Best Street Festivals in Chicago

Which are you most excited for?

SEPT 6: Sangria Fest

SEPT 6–8: Taste of Chicago

SEPT 6–OCT 12: Oktoberfest at Hubbard Inn

SEPT 13: Englewood Jazz Fest

SEPT 13–15: Grito Fest

SEPT 14: Wrigleyville Country Fest

SEPT 14–15: Ravenswood Art Walk

SEPT 20: Summer Cocktail Fest

SEPT 20–22: Riot Fest & Riot Land

SEPT 20–29: World Music Fest

SEPT 26: Cider Fest

SEPT 28–29: Randolph Street Market

#chicago #free #fall

Chicago
2024/9/3 Edited to

... Read moreChicago is renowned for its lively street festivals that celebrate the city's rich culture and diverse community. In September, the city comes alive with an array of events that cater to all interests. For instance, Sangria Fest, happening on September 6th, offers delicious drinks and a festive atmosphere. The Taste of Chicago from September 6-8 showcases food from local vendors, making it a must-visit for food lovers. Oktoberfest at Hubbard Inn runs from September 6 to October 12, embracing German culture with beer, food, and music. Jazz enthusiasts can look forward to the Englewood Jazz Fest on September 13th, featuring talented musicians from near and far. The Grito Fest, from September 13-15, celebrates Hispanic Heritage Month with vibrant performances and delicious food. Additionally, on September 14th, Wrigleyville Country Fest brings together country music lovers, while the Ravenswood Art Walk from September 14-15 showcases local artists and their creations. For cocktail enthusiasts, the Summer Cocktail Fest on September 20th promises exciting concoctions. Riot Fest & Riot Land, occurring from September 20-22, is a rock festival that attracts big-name bands alongside emerging artists, offering a diverse lineup for music fans. The World Music Fest from September 20-29 invites attendees to experience global sounds and cultures. Finally, Cider Fest on September 26th and the Randolph Street Market from September 28-29 round out the month with unique shopping and tasting experiences. These festivals not only highlight the city's diversity but also offer locals and visitors an opportunity to connect and celebrate together.

11 comments

CHI Bucket List's images
CHI Bucket ListCreator

Who wants to go to them all?

Related posts

A scenic view of the Chicago River flowing between tall city buildings under a clear sky, with a light blue banner overlay stating "3 Days in Chicago: Must-Visit Spots."
A boat cruises on the Chicago River with the city skyline in the background, overlaid with text detailing "Iconic Eats & Skyline Views" and a day's itinerary.
An aerial view of a city with numerous buildings extending towards a body of water, featuring an overlay with "Neighborhood Gems & Local Culture" and a day's itinerary.
3 Days in Chicago: Must-Visit Spots
3 days in Chicago = food, skyline views, and hidden gems. From deep dish to jazz bars, here’s how to make the most of a long weekend in the Windy City! What’s your must-do in Chicago? #ChicagoTravel #WindyCityAdventures #WeekendInChicago #TripUnlocked #Chicago
Trip Unlocked

Trip Unlocked

557 likes

Chicago Riverwalk >>>
The Chicago Riverwalk is a multi-use public open space located on the south bank of the main branch of the Chicago River, extending from Lake Michigan and the Outer Drive Bridge westward to Lake Street. The Chicago Riverwalk contains restaurants, bars, cafes, small parks, boat and kayak rentals,
CHI Bucket List

CHI Bucket List

2063 likes

Weekend Trip to Chicago 🥰
It’s always a vibe in Chicago ❤️‍🔥 Overall: 9/10 Things to do - Take the Chicago Architecture River Tour, Chicago River - Go to Starbucks Reserve Roastery - Go to Marc Jacobs - Oak Street - Go to Cloud Gate #chicagotrip #chicagoitinerary #contentcreator #blackgirltr
Erie Valentine💞👑

