From rooftop brunches and brewery festivals to baseball, waterfront dining, outdoor getaways, and family-friendly events, Memorial Day Weekend in Chicago marks the unofficial start of summer with no shortage of ways to celebrate. Whether you are looking for a long weekend staycation, patio dining, fireworks, live entertainment, or a quick escape from the city, these Chicago-area restaurants, hotels, festivals, and experiences are offering special programming throughout the holiday weekend.
The Bellevue

Photo Credit: The Bellevue
Spend Memorial Day Weekend dining al fresco at The Bellevue in Chicago’s Gold Coast. The neighborhood favorite will feature patio dining throughout the holiday weekend, along with its popular brunch service and elevated American fare. Guests can enjoy cocktails including the Banana Espresso Martini alongside brunch favorites and steak-and-eggs offerings from the restaurant’s expansive 100-seat patio near the lakefront.
Location: 1031 N Rush St, Chicago, IL 60611
Cindy’s Rooftop

Photo Credit: Cindy’s Rooftop
Celebrate Memorial Day with skyline views and brunch at Cindy’s Rooftop inside the Chicago Athletic Association Hotel. On Memorial Day Monday, the iconic rooftop restaurant will serve its brunch menu throughout the day in place of lunch service, featuring pancakes, egg dishes, pastries, brunch cocktails, and seasonal spritzes. Guests can also enjoy sweeping views of Millennium Park and Lake Michigan, along with the return of Navy Pier’s summer fireworks season.
Location: 12 S Michigan Ave Chicago, IL 60603
Camp Llama

Photo Credit: Bangtel
For those looking to escape the city for Memorial Day Weekend, Camp Llama offers a family-friendly A-frame farm retreat in Twin Lake, Michigan, near Muskegon. Designed for larger groups with accommodations for up to 29 guests, the property includes a pool, hot tub, fire pit, pond, and expansive outdoor space for games and activities. Camp Llama is also offering 20% off Memorial Day stays with the code “ChicagoPlanner20.”
Location: Twin Lake, Michigan
Fiya
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Photo Credit: Fiya
Fiya will celebrate Memorial Day Weekend with a special “Al Ha’esh” grill-centric menu inspired by Israeli open-fire cooking traditions. Available May 22–25, the limited-time menu from Chef Ben Blum features dishes including lamb burgers, falafel burgers, skewers, watermelon salad, grilled corn ribs, and seasonal sides. Guests can enjoy the holiday offerings indoors or on the restaurant’s spacious backyard patio in Andersonville.
Location: 5419 N. Clark Street, Chicago, IL 60640
Hyatt Lodge Oak Brook

Photo Credit: Hyatt Lodge
Hyatt Lodge Oak Brook is welcoming guests and locals alike for a multi-day Memorial Day Weekend celebration set across its 88-acre forest preserve property. The festivities include a Friday Car Show and Cookout featuring classic cars, outdoor bar service, music, and grilled favorites, along with Sunday’s Bike and Hike the Reserve event complete with guided biking, family-friendly activities, bounce houses, games, and refreshments. The resort-style property also offers scenic accommodations, on-site dining, and more than 30,000 square feet of event space.
Location: 2815 Jorie Blvd, Oak Brook, IL 60523
Mayfestiversary
Kick off Memorial Day Weekend at Mayfestiversary, the annual street festival from Begyle Brewing and Dovetail Brewery returning to Ravenswood for its 10th anniversary celebration. Taking place May 23–24, the free festival features more than 60 beers, live music, local food vendors, special anniversary releases, and family-friendly activities. The event also supports The Friendship Center, helping provide meals to Chicago neighbors facing food insecurity.
Location: Between Begyle Brewing and Dovetail Brewery in the Ravenswood Corridor.
Entrances located at:
• 1800 W Cuyler Ave
• 4114 N Ravenswood Ave
• 1820 W Belle Plaine Ave
Olio e Più

Photo Credit: Kristen Mendiola
Olio e Più will celebrate Memorial Day with special brunch and dinner service in River North, complete with patio dining and Italian Riviera-inspired cocktails. Guests can enjoy Bottomless Bubbles during brunch, Aperitivo Hour specials, and Martini Monday offerings featuring classic martinis for $10. The restaurant’s expansive corner patio provides a lively outdoor setting for handmade pastas, spritzes, and holiday weekend dining.
Location: 445 N Dearborn St.. Chicago, IL 60654
Schaumburg Boomers

Photo Credit: Schaumburg Boomers
The Schaumburg Boomers will kick off Memorial Day Weekend at Wintrust Field with a full lineup of baseball, fireworks, giveaways, and family-friendly entertainment. Weekend highlights include post-game fireworks, a hat giveaway, Hawaiian shirt giveaway, Bark in the Park, and Military Appreciation Day. Guests can also enjoy free parking, themed activities, and classic ballpark food throughout the holiday weekend.
Location: Wintrust Field, 11999 S Springinsguth Rd, Schaumburg, IL 60193
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