Title: £518 Cheap Flights from Sydney to Chicago (SYD to ORD) - Expedia.co.uk ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # £518 Cheap Flights from Sydney (SYD) to Chicago (ORD) [View £518 flight on Tue, 28 Oct 2025](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:SYD,to:ORD,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:517.30&airProductToken=AQpkCjEIxbIBEgM0NTEYkh4ggD0oj8T7AjDmyvsCOEVAAFgBagZZQkFTSUNyCEVOTjAwSDVUCi8IxbIBEgE5GIA9IK4cKIvM-wIwj9P7AjhFQAFYAWoGWUJBU0lDcghFTk4wMEg1VBIKCAEQARgBKgJFWRgBIgQIARABKAIoAygEMAE) - [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 ## Popular airlines from Sydney Airport (SYD) to Chicago O'Hare International Airport (ORD) - ![Emirates](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_EK.svg) Emirates [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"EK"}}]) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![Qantas Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QF.svg) Qantas Airways [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QF"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Cathay Pacific](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_CX.svg) Cathay Pacific [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"CX"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Air New Zealand](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NZ.svg) Air New Zealand [](https://www.expedia.co.uk/Flights-Search?leg1=from:syd,to:ord,departure:29/10/2025TANYT&leg2=from:ord,to:syd,departure:05/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NZ"}}]) ![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 Flights from Sydney (SYD) to Chicago (ORD) Prices were available within the past 7 days and start at £518 for one-way flights and £921 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, 8 Nov - Mon, 24 Nov SYD Sydney ORD Chicago £921 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:920.90&airProductToken=AQqDAQopCMGGARICMzQYkh4guI0BKLS9_AIwmsT8AjhHQABYAXIIR0xXTzkyQkEKKgjBhgESAzMwNBi4jQEgmF0osMX8AjDIx_wCOEdAAVgBcghHTkExQTBCQQoqCMGGARIEODk2NxiYXSCuHCiTyPwCMLjJ_AI4R0ABWAFyCEdOQTFBMEJBCoMBCioIwYYBEgQ4OTU4GK4cIJhdKLH3_QIwrvj9AjhHQABYAXIIR05BMUEwQkEKKgjBhgESAzMxMRiYXSC4jQEomPz9AjDi_v0COEdAAVgBcghHTkExQTBCQQopCMGGARICMzMYuI0BIJIeKND__QIwi4f-AjhHQAFYAXIIR0xYTzkyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAB) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, 8 Nov - Mon, 24 Nov SYD Sydney ORD Chicago £926 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:925.80&airProductToken=AQqEAQopCMGGARICMzQYkh4guI0BKLS9_AIwmsT8AjhHQABYAXIIR0xXTzkyQkEKKwjBhgESAzEwNhi4jQEgmM4BKLrF_AIwvsf8AjhHQAFYAXIIR05BMUEwQkEKKgjBhgESAzUwORiYzgEgrhwoosj8AjCayfwCOEdAAVgBcghHTkExQTBCQQqDAQoqCMGGARIEODk1OBiuHCCYXSix9_0CMK74_QI4R0AAWAFyCEdOQTFBMEJBCioIwYYBEgMzMTEYmF0guI0BKJj8_QIw4v79AjhHQAFYAXIIR05BMUEwQkEKKQjBhgESAjMzGLiNASCSHijQ__0CMIuH_gI4R0ABWAFyCEdMWE85MkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, 8 Nov - Mon, 24 Nov SYD Sydney ORD Chicago £937 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:936.50&airProductToken=AQpYCikIwYYBEgIzNBiSHiC4jQEotL38AjCaxPwCOEdAAFgBcghHTFdPOTJCQQorCMGGARIEMTA0OBi4jQEgrhwo_sT8AjD5xvwCOEdAAVgBcghHTkExQTBCQQqDAQoqCMGGARIEODk1OBiuHCCYXSix9_0CMK74_QI4R0AAWAFyCEdOQTFBMEJBCioIwYYBEgMzMDUYmF0guI0BKPH5_QIwy_z9AjhHQAFYAXIIR05BMUEwQkEKKQjBhgESAjMzGLiNASCSHijQ__0CMIuH_gI4R0ABWAFyCEdMWE85MkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, 8 Nov - Sat, 15 Nov SYD Sydney ORD Chicago £940 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:939.40&airProductToken=AQpYCikIwYYBEgIzNBiSHiC4jQEotL38AjCaxPwCOEdAAFgBcghHTFdPOTJCQQorCMGGARIEMTA0OBi4jQEgrhwo_sT8AjD5xvwCOEdAAVgBcghHTkExQTBCQQqDAQoqCMGGARIEODk1OBiuHCCYXSiRkv0CMI6T_QI4R0AAWAFyCEdOQTFBMEJBCioIwYYBEgMzMTEYmF0guI0BKPiW_QIwwpn9AjhHQAFYAXIIR05BMUEwQkEKKQjBhgESAjMzGLiNASCSHiiwmv0CMOuh_QI4R0ABWAFyCEdMV085MkJBEgoIARABGAEqAkFDGAEiBAgBEAEoAigDKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Sat, 8 Nov - Mon, 24 Nov SYD Sydney ORD Chicago £942 