October was the most popular month for Chicago trips planned on Anywayr (formerly Travelry), with 28.6% of trips, and September came next at 20.4%. If your group is aiming for the same weeks, two things will shape the trip more than the weather: the Chicago Marathon on the second Sunday of October, and the end of the lakefront swim season on Labor Day.
This Chicago travel data comes from 49 trips planned by 44 people. That is a small sample, so read the percentages as a rough picture of what planners chose.
The numbers
| Measure | Result |
|---|---|
| Trips planned | 49 |
| Unique planners | 44 |
| Average group size | 2.7 people |
| Median group size | 2 people |
| Average trip length | 5.9 nights |
| Median trip length | 4 nights |
When people go
| Month | Share of trips |
|---|---|
| October | 28.6% |
| September | 20.4% |
| August | 14.3% |
| December | 8.2% |
October. The Chicago Marathon is always on the second Sunday of October. The 2026 race on 11 October drew about 55,000 runners, and the 2027 race is on Sunday 10 October (Chicago Marathon). Most streets on the course close from 6am to about 4pm on race day, and roads around Grant Park close from Thursday to Monday (NBC Chicago). If nobody in your group is running, pick the weekend before or after.
In both 2026 and 2027, the weekend after the marathon is Open House Chicago, when around 200 buildings that are normally closed to the public open for free, with no tickets needed. The 2027 dates are 16 and 17 October (Open House Chicago). With 65.3% of planners picking Cultural Experiences, it is worth timing an October trip around it.
September and August. Chicago's lifeguarded swim season runs from the Friday before Memorial Day to Labor Day. After that, swimming at the city's beaches is not allowed (Chicago Park District). That matters here, because 51% of planners chose Beach & Water Sports. A September trip after Labor Day still gets the lakefront path and the beaches to sit on, but not the water.
December. The Christkindlmarket in Daley Plaza runs daily from 20 November to 24 December in 2026, with free entry (Christkindlmarket). For a December group it is the easiest evening out to plan around.
Who goes
- Couples: 40.8%
- Families: 32.7%
- Friends: 14.3%
- Solo: 12.2%
Couples and families make up most Chicago trips, and groups are small: a median of 2 people, with an average of 2.7. Friend groups are a small share at 14.3%.
If you are bringing a bigger group, where you stay matters more than for a couple. Compare group stays in Chicago and hotels in Chicago, and use Chicago's best neighbourhoods to decide how close to the Loop you need to be.
What people want to do
| Interest | Share of trips |
|---|---|
| Food & Dining | 77.6% |
| Cultural Experiences | 65.3% |
| Adventure & Outdoor Activities | 61.2% |
| History & Museums | 51% |
| Beach & Water Sports | 51% |
| Local Markets | 49% |
Food & Dining leads at 77.6%. For a group, that means booking the big dinners before the trip rather than walking in; see group dining in Chicago.
Cultural Experiences (65.3%) and Adventure & Outdoor Activities (61.2%) can pull a group in two directions. The Chicago Architecture Center river cruise suits both camps: it is 90 minutes outside on the river, about the buildings. It runs from mid-March to late November (15 March to 22 November in 2026), leaving from 112 East Wacker Drive (First Lady). A December group will need an indoor plan instead.
History & Museums and Beach & Water Sports tie at 51%. They suit different seasons, so an October group leaning towards museums is in step with the calendar, while a beach group should go in summer.
How long people stay
The average trip was 5.9 nights and the median 4. Most groups plan a long weekend, and a few much longer trips pull the average up. For a summer version of the trip, see Chicago in summer with a group.
How we counted
The data covers 49 Chicago trips planned on Anywayr by 44 unique planners, pulled on 28 September 2026, with admin and test trips removed. Trips can list more than one interest, so the interest figures add up to more than 100%.
To plan your own, add your dates and who is going to an Anywayr trip. It builds a day-by-day plan with places to stay, and the group can vote on stays on one shared trip page.