Title: $23 Cheap flights from Chicago, IL - Expedia.com ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $23 Cheap flights from Chicago, IL [View $23 flight on Sat, Apr 25, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:MDW,to:MCO,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:22.98&airProductToken=AQoxCi8IxnISBDE1MzYY7LABIMxwKPaliwMwn6eLAzhFQABYAWoEUENfMXIHSzIxU1hTMhIMCAEQARgBKgJGOTIAGAEiBAgBEAEoAigDMA0) [Chicago Travel Guide](https://expedia.com/Chicago.dx178248)[Hotels in Chicago](https://expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels)[Things to do in Chicago](https://expedia.com/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Car Rentals in Chicago](https://expedia.com/Car-Rentals-In-Chicago.d178248.Car-Rental-Guide)[Chicago Vacation Packages](https://expedia.com/Chicago.d178248.Destination-Travel-Guides) ## Popular airlines from Chicago - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines ## Today's featured flight deals from Chicago Nonstop Carry-on included Lower price than typical - Chicago (ORD)San Juan (SJU) Mon, Mar 30 Sat, Apr 4 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 3 hours ago 40% less than typical $486 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SJU,departure:3/30/2026TANYT&leg2=from:SJU,to:ORD,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-97d49ea2cb7c4fac9a1226c1e6885ab1-1239-1-st-v5-sos-97d49ea2cb7c4fac9a1226c1e6885ab1-1083-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAeeWzlyQASeQAQCqAQcKA0NISRAAsgEHCgNTSlUQAA~AQo0CjIIwYIBEgQxMDYwGK4cILKiASjeh4kDMPiJiQM4QkAAWAFqBUJBU0lDcghPTk4yQURCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpgCi8IwmwSBDE0NjIYsqIBIMGTASi0vokDMKjAiQM4WkAAWAFqAkFOcghaSTBBVUVZNQotCMJsEgMzMTEYwZMBIK4cKP3CiQMwscSJAzhPQAFYAWoCQU5yCE9JNEFCRVk1EgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ&medianPrice=1040.00&displayPrice=485.62&src=dflp) - Chicago (ORD)San Juan (SJU) Mon, Mar 30 Sat, Apr 4 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 6 hours ago 45% less than typical $431 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SJU,departure:3/30/2026TANYT&leg2=from:SJU,to:MDW,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-8f218aceb7e14537b38778393bf6e160-2002-1-st-v5-sos-8f218aceb7e14537b38778393bf6e160-1846-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAcvIzVyQASeQAQCqAQcKA0NISRAAsgEHCgNTSlUQAA~AQo0CjIIwYIBEgQxMDYwGK4cILKiASjeh4kDMPiJiQM4QkAAWAFqBUJBU0lDcghPTk4yQURCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQpwCjYIxJgBEgQxODQwGLKiASDgXCjAuokDMLq8iQM4RUAAWAFqCU1BSU5CQVNJQ3IIVU5OQzBOQloKNgjEmAESBDEwNzYY4Fwg7LABKP--iQMw87-JAzhFQAFYAWoJTUFJTkJBU0lDcghVTk5DME5CWhIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE&medianPrice=1040.00&displayPrice=430.50&src=dflp) - Chicago (ORD)San Juan (SJU) Mon, Mar 30 Sat, Apr 4 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 4-day trip found 6 hours ago 50% less than typical $412 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:SJU,departure:3/30/2026TANYT&leg2=from:SJU,to:ORD,departure:4/4/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-301ce35e008e4adaae337cee6d02020e-1339-1-st-v5-sos-301ce35e008e4adaae337cee6d02020e-1178-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAbS0zVyQAQGQAQOqAQcKA09SRBABsgEHCgNTSlUQAQ~AQo0CjIIwYIBEgQxMDYwGK4cILKiASjeh4kDMPiJiQM4QkAAWAFqBUJBU0lDcghPTk4yQURCWhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs.AQphCi8I15wBEgQzMDcyGLKiASDMcCjSvokDMJXAiQM4Q0AAWAFqA1dHQXIHQ0xBM1IyRgouCNecARIEMzg4MhjMcCCuHCjSw4kDMJXFiQM4Q0ABWAFqA1dHQXIHQ0xBM1IyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE&medianPrice=1040.00&displayPrice=411.50&src=dflp) - Chicago (ORD)Miami (MIA) Sat, Mar 21 Sat, Mar 28 