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:24/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:941.40&airProductToken=AQqEAQopCMGGARICMzQYkh4guI0BKLS9_AIwmsT8AjhHQABYAXIIR0xXTzkyQkEKKwjBhgESAzEwNhi4jQEgmM4BKLrF_AIwvsf8AjhHQAFYAXIIR05BMUEwQkEKKgjBhgESAzUwORiYzgEgrhwoosj8AjCayfwCOEdAAVgBcghHTkExQTBCQQpYCisIwYYBEgQxMDQ5GK4cILiNASi0-_0CMMf9_QI4R0AAWAFyCEdOQTFBMEJBCikIwYYBEgIzMxi4jQEgkh4o0P_9AjCLh_4COEdAAVgBcghHTFhPOTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMAE) ![Qantas Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/QF.gif) Sat, 8 Nov - Sat, 15 Nov SYD Sydney ORD Chicago £1,003 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1003.00&airProductToken=AQpUCigI0YwBEgQ0MTExGJIeIIu4ASi0vfwCMO3D_AI4T0AAWAFyBU9KVzRCCigI0YwBEgQ0NTQ4GIu4ASCuHCiAxvwCMPjH_AI4T0ABWAFyBU9KVzRCClQKKAjRjAESBDQ1NDgYrhwgi7gBKKOX_QIwupn9AjhPQABYAXIFT0pXNEIKKAjRjAESBDQxMTIYi7gBIJIeKLWa_QIwyKH9AjhPQAFYAXIFT0pXNEISCggBEAEYASoCUUYYASIECAEQASgCKAMoBDAB) ![Cathay Pacific](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/CX.gif) Wed, 5 Nov - Fri, 7 Nov SYD Sydney ORD Chicago £1,073 Return found 6 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:05/11/2025TANYT&leg2=from:ORD,to:SYD,departure:07/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1072.60&airProductToken=AQpsCjQIw7ABEgMxNjIYkh4gxzIoxZv8AjD6n_wCOE5AAFgBaglFQ09OTElHSFRyCE5SMjFBVUlSCjQIw7ABEgM4MDYYxzIgrhwo86j8AjDPr_wCOE5AAVgBaglFQ09OTElHSFRyCE5SMjFBVUlSCmwKNAjDsAESAzgwNxiuHCDHMijTu_wCMI7D_AI4TkAAWAFqCUVDT05MSUdIVHIITlIyMUFVSVIKNAjDsAESAzE2MRjHMiCSHijAw_wCMOvH_AI4TkABWAFqCUVDT05MSUdIVHIITlIyMUFVSVISCggBEAEYASoCQ1gYASIECAEQASgCKAMoBDAB) ![Turkish Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TK.gif) Sat, 8 Nov - Sat, 15 Nov SYD Sydney ORD Chicago £1,097 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1096.60&airProductToken=AQpUCigI1JYBEgMxNzUYkh4gyJwBKIfC_AIwkcz8AjhXQABYAXIGV0YzWFBDCigI1JYBEgMxODUYyJwBIK4cKPPV_AIwpdv8AjhXQAFYAXIGV0YzWFBDClIKJgjUlgESATYYrhwgyJwBKKyY_QIwrJ39AjhXQABYAXIGV0YzWFBDCigI1JYBEgMxNzQYyJwBIJIeKJWo_QIw1LH9AjhXQAFYAXIGV0YzWFBDEgoIARABGAEqAlRLGAEiBAgBEAEoAigDKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, 26 Oct - Wed, 29 Oct SYD Sydney ORD Chicago £1,158 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:26/10/2025TANYT&leg2=from:ORD,to:SYD,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1157.90&airProductToken=AQpYCikIwYIBEgI3MhiSHiCLuAEolKv7AjDNsfsCOE9AAFgBcghPTFcwQVROMAorCMGCARIEMTAwORiLuAEgrhwow7n7AjC1u_sCOE9AAVgBcghPTFgwQVROMApaCisIwYIBEgQyNDk5GK4cIKOxASiZ1_sCMLTY-wI4T0AAWAFyCE9MWDBBVE4wCisIwYIBEgQ3MjYyGKOxASCSHiiW2fsCMKvh-wI4T0ABWAFyCE9MWDBBVE4wEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![All Nippon Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/NH.gif) Fri, 17 Jul - Mon, 20 Jul SYD Sydney ORD Chicago £1,205 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:17/07/2026TANYT&leg2=from:ORD,to:SYD,departure:20/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1204.50&airProductToken=AQqEAQopCM6QARIDODgwGJIeIKcbKI_KkgMw3c6SAzhVQABYAXIIVUZBNFRRWVUKKgjOkAESAzEyNhinGyCLuAEo9dWSAzDr2pIDOFVAAVgBcghVRkE0VFFZVQorCM6QARIENzI0MBiLuAEgrhwomd6SAzCd4JIDOExAAVgBcghMRkE3VFFZTApWCikIzpABEgMxMTEYrhwgpxsotfGSAzDf95IDOExAAFgBcghMRkE3VFFZTAopCM6QARIDODc5GKcbIJIeKLn4kgMw_fySAzhMQAFYAXIITEZBN1RRWUwSCggBEAEYASoCTkgYASIECAEQASgCKAMoBDAB) ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.co.uk/Flights-Search?leg1=from:SYD,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:SYD,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from £1,069](https://www.expedia.co.uk/Flights-Search?leg1=from:SYD,to:ORD,departure:29/10/2025TANYT&leg2=from:ORD,to:SYD,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Sydney to Chicago route information | Origin airport | Kingsford Smith Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | Air Canada, Air New Zealand, All Nippon Airways, Asiana Airlines, Cathay Pacific, Emirates, Etihad Airways, Fiji Airways, JetBlue Airways, Korean Air, Qantas Airways, Qatar Airways, Turkish Airlines | | Return price | £921 | | Distance | 14775 km | ## Compare flights from Sydney to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Sydney to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Kingsford Smith Intl. to O'Hare Intl..   To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.  Grab a great deal on your flight from Kingsford Smith Intl. (SYD) to O'Hare Intl. (ORD) The easiest way to view the best deals on flights from Sydney to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Kingsford Smith Intl. to O'Hare Intl. start at just £921 and range up to £1,205.   