The leaves along Chicago’s lakefront are starting to turn, and the city’s fall weather is about to hit its peak. That same window is one of the busiest parts of Chicago’s fall season. If you’ve been eyeing a getaway, October gives you plenty to plan around, and the Chicago Marathon on Oct. 11 is only one piece of it.
Between Oct. 8 and 25, the city fits in a film festival, a free architecture weekend and a fashion week. The Art Institute of Chicago also just opened a new Mary Cassatt exhibition. If you only have one weekend, aim for Oct. 17-18, when all four overlap.
Chicago’s Marathon Is Bringing Its Biggest Field Yet
The Chicago Marathon returns Sunday, Oct. 11, for its 48th running. Organizers expect more than 55,000 participants, the largest field in the race’s history.
Runners start and finish in Grant Park. Not running? You can still cheer from the sidelines.
What Else Is on the October Calendar
Here’s what else you can work into the trip:
- The Chicago International Film Festival, Oct. 14-25: The 62nd edition bills itself as North America’s longest-running competitive film festival. This year it adds its first Physical Media Fair for film collectors.
- Open House Chicago, Oct. 17-18: The Chicago Architecture Center opens more than 200 sites for free, including many that don’t usually welcome the public. Some sites, including the Chicago Board of Trade Building, open Saturday only.
- Chicago Fashion Week, Oct. 8-18: Its final days overlap with Open House weekend.
- “Mary Cassatt: After Impressionism,” Art Institute of Chicago: The museum’s first Cassatt exhibition in more than 25 years runs through Jan. 3, 2027. Most visitors need a $7 exhibition ticket on top of general admission.
Where to Stay Downtown
The Ritz-Carlton, Chicago is on the Gold Coast at Water Tower Place, along the Magnificent Mile. Its Torali restaurant serves prime steak and handmade pastas, and you can take in city and lake views from Rooftop at Torali on the 12th floor.
Arlo Chicago puts you steps from Millennium Park, inside the 1916 Atlantic Bank building. Its bistro, About Last Knife, serves meals any time of day. Each night’s stay also sends 50 cents to Deborah’s Place, which helps women who are homeless in Chicago.
Open House is the easiest part of the trip to wing. Sites let visitors in on a first-come, first-served basis, so you won’t need tickets or reservations. Pick a neighborhood the night before, and wear shoes you can walk in all day.