Erie Valentine💞👑

344 likes

NYC STYLE STREET CART FOOD IN CHICAGO 🐑
Halaleez: 8.8/10 & $47.64 🐑 Food: 8.9/10 Quality: 8.5/10 Service: 8.7/10 Price: 9.1/10 OVERALL: 8.8/10 400 S Financial Pl, Chicago, IL 60605 #halaleezchicago #chicagohalalfood #chicago
SERGELATO

SERGELATO

115 likes

1950s Hong Kong Street Food Spot in Chicago
Ken Kee is one of the best Chinese restaurants in Chicago serving up the best Hong Kong style cuisine! Visit them in Chinatown #chicagochinatown #chicagofood #chicagofoodie #chicagorestaurants #chicagoeats
Kayleejochicago

Kayleejochicago

114 likes

The 3 Best Mid-Range Hotels in Chicago
– 📍 Swissotel Chicago — just steps from the Chicago River and Millennium Park. 📍 Aloft Chicago Mag Mile — only 5 mins to Michigan Avenue and the Magnificent Mile. 📍 LondonHouse Chicago, Curio Collection by Hilton — around a 10-min walk to the Chicago Art Museum. #chicagohotel #chicagotrav
My Little Escapes

My Little Escapes

55 likes

Chicago St. Patrick’s Day hits different🍀
The Chicago River is dyed green for St. Patrick's Day by the Chicago Plumbers union, which uses 2 boats to spray a vegetable-based powder that turns green when it comes into contact with water, so it’s completely safe for the wild life! The union first dyed the river in 1962, using 100 pound
CADE ALEX

CADE ALEX

111 likes

Shop on N. Clark Street, Chicago IL🛍️
Ran over to North Clark street to see what they had! During my high school days I’d go pick up jewelry and little cute purses for the low😂. If you’re looking to start a cute accessory business for yourself or simply like cute throw on items, go scout the block 💕. Some store do require you to have
KENNEDY

KENNEDY

1521 likes

People play beach volleyball on a sandy court in Chicago, with the city skyline, including the John Hancock Center and The Drake Hotel, visible under a partly cloudy sky.
Beach volleyball players are active on a sandy court at dusk, with the illuminated Chicago skyline in the background. A volleyball is in mid-air, showcasing the evening league atmosphere.
Multiple beach volleyball courts are filled with players on a sandy beach, set against a backdrop of Chicago's urban buildings and green trees under an overcast sky.
Beach Volleyball leagues in Chicago 🏐
Have you heard that beach volleyball is the new hottest thing to do in Chicago?! Well if you haven’t yet, now you have! This is your sign to join a volleyball league this summer. Whether you’re playing at North Avenue Beach or Oak Street Beach , you’re sure to have a great time with an incre
sydneyblandford

sydneyblandford

8 likes

Things to do in Chicago at Night ✨
Things to do in Chicago at night 🥂 Z Bar : Grab a drink at a rooftop lounge and enjoy the views of the city. This rooftop lounge offers a cozy fire and blankets for those fresh nights. Millennium Park : Check out the park in the evening off of Michigan Avenue. Walk around “the Bean” and r
RoseGoes-

RoseGoes-

412 likes

A group of seven friends smiling for a photo outdoors, with a building and cloudy sky in the background, likely at North Avenue Beach after a volleyball game.
A panoramic view of the Chicago skyline at dusk, with beach volleyball courts and players in the foreground under a cloudy sky.
People playing beach volleyball on a sandy court, with a net displaying "CHICAGOSOCIAL.COM" and "CHICAGO SPORT & SOCIAL CLUB" logos under a cloudy sky.
Chicago Beach Volleyball League
The best way to make friends in the city and take advantage of Chicago summer is to join a Beach Volleyball League! 🏐🌞 My friends and I signed up with Chicago Sport Social Club and we play every Thursday at North Ave Beach just in time for the prettiest sunset skyline view! Starting mid-to-late May
megan

