Cheap Chicago Flights and Deals Dep: Mar 21 Rtn: Apr 02JAXJacksonvilleCHIChicago$84.58 Dep: Apr 08 Rtn: Apr 29PSPPalm SpringsCHIChicago$88.59 Dep: May 01 Rtn: May 02NYCNew York CityCHIChicago$95.30 Dep: Apr 30 Rtn: May 07AUSAustinCHIChicago$97.57 Dep: May 01 Rtn: May 08DFWDallasCHIChicago$106.58 Dep: Apr 09 Rtn: Jun 08CVGCincinnatiCHIChicago$107.60 Dep: Mar 26 Rtn: Mar 30DENDenverCHIChicago$112.58 Dep: Mar 26 Rtn: Apr 02TPATampaCHIChicago$114.60 Dep: Apr 30 Rtn: May 01HOUHoustonCHIChicago$115.56 Dep: Mar 26 Rtn: Apr 02ORLOrlandoCHIChicago$119.58Ref:iS4b-LDTBkaPTma2VlBdlA * All fares above were last found on: Mar 20, 2019 and 12:05:49 AM. Fares are round trip. Fares incl. all fuel surcharges, our service fees and taxes. Displayed fares are based on historical data, are subject to change and cannot be guaranteed at the time of booking. See all booking terms and conditions.