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip found 3 hours ago 55% less than typical $293 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/21/2026TANYT&leg2=from:MIA,to:ORD,departure:3/28/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-1bf5bff6a56d4dbaa20800cc2da3ec6d-1042-1~8.S.1~AQoGCAEQ-5ADEgcI1AQQARgBKAJYAnAAegNiZnOIAeCazlyqAQcKA0NISRAAsgEHCgNNSUEQAQ~AQozCjEIwYIBEgQyOTAxGK4cIIwCKN-giAMwnKKIAzhCQABYAWoFQkFTSUNyCFFWRlVaTkJYCmYKMQjBggESBDM4MTQYjAIgoQMom-mIAzC26ogDOEJAAFgBagVCQVNJQ3IIUVdBTElPQlgKMQjBggESBDQ3MDQYoQMgrhwo_uuIAzDw7IgDOEJAAVgBagVCQVNJQ3IIUVdBTElPQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=878.00&displayPrice=292.60&src=dflp) - Chicago (ORD)Miami (MIA) Sat, Mar 21 Sun, Mar 29 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 7-day trip found 8 hours ago 40% less than typical $334 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/21/2026TANYT&leg2=from:MIA,to:ORD,departure:3/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-dc4de51afdd345088bc2723d8d185b0e-809-1-st-v5-sos-dc4de51afdd345088bc2723d8d185b0e-810-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZL_zFyQAQCQAQuqAQcKA09SRBAAsgEHCgNNSUEQAA~AQozCjEIwYIBEgQyNDE5GK4cIIwCKISgiAMwx6GIAzhCQABYAWoFQkFTSUNyCFFWQVVaT0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQplCjEIwYIBEgQxNzY1GIwCIO9ZKMD0iAMw7fWIAzhCQABYAWoFQkFTSUNyCE5XQVpaT0JYCjAIwYIBEgM5NTUY71kgrhwosfaIAzDM94gDOEJAAVgBagVCQVNJQ3IITldBWlpPQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=722.00&displayPrice=333.59&src=dflp) - Chicago (ORD)Miami (MIA) Fri, Mar 20 Fri, Mar 27 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 6-day trip just found 55% less than typical $248 [](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:MIA,departure:3/20/2026TANYT&leg2=from:MIA,to:ORD,departure:3/27/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-eb04674b276441289f1570b5d990c9b0-1552-1-st-v5-sos-eb04674b276441289f1570b5d990c9b0-1448-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdbpzlyQASyQAR6qAQcKA09SRBAAsgEHCgNNSUEQAA~AQozCjEIwYIBEgQyNDE5GK4cIIwCKOSUiAMwp5aIAzhCQABYAWoFQkFTSUNyCFFWQVVaT0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQpuCjUIxJgBEgQxMjQ5GIwCIOBcKNjdiAMw196IAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTlCRwo1CMSYARIEMTE0NxjgXCCuHCiH34gDMITgiAM4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkE5QkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB&medianPrice=716.00&displayPrice=247.60&src=dflp) - Chicago (MDW)Las Vegas (LAS) Mon, Mar 16 Fri, Mar 20 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 4-day trip found 19 hours ago 50% less than typical $357 [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LAS,departure:3/16/2026TANYT&leg2=from:LAS,to:MDW,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-bb984807108949be801708bc2d8802f3-3635-1-st-v5-sos-bb984807108949be801708bc2d8802f3-3547-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAczMylyqAQcKA01EVxAAsgEHCgNMQVMQAA~AQoxCi8I15wBEgM1MTIY7LABIIuQASjR6YcDMMHrhwM4UEAAWAFqA1dHQXIHUExOVVAyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQpyCjcIxJgBEgQyNzQzGIuQASDjtAEoqJiIAzCJmogDOEVAAFgBaglNQUlOQkFTSUNyCFhBVk5BMEJHCjcIxJgBEgQ1MjE4GOO0ASDssAEorpuIAzCBnIgDOEVAAVgBaglNQUlOQkFTSUNyCFhBVk5BMEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ&medianPrice=892.00&displayPrice=356.60&src=dflp) - Chicago (MDW)Las Vegas (LAS) Sat, Mar 21 Tue, Mar 24 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 6 hours ago 50% less than typical $283 [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LAS,departure:3/21/2026TANYT&leg2=from:LAS,to:MDW,departure:3/24/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-60ee4c7751934ddb976ef4a09b423b0b-6303-1-st-v5-sos-60ee4c7751934ddb976ef4a09b423b0b-6223-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAYfNzVyQAR2QAR2qAQcKA01EVxAAsgEHCgNMQVMQAA~AQoxCi8I15wBEgM1MTIY7LABIIuQASiDoYgDMPiiiAM4RUAAWAFqA1dHQXIHRUROVlIyRhIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQpvCjUIxJgBEgM3MjAYi5ABIOBcKIDFiAMw4saIAzhFQABYAWoJTUFJTkJBU0lDcghWQVZOQzJCRwo2CMSYARIEMTA2MxjgXCDssAEoy8iIAzDAyYgDOEVAAVgBaglNQUlOQkFTSUNyCFZBVk5DMkJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ&medianPrice=782.00&displayPrice=282.60&src=dflp) - Chicago (MDW)Las Vegas (LAS) Sat, Mar 14 Sat, Mar 21 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 7-day trip found 19 hours ago 45% less than typical $387 [](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:LAS,departure:3/14/2026TANYT&leg2=from:LAS,to:MDW,departure:3/21/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-a9d8e747b6b6438bb5690a340700f5d9-6332-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gB49DKXKoBBwoDTURXEACyAQcKA0xBUxAA~AQoyCjAI15wBEgQzNTcyGOywASCLkAEoqtOHAzCf1YcDOFBAAFgBagNXR0FyB1BMTlVQMkYKYgovCNecARIEMTAwNRiLkAEgg2kogqOIAzDwo4gDOFBAAFgBagNXR0FyB1BMQVVQMkYKLwjXnAESBDI2MTMYg2kg7LABKL-miAMw0KeIAzhQQAFYAWoDV0dBcgdQTEFVUDJGEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ&medianPrice=962.00&displayPrice=386.60&src=dflp) ## Cheapest flights from Chicago These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Sat, Apr 25 - Thu, Apr 30 MDW Chicago MCO Orlando $46 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:MCO,departure:4/25/2026TANYT&leg2=from:MCO,to:MDW,departure:4/30/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:45.96&airProductToken=AQoxCi8IxnISBDE1MzYY7LABIMxwKPaliwMwn6eLAzhFQABYAWoEUENfMXIHSzIxU1hTMgoxCi8IxnISBDM4NTMYzHAg7LABKPXbiwMwpd2LAzhFQABYAWoEUENfMXIHSzIxRFhTMhIMCAEQARgBKgJGOTIAGAEiBAgBEAEoAigDMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, May 11 - Fri, May 15 ORD Chicago TPA Tampa $46 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TPA,departure:5/11/2026TANYT&leg2=from:TPA,to:ORD,departure:5/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:45.96&airProductToken=AQowCi4IxnISBDEyNTIYrhwg8wMost2MAzDp3owDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIEMTQxNRjzAyCuHCivjI0DMOqNjQM4RUAAWAFqBFBDXzFyB0syMURYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Fri, Apr 17 - Mon, Apr 20 ORD Chicago DFW Dallas $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:DFW,departure:4/17/2026TANYT&leg2=from:DFW,to:ORD,departure:4/20/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQoxCi8IxnISBDMyNDMYrhwgo7EBKIPKigMwrMuKAzhFQABYAWoEUENfMXIHSzIxSVhTMgoxCi8IxnISBDMyNDQYo7EBIK4cKOzzigMwh_WKAzhFQABYAWoEUENfMXIHSzIxTlhTMhIKCAEQARgBKgJGORgBIgQIARABKAIoAzAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Apr 13 - Wed, Apr 15 ORD Chicago LAS Las Vegas $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:LAS,departure:4/13/2026TANYT&leg2=from:LAS,to:ORD,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQoxCi8IxnISBDM2NDcYrhwgi5ABKL6kigMww6aKAzhFQABYAWoEUENfMXIHSzIxTlhTMgoxCi8IxnISBDIxNDYYi5ABIK4cKJiyigMw_LOKAzhFQABYAWoEUENfMXIHSzIxWFhTMhIMCAEQARgBKgJGOTIAGAEiBAgBEAEoAigDMA0) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Apr 20 - Sat, Apr 25 ORD Chicago MIA Miami $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:MIA,departure:4/20/2026TANYT&leg2=from:MIA,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDM2MzAYrhwgjAIopvGKAzDt8ooDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIEMjY3MRiMAiCuHCiRq4sDMOusiwM4RUAAWAFqBFBDXzFyB0syMVNYUzISDAgBEAEYASoCRjkyABgBIgQIARABKAIoAzAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Mon, Apr 20 - Sat, Apr 25 ORD Chicago FLL Fort Lauderdale $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:FLL,departure:4/20/2026TANYT&leg2=from:FLL,to:ORD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDIyMDUYrhwg5Voo0--KAzCY8YoDOEVAAFgBagRQQ18xcgdLMjFEWFMyCjAKLgjGchIEMjIwNhjlWiCuHCjvqYsDMMmriwM4RUAAWAFqBFBDXzFyB0syMVNYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Thu, Apr 9 - Mon, Apr 13 MDW Chicago DFW Dallas $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:MDW,to:DFW,departure:4/9/2026TANYT&leg2=from:DFW,to:MDW,departure:4/13/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQoyCjAIxnISBDE4ODcY7LABIKOxASjT9YkDMPz2iQM4RUAAWAFqBFBDXzFyB0syMVJYUzIKMgowCMZyEgQyODgyGKOxASDssAEos6SKAzC9pYoDOEVAAFgBagRQQ18xcgdLMjFOWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Tue, Apr 21 - Sat, Apr 25 RFD Rockford DFW Dallas $143 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:RFD,to:DFW,departure:4/21/2026TANYT&leg2=from:DFW,to:RFD,departure:4/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:142.14&airProductToken=AQpmCjEIwYIBEgQ2NTcyGLEZIK4cKLT3igMwjviKAzhCQABYAWoFQkFTSUNyCE9WQUlYU0JWCjEIwYIBEgM0ODEYrhwgo7EBKLv4igMw3PmKAzhCQAFYAWoFQkFTSUNyCE9WQUlYU0JWCmYKMQjBggESAzM5MRijsQEgrhwo-KOLAzCPpYsDOEJAAFgBagVCQVNJQ3IIT1ZBSVhTQlYKMQjBggESBDY1NzQYrhwgsRkoyqWLAzCpposDOEJAAVgBagVCQVNJQ3IIT1ZBSVhTQlYSDAgBEAEYASoCQUEyABgBIgQIARABKAIoAygEMAs) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 7 - Tue, Apr 14 ORD Chicago DAL Dallas $143 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:DAL,departure:4/7/2026TANYT&leg2=from:DAL,to:ORD,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:142.80&airProductToken=AQowCi4I15wBEgQzNjgyGK4cIINYKNfciQMw7d2JAzhWQABYAWoDV0dBcgdWWk5WSDJMCjAKLgjXnAESBDE3MjgYg1ggrhwo-amKAzCKq4oDOFZAAFgBagNXR0FyB1ZaTlZIMkwSDAgCEAEYAioCV04yABgBIgQIARABKAIoAygEMAE) ![Volaris](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/Y4.gif) Thu, Apr 16 - Sat, Apr 18 ORD Chicago NLU Mexico City $302 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ORD,to:NLU,departure:4/16/2026TANYT&leg2=from:NLU,to:ORD,departure:4/18/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:301.13&airProductToken=AQpfCi0I2WgSBDE3MDUYrhwg5lgo6cKKAzDfxIoDOEFAAFgBagRaZXJvcgZBTENTUzIKLgjZaBIEMTI5MhjmWCDtogEo68WKAzC2xooDOEFAAVgBagRaZXJvcgZBTENTUzIKXwouCNloEgQxMjkzGO2iASDmWCiz24oDMP_bigM4QUAAWAFqBFplcm9yBkFMQ1NTMQotCNloEgQxNzAyGOZYIK4cKLvcigMws96KAzhBQAFYAWoEWmVyb3IGQUxDU1MxEgoIARABGAEqAlk0GAEiBAgBEAEoAigDKAQwDQ) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## How to Find Cheap Flights from Chicago, IL #### How much is a flight from Chicago? This week, flights from Chicago are available between $46 – $302\. #### How to find cheap flights from Chicago? Expedia makes it easy to compare cheap flights from Chicago to many destinations. Check out excellent deals on domestic and international flights from Chicago. Once you select an offer, use our filters and sort by “Price (Lowest)” to see some of the cheapest and suitable options. #### How can I get the best deal on flights from Chicago? On Expedia, you have some of best airline ticket deals at your fingertips. Whether it’s a beach escape with your partner, a family vacation with your kids, or business trip with colleagues, these low airline ticket prices mean more savings for you. An excellent strategy for finding some of the best deals on flights from Chicago is to be flexible with your dates. Within each offer, you can compare prices for similar timeframes using our “Show flexible dates” feature. Depending on your destination, direct flights from Chicago may be more expensive. Airlines with strict bag policies or fees can also impact your costs. #### What is the best airline to fly from Chicago? At Expedia, we give you all the available options from our reputable partners. Select the airline that best suits your preferences and membership loyalties. You can fly from