To find an even better deal, try   - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Sydney and Chicago - booking your flight during November, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper  Why you should book your Sydney to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Kingsford Smith Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.   Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.   ## Frequently asked questions ### How much is a flight from SYD to ORD? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price quoted for a round-trip flight between Mascot Airport and ORD was £921. Great fares don't last forever, so book yours today. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Sydney Airport to O'Hare Airport? > This varies from airline to airline, as each has its own set of terms and conditions. Head to the [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033), where there are easy-to-follow instructions on how to cancel your flight online. ### How do I find cheap flights from Mascot Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for SYD to ORD flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from Kingsford Smith Intl. Airport (SYD) to O'Hare Intl. Airport (ORD)? > The distance is around 14,900 kilometres. Travel pillow? Check. Toiletries? Double check. We recommend you pack all the essentials for this long-haul Sydney to Chicago flight. ### Which airlines fly direct from Mascot Airport to O'Hare Intl. Airport (ORD)? > Direct flights aren't available, so you'll have to make at least one stop between Sydney Airport and ORD. Make the most of the layover time to stretch your legs and freshen up. ### Are Sydney Airport to ORD flight tickets cheaper when they're purchased at the last minute? > Booking your trip from Sydney Airport to O'Hare Airport at the last minute could save you some cash. However, it might cost you a whole lot more! If you'd prefer not to take the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Lake Of The Ozarks (AIZ) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/aiz/chi/lake-of-the-ozarks-to-chicago) - [Flights from Amsterdam (AMS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ams/chi/amsterdam-to-chicago) - [Flights from Atlanta (ATL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/atl/chi/atlanta-to-chicago) - [Flights from Abu Dhabi (AUH) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/auh/mdw/abu-dhabi-to-chicago) - [Flights from Wilkes-Barre (AVP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/avp/chi/wilkes-barre-to-chicago) - [Flights from Beirut (BEY) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bey/chi/beirut-to-chicago) - [Flights from Birmingham (BHX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bhx/chi/birmingham-to-chicago) - [Flights from Bitam (BMM) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bmm/chi/bitam-to-chicago) - [Flights from Basel (BSL) to Chicago (PWK)](https://www.expedia.co.uk/lp/flights/bsl/pwk/basel-to-chicago) - [Flights from Burbank (BUR) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/bur/mdw/burbank-to-chicago) - [Flights from Baltimore (BWI) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bwi/chi/baltimore-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Carlisle (CAX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/cax/chi/carlisle-to-chicago) - [Flights from Cambridge (CBG) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/cbg/chi/cambridge-to-chicago) - [Flights from Chub Cay (CCZ) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ccz/chi/chub-cay-to-chicago) - [Flights from Craig (CGA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/cga/chi/craig-to-chicago) - 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[Flights from Edinburgh (EDI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/edi/mdw/edinburgh-to-chicago) - [Flights from Emden (EME) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/eme/chi/emden-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Frankfurt (FRA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/fra/chi/frankfurt-to-chicago) - [Flights from Galesburg (GBG) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gbg/mdw/galesburg-to-chicago) - [Flights