Departures · CHI
Cheap flights from Chicago.
15 routes from Chicago are under their usual price, up to 60% below. Members get the dates and the booking link the morning we find each one.
- Routes under usual
- 15
- Biggest drop
- -60%
- Prices seen
- 29 Oct
Cheap right now.
Prices seen 29 Oct 2026
-
-60%
Return · Dec 2026ManilaUS$611 US$1,515 -
-56%
Return · Nov 2026RomeUS$302 US$693 -
-53%
Return · Nov 2026MiamiUS$169 US$359 -
-53%
One way · Dec 2026StockholmUS$267 US$568 -
-48%
Return · Dec 2026Mexico CityUS$316 US$609 -
-47%
Return · Mar 2027CancunUS$242 US$459 -
-43%
One way · Nov 2026LisbonUS$203 US$354 -
-43%
Return · Nov 2026LondonUS$735 US$1,284 -
-40%
Return · Apr 2027BangkokUS$536 US$886 -
-38%
One way · Dec 2026Abu DhabiUS$607 US$974 -
-38%
Return · Dec 2026IstanbulUS$833 US$1,354 -
-35%
One way · May 2027TokyoUS$438 US$672 -
-33%
One way · Dec 2026PhuketUS$540 US$808 -
-32%
Return · Jan 2027Kuala LumpurUS$914 US$1,341 -
-31%
Return · Dec 2026DohaUS$891 US$1,293
How it works
Prices here. Dates for members.
We check every route from Chicago every day against what it usually costs for the same month and trip length. The prices on this page are real. The dates that work and the booking links go to members first, by email, before the fares are gone.
Join from Chicago- We search every routeFrom Chicago, months ahead, every day
- We keep the real dropsOnly fares well under the usual price
- You book directDates and the link, in your inbox
Prices are the cheapest fares we found from Chicago, in USD, for one adult, and can change when you click.