Food & Drink in Chicago
Tastings, classes, pop-ups, omakase you have to book a month out.
Big Irish Jay at Riddles Comedy Club
Big Irish Jay Hollingsworth headlines Riddles Comedy Club for a full weekend of stand-up. $25 cash cover, two-drink minimum.
Noche Caribena: Caribbean Arts Night
Caribbean and Puerto Rican cultural performance night. Lechon, empanadas, and street food. Rhythmic, immersive, welcoming. Performance 6PM Saturday.
Taste of Orland Park 2026
Signature tasting booths from the southwest suburbs' top restaurants. Massive, festive, welcoming. Aug 7-9 afternoon to late evening.
Ten Cat Swing Summer Series Finale at Banging Gavel
Swing and acoustic jazz night at Banging Gavel Brews. Sophisticated, intimate, soulful. Upscale brewpub menu and charcuterie. 6:30-9:30PM Thursday.
Cruising The Waves Yacht Party
You're floating down the Chicago River and out onto Lake Michigan while a top-shelf open bar keeps the good times flowing—and then Navy Pier's fireworks explode across the skyline right in front of you. This inaugural yacht experience pairs live DJs, dinner, and unobstructed water views with the kind of vantage point landlubbers will never have.
Lollapalooza 2026
Four days of the biggest names in music take over Grant Park for Lollapalooza 2026. 170+ bands across 8 stages, street food, after-shows at venues acr
90s House Music Vinyl Tribute
Free outdoor riverside DJ set at Ping Tom Park pagoda in Chinatown. 90s house music on vinyl with scenic river views. 6:30-9:30 PM.
Orland Park Summer Brewfest and Food Truck Rally
Craft beer fest with 15+ food trucks, microbrewery sampling pavilions, and live music at the Civic Center. 4-10PM Saturday.
Silver Room Block Party
The Silver Room Block Party takes over Salt Shed's sprawling Goose Island grounds with 40 performances across indoor and outdoor stages—expect everything from emerging local acts to established names, all while 20 Chicago vendors set up shop around you. The fairground vibe means you've got room to breathe, skip between stages, and actually grab food without missing the headliners.
Taste of Chicago Pop-Up — Pullman
Free local culinary showcase at Pullman Park Commons. Dozens of South Side food trucks and neighborhood restaurants. Noon-8 PM.
Bucktown Garden Walk and Block Party
Community arts, live music, craft food vendors, honey tastings, and beer gardens centered at Churchill Park. Lively, welcoming, open-air. Mid-summer w
Pitchfork Music Festival 2026
Three days of indie, hip-hop, and electronic music curated by Pitchfork in Union Park. Smaller than Lolla, weirder than Riot Fest, and exactly the vib
Splou Yorkcity Live at Riddles
Splou Yorkcity takes the Riddles stage for a Sunday afternoon set. 5 PM showtime. $25 cash cover.
90s R&B Sing-A-Long Interactive Lounge
90s R&B sing-along with candle crafting in Logan Square. BYOB-friendly, nostalgic, interactive.
East Side Eats Festival
Community cookout and live music at St. Simeon Serbian Orthodox grounds on the East Side. Traditional neighborhood comfort food, grilled dishes, and f
Chosen Few Picnic & House Music Festival
Chicago's legendary soulful house music celebration at Jackson Park. The original house music picnic — massive grounds, soul food trucks, and dancing
Blue Violet Late-Night Social
High-energy Latin and Afrobeat social at Hubbard Inn in River North. Weekly recurring Friday midnight track with elite cocktail mixology and VIP table
Square Roots Craft Brew & Music Festival
Live indie music and craft brewery festival in Lincoln Square. Over 40 regional craft beer taps, local food vendors, and three days of music. Runs thr
Taste of Chicago 2026
Chicago's legendary food festival returns to Grant Park with five days of the city's best restaurants, food trucks, and pop-ups. Free admission to the
4th on 53rd Parade & Festival
Free Fourth of July parade and cultural festival in downtown Hyde Park. Morning parade through late afternoon festival with local food stations.
Ashley Walls Country-Pop Fest and Fireworks at Harmony Square
Holiday country concert with fireworks at Harmony Square. Festive, loud, all-American. Food trucks and beverage tents. 7:30PM Friday.
International Festival of Life — Reggae & World Music
World, Afrobeat, and reggae concerts at Union Park running the entire Fourth of July weekend. Authentic Jamaican jerk pits, West African cuisine, and
Thursday Night Beats & Bites — South Loop
Free weekly rooftop beats, food trucks, and lawn games at Roosevelt Collection in the South Loop. Every Thursday in July.
Argyle Night Market
Asian night market on Argyle Street in Uptown's Little Vietnam. Weekly Thursday evening series with live street cooking, dim sum, Vietnamese BBQ, and
Midweek Jazzin' at the Shedd
Premium lakefront jazz cocktail series at the Shedd Aquarium. Wednesday after-hours with live jazz, upscale drinks, and aquatic ambiance. Recurring we
Maxwell Street Market Summer Series
Free historic open-air flea and food market on South Halsted. Famous Mexican street food stalls, hand-pressed tacos, and live DJs. Every Sunday.
