Marathon Weekend Guide: The 12 Best Things to Do in Chicago This Weekend

This is one of those weekends that reminds you why you live here.

The 48th Bank of America Chicago Marathon takes over the city on Sunday — 55,000 runners from around the world racing through 29 neighborhoods, with well over a million spectators lining the course. And Saturday? The city just declared October 10 "Best Big City Day," celebrating a full decade as Condé Nast Traveler's best big city in America. There's a floating house-music party on the Riverwalk, a limited-edition "Perfect 10" beer from Goose Island, and a special cheesecake flight from Eli's. That's just Saturday afternoon.

Whether you're cheering, sipping, or steering clear of the crowds, here's how to do marathon weekend right.

Sunday: The Marathon

The main event. The 26.2-mile course starts and ends at Columbus Drive in Grant Park, with runners on the course from 7:00 AM to 4:00 PM on Sunday, October 11. If you've never spectated, do it at least once — the energy in Boystown (Mile 7.5), Pilsen, and Chinatown (Mile 21.5) is unreal.

A few pro tips: do NOT attempt to drive downtown. Take the CTA — the Red Line to Addison for the Boystown stretch, or Cermak-Chinatown for the late-race drama when runners are digging deep. Bring a cowbell. And cheer for the back-of-the-pack runners harder than the elites — they're the ones who need it most.

Saturday: Best Big City Day

Saturday afternoon, get yourself to the Riverwalk near City Winery for the city's big celebration — a floating house-music party with pioneering Chicago DJ Lori Branch starting around 3:30. It's free, it's on the water, and it's the kind of only-in-Chicago moment that makes a great story on Monday morning.

Lincoln Park Wine Fest (Oct 9–11)

Celebrating its 10th year, the Lincoln Park Wine Fest takes over Jonquil Park (1001 W. Wrightwood Ave.) with wines from around the world, food vendors, and DJs. Sessions run Friday evening, all day Saturday, and Sunday. General admission starts around $30, organized into two-hour tasting windows that make it easy to pair with dinner in the neighborhood. Bonus: proceeds support the Wrightwood Neighbors Association and local park initiatives.

Lincoln Brunch Fest (Saturday, 10 AM–2 PM)

Third annual, right on Lincoln Avenue — local food, local businesses, live music. The perfect Saturday-morning warm-up before the afternoon festivities.

Tenderfest at Navy Pier (Saturday)

Because sometimes you just want chicken tenders by the lake. This one's exactly what it sounds like, and honestly, that's the whole pitch.

Chicago Fashion Week (Oct 8–18)

Now in its third year, with 50+ runway shows, pop-ups, and designer showcases scattered across the city — spotlighting Chicago's own design community. Check the schedule and pick your lane: runway, streetwear, or local shopping.

Historic Pullman House Tour (Oct 10–11)

A rare chance to step inside beautifully preserved private homes in historic Pullman on the Far South Side and go back to the 19th century for an afternoon. If you're into architecture or Chicago history, this one's a hidden gem.

Chicago Zine Fest (Saturday)

Head to the Harold Washington Library for a celebration of independent publishing — zines, comics, and small-press weirdness from local makers.

Out in the Western Suburbs

Don't sleep on the suburbs this weekend:

- St. Charles Scarecrow Festival (Oct 9–11): One of the Fox Valley's best fall traditions — scarecrows everywhere, vendors, food, and entertainment in downtown St. Charles along the river.

- Naperville Festive Fall Festival (Saturday, 2–4 PM): Free trunk-or-treat, games, inflatables, and crafts at Naperville Church of Christ (2035 E. 75th St.). Bring a non-perishable food item for the West Suburban Community Pantry.

- Boo! at the Zoo (Brookfield Zoo, through Oct 25): The classic family Halloween event — costumes encouraged, trick-or-treat stations, and the animals couldn't care less about your costume.

- Sonny Acres Farm (West Chicago): The longtime western-suburban fall staple — pumpkin patch, haunted hayride, barn experiences, and all the seasonal food you can handle, running weekends through the end of October.

Sports & Concerts

- Chicago Fire vs. New York City FC — Saturday at Soldier Field

- Chicago Blackhawks vs. Carolina Hurricanes — Saturday at the United Center

- Olivia Rodrigo: The Unraveled Tour — Sunday and Monday at the United Center

Don't Forget Monday

Monday is Columbus Day, and the Chicago History Museum is offering free admission for Illinois residents. The Columbus Day Parade steps off at noon. An easy way to stretch the weekend one more day.

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There's no better weekend to be a Chicagoan — or to start thinking about becoming one. If the suburbs are calling your name, you know where to find me.

— Jeff