Chicago with: Frontier Airlines, American Airlines, Southwest Airlines, Aeromexico, Volaris. #### What is the best month to fly from Chicago? One of the cheapest times to fly from Chicago airport(s) is April, based on the current list of flights available now. Prices on plane tickets vary considerably throughout the year due to availability and seasonal demand. #### Are there any last-minute flights from Chicago? Expedia is the place to find last-minute flights from Chicago, making it easy for you to compare prices on flights in the near future for different combinations of travel dates and from multiple airlines. We source some of the best deals for you and display some of the best offers available over the next 2 weeks. #### Why book your ticket with Expedia? Booking flights from Chicago with Expedia is the obvious choice to get low prices, save money, and see more value from every dollar spent. We show you some of the best deals happening right now and provide a vast inventory of airlines and flight routes to choose from, so you can find some of the cheapest flights from Chicago. You can customize your journey to your timeline, route preferences, budget, rewards programs, and more. #### Can I change/cancel my flight? Some flights can be changed or canceled, but fees and refunds will depend on the unique terms of your flight agreement. Airlines have different rules and restrictions for exchanging or refunding flights. For more information, go to your itinerary or visit our [customer service portal](https://www.expedia.com/service/). We recommend choosing flights with no change fees for the most flexibility. Filter by “Flexible change policies” to see flights with no change fees. \*Data specialists from both ARC and Expedia Group analysed ARC's global flight data to distil actionable information to help people save money on travel. While it's impossible to guarantee when to find the lowest prices, after examining the variables, we were able to observe trends. Analysis based on ARC, round-trip flight data between 1 October 2017 - 30 September 2018 for Economy and Premium cabin ATPs on a global basis. ## Travel information ## Flights from Chicago: Essential Travel Information | Cheapest flight from Chicago | $46 (roundtrip) | | ---------------------------------- | ----------------------------------------------------------------------------- | | Best airlines to fly from Chicago | Frontier Airlines, American Airlines, Southwest Airlines, Aeromexico, Volaris | | Cheapest month to fly from Chicago | April | | Chicago IATA code | CHI | | Chicago Country/State | Illinois | | Airline ticket deals from Chicago | $46 - $302 | \*Flight schedules are subject to change. ## Explore a world of travel with Expedia - Lodging - Packages - Cars - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Riverwalk ](https://www.expedia.com/Chicago-Riverwalk-Hotels.0-l553248621533116610-0.Travel-Guide-Filter-Hotels) - [Hotels near Magnificent Mile ](https://www.expedia.com/Magnificent-Mile-Chicago-Hotels.0-n800025-0.Travel-Guide-Filter-Hotels) - [Hotels near Grant Park ](https://www.expedia.com/Grant-Park-Hotels.0-l507389-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Cheap-Hotels.0-n6350699-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels near The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels.0-n800024-0.Travel-Guide-Filter-Hotels) - [Hotels near Millennium Park ](https://www.expedia.com/Millennium-Park-Hotels.0-l6069201-0.