Title: Cheap Flights to South Side - Expedia.co.uk ![Chicago, IL featuring interior views and an airport as well as a couple](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by by Midway Intl Airport ![](https://images.trvl-media.com/place/5719117/eadab43c-a88e-4198-bdcd-703715c2ebbd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # £314 Cheap Flights to South Side [View £314 flight on Tue, 3 Mar 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:LGW,to:ORD,departure:03/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:313.38&airProductToken=AQpnCjIIwYIBEgQ3MDEyGMuxASDMcCio0IYDMPbUhgM4T0AAWAFqBUJBU0lDcghPTFg1QzVCNAoxCMGCARIEMTU4NRjMcCCuHCjw24YDMK7dhgM4QkABWAFqBUJBU0lDcghPTFg1QzVCNBIKCAIQARgCKgJBQRgBIgQIARABKAIoAygEMAs) - [Return](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only [South Side Travel Guide](https://expedia.co.uk/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.co.uk/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Things to do in South Side](https://expedia.co.uk/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[South Side Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-South-Side.d553248635074842823.Car-Hire-Guide)[South Side Holidays](https://expedia.co.uk/South-Side.d553248635074842823.Holidays-City-Breaks) ## Popular airlines - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines ![notification illustration](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\* ![deals illustration](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\* ![trophy illustration](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) ## Cheap round-trip flights to South Side Prices were available within the past 7 days and start at £314 for one-way flights and £399 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![TAP Portugal](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TP.gif) Thu, 29 Jan - Sun, 1 Feb LGW London ORD Chicago £399 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LGW,to:ORD,departure:29/01/2026TANYT&leg2=from:ORD,to:LGW,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:398.38&airProductToken=AQpsCjUI1KABEgQxMzM3GMuxASCLkgEooN-DAzDA4IMDOE9AAFgBagdESVNDSU5UcghPRjBEU0lINwozCNSgARIDMjQzGIuSASCuHCjL6IMDMIXtgwM4T0AAWAFqB0RJU0NJTlRyCE9GMERTSUg3CmwKMwjUoAESAzI0NBiuHCCLkgEo8YWEAzDMiYQDOE9AAFgBagdESVNDSU5UcghPRjBEU0lINwo1CNSgARIEMTMzNhiLkgEgy7EBKOyKhAMwkYyEAzhPQABYAWoHRElTQ0lOVHIIT0YwRFNJSDcSCggBEAEYASoCVFAYASIECAEQASgCKAMoBDAN) ![Scandinavian Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SK.gif) Sat, 15 Nov - Sat, 22 Nov LHR London ORD Chicago £411 Return found 2 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LHR,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:LHR,departure:22/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:410.32&airProductToken=AQplCjEI05YBEgM1MDIY64kBIOI7KOyQ_QIw2pH9AjhUQABYAWoFTElHSFRyCFRMRVU2R0hUCjAI05YBEgM5NDMY4jsgrhwoqpL9AjDVlv0COFRAAVgBagVMSUdIVHIIVExFVTZHSFQKZQowCNOWARIDOTQ0GK4cIOI7KNDm_QIwter9AjhUQABYAWoFTElHSFRyCFRMRVU2R0hUCjEI05YBEgM1MDUY4jsg64kBKMPs_QIwwO39AjhUQAFYAWoFTElHSFRyCFRMRVU2R0hUEgoIARABGAEqAlNLGAEiBAgBEAEoAigDKAQwAQ) ![Icelandair](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/fi.gif) Wed, 7 Jan - Thu, 15 Jan LGW London ORD Chicago £446 Return just found [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LGW,to:ORD,departure:07/01/2026TANYT&leg2=from:ORD,to:LGW,departure:15/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:445.18&airProductToken=AQplCjEIxpIBEgM0NzEYy7EBIIopKOvlgQMwuOeBAzhPQABYAWoFTElHSFRyCE9KMlFHQkxUCjAIxpIBEgM4NTMYiikgrhwo_ueBAzCY64EDOE9AAVgBagVMSUdIVHIIT0oyUUdCTFQKZQowCMaSARIDODUyGK4cIIopKN7FggMw1ciCAzhPQABYAWoFTElHSFRyCE9KMlFHQkxUCjEIxpIBEgM0NzAYiikgy7EBKIzJggMwz8qCAzhPQAFYAWoFTElHSFRyCE9KMlFHQkxUEgoIARABGAEqAkZJGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, 3 Dec - Wed, 10 Dec LGW London ORD Chicago £485 Return found 8 