreciate the original sound, creative evolution, and Prince’s experience in an extraordinary way. 

Get lost in the world of diamonds and pearls for more sophistication. You will also be pleased to get involved in the audiovisual dance party. The Prince’s best hits are also in hand to accompany your summer weekend. Your plan should include a range of classic photos, memorabilia, and outfits.

19. Discover a Summer Street Festival

fun things to do in chicago this weekend
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Chicago has an unrivaled selection of summer street festivals along its parks and streets. The places are always packed every week. Be a part of the happy crowds to allocate your summertime. The events are so welcoming, whether you find live music performances, authentic foods, or signature beverages. 

The events provide fun things to do around your neighborhood, with complete street vendors and a warm atmosphere. Get close to the nearest summer street festival. Invite your family and friends to gather together without exception.

20. Take a Bike Ride

fun things to do in chicago this weekend
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Biking on the North Branch trail is one of the fun things to do in Chicago this weekend. The location offers a 16-mile bike trail that you will love. Pedal your bikes on the well-paved patch bringing you more experience. The track is also low-stressed. Take advantage to have refreshment and release your boredom after busy workdays.

The place is an excellent way to escape from the crowded city. Whether you take a solo bike trip or a group trip, freak out on riding bikes throughout the northern suburbs. During your ride, get a taste of what it’s like to sip authentic cocktails across the trill.


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What can a teenager do on the weekend?

An array of fun things to do are available to spend your weekend. You can visit the significant live music performance, attend live sports, adore artworks at the exhibition, spot aerial firework shows, and more.   

Is NYC or Chicago better?

Living cost in Chicago is 85% lower than in New York City. Even providing a lower cost of living, Chicago offers weather, public transportation, culture, and attractions as impressive as NYC. The Windy City never fails to offer fantastic options. It offers fun things to enjoy. 

Should I go to Chicago alone?

Chicago is a perfect place to make a solo trip. The City comes with accessible public transportation and more free-admission destination. Get an experience to explore Chicago whether you take a solo trip or group tour.

Why is Chicago so popular?

Some reasons make Chicago so popular. The city offers an inclusive and welcoming spirit, iconic landmarks, world-class shopping centers, friendly neighborhoods, and more. 

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