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Luxury-Hotel.0-n6350699-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Hotels near River North ](https://www.expedia.com/River-North-Chicago-Hotels.0-n6350695-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Union Station ](https://www.expedia.com/Chicago-Union-Station-Hotels.d6129885.Travel-Guide-Hotels) - [Hotels near Michigan Avenue ](https://www.expedia.com/Michigan-Avenue-Hotels.0-l6156167-0.Travel-Guide-Filter-Hotels) - [Hotels near Soldier Field ](https://www.expedia.com/Soldier-Field-Hotels.0-l6058043-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Theatre ](https://www.expedia.com/Chicago-Theatre-Hotels.0-l6064049-0.Travel-Guide-Filter-Hotels) - [Hotels with a View in Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Hotels-With-View.0-n6350699-0-tHotelswithView.Travel-Guide-Filter-Hotels) - [Hotels near Art Institute of Chicago ](https://www.expedia.com/Art-Institute-Of-Chicago-Hotels.0-l6064021-0.Travel-Guide-Filter-Hotels) - [Hotels near State Street ](https://www.expedia.com/State-Street-Hotels.0-l6175182-0.Travel-Guide-Filter-Hotels) - [Hotels near CIBC Theatre ](https://www.expedia.com/CIBC-Theatre-Hotels.0-l553248621563220853-0.Travel-Guide-Filter-Hotels) - [Hotels near Theatre District ](https://www.expedia.com/Theatre-District-Chicago-Hotels.0-n651190586167894016-0.Travel-Guide-Filter-Hotels) - [Motels in Monroe Station ](https://www.expedia.com/Monroe-Station-Motels.d6189309-aaMotels.Travel-Guide-Accommodation) - [Central Chicago Hotels ](https://www.expedia.com/Central-Chicago-Hotels.d553248635976475413.Travel-Guide-Hotels) - [Condo Rentals in Monroe Station ](https://www.expedia.com/Monroe-Station-Condos.d6210064-aaCondos.Travel-Guide-Accommodation) - [Cheap Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Cheap-Hotels.0-n800024-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels near Sullivan Center ](https://www.expedia.com/Sullivan-Center-Hotels.0-l553248621533116571-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Theatre District ](https://www.expedia.com/4Star-Theatre-District-Chicago-Hotels.s40-n651190586167894016-0.Travel-Guide-Filter-Hotels) - [Hotels near Chagall's Four Seasons ](https://www.expedia.com/Chagalls-Four-Seasons-Hotels.0-l553248621533116569-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Theatre District ](https://www.expedia.com/3Star-Theatre-District-Chicago-Hotels.s30-n651190586167894016-0.Travel-Guide-Filter-Hotels) - [Hotels with Suites in Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Hotel-Suites.0-n6350699-0-tHotelSuites.Travel-Guide-Filter-Hotels) - [Hotels near Marquette Building ](https://www.expedia.com/Marquette-Building-Hotels.0-l553248621533116542-0.Travel-Guide-Filter-Hotels) - [Hotels near Chase Tower ](https://www.expedia.com/Chase-Tower-Hotels.0-l553248621555594882-0.Travel-Guide-Filter-Hotels) - [Hotels near Haskell Building ](https://www.expedia.com/Haskell-Building-Hotels.0-l6065133-0.Travel-Guide-Filter-Hotels) - [Hotels near Navy Pier ](https://www.expedia.com/Navy-Pier-Hotels.0-l6069215-0.Travel-Guide-Filter-Hotels) - [Hotels near Adams-Wabash Station ](https://www.expedia.com/Adams-Wabash-Station-Hotels.d6210258.Travel-Guide-Hotels) - [Hotels near Madison-Wabash Station ](https://www.expedia.com/Madison-Wabash-Station-Hotels.d6210251.Travel-Guide-Hotels) - [Hotels with Suites in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotel-Suites.0-n800024-0-tHotelSuites.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Downtown Chicago ](https://www.expedia.com/4Star-Downtown-Chicago-Chicago-Hotels.s40-n6350699-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Loop Synagogue ](https://www.expedia.com/Chicago-Loop-Synagogue-Hotels.0-l553248621555594887-0.Travel-Guide-Filter-Hotels) - [Hotels near House of Blues Chicago ](https://www.expedia.com/House-Of-Blues-Chicago-Hotels.0-l6227753-0.Travel-Guide-Filter-Hotels) - [Hotels near Daley Plaza ](https://www.expedia.com/Daley-Plaza-Hotels.0-l553248621533116574-0.