Title: Cheap Flights from Chicago from £75 - Expedia.co.uk ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/32a5a1b7-682e-4c22-a8ab-4b736795e0ea/expedia_fallback.webp?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap flights from Chicago, IL ## 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_UA.svg) United - ![](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_AS.svg) Alaska Airlines - ![](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_B6.svg) JetBlue Airways - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 25% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.co.uk/login) ## Cheapest flights from Chicago These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 17 Jun - Tue, 30 Jun MDW Chicago MCO Orlando £148 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:MDW,to:MCO,departure:17/06/2026TANYT&leg2=from:MCO,to:MDW,departure:30/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:147.70&airProductToken=AQpFCiEIxJgBEgQxNzI4GOywASDgXCjz_Y8DMPT-jwM4RUAAWAEKIAjEmAESBDExNjIY4FwgzHAo7P-PAzDIgJADOEVAAVgBCkUKIAjEmAESBDE0NjMYzHAg4FwotYuRAzCYjJEDOEVAAFgBCiEIxJgBEgQyNDE3GOBcIOywASjkjJEDMNyNkQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, 30 Jun - Wed, 1 Jul ORD Chicago MCO Orlando £148 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:MCO,departure:30/06/2026TANYT&leg2=from:MCO,to:ORD,departure:01/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:147.70&airProductToken=AQpECiAIxJgBEgQxMjY0GK4cIOBcKNaKkQMw0ouRAzhFQABYAQogCMSYARIEMTY1OBjgXCDMcCiFjJEDMOGMkQM4RUABWAEKRgohCMSYARIEMTIwMRjMcCDjtAEo2JWRAzD2lpEDOEVAAFgBCiEIxJgBEgQzNjczGOO0ASCuHCjSl5EDMLGYkQM4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, 9 May - Tue, 12 May ORD Chicago DFW Dallas £150 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:DFW,departure:09/05/2026TANYT&leg2=from:DFW,to:ORD,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:150.00&airProductToken=AQo0CjIIwYIBEgQxNTU1GK4cIKOxASitwowDMM_DjAM4QkAAWAFqBUJBU0lDcghPVkFJWFRCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, 25 Aug - Wed, 2 Sept ORD Chicago MIA Miami £165 Return found 5 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:MIA,departure:25/08/2026TANYT&leg2=from:MIA,to:ORD,departure:02/09/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:164.90&airProductToken=AQpECiAIxJgBEgQxMjQ3GK4cIOBcKLqBlgMwtIKWAzhFQABYAQogCMSYARIEMTMzMhjgXCCMAijkgpYDMNmDlgM4RUABWAEKRAogCMSYARIEMTI2MRiMAiDgXCi125YDMKzclgM4RUAAWAEKIAjEmAESBDI4OTQY4Fwgrhwo5NyWAzDk3ZYDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, 9 May - Tue, 12 May ORD Chicago DAL Dallas £165 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:DAL,departure:09/05/2026TANYT&leg2=from:DAL,to:ORD,departure:12/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:164.90&airProductToken=AQptCjUIxJgBEgQxNTE2GK4cIOBcKPbCjAMw7MOMAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTVCQwo0CMSYARIDNTEyGOBcIINYKNfEjAMw28WMAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTVCQwptCjQIxJgBEgM1MTIYg1gg4Fwoq-iMAzCs6YwDOEVAAFgBaglNQUlOQkFTSUNyCFZBVlNBNUJDCjUIxJgBEgQxMTk5GOBcIK4cKKvqjAMwr-uMAzhFQAFYAWoJTUFJTkJBU0lDcghWQVZTQTVCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, 17 May - Thu, 21 May ORD Chicago TPA Tampa £172 Return found 3 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:TPA,departure:17/05/2026TANYT&leg2=from:TPA,to:ORD,departure:21/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:171.50&airProductToken=AQoyCjAIwYIBEgMzNTMYrhwg8wMo8aGNAzCZo40DOEJAAFgBagVCQVNJQ3IITldBVVpOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sat, 23 May - Wed, 10 Jun ORD Chicago PHX Phoenix £185 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PHX,departure:23/05/2026TANYT&leg2=from:PHX,to:ORD,departure:10/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:184.20&airProductToken=AQpFCiAIwaYBEgQxNDcwGK4cIJJoKOjgjQMw_eKNAzhYQABYAQohCMGmARIEMzE5NBiSaCDvuQEomuSNAzDx5I0DOFhAAVgBCkUKIQjBpgESBDIwMjgY77kBIJJoKJWvjwMw56-PAzhYQABYAQogCMGmARIEMTQ5MxiSaCCuHCiXsI8DMJSyjwM4WEABWAESCggBEAEYASoCQVMYASIECAEQASgEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sun, 16 Aug - Tue, 18 Aug ORD Chicago LAS Las Vegas £186 Return found 5 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:LAS,departure:16/08/2026TANYT&leg2=from:LAS,to:ORD,departure:18/08/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:185.30&airProductToken=AQphCi4IwaYBEgQxNDcwGK4cIJJoKOiblQMw-p2VAzhYQABYAWoCU1ZyCEdINE9BSkJOCi8IwaYBEgQyMjU1GJJoIIuQASjSn5UDMKqglQM4WEABWAFqAlNWcghHSDRPQUpCTgphCi8IwaYBEgQyMjgyGIuQASCSaCiSt5UDMOG3lQM4WEAAWAFqAlNWcghHSDRPQUpCTgouCMGmARIEMTQ5MxiSaCCuHCi3uJUDMLS6lQM4WEABWAFqAlNWcghHSDRPQUpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, 19 May - Thu, 4 Jun ORD Chicago MCO Orlando £199 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:MCO,departure:19/05/2026TANYT&leg2=from:MCO,to:ORD,departure:04/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:198.40&airProductToken=AQoiCiAI1YIBEgQxNDEwGK4cIMxwKLe2jQMw5reNAzhHQABYAQoiCiAI1YIBEgQyNjgzGMxwIK4cKNTnjgMwkOmOAzhLQABYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, 11 Jun - Wed, 24 Jun ORD Chicago MCO Orlando £203 Return found 4 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:ORD,to:MCO,departure:11/06/2026TANYT&leg2=from:MCO,to:ORD,departure:24/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:202.50&airProductToken=AQpBCh8IwmwSBDEyMDYYrhwgqVEonrWPAzCqto8DOExAAFgBCh4IwmwSAzM4MxipUSDMcCjmto8DMKC4jwM4TEABWAEKQAoeCMJsEgMzODQYzHAgqVEo18iQAzCBypADOExAAFgBCh4IwmwSAzQwNRipUSCuHCiyy5ADMN7MkAM4TEABWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) Find available prices by choosing your travel dates. \*Available to Expedia members. 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