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LGW,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:LGW,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:484.18&airProductToken=AQqbAQoyCMGCARIENzAxMhjLsQEgzHAo6Nv-AjC24P4COE9AAFgBagVCQVNJQ3IIT0xVMUMxQjQKMQjBggESAzg2MxjMcCDimgEo0-H-AjC_4v4COEJAAVgBagVCQVNJQ3IIT0xVMUMxQjQKMgjBggESBDEwMzkY4poBIK4cKLLj_gIws-T-AjhCQAFYAWoFQkFTSUNyCE9MVTFDMUI0CpwBCjIIwYIBEgQxMDg2GK4cIOKaASjMrP8CMMyt_wI4QkAAWAFqBUJBU0lDcghPTFg4QzFCNAoyCMGCARIEMTMwMRjimgEg8wMo7a7_AjDXr_8COEJAAVgBagVCQVNJQ3IIT0xYOEMxQjQKMgjBggESBDcwMTQY8wMgy7EBKN6w_wIw3LT_AjhPQAFYAWoFQkFTSUNyCE9MWDhDMUI0EgoIAhABGAIqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Swiss International Air Lines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/LX.gif) Mon, 16 Feb - Thu, 26 Feb LCY London ORD Chicago £487 Return found 6 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LCY,to:ORD,departure:16/02/2026TANYT&leg2=from:ORD,to:LCY,departure:26/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:486.11&airProductToken=AQppCjQIzLABEgM0NjUYy8ABILk8KM6qhQMwrauFAzhLQABYAWoIRUNPTElHSFRyCEtMVTVEWEJRCjEIzLABEgE4GLk8IK4cKJqzhQMw_LeFAzhLQAFYAWoIRUNPTElHSFRyCEtMVTVEWEJRCmkKMQjMsAESATkYrhwguTwosp6GAzDEooYDOEtAAFgBaghFQ09MSUdIVHIIS0xVNURYQlEKNAjMsAESAzQ1Nhi5PCDLwAEonqOGAzCCpIYDOEtAAVgBaghFQ09MSUdIVHIIS0xVNURYQlESCggCEAEYAioCTFgYASIECAEQASgCKAMoBDAL) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (MDW) ### August is typically the cheapest month to fly From £66 - £417 per traveller. ## Frequently asked questions ### How do I find cheap flights to South Side that have flexible change policies? > When it comes to travelling these days, flexibility is crucial. That's why we have a "No change fee" search function to help you track down flexible, affordable tickets to South Side. It's near the top left of your screen directly underneath the "Flexible change policies" subheading. ### Which airlines fly to South Side? > When you're ready to book your ticket to or near South Side, these well-known airlines look forward to welcoming you aboard: > > > > - United Airlines - 12,950 flights to or near South Side each month, including 12,950 flights to O'Hare Intl. Airport (ORD) per month. > - American Airlines - 8,855 flights to or near South Side each month, including 8,855 flights to O'Hare Intl. Airport (ORD) per month. > - Delta Air Lines - 1,222 flights to or near South Side each month, including 1,222 flights to O'Hare Intl. Airport (ORD) per month. ### How can I find cheap tickets to South Side? > Book well ahead of time, consider nearby airports, avoid peak travel periods — you're not short of ways! One more is to use Expedia's "flexible dates" function. Find a South Side flight, then compare the prices for nearby dates. In the last seven days, the lowest price for a flight to South Side was £399. ### How much is a flight to South Side? > In the last seven days, return tickets to South Side sold from just £399 and reached a maximum price of £487. For one-way journeys departing from London (LGW), the lowest price during this time was only £314. ### What are the most popular airports to fly into in South Side? > Get set to pack your bags and fly into O'Hare Intl. Airport (ORD), South Side's major flight hub. Lock in a seat on one of the 25,318 flights that touch down at this top destination every month. ### When is the cheapest time to fly to South Side? > Jet off on a Tuesday to increase your chances of picking up the cheapest deal to South Side. Mondays are usually the second most affordable day to depart. Saturday is typically the costliest day to fly anywhere. ### How much is a plane ticket to South Side? > In the last seven days, tickets to South Side varied between £399 and £487. Prices generally depend on the departure time, cabin class, airline and how early the fare is booked. ### What months are the cheapest to book a flight to South Side? > February is the most affordable month to book your South Side holiday. Tickets are at a premium during the month of December, so keep clear of this time if you can. ## Book with confidence ### Expedia flights