Labor Day weekend in Chicago is more than just a long holiday — it’s the city’s unofficial farewell to summer.
As the days get shorter and the season winds down, there’s no better time to soak up street festivals, lively parties, food fairs, and all the cultural events the city has to offer.
For me, this weekend is all about balance: splitting time between outdoor adventures with friends and solo moments along the lakefront.
This guide has you covered for every way to celebrate Labor Day weekend, whether you’re planning a full-on adventure or just a few small escapes around the city.
Things to Do Over Labor Day Weekend in Chicago
From major festivals to local favorites, there are plenty of ways to spend the long weekend. Here are some of the best ways to enjoy Chicago this Labor Day.
Celebrate culture and community at a Chicago Street Festival
Here are major festivals and events taking place in Chicago during Labor Day weekend.
- August 28 – 31, 2025: Chicago Jazz Festival
- August 29 – 31, 2025: North Coast Music Festival
- August 29 – 31, 2025: ARC Music Festival
- August 30 – 31, 2025: WingOut Chicago
- August 31, 2025: Bike the Drive
- August 30 – September 1, 2025: African Festival of the Arts
- August 29 – September 1, 2025: Taste of Polonia
Haute Tip: When going with groups, I always try to split meals. You can try more food options this way!
Watch the Labor Day Weekend Fireworks at Navy Pier
Catch the final fireworks show of the summer on Saturday, August 30th, along the Chicago skyline. View from the pier, the Riverwalk, or even from a kayak or boat for a unique perspective.
Hit up a Chicago Beach
Hit up Chicago’s beaches this Labor Day weekend. From the iconic North Avenue and Oak Street to hidden gems like 12th Street and South Shore. Lounge in the sun, rent a paddleboard, or catch skyline views while sipping a cocktail at a beachside bar.
Indulge in Labor Day Bites & Sips
Labor Day is perfect for patios, rooftops, and lakeside dining. Here are some highlights of restaurants offering specials and deals during the long weekend:
- The Grillroom Chophouse & Wine Bar (Downtown) – Pre-Labor Day half-price bottles of wine & daily happy hour 3–6 PM with $10 select wines, $10 Margaritas, $12 Half Dozen Oysters, $12 Meatball, $12 Tuscan Toast.
- Uvae Kitchen & Wine Bar (Andersonville) – Happy hour with $2 oysters & shrimp cocktail, $5 draft bubbles. Patio dining available.
- Aura on the Lake (Edgewater) – Beachfront dining & cocktails from 11 AM daily. Live music Friday 5–8 PM, DJ Sunday 3–7 PM. Dog-friendly & cabanas available.
- Central Park Bar (Avondale) – Labor Day Patio Happy Hour with half-price drinks (excluding shots) on the expansive outdoor space.
- Graystone Tavern (Wrigleyville) – Cubs Pregame & Watch Party with game-day specials ($5–$35) including pizza puffs, nachos, Old Style, Cubbie Bombs, Miller Lite & Coors buckets. TVs + patio games.
- Ina Mae Tavern (Wicker Park) – Labor Day Patio Party featuring $25 plates (boiled shrimp, corn & potatoes) plus a Hurricane or Ina Whiskey Punch. Live music 1–4 PM; $10 boozy frozen cocktails.
- Lottie’s Pub (Wicker Park) – Maker’s Mark BBQ & cornhole. Happy hour 12–5 PM with $4 Mich Ultra, $5 Kona Big Wave, $9 Maker’s Lemonade Mason Jars, $10 Kentucky Mule, $10 BBQ Chicken Tenders, $10 Smokehouse Burgers. Maker’s Mark sampling at 2 PM; Trivia at 7 PM with prizes.
Pick Apples and Grab Other Fall Treats at a U-Pick Farm
Load up on the freshest apples and sweets at a nearby Chicago U-pick farm before everyone else. Load up on the freshest apples and seasonal treats at nearby Chicago U-pick farms before the crowds arrive. Try farms in Illinois and Indiana that are less than an hour away, like Kuipers, County Line Orchard, All Seasons Orchard.
Play & Connect at Black Girl Field Day
Celebrate joy, movement, and sisterhood at this afternoon festival designed for and by Black women, featuring pickle ball lessons, field games, wellness juice, outdoor movies, and a cozy lounge to unwind. The event takes over Fulton Market on Saturday, August 30, from 3 to 7 p.m.
Take a Dip at Rooftop and Public Pools
Cool off before the season ends at Chicago’s best pools. Lounge and swim at rooftop favorites like Soho House, Solana at The Robey, and Cabra at the Hoxton Hotel, or take a refreshing dip at local public pools.
Labor Day Parties
Turn up your Labor Day weekend with live performances, dancing, and good times all day and night.
- Holiday Weekend Kickoff FRIDAY Happy Hour/Day Party at Chemistry
- Howl at the Moon Chicago’s Pop Weekend
- Culture Shock Golf Weekend
- Ratio’s Labor Day Event
- Views & Vibes: Labor Day Weekend
- R&B Mimosa Fest
- Cream And Orange Dreamsicle Virgo Bash
- Sincerely, Summer
- Sundays Are For Lovers
- Pretty Things at Cerise Rooftop
- For the Love of R&B and Reggae at The Reading Room
- Sounds of Summer
Experience an R&B Weekend at Country Club Hills Amphitheater
Get ready for back-to-back nights of R&B legends at the Country Club Hills Amphitheater. On Saturday, August 30, Dru Hill takes the stage with Ginuwine’s signature vocals. Then, close out the weekend on Sunday, August 31, with The Whispers delivering timeless classics alongside Shalamar.
Catch a Chicago Baseball Game
Soak up the last of summer baseball in both sides of town during Labor Day Weekend. The Chicago White Sox face the New York Yankees all weekend long at Guaranteed Rate Field. Meanwhile, the Chicago Cubs take on the Atlanta Braves at Wrigley Field to close out the long holiday weekend on Monday, September 1.
Dance All Night at Chicago Loves Bachata Day
Move nonstop across three dance rooms with four DJs, workshops, and music spanning sensual bachata to salsa and mambo, plus special performances from international guests Christian y Gabriella. The celebration kicks off at Dance Center Chicago, 3868 N. Lincoln Ave., on Saturday, August 30, beginning at noon and continuing through 3 a.m. Sunday, August 31.
Meet Your Match at Pup Social’s Adopt & Shop
Sip, shop, and play with adoptable pups while browsing local pet brands, enjoying drink tastings, and entering raffles at Chicago’s first off-leash bar and park. Stop by Pup Social, 2200 N Ashland Ave, on Saturday, August 30, from 12 to 6 p.m.
Just as Memorial Day marks the start of summer, Labor Day weekend is the finale — a time to celebrate, reflect, and make the most of the season’s last hurrah. From music and art to food and culture, Chicago offers an endless array of ways to spend the holiday weekend.
What are your Labor Day plans in Chicago? Share your favorite spots or experiences in the comments below — I’d love to hear how you’re celebrating!
