Summer on the Horizon: What to Look Forward to in Chicago Starting May 2025

As spring gives way to longer days and warmer weather, Chicago starts to buzz with the energy that only summer can bring. Starting in May, the city wakes up early, stays out late, and puts on one of the most spectacular warm-weather seasons in the country. Whether you're planning your first visit or making your annual return, summer 2025 promises iconic events, lakefront views, and unforgettable experiences—many of them just steps from The Chicago Hotel Collection’s boutique properties.

From rooftops to river cruises, neighborhood festivals to museum nights, here’s your guide to what’s coming and why May is the time to book your summer stay in Chicago.

🌇 Rooftops, Patios & Alfresco Everything

May is when outdoor dining kicks into full swing across Chicago. Restaurant patios, beer gardens, and rooftop lounges open for the season, and reservations start filling up fast.

In River North, pop over to RPM Seafood for riverside views and fresh catch, or sip cocktails at LondonHouse’s rooftop for panoramic skyline scenes. Near Mag Mile, Cindys Rooftop continues to be a seasonal favorite, overlooking Millennium Park and Lake Michigan.

Guests staying at The Chicago Hotel Collection River North or Mag Mile are within easy walking distance of the city’s top rooftop bars and patio dining hotspots. And if you're at The Chicago Hotel Collection Ambassador Gold Coast, the tree-lined streets are filled with historic charm and sidewalk cafés worth exploring on a slow morning or golden-hour stroll.

🛥️ Lakefront Season Begins

Chicago’s 18-mile Lakefront Trail becomes a must-do the moment temperatures rise. Whether you want to walk, jog, bike, or people-watch, this scenic path links beaches, parks, museums, and neighborhoods in one beautiful route.

Lake Michigan itself also becomes part of the adventure. Starting in May, river cruises and lake tours resume full service. The Chicago Architecture Foundation River Cruise is a must-see for first-timers and locals alike. For more excitement, take a ride on the Seadog speedboat, or schedule a sunset cruise with drinks and skyline views.

Navy Pier, just minutes from the Mag Mile and Gold Coast properties, comes alive with outdoor dining, street performers, and fireworks shows every Wednesday and Saturday night from Memorial Day through Labor Day.

🎶 Festival Season Kicks Off

Chicago is known for its summer festival scene—and it all begins in May.

Highlights to watch for:

• Chicago Mayfest (May 17–19): A kickoff to street fest season in Lincoln Park with food, live bands, and neighborhood energy.

• Mole de Mayo (May 24–26): A celebration of Mexican culture in Pilsen featuring music, lucha libre wrestling, and incredible mole tastings.

• Belmont-Sheffield Music Fest (Memorial Day Weekend): Near Wrigleyville, this fest brings live music, food vendors, and drinks to the heart of Lakeview.

Whether you’re heading to a neighborhood block party or planning for bigger festivals later in the summer (like Lollapalooza or Taste of Chicago), May gives you the first taste of what’s to come—with fewer crowds and better hotel availability.

⚾ Game On: Cubs, Sox & Beyond

Baseball season is in full swing by May, and there’s no better way to spend an afternoon than in the stands at Wrigley Field or Guaranteed Rate Field.

Stay at The Chicago Hotel Collection Wrigleyville to be steps from the action, or catch an easy Red Line ride from our River North or Mag Mile locations. After the game, Wrigleyville’s bar scene is perfect for post-game drinks, live music, or rooftop hangouts overlooking the diamond.

Other major sporting events in May include:

• Chicago Fire matches at Soldier Field

• Chicago Sky home games as WNBA season tips off

• Major tennis and running events around the city

No matter which team you’re cheering for, The Chicago Hotel Collection puts you within reach of the action.

🖼️ Culture Comes Outdoors

Chicago’s museums, art galleries, and cultural institutions come alive in the summer—but May is a sweet spot before the peak crowds arrive.

• The Art Institute of Chicago offers special exhibitions all season long and is just minutes from our Mag Mile and Gold Coast hotels.

• Museum of Contemporary Art and Chicago History Museum also host late hours and outdoor installations beginning in May.

• Chicago Symphony Orchestra and Lyric Opera often offer spring performances or previews for their summer series.

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Many institutions begin outdoor programming this time of year too, like the Grant Park Music Festival and Movies in the Parks, both of which are completely free.

🛍️ Shop, Stroll, and Soak It All In

May is the perfect time to enjoy Chicago’s world-famous shopping districts before the peak summer rush. Stroll down the Magnificent Mile for flagship stores, designer boutiques, and easy access to Oak Street’s luxury shops.

Guests staying at our Mag Mile and Gold Coast properties have the best of both worlds: upscale shopping just outside their door and a quiet, boutique hotel to return to at the end of the day.

📅 Plan Ahead for Memorial Day Weekend

Memorial Day Weekend (May 24–27, 2025) marks the unofficial start of summer in Chicago. That weekend includes:

• The start of fireworks at Navy Pier

• Lakefront festivals and food fairs

• Special museum events and concerts

• Packed patios and rooftop openings

It’s also one of the busiest weekends of the season—so if you’re planning to visit, booking early is essential to secure the best rates and locations.

🛎️ Where to Stay: The Chicago Hotel Collection

No matter your summer itinerary, The Chicago Hotel Collection has a property perfectly located for your plans:

• Mag Mile: Ideal for shopping, Navy Pier, and lakefront access

• River North: Walkable to nightlife, rooftop dining, and downtown culture

• Wrigleyville: Steps from Cubs games, concerts, and vibrant bars

• Ambassador Gold Coast: Historic charm near beaches, Oak Street, and upscale dining

Each stay includes access to our Guest Benefits Package, which unlocks discounts on tours, attractions, and future travel perks.

☀️ Summer Starts Now

May is the best time to lock in your summer plans before the season heats up. With fewer crowds, better rates, and early access to the city’s top experiences, it’s the ideal time to explore Chicago while staying with The Chicago Hotel Collection.

Book Direct and Save at any of our boutique locations and enjoy access to exclusive perks, flexible check-in, and the best available rates—only on our official website.