to South Side Searching for cheap flights to South Side? No travel company presents more choices than Expedia if you're looking to compare flights to South Side. With more airlines, cheaper flights, fewer stops, and more departure and arrival times travellers should ensure they search on Expedia before any holiday to Chicago. Expedia provides the cheapest flights to many destinations in Chicago and you may find even greater savings if you combine your flight with a hotel stay in South Side. Expedia is the largest online travel agency which means that Expedia have access to cheap flights. So make sure you check Expedia regularly for these bargain flights because the cheapest airline tickets sell out fast. Expedia is not only free for everyone to use but it quick and easy to use. Find the lowest flight prices guaranteed and book directly through Expedia. Browse through hundreds of cheap flight offers to find the one that suits your budget by simply inputting your travel dates. Expedia will then find the cheapest flights to South Side for that period and let you choose your preferred time and airline. If you need additional assistance, Expedia Customer Service representatives are available from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends. Our capable staff will be able to help you with any questions regarding your South Side flight, or other booking questions that may arise. When you book flights with Expedia you can rest assured that you have booked the best flight at the lowest price. ## Travel information | Destination airport | O'Hare Intl. | | --- | --- | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Return price | £398 | ## Trending flights to South Side Prices were available within the past 7 days and start at £314 for one-way flights and £399 for round trip, for the period specified. Be sure to select the 'Direct flights only' box above if you are looking for a non stop route. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![TAP Portugal](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TP.gif) Thu, 29 Jan - Sun, 1 Feb LGW London ORD Chicago £399 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:LGW,to:ORD,departure:29/01/2026TANYT&leg2=from:ORD,to:LGW,departure:01/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:398.38&airProductToken=AQpsCjUI1KABEgQxMzM3GMuxASCLkgEooN-DAzDA4IMDOE9AAFgBagdESVNDSU5UcghPRjBEU0lINwozCNSgARIDMjQzGIuSASCuHCjL6IMDMIXtgwM4T0AAWAFqB0RJU0NJTlRyCE9GMERTSUg3CmwKMwjUoAESAzI0NBiuHCCLkgEo8YWEAzDMiYQDOE9AAFgBagdESVNDSU5UcghPRjBEU0lINwo1CNSgARIEMTMzNhiLkgEgy7EBKOyKhAMwkYyEAzhPQABYAWoHRElTQ0lOVHIIT0YwRFNJSDcSCggBEAEYASoCVFAYASIECAEQASgCKAMoBDAN) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - [4 Star Hotels in McKinley Park](https://www.expedia.co.uk/4Star-McKinley-Park-Chicago-Hotels.s40-n6132389-0.Travel-Guide-Filter-Hotels) - 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[Hotels near Wintrust Arena](https://www.expedia.co.uk/Wintrust-Arena-Hotels.0-l553248634328853320-0.Travel-Guide-Filter-Hotels) - [Flights to Berwyn](https://www.expedia.co.uk/Cheap-Flights-To-Berwyn.d79328.Travel-Guide-Flights) - [Flights to Blue Island](https://www.expedia.co.uk/Cheap-Flights-To-Blue-Island.d80954.Travel-Guide-Flights) - [Flights to Central Chicago](https://www.expedia.co.uk/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights) - [Flights to Chicago](https://www.expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Cicero](https://www.expedia.co.uk/Cheap-Flights-To-Cicero.d89615.Travel-Guide-Flights) - [Flights to Darien](https://www.expedia.co.uk/Cheap-Flights-To-Darien.d181404.Travel-Guide-Flights) - [Flights to Evanston](https://www.expedia.co.uk/Cheap-Flights-To-Evanston.d8049.Travel-Guide-Flights) - [Flights to Far North Side](https://www.expedia.co.uk/Cheap-Flights-To-Far-North-Side.d553248635976475356.Travel-Guide-Flights) - [Flights to Far Southwest Side](https://www.expedia.co.uk/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights) - [Flights