Cheap Chicago Flights and Deals Dep: Feb 08 Rtn: Feb 12ATLAtlantaCHIChicago$123.60 Dep: Feb 14 Rtn: Feb 17PHXPhoenixCHIChicago$139.58 Dep: Feb 05 Rtn: Feb 07BOSBostonCHIChicago$158.60 Dep: Feb 14 Rtn: Feb 18HOUHoustonCHIChicago$167.60 Dep: May 17 Rtn: May 20LAXLos AngelesCHIChicago$221.58 Dep: Feb 22 Rtn: Feb 24NYCNew York CityCHIChicago$223.60 Dep: Feb 14 Rtn: Feb 19SJUSan JuanCHIChicago$232.55 Dep: Apr 12 Rtn: Apr 14DFWDallasCHIChicago$248.58 Dep: Feb 07 Rtn: Feb 11SFOSan FranciscoCHIChicago$251.60 Dep: Jun 25 Rtn: Jul 01ORLOrlandoCHIChicago$257.60Ref:DMEd8J3R2EG35HYiP7Rrzw * All fares above were last found on: Jan 15, 2019 and 9:26:47 PM. 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.