Chicago’s Labor Day celebrations have summer going out on a high note


Ready for the holiday? Chicago’s Labor Day Celebrations will make you wish that summer fun would last a couple more weekends.

Labor Day celebrations might mark the unofficial end of summer, but that doesn’t mean the parties are low-key. Chicago is ready to make this holiday weekend a festive one. From lakefront hot spots to rooftop parties, these Labor Day specials will make you wish that fall would never come.

Here are some of FoodSided’s suggestions for Labor Day celebrations in Chicago.


Located on the 24th floor of the Hyatt Centric The Loop Chicago, the breathtaking views are matched with stunning cocktails and delicious bites. On Sunday, September 2, groups of six or more will be treated to complimentary champagne toasts. Let’s all raise a glass to those great summer moments.

ROOF on theWit

If you didn’t get to jet off for the holiday weekend, feel like you did at ROOF on theWit. When you step into this paradise, it appears as if you’ve jetted off to Tahiti. Drinks, bites and music. On September 1, DJ Vinny Ventiera (The Bachelorette and Bachelor in Paradise) will be setting the mood with music. Who needs a 10 hour plane ride when you can have the French Polynesian Island in Chicago?

Labor Day celebrations, photo provided by Castaways

End-of-Season at Castaways

Enjoy one last day on the lakefront at Castaways, the North Avenue Beach hotspot. Throughout the weekend, there will be live entertainment. Plus, find your inner “om” with Yoga on the Boat on Sunday. In addition to yoga, guests can enjoy mimosas, fresh juice and refreshment.

Commonwealth Tavern in Roscoe Village

For some people, the holiday weekend marks the kick-off of college football. Commonwealth Tavern will host a Notre Dame Season opener. There will be both food and drink specials to mark the occasion. Also, on Sunday, Commonwealth Tavern will host a brunch. From a Bloody Mary Bar to Brunch Schnitzel, the menu is quite enticing.

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Easy Bar

Why not sip to the end of summer with a special cocktail called “The Duffy.” This cocktails mixes El Tesoro Anejo Tequila with bitters, orange swath and a luxardo cherry. Who wouldn’t want to sip on this delightful cocktail? Plus, your four legged family members are welcome on the dog-friendly patio. Here’s to the end of summer.


What do you do on a day off? Enjoy a cocktail, of course. Estelle’s will be serving a specialy “Hoffa’s Manhattan” for just $8 on Labor Day. In addition to other drink specials, burgers will be half-price.

Hubbard Inn

Why not enjoy some delicious seafood for the holiday weekend. Grab some friends and enjoy a Seafood Platter that has a bounty of seafood. Pair that platter with a build-your-own-sangria pitcher and it makes for a delicious event.

Labor Day Celebration, photo provided by Hubbard Inn

Also, both Saturday and Sunday will feature a Bottomless Brunch. For just $20, with the purchase of a plate, guests can enjoy bottomless mimosas and bloody marys. Remember it’s a three-day weekend, so it’s time to celebrate.

Joy District and Parlay at Joy District

On Labor Day, enjoy a rooftop party at Joy District. Sip on cocktails like Lost Cause, Cucumber Cooler and Nextflix and Chile. Later in the afternoon, Parlay will be serving Double Stack Burger Sliders, pizza and the Parlay Burger. You might want to forget about going to work on Monday.

The Miller Lite Beer Garden at Navy Pier

Navy Pier is a great spot to celebrate the holiday weekend. Head to the Miller Lite Beer Garden for various specials. Plus, the location will be hosting “Live on the Lake!” music. Don’t forget to stay for fireworks on Saturday.

Fogo de Chão

Have a craving for a lot of meat? Kids will enjoy a free dinner, lunch or brunch at Fogo de Chão on Labor Day. With the purchase of a full-priced meal, kids eat free.

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Do you have Labor Day celebrations on the calendar? Share how you are celebrating the holiday by tagging #FoodSided with all your delicious bites and sips.