September in Chicago: Festivals, Sports, and City Adventures

As summer winds down, September in Chicago strikes the perfect balance between lively events, crisp weather, and a relaxed atmosphere. The city comes alive with festivals, sports, and cultural happenings — making it one of the best times of year to visit. Whether you’re here for world-class music, championship sports, or simply to explore the neighborhoods, September offers something for everyone. And with The Chicago Hotel Collection’s prime locations — Mag Mile, River North, Wrigley, and the Ambassador Gold Coast — you’ll be right in the heart of it all.

Chicago Jazz Festival 🎷

Labor Day weekend kicks off the month with the Chicago Jazz Festival, a beloved tradition showcasing both local talent and international stars. Millennium Park transforms into a haven for music lovers, with free performances filling the late-summer air. Spread out a blanket, grab a snack from a local vendor, and soak up the sounds of saxophones and trumpets echoing under the city skyline.

Where to stay: Our Mag Mile and River North locations put you within walking distance of Millennium Park, so you can come and go as you please without worrying about long commutes or crowded trains.

Riot Fest 🎸

By mid-September, Chicago hosts one of the country’s biggest alternative music festivals — Riot Fest in Douglass Park. With a lineup that spans punk, rock, hip-hop, and everything in between, this is the place for anyone who wants a weekend of high-energy music and festival fun. The atmosphere is electric, and Chicago’s skyline makes a perfect backdrop.

Pro tip: After a full day at Riot Fest, retreat to the comfort of your CHC guest room, where your all-inclusive stay means you’ll have nightly cocktails, dinner credits, and breakfast waiting without worrying about extra costs.

Chicago Gourmet 🍷

For food and wine enthusiasts, Chicago Gourmet is the event of the season. Hosted at Millennium Park, this culinary festival brings together top chefs, mixologists, and sommeliers for tastings, demonstrations, and one-of-a-kind dining experiences. Imagine sipping fine wine while sampling bites from Chicago’s most celebrated kitchens — it’s foodie heaven.

Where to stay: The Ambassador Gold Coast offers a charming neighborhood escape while still keeping you close to downtown. Pair the elegance of the Gold Coast with your all-inclusive perks — breakfast, cocktails, and dinner credits included with your stay.

Sports Fever: Cubs & Bears 🏟️

Chicago is a sports city, and September is when the energy hits its peak.

• Chicago Cubs: Cheer on the Cubs as they wrap up their season at historic Wrigley Field. September games are often some of the most exciting, with playoff hopes hanging in the balance.

• Chicago Bears: As football season kicks off, Soldier Field becomes the center of attention. Tailgating, cheering crowds, and crisp fall air create the ultimate game-day vibe.

Where to stay: If baseball is on your list, our Wrigley location puts you steps from the action. For football weekends, Mag Mile and River North offer easy access to Soldier Field — with the bonus of an all-inclusive stay that keeps game-day costs under control.

Early Fall Adventures 🌆

Beyond the festivals and sports, September is the perfect time to explore Chicago’s cultural and natural highlights.

• Architecture River Cruises: The cooler weather makes for the most enjoyable rides along the Chicago River. With the city skyline bathed in golden sunlight, it’s a breathtaking experience.

• Neighborhood Strolls: Wander through Lincoln Park, the Gold Coast, or Wicker Park to enjoy boutique shopping, cozy coffee shops, and local eateries without the heavy summer crowds.

• Museums & Theater: September also marks the start of theater season, with Broadway in Chicago and neighborhood playhouses launching new productions. Pair that with timeless favorites like the Art Institute or the Museum of Contemporary Art, and you have endless options for indoor exploration.

Why Stay with The Chicago Hotel Collection?

When planning your September getaway, your choice of hotel makes all the difference. The Chicago Hotel Collection is proud to be Chicago’s only all-inclusive hotel brand — meaning your stay isn’t just about the room. It’s about value, convenience, and experiences built into every reservation.

Here’s what’s always included when you book direct with us:

• Daily breakfast buffet for two (a $70 value)

• Two complimentary cocktails each night (a $32 value)

• Nightly dinner credit to enjoy during your stay

• Exclusive local and worldwide perks for added savings even after checkout

Unlike other hotels that charge extra for these amenities, we make them part of your stay — no hidden surprises, no inflated add-ons. Just one straightforward, all-inclusive experience.

Make September Your Month in Chicago 🌟

From the smooth sounds of the Jazz Festival to the roar of the Bears crowd, September offers a taste of everything that makes Chicago special. Add in world-class dining, vibrant neighborhoods, and unforgettable events, and you’ve got the makings of a perfect city getaway.

Make the most of it by booking your stay directly with The Chicago Hotel Collection. As Chicago’s only all-inclusive hotels, you’ll enjoy unmatched value and convenience — and when you book direct, you save even more.

👉 Book direct today at www.thechicagohotelcollection.com and experience September in Chicago the all-inclusive way.