megan

6 likes

An aerial view of a bustling street festival in Chicago with numerous people, vendor tents, and buildings under a bright sky. The image has a text overlay that reads 'FESTIVALS I'M LOOKING FORWARD TO In Chicago'.
A person holds a tamale in the foreground, with a large, colorful sign for the 'Tacos y Tamales Festival' in the background. The sign features skeleton musicians and vibrant decorations.
A wide shot of a large crowd gathered at an outdoor festival, with the Chicago skyline visible in the distance under a cloudy sky. Tents are also visible among the attendees.
Chicago Festivals I’m looking forward to
Let’s be real: it’s not a true Chicago summer without hitting as many street fests as you can. Here are some I’m looking forward to: 🌮 Tacos y Tamales Festival (July 18–20) in Pilsen. If you are a foodie this one’s for you. Here you can eat, dance, and shop your way through while celebrat
chicago_forfree

chicago_forfree

7 likes

INDIAN VEGETARIAN FOOD NEAR CHICAGO 🇮🇳
Jay Bhavani: 8.1/10 & $60.93 🇮🇳 Food: 8/10 Quality: 8.2/10 Service: 7.9/10 Price: 8.4/10 OVERALL: 8.1/10 1165 Barrington Rd, Hoffman Estates, IL 60169 #jaybhavani #indianfood #indianstreetfood
SERGELATO

SERGELATO

37 likes

2025 Summer Chicago 🌸✨
Summertime in Chicago is unbeatable! There are so many things to do and beautiful sites to see. If you’re looking to visit Chicago in the summer, consider planning your trip around some of these incredible events. Music Festivals: 1. Sueños Music Festival (May 24-25) is a two-day Latin music
outdoorsieabbie

outdoorsieabbie

18 likes

7 Things I'm Doing in Chicago This Summer
Summertime Chi is a whole vibe! From festivals and rooftop views to art, food, and enjoying movies in the park, here are 7 things I'm making time for. Whether you're a local or visiting, here are some of my fav ways to enjoy Chicago. Which one would you try first? #chicagofun #things
Kendra | Travel, Food, & Livin

Kendra | Travel, Food, & Livin

15 likes

A paved path along Oak Street Beach in Chicago, with people walking and jogging. The city skyline, including prominent skyscrapers, is visible across the water under a partly cloudy sky.
A wide view of Oak Street Beach in Chicago, showing numerous people relaxing on the sand and near the water. Tall city buildings line the background under a bright, cloudy sky.
A red patterned picnic blanket and a striped cooler bag are laid out on the sand at Oak Street Beach. In the background, people are seen relaxing on the beach and wading in the water.
🏖️ I caught some tan lines at Oak Street Beach
If you’re ready to get your beach onnnnn, head to Oak Street Beach in Streeterville . Personally, I think this is where you can get the best views of the Chicago skyline with easy access to take a dip in the scorching heat. I recommend saving your money and packing a cooler with water and
chicago_forfree

chicago_forfree

6 likes

📸 Must-Visit Photo Spots in Chicago! 🏙✨
Chicago, the third-largest city in the U.S., is a paradise for photographers! With its Gotham-like skyline, iconic landmarks, and urban charm, this city offers some of the best photo spots you can’t miss. Whether you’re a beginner or a pro, these 9 locations will help you capture stunning shots wit
Lily Brown

Lily Brown

52 likes

How to save money at concerts/festivals ✨
Part 2 of how you can save your money at concerts/festivals so you can enjoy them and have a good time, guilt-FREE! Just because inflation has made concerts super expensive, doesn’t mean we have to pay the full price and break our wallets. What are some of your best tips for saving money at c
Kim Liao

Kim Liao

26 likes

PART TWO OF MY TOP 22 BURGERS IN CHICAGO 🍔
Part 2: my top 22 burgers in Chicago 🍔 Burger Spots: 11-16 11. The Region - Roscoe Village 12. Charlie Martin’s - River North 13. Tacos Sublime - Bridgeport 14. Leavitt Street Inn - Bucktown 15. Community Tavern - Portage Park 16. Small Cheval - West Loop #chicagoburger #bestburgersinch
SERGELATO

