Memorial Day Weekend in Chicago is just a few short weeks away, and now is the perfect time to shore up some plans for your day off!
Whether you’re looking for relaxed bar hangs, high-energy boat and beach parties, or just a nice outdoor patio, there’s something for everybody to do in the Windy City.
Here’s your guide to all the can’t-miss Memorial Day Weekend events in Chicago for 2026.
All White Attire Cruise Aboard the Spirit of Chicago Yacht
Hop aboard the Spirit of Chicago super yacht for the ultimate Memorial Day Weekend cruise party!
With 4 decks, 2 DJs, and 2 floors of music, this yacht bash promises a high-energy celebration and the perfect start to summer.
Tickets start at just $23.79, click here to grab yours.
Memorial Day Patio Party and FREE Bingo at Central Park Bar
Central Park Bar is here to help you enjoy your day off on Monday, May 25, with a full evening of festivities.
The party starts at 4 p.m. with a half-price happy hour, followed by free bingo from 7 to 10 p.m.
Guests can sip all their favorite cocktails and cans, enjoy the expansive outdoor patio, and relax around fire pits and porch swings.
Drinks deals and Doodle Meetup at Cody’s Public House
Cody’s Public House in Lakeview is your one-stop spot for all the Memorial Day Weekend fun.
On Sunday, May 24, Cody’s will host a tail-wagging puppy social meetup. Dog owners are welcomed to bring their four-legged friend along from 1 – 4 p.m.
Guests will specials like $5 Kona Big Wave Golden Ale. Doggies will enjoy complimentary pup cups.
On Monday, May 25, the good times keep rolling with a special happy hour from 12 – 3 p.m. featuring $5 Mimosas, $10 Aperol Spritz and $30 Surfside Buckets.
Chicago Memorial Day Weekend Bar Crawl
The ultimate Memorial Day bar crawl in Chicago is going down in West Loop on Saturday, May 23.
Check-in runs from 4 – 7 p.m. at PB&J: Pizza, Beer, and Jukebox.
Tickets include free entry to all participating West Loop bars, exclusive drink specials, professional photo ops, and access to a fun-filled after party.
Memorial Day Happy Hour and Patio Hang at Tune-Up
Tune-Up is one of the latest additions to the Chicago bar scene, and this Memorial Day is your chance to see what the hype is all about!
The auto-shop-turned-cocktail lounge is celebrating with a half-price happy hour on Monday, May 25, from 4 – 7 p.m.
Stick around all night and sip creative cocktails on the lively outdoor patio or hang in the spacious and artfully designed interior.
Memorial Day Weekend Cubs Specials at Graystone Tavern
The Chicago Cubs are facing off against the Houston Astros this Memorial Day Weekend. And the Graystone Tavern in Wrigleyville is your official home base!
Just a block from Wrigley Field, the Graystone is serving up drink deals and delicious pre-game eats all weekend long.
Highlights include $5 corn dogs, $5 Old Style tall boys, $6 Cubbie Bombs, $8 cold brew Irish coffee, $10 Chicago Handshakes, and $30 Surfside buckets.