Friday, May 23: Kick Off the Weekend

Chicago Riverwalk + Architecture Cruise

Start your weekend with a scenic stroll or hop on a late afternoon architecture boat tour on the Chicago River. Pro tip: Grab a drink from City Winery or Island Party Hut and watch the sunset reflect off the skyline.

Rooftop Happy Hour

• Cindy’s (Millennium Park views)
• LondonHouse Rooftop (Riverwalk glam)
• Utopian Tailgate (colorful and quirky in Old Town)
  

Live Music + Nightlife

Check out:

• Smart Bar for electronic beats
• House of Blues for some live soul and funk
• Or a chilled-out evening at Jazz Showcase

Saturday, May 24: Festival Fun & Outdoor Adventures

Mayfest in Lincoln Park

A Chicago classic! Think craft beers, cover bands, and bratwursts. Great for groups, day drinking, and dancing under the sun. 

Hit the Beach

It’s (unofficially) beach season! Grab your towel and head to:

• North Avenue Beach (party vibe)
• Montrose Beach (chill and dog-friendly)
• Oak Street Beach (close to downtown)
  

Shop & Stroll

• Hit up Randolph Street Market Festival for vintage finds, vinyl, and local bites.
• Wander the West Loop for boutique shopping and killer eats.

Eat Like a Local

You must squeeze in a:

• Deep dish from Lou Malnati’s or Pequod’s
• Italian beef from Al’s Beef
• Street tacos from Antique Taco or Big Star

Sunday, May 25: Celebrate & Chill

Lake Michigan Boat Party or Cruise

Rent a boat with friends or book a BYOB cruise. Chicago’s skyline from the water is chef’s kiss.

Movies in the Parks (Opening Weekend!)

• Chicago Park District’s Movies in the Parks series usually kicks off Memorial Day weekend. Bring a blanket and catch a free movie under the stars.
  

Sunday Funday

• Brunch at The Publican, Beatrix, or Wildberry Pancakes
• Hit a Sunday day party at places like Bounce, Celeste, or Revel Fulton Market

Monday, May 26: Memorial Day Tribute & Relaxation

Chicago Memorial Day Parade

Head downtown to State Street at noon for the official parade honoring U.S. service members. It’s one of the largest Memorial Day parades in the country.

Picnic & Chill in the Parks

Unwind in:

• Millennium Park (great for photos and people-watching)
• Humboldt Park (beautiful lagoon and Puerto Rican culture)
• Promontory Point (epic skyline views)
• Pack a picnic, bring a speaker, and relax with friends.