to Harvey](https://www.expedia.co.uk/Cheap-Flights-To-Harvey.d8292.Travel-Guide-Flights) - [Flights to Hillside](https://www.expedia.co.uk/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights) - [Flights to Hometown](https://www.expedia.co.uk/Cheap-Flights-To-Hometown.d6132133.Travel-Guide-Flights) - [Flights to Lavergne](https://www.expedia.co.uk/Cheap-Flights-To-Lavergne.d6132171.Travel-Guide-Flights) - [Flights to Melrose Park](https://www.expedia.co.uk/Cheap-Flights-To-Melrose-Park.d8800.Travel-Guide-Flights) - [Flights to North Side](https://www.expedia.co.uk/Cheap-Flights-To-North-Side.d553248635976475406.Travel-Guide-Flights) - [Flights to Northwest Side](https://www.expedia.co.uk/Cheap-Flights-To-Northwest-Side.d553248635976475367.Travel-Guide-Flights) - [Flights to O'Hare Intl.](https://www.expedia.co.uk/Cheap-Flights-To-OHare-Intl.d4477519.Travel-Guide-Flights) - [Flights to Oak Brook](https://www.expedia.co.uk/Cheap-Flights-To-Oak-Brook.d9218.Travel-Guide-Flights) - [Flights to Oak Lawn](https://www.expedia.co.uk/Cheap-Flights-To-Oak-Lawn.d9227.Travel-Guide-Flights) - [Flights to Orland Park](https://www.expedia.co.uk/Cheap-Flights-To-Orland-Park.d9270.Travel-Guide-Flights) - [Flights to Park Ridge](https://www.expedia.co.uk/Cheap-Flights-To-Park-Ridge.d143564.Travel-Guide-Flights) - [Flights to Riverdale](https://www.expedia.co.uk/Cheap-Flights-To-Riverdale.d6132178.Travel-Guide-Flights) - [Flights to Rosemont](https://www.expedia.co.uk/Cheap-Flights-To-Rosemont.d7581.Travel-Guide-Flights) - [Flights to Rush Street](https://www.expedia.co.uk/Cheap-Flights-To-Rush-Street.d6175183.Travel-Guide-Flights) - [Flights to Skokie](https://www.expedia.co.uk/Cheap-Flights-To-Skokie.d6903.Travel-Guide-Flights) - [Flights to South Suburbs](https://www.expedia.co.uk/Cheap-Flights-To-South-Suburbs.d6264251.Travel-Guide-Flights) - [Flights to Southwest Side](https://www.expedia.co.uk/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights) - [Flights to Tinley Park](https://www.expedia.co.uk/Cheap-Flights-To-Tinley-Park.d55204.Travel-Guide-Flights) - [Flights to Willowbrook](https://www.expedia.co.uk/Cheap-Flights-To-Willowbrook.d7870.Travel-Guide-Flights) - [Flights to Wilmette](https://www.expedia.co.uk/Cheap-Flights-To-Wilmette.d54976.Travel-Guide-Flights) - [Visit Grand Boulevard](https://www.expedia.co.uk/Chicago-Grand-Boulevard.dx6132310) - [Visit Hyde Park](https://www.expedia.co.uk/Chicago-Hyde-Park.dx117842) - [Visit Jackson Park Highlands](https://www.expedia.co.uk/Chicago-Jackson-Park-Highlands.dx6132329) - [Visit Near South Side](https://www.expedia.co.uk/Chicago-Near-South-Side.dx6132399) - [Visit Prairie District](https://www.expedia.co.uk/Chicago-Prairie-District.dx553248635976473159) - [Visit South Commons](https://www.expedia.co.uk/Chicago-South-Commons.dx6132263) - [Chicago Holidays](https://www.expedia.co.uk/Chicago.d178248.Holidays-City-Breaks) - [Essex Holidays](https://www.expedia.co.uk/Essex.d6132371.Holidays-City-Breaks) - [Hyde Park Holidays](https://www.expedia.co.uk/Hyde-Park.d117842.Holidays-City-Breaks) - [Robie House](https://www.expedia.co.uk/Robie-House-Hyde-Park.d6064059.Attraction) - [Sr Crown Hall](https://www.expedia.co.uk/SR-Crown-Hall-Bronzeville.d553248621533116346.Attraction) - [S.s. Peter and Paul Church](https://www.expedia.co.uk/SS-Peter-And-Paul-Church-McKinley-Park.d6247219.Attraction) - [Car hire near Lake Meadows Park](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lake-Meadows-Park.d6132351.Car-Hire-Guide) - [Enterprise Rental Cars in Hyde Park](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Hyde-Park.d117842-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in Southwest Side](https://www.expedia.co.uk/Enterprise-Car-Rentals-In-Southwest-Side.d553248635976475403-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Hyde Park](https://www.expedia.co.uk/Europcar-Car-Rentals-In-Hyde-Park.d117842-c14.Car-Rental-Guide-Suppliers) \*Available to Expedia members.