Chicago festivals Are Back: Summer 2025 Events Worth Traveling For

Plan your stay with The Chicago Hotel Collection and step into Chicago’s most exciting summer yet.

Summer in Chicago doesn’t ease in—it shows up loud. From lakefront music festivals to open-air art fairs and the smell of barbecue in the streets, the city turns into one massive celebration once the weather turns. If you’ve been waiting to make a trip, now’s the time.

Whether you’re new to the city or a returning guest, The Chicago Hotel Collection puts you within walking (or quick rideshare) distance of the biggest events—and the best spots to wind down after. Here’s what’s coming up in summer 2025 and why you’ll want to lock in your stay early.

🎶 Chicago Blues Festival

June 6–8 | Millennium Park

The world’s largest free blues festival kicks off the summer in style. Big names and local talent light up Millennium Park all weekend, bringing in crowds and good vibes. Our Mag Mile and River North locations are just blocks from the action—so you can walk back to your suite after a full day of music.

🎭 Old Town Art Fair

June 14–15 | Old Town Triangle

Cobblestone streets, historic brownstones, and hundreds of curated artists—that’s what you’ll find at this long-running Chicago favorite. Just minutes from The Chicago Hotel Collection Ambassador Gold Coast, this fair is perfect for a slow morning, some art browsing, and great eats nearby.

🎨 Gold Coast Art Fair

June 22–23 | Grant Park

One of the oldest art festivals in the country brings over 200 artists to Grant Park. From ceramics and jewelry to large-scale paintings, you’ll find something worth stopping for. Staying at our Gold Coast or Mag Mile locations makes it easy to shop and stroll without worrying about parking or long commutes.

🎸 Windy City Smokeout

July 10–13 | United Center

A heavy-hitter on the summer calendar. This four-day festival combines top-tier country artists with the best BBQ pitmasters in the U.S. Expect packed crowds, cold beer, and a full weekend of live shows. Our River North location gives you quick access to the festival and downtown nightlife afterward.

🍕 Taste of Chicago

July 25–27 | Grant Park

This one’s legendary for a reason. Sample dishes from dozens of the city’s most iconic restaurants, all in one spot. Deep dish, elotes, birria, sliders, sweets—if it’s served in Chicago, it’s here. The Chicago Hotel Collection Mag Mile and Gold Coast are both within minutes of Grant Park, so you can head back for a midday break or change before round two.

🎆 Navy Pier Fireworks & Live on the Lake

Wednesdays & Saturdays, All Summer

Summer nights in Chicago hit different—especially when the sky lights up over Lake Michigan. Navy Pier’s weekly fireworks shows are free, crowd-pleasing, and just a short walk from our Mag Mile location. Plan a dinner by the water, catch the show, and then call it a night in comfort.

Festival Vibes All Day, Chicago Nights After

After the festivals wrap up, Chicago doesn’t slow down. The city’s late-night scene is as strong as ever, especially in the neighborhoods surrounding our hotels. Grab a steak at Gibsons near the Gold Coast, hit up Celeste or TAO in River North for a proper night out, or catch a Cubs night game followed by a beer at Smoke Daddy in Wrigleyville.

If you’re winding down instead of going out, take a walk along the lakefront path or the Riverwalk—both offer quiet city views and cool breezes, perfect for ending the day.

Stay Close to Everything

With four boutique properties in the city’s best neighborhoods, you’re never far from the action:

• Wrigleyville: Steps from Cubs games, sports bars, and summer street fests

• River North: Near high-end dining, nightlife, and Loop-area events

• Mag Mile: Close to Grant Park, Navy Pier, Millennium Park, and shopping

• Ambassador Gold Coast: Nestled near Old Town, the beach, and quieter upscale corners of the city

Each property has its own vibe, but all share the same benefits when you book direct—more space, more style, and perks you won’t get anywhere else.

Book Direct and Get More

When you book directly through The Chicago Hotel Collection, you unlock exclusive advantages, including:

• Access to discounted local attractions

• Flexible room types, including one- and two-bedroom suites perfect for groups

• Priority room selection and upgrades when available

Don’t just book a place to sleep. Book a stay that gives you more to enjoy before and after the festival fun.

Summer is calling. Plan your getaway with The Chicago Hotel Collection and make 2025 a summer worth remembering. Book direct and stay where it matters.