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels-Hilton-Hotels.0-n6350699-0--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Luxury-Hotel.0-n800024-0-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Loop ](https://www.expedia.com/4Star-The-Loop-Chicago-Hotels.s40-n800024-0.Travel-Guide-Filter-Hotels) - [Boutique Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Boutique-Hotel.0-n800024-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Hotels near Jackson Station ](https://www.expedia.com/Jackson-Station-Hotels.d6189302.Travel-Guide-Hotels) - [Condo Rentals in Jackson Station ](https://www.expedia.com/Jackson-Station-Condos.d6189302-aaCondos.Travel-Guide-Accommodation) - [Hotels near Kluczynski Building ](https://www.expedia.com/Kluczynski-Building-Hotels.0-l553248621533116540-0.Travel-Guide-Filter-Hotels) - [Hotels near Washington Station ](https://www.expedia.com/Washington-Station-Hotels.d6210071.Travel-Guide-Hotels) - [Hotels near Jackson Station ](https://www.expedia.com/Jackson-Station-Hotels.d6210057.Travel-Guide-Hotels) - [Hotels near Cloud Gate ](https://www.expedia.com/Cloud-Gate-Hotels.0-l6182888-0.Travel-Guide-Filter-Hotels) - [Hotels near Miró's Chicago ](https://www.expedia.com/Miros-Chicago-Hotels.0-l553248621533116567-0.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Symphony Orchestra ](https://www.expedia.com/Chicago-Symphony-Orchestra-Hotels.0-l553248621533126470-0.Travel-Guide-Filter-Hotels) - [Hotels near Monadnock Building ](https://www.expedia.com/Monadnock-Building-Hotels.0-l6069203-0.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Free-Parking.0-n800024-0-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Marriott-Hotels-Resorts.0-n800024-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Hot-Tubs.0-n800024-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels near Chicago Temple ](https://www.expedia.com/Chicago-Temple-Hotels.0-l553248621561883126-0.Travel-Guide-Filter-Hotels) - [Resorts & Hotels with Spas in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Spa-Hotel.0-n800024-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels near Richard J. Daley Center ](https://www.expedia.com/Richard-J-Daley-Center-Hotels.0-l6175173-0.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotel-With-Early-Check-In.0-n800024-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - [Family Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Family-Hotel.0-n800024-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Hotels near Afrocentric Bookstore ](https://www.expedia.com/Afrocentric-Bookstore-Hotels.0-l553248621555594812-0.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Complimentary-Breakfast.0-n800024-0-tHotelswithComplimentaryBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with a Gym in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Fitness-Center.0-n800024-0-tHotelswithFitnessCenter.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Indoor-Pool.0-n800024-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Pet-Friendly-Hotel.0-n800024-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Best-Western.0-n800024-0--bBestWestern.