Fall adventures Await 🍂

There’s something magical about Chicago when September rolls in. The summer heat softens into crisp breezes, the leaves begin their slow golden transformation, and the city hums with the energy of a new season. For travelers, it’s the sweet spot—warm enough for patio dining and Riverwalk strolls, cool enough for cozy sweaters and pumpkin spice. Add in world-class events, vibrant neighborhoods, and unforgettable views, and it’s clear: September is the perfect time to experience the Windy City.

If you’re staying with us at The Chicago Hotel Collection, you’re right at the center of it all. From skyline sunsets on our rooftop terraces to Chicago-style eats just steps from your suite, September adventures are waiting at your doorstep.

Food Festivals & Culinary Delights

Chicago’s food scene is legendary, and September brings out the best of it.

• Taste of Chicago (Sept 5–7, Grant Park) – Sample bites from iconic eateries and hidden gems all in one place. Expect music stages, local vendors, and that electric Chicago energy.

• Chicago Gourmet (Sept 25–28) – A high-end culinary festival with celebrity chefs, wine pairings, and creative dining experiences. Millennium Park becomes a foodie’s playground.

  

• Farmers Markets – Don’t miss Green City Market in Lincoln Park or Logan Square’s Sunday market for fresh cider, pastries, and produce bursting with fall flavor.

Tip: After indulging downtown, return to the hotel for a complimentary nightcap with our Guest Benefits Package, which includes drink tickets for each evening of your stay.

Festivals & Cultural Experiences

Chicago’s creative spirit takes center stage in September.

• World Music Festival (Sept 20–Oct 6) – Free performances across the city, with global sounds from Africa, Asia, and Latin America filling local venues.

• Ravenswood ArtWalk (Sept 14–15) – Wander galleries and open studios, shop from local artisans, and enjoy food trucks and craft beer along this charming arts corridor.

• Chicago Architecture Biennial (opens Sept 19) – Explore cutting-edge exhibits and installations across iconic spaces like the Chicago Cultural Center.

Each festival offers a different perspective on the city—whether it’s the beat of a drum, the stroke of a paintbrush, or the bold lines of modern design.

Family-Friendly Fall Fun

Traveling with kids? September is packed with options that mix fun with fall vibes.

• Lincoln Park Zoo Fall Fest – Pumpkin patches, rides, and seasonal treats, all with free zoo admission.
  

  

• Jack’s Pumpkin Pop-Up – A Goose Island escape with carnival games, corn mazes, and thousands of pumpkins—perfect for family photos.

  

• Chicago Botanic Garden’s Night of 1,000 Jack-o’-Lanterns – While technically creeping into October, this enchanting display kicks off late September with glowing, artist-carved pumpkins.

After a day of adventure, head back to the hotel and relax—our spacious suites offer room for the whole family.

Outdoor Adventures & Iconic Views

Chicago’s skyline shines brightest in September’s crisp light.

• Architectural Boat Tours – Glide along the Chicago River and learn the stories behind the city’s most famous skyscrapers. With cooler weather and fewer crowds, September is the ideal time.

• Chicago Riverwalk – Sip wine by the water, explore public art, or simply stroll with stunning views.

• Parks & Nature – For fiery foliage, visit Lincoln Park, Grant Park, or Jackson Park’s Japanese Garden. Want a quick trip? Morton Arboretum, just outside the city, offers 1,700 acres of color.

Back at the Ambassador Gold Coast, Astor Terrace, or River North locations, you’ll find rooftops and lounges perfect for your own golden-hour moment.

Sports & Entertainment

Fall means game time in Chicago.

• Baseball – Catch the Cubs at Wrigley Field or the White Sox at Guaranteed Rate Field. Nothing says fall like ballpark hot dogs and a cool breeze.

• Football – The Chicago Bears kick off their season at Soldier Field, and the city buzzes with tailgates and team spirit.

• Concerts & Shows – From Lollapalooza aftershows to Broadway in Chicago, September’s calendar is always packed.

Whether you’re here for sports or shows, our hotels are a quick ride from all the action.

Why Stay with The Chicago Hotel Collection?

September may be the star, but your stay should shine too. At The Chicago Hotel Collection, we make sure every guest feels like a local insider:

• Prime Locations – Stay in the heart of the action: Mag Mile, River North, Wrigley, or Gold Coast. Each puts you steps from Chicago’s top attractions.

• Spacious Suites – More than a room—our suites give you space to spread out, relax, or get ready for a night out.

• Enjoy daily breakfast for two, drink tickets, discounts to Chicago attractions, and more.

• Flexible Options – From intimate getaways to group travel, our properties can host your trip your way.

Your September Adventure Starts Here

Chicago in September is alive with energy, flavor, and unforgettable moments. Whether you’re cheering at Wrigley, wandering an art walk, or sipping cider along the Riverwalk, fall memories are waiting around every corner.

And the best way to experience it all? By staying with us.

📍 Choose your perfect location with The Chicago Hotel Collection and enjoy the comfort of suites, perks of the Guest Benefits Package, and unmatched access to the city’s best fall experiences.

👉 Book direct today at thechicagohotelcollection.com and save.

Your fall in Chicago starts with us. 🍁