30 Amazing Things To Do On Labor Day Weekend In Chicago

Colby Smith • September 2, 2020

Make your three-day weekend count!

Summer’s on the out and fall’s almost here. Seize the warm rays of sunshine while you can before it gets to cold with these 30 amazing things to do for Labor Day Weekend in Chicago!

1. Experience Gorgeous Outdoor Candlelight Concerts

You can still experience an absolutely magical (and safe) summer here in Chicago, and part of that is thanks to the amazing outdoor spaces the city has to offer. Luckily, Fever Originals is bringing its wildly popular Candlelight concert series to open-air venues for the season, from stunning rooftops and terraces to enchanting secret gardens.

2. Eat The Most Expensive PB&J In The World

PB&J is West Loop’s newest hangout. The bar/restaurant — shorthand for pizza, beer, and jukebox — is complete with a jukebox, pool table, craft cocktails, and an enticing menu. Most notable patrons will find, is their Golden Goose a not-so-simple peanut butter and jelly sandwich that prices at $350. How on earth can a pb&j cost hundreds of dollars, you ask. The sandwich, which requires a day-in-advance order contains the following ingredients the world’s most expensive jelly (Maison Dutriez’s Red Currant Jam) that is hand seeded using goose quills, as well as — amongst other things — toasted edible gold leaf bread.

3. Bob Down The River In An Electric Donut Boat

Seize the last stages of summer by setting sail on the Chicago River with the latest in Chicago Electric Boats’ new donut boat. The ring-shaped water cruiser allows for a group up to 6 passengers, all seated around a circular table in the middle for beverages, snacks, and other provisions necessary for the sea-bound voyage. The donut cruisers leave from the Rockwell on the River port. Prices begin at $165 for an hour cruise on the river with options to go up to 4 hours.

4. Watch The Kentucky Derby

Make your way to Lincoln Park’s barbeque-centric sports bar this Labor Day Weekend. There will be plenty of indoor and outdoor space for laid-back and safe viewing! The Derby action will be broadcast indoors and on the convertible patio, which is decked out with a pool table, giant Connect Four, giant Jenga and more. You’ll get to enjoy the Kentucky Derby action with a White Claw Hard Seltzer in one hand and a yummy appetizer in the other!

5. Get Back Into The Ballpark Spirit

Baseball is officially back. While the stands are a no-go for the time being, you can still get the ballpark experience with this grand-slam Cubs Home Game Package deal that includes bottomless drinks and unlimited cheese and pepperoni pizza in the heart of Wrigleyville at HVAC!

6. Rock Out At A Drive-In Concert

Lakeshore Drive-In is reviving Chicago’s live experience industry. They have come together to create a socially responsible event series that puts gigs in the hands of industry professionals and creates space for Chicagoans to get back to enjoying live entertainment safely. You’ll discover here that Chicago’s music, arts, and culture are unlike any other. The Lakeshore Drive-In will combine local talent with national leaders to showcase truly unique experiences!

7. Fasten Your Seatbelt For Action-Packed Entertainment

Fever is teaming up with CHI Together to fuel your evenings with non-stop fun! From Wednesdays through Sundays, Soldier Field is bringing you clutch entertainment. Moviegaters are invited to post up and popcorn for the evening screenings at 8:30 pm — but trust us, you’ll want to come early for these previews! Gates open at 7:00 pm, where in attendants can enjoy live music from local DJs, comedians, games, prizes, and more!

8. Vibe Out In The Lanes

Bowling may bring back nostalgic memories of elementary school birthday parties, but that doesn’t mean it isn’t just as fun for adults—it just depends on the setting! And Bowlero and Bowlmor Lanes are definitely made for grown-ups. Combining the best of bowling, dining and nightlife, it’s the perfect spot for your next night out. Lanes are backlit with bright neon colors for the ultimate retro vibes, along with interactive arcade games and throwback hits playing at all times.

9. Strengthen Your Core And Your Mind With An Evening Of Rooftop Yoga And Meditation

After the holiday weekend, you might need to a day to re-energize ahead of the week. Mindful Mondays at Ace Hotel Rooftop will provide a pleasant opportunity for you to center your focus through a yoga flow and meditation session. Attendants will also receive a wellness kit as a takeaway from the experience. Fever will be hosting Mindful Mondays throughout August until October, come enjoy an open-air yoga experience at this West Loop rooftop.

10-11. Pop In To A Pop-Up

Pop-culture pop ups are in season. While you might have missed the short-lived Saved By The Bell pop-up, you still have time to catch a couple more. Grab the burger of the day at Replay’s Bob’s Burgers Pop Up, where the Belcher’s are cooking up a Grand Re- Re- Opening with a slew of excellent margaritas and not-human-meat burgers!