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in The Loop ](https://www.expedia.com/The-Loop-Chicago-Hotels-Hotels-With-Balconies.0-n800024-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Loop ](https://www.expedia.com/5Star-The-Loop-Chicago-Hotels.s50-n800024-0.Travel-Guide-Filter-Hotels) - [Visit Downtown Chicago ](https://www.expedia.com/Chicago-Downtown-Chicago.dx6350699) - [Visit The Loop ](https://www.expedia.com/Chicago-The-Loop.dx800024) - [Cibc Theatre ](https://www.expedia.com/CIBC-Theatre-Downtown-Chicago.d553248621563220853.Vacation-Attraction) - [Chase Tower ](https://www.expedia.com/Chase-Tower-Downtown-Chicago.d553248621555594882.Vacation-Attraction) - [Visit Theatre District ](https://www.expedia.com/Chicago-Theatre-District.dx651190586167894016) - [Sullivan Center ](https://www.expedia.com/Sullivan-Center-Downtown-Chicago.d553248621533116571.Vacation-Attraction) - [State Street ](https://www.expedia.com/State-Street-Bronzeville.d6175182.Vacation-Attraction) - [Chagall's Four Seasons ](https://www.expedia.com/Chagalls-Four-Seasons-Downtown-Chicago.d553248621533116569.Vacation-Attraction) - [Marquette Building ](https://www.expedia.com/Marquette-Building-Downtown-Chicago.d553248621533116542.Vacation-Attraction) - [Haskell Building ](https://www.expedia.com/Haskell-Building-Downtown-Chicago.d6065133.Vacation-Attraction) - [Daley Plaza ](https://www.expedia.com/Daley-Plaza-Downtown-Chicago.d553248621533116574.Vacation-Attraction) - [Chicago Loop Synagogue ](https://www.expedia.com/Chicago-Loop-Synagogue-Downtown-Chicago.d553248621555594887.Vacation-Attraction) - [Monadnock Building ](https://www.expedia.com/Monadnock-Building-Downtown-Chicago.d6069203.Vacation-Attraction) - [Miró's Chicago ](https://www.expedia.com/Miros-Chicago-Downtown-Chicago.d553248621533116567.Vacation-Attraction) - [Richard J. Daley Center ](https://www.expedia.com/Richard-J-Daley-Center-Downtown-Chicago.d6175173.Vacation-Attraction) - [The Loop Vacations ](https://www.expedia.com/The-Loop.d800024.Destination-Travel-Guides) - [Willis Tower ](https://www.expedia.com/Willis-Tower-Downtown-Chicago.d6064069.Vacation-Attraction) - [Chicago Temple ](https://www.expedia.com/Chicago-Temple-Downtown-Chicago.d553248621561883126.Vacation-Attraction) - [Marshall Field Building ](https://www.expedia.com/Marshall-Field-Building-Downtown-Chicago.d553248621533116570.Vacation-Attraction) - [Picasso Statue ](https://www.expedia.com/Picasso-Statue-Downtown-Chicago.d6069235.Vacation-Attraction) - [Chicago Cultural Center ](https://www.expedia.com/Chicago-Cultural-Center-Downtown-Chicago.d6064037.Vacation-Attraction) - [Depaul University-Loop Campus ](https://www.expedia.com/DePaul-University-Loop-Campus-Downtown-Chicago.d6227480.Vacation-Attraction) - [Rookery ](https://www.expedia.com/Rookery-Downtown-Chicago.d553248621533116543.Vacation-Attraction) - [Van Car Rentals near CIBC Theatre ](https://www.expedia.com/Van-Car-Rentals-In-CIBC-Theatre.d553248621563220853-tVan.Car-Rental-Guide-Class) - [Car rentals near Sullivan Center ](https://www.expedia.com/Car-Rentals-In-Sullivan-Center.d553248621533116571.Car-Rental-Guide) - [Car rentals near Theatre District ](https://www.expedia.com/Car-Rentals-In-Theatre-District.d651190586167894016.Car-Rental-Guide) - [Car rentals near Chagall's Four Seasons ](https://www.expedia.com/Car-Rentals-In-Chagalls-Four-Seasons.d553248621533116569.Car-Rental-Guide) - [Car rentals near State Street ](https://www.expedia.com/Car-Rentals-In-State-Street.d6175182.Car-Rental-Guide) - [Car rentals near Chase Tower ](https://www.expedia.com/Car-Rentals-In-Chase-Tower.d553248621555594882.Car-Rental-Guide) - [Car rentals near The Loop ](https://www.expedia.com/Car-Rentals-In-The-Loop.d800024.Car-Rental-Guide) - [Car rentals near Richard J. Daley Center ](https://www.expedia.com/Car-Rentals-In-Richard-J-Daley-Center.d6175173.Car-Rental-Guide) - [Enterprise Rental Cars in The Loop ](https://www.expedia.com/Enterprise-Car-Rentals-In-The-Loop.d800024-c15.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in The Loop ](https://www.expedia.com/Avis-Car-Rentals-In-The-Loop.d800024-c41.Car-Rental-Guide-Suppliers) \*Available to One Key members.