Group trip to Chicago
Summer Chicago is undefeated. Boat party, deep dish, then argue about deep dish.
Free to plan. Pay only when you send it to the group: $2 per person, never more than $20.
What it costs, month by month
Per person for stay, activities and a round-trip flight, 3 nights, for a group of about 6 to 8 sharing. Rough ranges to sanity-check a plan, not quotes.
See the numbers
| Month | Per person | Season |
|---|---|---|
| January | $450 to $850 | Off-season |
| February | $450 to $850 | Off-season |
| March | $450 to $850 | Off-season |
| April | $450 to $850 | Off-season |
| May | $450 to $850 | Off-season |
| June | $600 to $1,150 | Busiest |
| July | $600 to $1,150 | Busiest |
| August | $600 to $1,150 | Busiest |
| September | $500 to $950 | Great |
| October | $450 to $850 | Off-season |
| November | $450 to $850 | Off-season |
| December | $450 to $850 | Off-season |
Group favorites in Chicago
- Architecture boat tour $$ (mid-range)Map
- Lake Michigan boat day $$$ (splurge)Map
- Wrigley game $$ (mid-range)Map
- Deep dish debate $ (budget)Map
What it costs to fly from your city
Recent real round-trip fares for June. Your airport stays on this device.
Where to stay in Chicago
Live prices for a group of 6. Booking through these links supports Trip Pulse at no extra cost to you.
Getting the group to actually say yes is the hard part
Put Chicago up against one or two other options and send everyone a private link. They say if they're in, which dates work and a budget only Trip Pulse sees. You get the pick that keeps the most people in.
- Start with Chicago already filled in with typical prices.
- Add a second option or let the group suggest one.
- Send it: $2 per person, $8 minimum, never more than $20.
If Chicago isn't quite it
All 33 trip ideasPrices are rough ranges reviewed September 2026 and move with season and demand. Always check before you book.