weekend.flights — start over
We show you when and where you can go.
FromChicagoFri–Sundirect1 adult
Cheap weekend flights from Chicago
The cheapest weekend from Chicago is Orlando, at €151 return. February is the cheapest month, and London, Fort Lauderdale and Amsterdam turn up as the best fare most often.
15 weekends ahead35 destinations · 24 countries · checked
Prices move. This page is rebuilt daily and shows the cheapest trip per weekend. The board searches live and knows every airline on the route.
Search live from ChicagoWeekend flights from Chicago: quick answers
How cheap is a weekend flight from Chicago?
Right now the cheapest is €151 return to Orlando. Across the next six months, half of all weekends have a trip at €386 or less.
What is the cheapest month for a weekend trip from Chicago?
February, where the best weekend fare is €151 return.
Where can you fly for a weekend from Chicago?
35 destinations in 24 countries have direct Friday-to-Sunday round trips in the months ahead. London, Fort Lauderdale and Amsterdam come up as the cheapest most often.
Do I need to take days off work?
It depends on the weekend you pick. Every trip on this page leaves on Friday and returns on Sunday, so the work week stays intact, though an early Friday departure can still mean leaving work after lunch. On the live board you can also choose Long weekends (Thursday to Monday shapes) or hunt bridge days around public holidays, and those do cost a day or two of leave.
How fresh are these prices?
This page was rebuilt on October 18, 2026 and refreshes daily. Fares are from Kiwi.com; the final price is always the one at checkout.