Cheapest time to fly to Chicago

The typical cheapest 7-night round trip from a US city: $236 for November and $346 for June.

1. -30%Cheapest timeNovember 2026Typically $236 round tripChecking fares…
2. -22%December 2026Typically $236 round tripChecking fares…
3. -23%January 2027Typically $239 round tripChecking fares…
4. -16%February 2027Typically $242 round tripChecking fares…
5. 0%March 2027Typically $290 round tripChecking fares…
6. +2%April 2027Typically $325 round tripChecking fares…
7. 0%May 2027Typically $330 round tripChecking fares…
8. +10%June 2027Typically $346 round tripChecking fares…
9. +8%July 2027Typically $345 round tripChecking fares…
10. +7%August 2027Typically $343 round tripChecking fares…

• Best time to visit ChicagoWeather, crowds and what's on

• JapanNovember to February
• TokyoDecember to February
• HawaiiJanuary and November
• Las VegasNovember to January
• LondonAbout the same all year
• New YorkNovember
• ItalyJanuary to February
• ThailandAbout the same all year
• Puerto RicoNovember to December
• ParisDecember to February
• FloridaNovember to January
• IrelandAbout the same all year
• OrlandoNovember
• CancunNovember to December
• SpainAbout the same all year
• the PhilippinesSeptember
• GreeceAbout the same all year
• VietnamNovember
• SeattleNovember
• RomeJanuary to February
• MexicoNovember to December
• IcelandFebruary to March and November
• GermanyAbout the same all year
• Costa RicaAbout the same all year
• PortugalJanuary to February and November
• New OrleansNovember to January
• MiamiJanuary and November
• Los AngelesNovember
• BrazilNovember
• the NetherlandsNovember to December
• BangkokAbout the same all year
• FranceDecember to February
• CanadaNovember to December
• the Dominican RepublicNovember to December
• South KoreaAbout the same all year
• IndonesiaAbout the same all year
• JamaicaNovember
• El SalvadorAbout the same all year
• United KingdomAbout the same all year