Or, if 2020 hasn’t shrunken your appetite for nostalgia. You can also beam into the Honey, I Shrunk The Kids pop-up at The Sixth Bar for a novelty cocktail list with food items to boot — all inspired by beloved children’s trilogy.

12. Chow Down On Bottomless BBQ

Chef Josh Scheid will be manning the grill on the patio at Old Grounds Social, cooking a Labor Day Weekend feast! Come eat, drink, and enjoy social distanced fun with your loved ones. This tantalizing all you can eat BBQ will keep you coming back for more and you get to wash down the grub with a complimentary well drink, beer or White Claw Hard Seltzer! There’s no better way to celebrate Labor Day Weekend!

13. Slay The Competition At Old Grounds Social’s Drag Bingo Night

Have the past few months been a little less-than-dazzling? We feel that. To put a little sparkle back into our lives, the queens over at Old Grounds Social are hosting Drag Bingo on Thursdays with dancers, prizes, drink deals including $20 domestic beer buckets, $25 champagne buckets, and shot specials throughout the night for a fabulously fun time!

14. Get Back To Brunching

Hubbard Inn’s weekend bottomless brunch deal is heaven on, well, in Chicago! This ticket gets you two hours of free-flowing mimosas and sangria and one brunch entree. Hubbard is a patio and open-air restaurant located in the center of the action in the heart of River North.

15-16. Picnic With A Twist

You might of had a picnic before — the classic basket packed with sandwiches and potato salad, red checkered cloth, and maybe a bottle of wine. But you can step up your picnic game with a Self-Guided Foodie Adventure for friends. Solve personally-curated clues and riddles sent to your smartphone that’ll take you on a journey to collect your special gourmet picnic food bit by bit. Each clue you solve will lead you closer to your next picnic food pickup and even closer to your final stunning secret picnic spot!

Or, for something a little more romantic. You can opt to embark on the picnic foodie adventure with a Mystery Date. This experience for two is all-inclusive, all you need to do is select the date and everything will be planned for you. You can expect a 3-4 hour picnic experience where you discover new parts of Chicago while supporting small business with this stress-free date!

17-19. Get Dinner With A Waterfront View

We may be miles away from the ocean but that doesn’t mean we can still enjoy some top-notch waterfront views. From bohemian hideouts by the river to beachy hangouts by the lake, these 9 stunning waterfront spots are all currently open for outdoor dining with new safety measures in place.

20. Hit Up The Largest Outdoor Adventure Park In America

Feel like you need a little taste of the action this summer? Take a short drive down to Lemont, where The Forge: Lemont Quarries just opened. From mountain biking and climbing walls to yoga to a tactical laser tag course, the 300-acre park is packed with everything you can think of with something for everyone!

21-22. Stroll Through A Garden

With autumn on the horizon, and winter to swiftly follow, it’s only a matter of time before the blossoming gardens around Chicago begin to lose their color. Discover some of the Windy City’s most spectacular secret gardens to stop and smell the roses!

The Morton Arboretum, has opened up their one-acre maze garden to sweeten the last stages of summer.

23-25. Grab A Donut

Donuts are a craving that you just can’t shake. Whether it’s your first thought in the morning or your last bright idea of the night, the donut-craving is real. Fulfill your deepest donut desires in the Windy City with our list of donut hole-in-the-walls in Chicago!

26. Hit Up Navy Pier Before They Close For The Year

Photo credit: @Jonathan J. Castellon via Unsplash

Due to a low visitor attendance caused by the conditions surrounding the pandemic, the city destination decided that it will cease all operations for the remainder of the year following Labor Day Weekend. On Friday, the Pier will host an Artisan Market on Friday, September 4, that will showcase local artists from across the city.

27-29. Dine Out On Beautiful Outdoor Patios

patios Chicago — Photo: @beatnikontheriver

Summer’s here and that means it’s time for some top-notch al-fresco dining! From riverside oasis to multi-tiered patios, there’s tons of awesome options. These 10 amazing places are all currently open for outdoor dining with new safety measures in place.

30. Embark On A Quest For Giant Trolls At The Morton Arboretum

The Morton Arboretum is home to a cornucopia of gardens, collections, and natural exhibits for Chicagoans to explore. Additionally, the Arboretum is also home to 6 gigantic trolls lingering in hide-aways to protect its wooden areas. The legend of The Arboretum goes that the 6 trolls first appeared in its wooded areas in 2018. Designed by Danish artist, Thomas Dambo, using reclaimed wood, the trolls — ranging from 15 – 30-feet high, and one 60-foot long —have remained on the grounds in protection of its trees. [Featured image: Jonathan J. Castellon via Unsplash]