SERGELATO

73 likes

Chicago Christmas Tree Lighting Date
Chicago Christmas Tree Lighting on Friday, November 21! 👇 📲SAVE this post Let's go to the 112th  annual City of Chicago Christmas Tree Lighting at Millennium Park! 🗓️November 21, 2025 🎄Pre-show at 5pm | main event at 6pm ⏰Get here early — the pre-show begins at 5pm with a lot of gr
Marisol - Globe Traveler

Marisol - Globe Traveler

27 likes

SUMMER IN THE CITY: CHICAGO EDITION ☀️🌊🚕
I love the city for many reasons, and these are some of my favorite places to go in Chicago! They are definitely worth seeing! - - - ⭐️Overall rating: /10/10 Chicago #chicagotrip #chicagoexplore #chicagolifestyle #navypier #beach #concert #funthingstodo #city #summer
naudia 🤍

naudia 🤍

268 likes

Devon Street Avenue Chicago 🇺🇸
#gettoknowme #chicago #lifeus #pakistaniusa #indianusa #pakistaniusa #indianusa #desipeople #latinpeopleinusa #travel #chicagofood #artist #chicagophotographer #viral #nfl #nba #chicagolife #smallbusiness #sanfrancisco #chicagobulls #atl #downtownchicago #chicagobears #food #instagra
DESI CHICAGO VIBE

DESI CHICAGO VIBE

9 likes

Travel Diary: Chicago
I got to spend a few hours in Chicago today after taking my first sleeper train into the city. It wasn’t nearly as cold as I thought it was going to be, but I’m still glad I planned for the weather! Tomorrow I’ll post some of the pics from the Art Institute, but in the meantime, enjoy Adams Str
Liz

Liz

9 likes

The Best Beaches in Chicago
It's about that time of year - summer in the city! Here are our top 2 beaches in Chicago where you can enjoy the lakefront and cool off in the city this summer. Chicago beaches are the perfect place to spend a day with friends, play volleyball, get some sun, and go for a swim in Lake Michigan.
Baggagegirls

Baggagegirls

619 likes

Ohio Street Beach Chicago Downtown Video |Desi Chi
Ohio Street Beach Chicago Downtown Video |Desi Chicago Vibe
DESI CHICAGO VIBE

DESI CHICAGO VIBE

10 likes

🌊 Beautiful Chicago River: A Must-See Day & Night!
The Chicago River is one of the most breathtaking spots in the city, flowing through Downtown Chicago before meeting Lake Michigan. Whether you’re walking along the Chicago Riverwalk, taking a boat tour, or enjoying skyline views from a rooftop bar, this scenic destination is a must-visit! 📍 Exa
Lily Brown

Lily Brown

4 likes

Chicago trip 2025🫶
This was such a fun little trip with my family I took over thanksgiving! Chicago is amazing and if you get the chance to see it you should! We had so much fun especially my kids at the aquarium! #chicago #Lemon8 #roadtrip #travel2025 #lemon8challenge Shedd Aquarium Art of Pizza on Stat
Rylan matu

Rylan matu

13 likes

✨Chicago’s Hidden Gems: Comedy, and Culture✨
🎉 Hey Friends! Ready for a virtual tour of some of Chicago’s most iconic sights? 🏙️✨Part 3 First up, the Laugh Factory 🎭 – a legendary comedy club that has seen performances from the best in the biz. This stage has echoed with laughter for decades, making it a must-visit for comedy lovers. N
Live4Travel 💎

Live4Travel 💎

23 likes

GREEK STREET FOOD IN CHICAGO 🇬🇷
trying Greek street food at the Old Town Art Fair 🖼️! Two Greeks and a Grill have pop ups this entire summer and worth the try if you can catch them! 🇬🇷 Name: Two Greeks and a Grill in Chicago, Illinois📍 Repeats: Pork Souvlaki, Feta Fries, Ice Cream follow them on instagram for their pop ups!
SERGELATO

