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A paradise for food and wine—come to Chicago and enjoy the charming summer.

Published: 2026-09-24 👁 100 views
Last updated 2026-09-24 — A paradise for food and wine—come to Chicago and enjoy the charming summer. Chicago’s summer is truly one-of-a-kind, as the city buzzes with life and the excitement level is at an all-time high. Locals and visitors alike flock outdoors to join the lively street scenes and a wide variety of festive celebrations. One highlight you simply can’t miss ...
A paradise for food and wine—come to Chicago and enjoy the charming summer.

      Chicago’s summer is truly one-of-a-kind, as the city buzzes with life and the excitement level is at an all-time high. Locals and visitors alike flock outdoors to join the lively street scenes and a wide variety of festive celebrations. One highlight you simply can’t miss is the diverse range of food festivals, both big and small, that attract food lovers from around the globe. Whether you’re a die-hard fan of American burgers or a loyal devotee of local wines, we’ve handpicked some of Chicago’s top street festivals that promise to be a foodie’s dream this summer!

2019 Chicago Friday Night Flights (Chicago Friday Night Flights 2019)
      The annual Chicago Friday Night Flights will take place on May 31st at Gallagher Way, right next to the iconic Wrigley Field. The opening event will feature 32 craft beer exhibitors, while well-known local restaurants Big Star and Smoke Daddy will serve up delicious bites to pair with your brews. Following the launch, the festival will continue with a series of neighborhood-focused tastings across four different corners of the city—don’t miss out if you love beer.
For specific schedules and details, please visit: www.choosechicago.com/fridaynightflights
   
Dates: May 31 – September 13, 2019
 Ticket Prices: Pre-sale tasting passport $20 / gate price $25 (includes 10 tasting tickets of 3 oz alcoholic beverages each); plus, there will be a variety of live music performances and gourmet food available for purchase on-site.

2019 Taste of Randolph Street (Taste of Randolph Street 2019)
      As one of Chicago’s best sidewalk food festivals, the Taste of Randolph Street will be held in the bustling West Loop district—a prime showcase opportunity for Chicago’s most renowned restaurants. Showcasing a rich mix of dining options across six of the city’s most famous culinary blocks, the 2019 Taste of Randolph Street will feature over 16 top-tier restaurants known for their exceptional menus and irresistible unique flavors. Additionally, live stage performances by some of the hottest and most promising bands and singers in the U.S. will keep you entertained all day long. While enjoying the food, engage both your taste buds and senses with a full-on audiovisual experience—you won’t want to miss it. This year’s performers include indie rock band Real Estate, R&B singer Anderson East, electronic pop duo Holy Ghost!, Vulfpeck guitarist Cory Wong, and NYC rock artist Cults.

Location: 900 W Randolph Street, Chicago
Dates: June 14–16, 2019
Ticket Price: Suggested donation of $10 per person

2019 Chicago Food Truck Fest (Chicago Food Truck Fest 2019)
      The Chicago Food Truck Fest is one of the top mobile food festivals in the U.S., drawing long lines of foodies every year. This year, the festival will take place in Chicago’s South Loop, featuring 40-50 food vendors offering delicious creations by top chefs. They’ll also have sangria and a selection of local wines to complement your meal—what a treat for your taste buds this year. And of course, don’t forget to enjoy the great live music performances and fun games that will delight both your stomach and your soul.

Location: 1600-1800 S. Wabash Ave, Chicago
Dates: June 22–23, 2019
Time: Noon to 10 PM
Ticket Price: General free admission or VIP ticket for $10
For more information about the event, please visit: http://www.chicagofoodtruckfestival.com/

2019 Taste of Chicago (Taste of Chicago 2019)
      Launched on July 4, 1980, the Taste of Chicago is the world’s largest free outdoor food festival. This year, 82 vendors will be participating, each showcasing their signature dishes and drinks. The renowned Taste of Chicago is the city’s hottest summer event, celebrating the city’s diverse culinary culture. Alongside amazing food, the festival also draws many families with live music performances and special family-friendly entertainment.

Dates: July 10–14, 2019
Time: Wednesday to Friday, 11 AM to 9 PM; Weekends, 10 AM to 9 PM
Location: Grant Park
Price: Free admission

 
2019 WINDY CITY SMOKEOUT (WINDY CITY SMOKEOUT 2019)
      Get ready—barbecue, craft beer, and country music come together perfectly at the annual Windy City Smokeout in Chicago. This year’s lineup features big names like Old Dominion, Chris Young, and Cole Swindell, all award-winning or rising stars in country music, along with warm-up acts including Lanco, Ashley McBryde, Eli Young Band, Jordan Davis, Jessie James Decker, and Jimmie Allen.
        The 2019 Windy City Smokeout will take place in a brand-new location—the parking lot of the United Center in Chicago—and will host over 20 world-famous barbecue restaurants. Get ready for finger-licking-good eats, with confirmed participants including Chicago’s Bub City, Nashville’s Martin’s Bar-B-Que and Peg Leg Porker, and Texas’ Salt Lick BBQ. The vendors are gearing up to deliver an unforgettable culinary and musical experience. How can you resist mouthwatering pork ribs from top ranches paired with a crisp, ice-cold beer? And don’t worry about limited beer choices—there will be plenty of national and local craft beers to go around.

Date: July 12–14, 2019
Location: Parking lot of the United Center in Chicago
Price: Tickets start at $40

2019 Chicago Gourmet
       Don’t forget to mark this special date on your calendar yet? Get ready to indulge in a mouthwatering extravaganza of top-tier wines and gourmet dishes.
       From September 27 to 29 over the entire weekend, a grand celebration of culinary talent will unfold in Millennium Park in downtown Chicago, as well as at the Harris Theater and the Chicago Athletic Association Hotel. Renowned chefs from across the U.S. will gather to deliver spectacular cooking demonstrations. In addition, there will be wine tastings featuring premium vintages and cocktail workshops for you to savor. With an abundance of exquisitely prepared food and drink, all set under the star-studded ambiance of the Chicago Gourmet, it’s an event you won’t want to miss.
       This year’s event brings together over 250 of Chicago’s most prestigious restaurants, chefs, wineries, and wine merchants. Wine paired with fine cuisine—expect delectable drinks and high-end, refined dishes that are sure to leave every guest enchanted, amazed, and with a soaring happiness index. So if you’re planning to go, be sure to save some room for more treats.
For more details and the full schedule of the 2019 Chicago Gourmet, visit: https://www.chicagogourmet.org/

Date: September 27–29, 2019
Location: Main venue at Millennium Park, along with additional satellite events at other venues
Price: Tickets start at $195







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