Memorial Day Weekend in Chicago and Beyond: Where to Go, What to Do, and Where to Stay

Memorial Day weekend is a time to celebrate, relax, and enjoy the beginning of summer. Whether you’re in Chicago or looking for a quick getaway nearby, there’s no shortage of exciting activities, delicious food, and memorable experiences. From indulging in Chicago’s best brunches to exploring the city’s iconic architecture, or taking a relaxing retreat in Southwest Michigan, Memorial Day weekend offers something for everyone. Here’s your ultimate guide to making the most of the long weekend.

Things to Do in Chicago

Navy Pier – A-MAY-Zing Days of Play

For families looking for a fun and interactive experience, head to Navy Pier for the A-MAY-Zing Days of Play, a free event hosted by Jewel-Osco. This event features family-friendly activities, including a sweepstakes for incredible prizes. After the event, enjoy Navy Pier’s first fireworks of the season.

• Where: Navy Pier, Chicago, IL

• When: Memorial Day weekend, with a special event on May 24

• Cost: Free

• Perfect for: Families

Chicago Architecture Center – Explore the City’s Iconic Structures

Explore Chicago’s architectural wonders with a Chicago Architecture Center River Cruise or one of their expert-led walking tours. Voted the #1 boat tour in the U.S. by USA Today readers, the river cruise offers a deep dive into the city’s rich history and iconic buildings. If you prefer to stay on land, take a walking tour for a closer look at Chicago’s neighborhoods and structures.

• Where: Chicago Architecture Center, 111 E. Wacker Drive, Chicago, IL

• When: Memorial Day weekend (Friday, May 23 – Monday, May 26)

• Cruise Times: Multiple daily tours available

• Cost: Ticket prices vary

Lakefront Trail and Riverwalk – Explore Chicago’s Outdoors

Enjoy Chicago’s outdoor beauty by taking a scenic stroll or bike ride along the Lakefront Trail or Chicago Riverwalk. Whether you prefer a leisurely walk or an active adventure, these scenic spots offer something for everyone. Explore the beach, rent a kayak, or simply relax and take in the views.

• Where: Lakefront Trail, Chicago Riverwalk

• When: All Memorial Day weekend

• Cost: Free

Dining & Experiences

The Bellevue Chicago – Start Your Weekend Right

Kick off your Memorial Day weekend with a vibrant brunch or happy hour at The Bellevue in Chicago’s Gold Coast. From 11 a.m. to 2:30 p.m., enjoy Chef Russell Kook’s elevated takes on American classics, such as the Breakfast Sandwich and Challah French Toast. Their happy hour, available Monday through Thursday from 3 p.m. to 6 p.m., offers $10 bites like Spicy Tuna Rolls and Crunchy Shrimp Rolls, paired with select wines. The spacious patio is an ideal spot to soak up the Chicago sun.

• Where: The Bellevue Chicago, 1031 N. Rush St., Chicago, IL

• When: Friday brunch from 11 a.m. – 2:30 p.m. (extended weekend brunch on Sat-Sun from 10 a.m. – 2:30 p.m.)

• Reservations: Recommended

The Hampton Social – Memorial Day Brunch

For a coastal brunch vibe in Chicago, head to The Hampton Social. On Memorial Day, they will serve brunch from 11 a.m. to 3 p.m., featuring dishes like the Gatsby Breakfast, Wild Berry French Toast, and the Sunrise Beach Bowl. Pair your meal with a refreshing Hampton Skinny Margarita or a classic Bloody Mary.

• Where: The Hampton Social, All Chicagoland Locations

• When: Memorial Day, Monday, May 26 from 11 a.m. – 3 p.m.

• Cost: Prices vary

• Reservations: Highly recommended

The Shore Club – Beachfront Dining & Day Parties

Located along the lakefront, The Shore Club is an excellent spot to enjoy Memorial Day weekend. Lounge by the water with food and drinks, and enjoy day parties on the Oasis. They offer reservations for daybeds, sunbeds, and cabanas, making it a great place to relax and celebrate.

• Where: The Shore Club, Chicago, IL

• When: Memorial Day weekend

• Cost: Reservations required for daybeds, sunbeds, and cabanas

Additional Options

Here are a few more great places to explore in the city for dining and unique experiences:

• Rooftop Bars: Enjoy cocktails at Cindy’s Rooftop, LondonHouse, or The J. Parker.

• Patio Dining: Check out The Aviary, Girl & the Goat, or The Purple Pig for excellent outdoor dining.

Getaways

BANGTEL’s The Love Inn – A Cosmic Woodland Retreat

If you’re seeking a more tranquil escape, The Love Inn in Grand Rapids, Michigan, offers an enchanting woodland retreat. This space-themed A-frame cabin is perfect for stargazing on the spacious deck, lounging by the pool, or enjoying the fire pit. The pet-friendly retreat is offering 20% off Memorial Day weekend bookings.

• Where: The Love Inn, Grand Rapids, MI

• When: Memorial Day weekend (limited availability)

• Special: 20% off with code MEMORIAL20

• Booking: www.bangtel.com/love-inn

PostBoy in Southwest Michigan – Culinary Delights and Scenic Views

If you’re looking to escape the city, Southwest Michigan is the perfect Memorial Day weekend getaway. Known as the “Hamptons of the Midwest,” this region offers fantastic dining options like PostBoy, a chef-driven restaurant offering international-inspired New American fare. For craft spirits, visit Journeyman Distillery, and if you’re in the mood for local cider, head to Virtue Cider. Spend time at the pristine beaches along Lake Michigan’s shoreline, or enjoy hiking at Warren Dunes State Park.

• Where: New Buffalo, MI (PostBoy), Journeyman Distillery, Warren Dunes State Park

• When: Memorial Day weekend

• What to Do: Dining, outdoor adventures, wine/craft spirit tastings

• How to Get There: Easy Amtrak access from Chicago

Festivals & Events Around Chicago

Chicago offers an abundance of festivals and events to celebrate Memorial Day weekend:

• Sueños Music Festival (May 24–25): A premier reggaeton festival featuring top Latin music stars.

• Belmont-Sheffield Music Fest (May 23–25): Tribute bands, local artisans, and a lively beer garden.

• Mole de Mayo Festival (May 24–25): A celebration of Mexican culture in Pilsen, with food, music, and lucha libre wrestling.

• Alley Fest (May 25): Live music performances in a unique alley setting.

• Randolph Street Market (May 24–25): A European-style market with antiques, art, fashion, and decor.

• Prairie Arts Festival (May 23–29): Art, music, and family fun in the suburbs.

Sports & Outdoor Activities

• Cubs vs. White Sox – Crosstown Classic: A classic rivalry game at Wrigley Field.

• Kayaking and Paddleboarding: Rent kayaks or paddleboards along the Chicago River or at Ohio Street Beach.

• Architecture River Cruise: Explore Chicago’s architectural wonders on the city’s famous boat tour.

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Where to Stay in Chicago

• The Langham, Chicago: A luxury hotel offering stunning views of the Chicago River and Millennium Park.

• The Robey: A stylish boutique hotel in Wicker Park with a rooftop bar and city views.

• The Drake Hotel: A historic hotel offering classic elegance on the Magnificent Mile.

• Airbnb Options: Rent a lakeside apartment or a cozy loft in neighborhoods like Logan Square or Pilsen for a more personalized experience.