SERGELATO

20 likes

The Chicago suburbs have rainbow soup dumplings 🌈
Phat Phat in downtown Schaumburg is known for their rainbow soup dumplings and authentic Indonesian street food! #chicago #chicagosuburbs #chicagofoodie #chicagofood #chicagorecommendations
Hello Chicago

Hello Chicago

24 likes

Japanese Street Food at Japan Fest NYC
Visiting NYC during the summer means you’ll get to attend some of the best international food festivals in the world. In my last post, I shared my experience at Taiwan Fest and in this post, I’d like to spotlight Japan Fes (yes, without the ‘t’)! Hosted several times throughout the year, Japan Fes
sunny

sunny

15 likes

A woman stands on a Chicago sidewalk with buildings and trees in the background. Text overlays announce "MY FAVORITE (NON-TOURISTY) SPOTS IN CHICAGO" and "brat city," introducing a guide to local recommendations.
An outdoor patio at Avli Taverna in Lincoln Park, featuring vibrant purple bougainvillea, string lights, and white pergolas, suggesting a pleasant dining atmosphere for a "Girl Dinner."
A large variety of colorful sushi rolls are neatly arranged in a white box, resembling a pizza box, from Tanuki Sushi & Grill in Lakeview, highlighting the unique "Sushi in a Pizza Box" concept.
How to Be BRAT in Chicago (my fav spots) 🏙️
It’s officially my 3rd year in my favorite city of Chicago so here are a couple of my favorite little spots that don’t get enough attention. 1. The BEST Mediterranean dinner at Avli Taverna There are two locations for Avli (Lincoln Park and River North). Been to both but love the neighborhoo
Millie Britt

Millie Britt

297 likes

Burek Shop Chicago
5910 N Clark street #salad #chicagofoodscene #burekshop #balkanfood #food BUREK SHOP 3M Restaurant
Marija Mara Official

Marija Mara Official

1 like

🧂 🎶 Hands down my favorite music venue in Chicago
I stand by this statement: The Salt Shed is the best music venue in Chicago If you don’t know already, they transformed the old Morton Salt factory into this concert space with indoor and outdoor spaces. I’ve seen Mt. Joy inside (for New Years) and Wilco + Lake Street Dive outside in the su
chicago_forfree

chicago_forfree

6 likes

Chicago Street Photography
#photography #chicagophotoshoot #peopleofchicago #streetphotography #creator
Yamil Muro

Yamil Muro

7 likes

Chicago riverwalk
#ThingsToDo #lemon8challenge From Lake Michigan to Lake Street, this 1.25-mile waterfront promenade blends city energy with calm river charm 🌆🌊 . Wander through six distinct “coves” – the Marina for scenic dining, the Cove for kayaking, the River Theater’s tiered seating, Water Plaza’s fo
Warda

Warda

12 likes

A sunny view of Ohio Street Beach in Chicago, showing people on the sand, volleyball nets, and the city skyline with tall buildings, including the John Hancock Center.
A scenic view of a Chicago beach with people playing volleyball, the calm waters of Lake Michigan, and the city skyline under a partly cloudy sky.
A wide shot of a bustling Chicago beach, possibly Milton Lee Olive Park Beach, with many people swimming and relaxing, backed by the city's high-rise buildings.
Chicago Beaches on Lake Michigan 👇
One of my favorite activities to do in Chicago in the summer season is to enjoy a beach day at on one of the Lake Michigan beaches. 🔐Save for locations 1️⃣ Ohio Street Beach Ohio Street Beach 📍600 N Lake Shore Dr, Chicago, IL 60611 2️⃣ Montrose Beach Montrose Beach 📍4400 N Lake Sh
Marisol - Globe Traveler

Marisol - Globe Traveler

23 likes

Weekend Trip From Chicago: Lake Geneva, WI
If you want to get out of the city this summer, take a weekend trip to Lake Geneva, WI! Though you'll be in a different state, Lake Geneva is just 1.5 hours from Chicago and it's the perfect place for a weekend getaway in nature. The Abbey Resort & Avani Spa Grand Geneva Resort
Baggagegirls

Baggagegirls

10 likes

See more