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FromChicagoFri–Sundirect1 adult
Cheap weekend flights from Chicago
The cheapest weekend from Chicago is Las Vegas, at €129 return. October is the cheapest month, and San Juan, Atlanta and Boston turn up as the best fare most often.
15 weekends ahead37 destinations · 22 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 €129 return to Las Vegas. Across the next six months, half of all weekends have a trip at €262 or less.
What is the cheapest month for a weekend trip from Chicago?
October, where the best weekend fare is €129 return.
Where can you fly for a weekend from Chicago?
37 destinations in 22 countries have direct Friday-to-Sunday round trips in the months ahead. San Juan, Atlanta and Boston come up as the cheapest most often.
Do I need to take days off work?
Usually not: every trip on this page leaves on Friday and returns on Sunday, so the work week stays intact. An early Friday departure can still mean leaving work after lunch, so check the times on the card. For longer breaks, the live board has a Long weekends option that searches around public holidays.
How fresh are these prices?
This page was rebuilt on September 3, 2026 and refreshes daily. Fares are from Kiwi.com; the final price is always the one at checkout.