Orland Park 80s Rock Night at Centennial Park
Free outdoor 80s tribute band concert at Centennial Park Amphitheater. Casual, lively, open-air. Local food trucks, beer booths. 7PM Saturday.
Annual Black LGBTQ+ Beach Day
Massive inclusive beach celebration at 63rd Street Beach. High-energy, sun-drenched, celebratory. Beach-side food trucks and vendors. Starts 2PM Satur
Chicago Michelada Fest
Mexican heritage food and cocktail festival at Union Park. Authentic street vendors, competitive michelada bars, tacos. Festive, high-energy, rowdy. G
Julie Doiron, Carson McHone
Julie Doiron's whisper-soft vocals paired with Carson McHone's understated Americana make for an unexpectedly perfect pairing—expect hushed, introspective songwriting that'll make you forget about your phone for two hours. You'll catch them at Empty Bottle in Ukrainian Village, the kind of room where every acoustic guitar line hits different.
Retro 80s & 90s Summer Jam
Free outdoor DJ dance set at Navy Pier Wave Wall Stage. 80s and 90s hits on the waterfront. 5-8:30 PM.
Juneteenth Kickoff: Black Yacht Weekend
Elevated Juneteenth celebration with Afrobeats, curated minority food trucks, and premium bottle service. Energetic, rhythmic, soulful. 8PM Friday.
90s Flashback Open-Air Dance Party
Free retro 90s dance party next to Wrigley Field at Gallagher Way. Themed cocktails, outdoor dancing, and nostalgia. 6-9 PM.
Juneteenth 2026: Black Joy and Wellness
Cookout-style Juneteenth celebration at Promontory Point with lakefront views. Traditional cookout food, local catering, healing workshops. Welcoming,
Piqniq at Taste of Randolph
Massive street culinary celebration in the West Loop. The famous restaurant row comes alive with live music stages. Runs all weekend.
Juneteenth Festival Chicago 2026
Celebrating Black culture, history, and community with live music, art, food vendors, and family activities across multiple stages. Chicago largest Ju
Voltage! Speakeasy: An Immersive Cabaret Thriller
Immersive dance and theater inside a simulated 1920s marathon dance hall. Premium cocktails, spooky cabaret.
Black Yacht Weekend Main Harbor Gathering
Elite Black culture recreation event at 31st Street Harbor. Catered yacht menus, open-air harbor food tents, and tropical drinks. Luxurious, scenic, c
Gottlieb, Palace Guard, Lavender
At Reggies Music Joint.
NAIA — New Mediterranean on the Riverwalk
Pan-Mediterranean restaurant with 150 feet of river frontage, 500-person capacity. From the team behind Siena Tavern. Greek-Italian-Spanish-Levantine
Anti-Everything, Gray Ghost, Kat Baptista
At Reggies Bananna's Shack .
Artikal Sound System, Josh Heinrichs
At Reggies Rock Club.
Fallen Condition, Alenia, Rose of Demise, Wyvern
At Reggies Music Joint.
Son Little
With special opening act Tonina. All sales are final, no refunds/exchanges permitted, but tickets may be transferred through your TM Account. Garcia's is fully ADA compliant featuring wheelchair lifts and ramps between the various levels of the venue, assisted listening devices upon request, and allows official service animals. Premium Table seating is located closest to the stage offering the most intimate music experience for guests and includes table service. Reserved Table seating is located on our main floor, behind the Premium section, and also includes table service. Both Premium and Reserved table seating is cabaret style which means you may be sitting with other fans. Private Booths are available and depending on the booth seats 1 to 4, 5, or 6 guests. General Admission/Standing Room is located around the sides of the room on an elevated level for quality viewing and easy bar access. 21 & Over Show. Must be 21+ with a valid ID to purchase alcohol. At Garcia's Chicago.
Juneteenth Community Celebration — Chatham
Free cultural festival with live jazz, DJ sets, and 20+ minority-owned brand food samples in Chatham. Noon to 4 PM.
Worm, Dusk, Fer De Lance
At Reggies Rock Club.
Wraith, Witchtrap, the Black Moriah, Burial Oath
At Reggies Music Joint.
Naper Lights Summer Concert Series
Free outdoor concerts on the Naperville Riverwalk. Regional tribute bands and acoustic duos. Festive, welcoming, open-air. Weekend dates June through
Whiskey Fest Chicago 2026
Sample premium whiskeys, bourbons, and ryes from top distilleries. Live music, food pairings, expert-led tastings. 21+ only.
90s Night at the Zoo
Brookfield Zoo after dark with 90s music, themed cocktails, food stations, and animal encounters. Dress in your best 90s gear. 21+ event.
Food & Drink venues
14 Parish Restaurant & Rhum Bar
8000 Miles
Acadia
Adalina Italian
Adobe Gilas
Adobo Grill
Ain't She Sweet Cafe
Akahoshi Ramen
Alcove Evanston
All Together Now
All Well
Al's #1 Italian Beef
Al's #1 Italian Beef (Taylor Street)
ALTO Steakhouse at Wind Creek
Amaru
Amerikas
Andy's Jazz Club
Anteprima
A.P. Deli
Arbella
Arena Lanes
Artango Bar & Steakhouse
Asador Bastian