from Glasgow (GLA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gla/mdw/glasgow-to-chicago) - [Flights from Geneva (GVA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gva/mdw/geneva-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Hull (HUY) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/huy/mdw/hull-to-chicago) - [Flights from Washington (IAD) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/iad/mdw/washington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/ind/mdw/indianapolis-to-chicago) - [Flights from Isle of Man (IOM) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/iom/chi/isle-of-man-to-chicago) - [Flights from Iowa City (IOW) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/iow/mdw/iowa-city-to-chicago) - [Flights from Istanbul (IST) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ist/chi/istanbul-to-chicago) - [Flights from Jacksonville (JAX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/jax/chi/jacksonville-to-chicago) - [Flights from New York (JFK) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/jfk/mdw/new-york-to-chicago) - [Flights from Kigali (KGL) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/kgl/mdw/kigali-to-chicago) - [Flights from Karachi (KHI) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/khi/chi/karachi-to-chicago) - [Flights from Kaluga (KLF) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/klf/chi/kaluga-to-chicago) - [Flights from Kitadaito (KTD) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ktd/chi/kitadaito-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Le Havre (LEH) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/leh/chi/le-havre-to-chicago) - [Flights from London (LGW) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/lgw/mdw/london-to-chicago) - [Flights from London (LHR) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/lhr/mdw/london-to-chicago) - [Flights from Milan (LIN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lin/chi/milan-to-chicago) - [Flights from Little Rock (LIT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lit/chi/little-rock-to-chicago) - [Flights from Klamath Falls (LMT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lmt/chi/klamath-falls-to-chicago) - [Flights from London (LON) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/lon/ugn/london-to-waukegan) - [Flights from Liverpool (LPL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lpl/chi/liverpool-to-chicago) - [Flights from La Rochelle (LRH) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lrh/chi/la-rochelle-to-chicago) - [Flights from Lawrence (LWC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lwc/chi/lawrence-to-chicago) - [Flights from Manchester (MAN) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/man/mdw/manchester-to-chicago) - [Flights from Kansas City (MCI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/mci/mdw/kansas-city-to-chicago) - [Flights from Memphis (MEM) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/mem/ugn/memphis-to-waukegan) - [Flights from Mexico City (MEX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mex/chi/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mia/chi/miami-to-chicago) - [Flights from Malta (MLK) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mlk/chi/malta-to-chicago) - [Flights from Durham (MME) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/mme/mdw/durham-to-chicago) - [Flights from Manila (MNL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mnl/chi/manila-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from Naples (NAP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/nap/chi/naples-to-chicago) - [Flights from Nottingham (NQT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/nqt/chi/nottingham-to-chicago) - [Flights from Newcastle (NTL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ntl/chi/newcastle-to-chicago) - [Flights from Norwich (NWI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/nwi/mdw/norwich-to-chicago) - [Flights from Obock (OBC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/obc/chi/obock-to-chicago) - [Flights from Chicago (ORD) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/ord/ugn/chicago-to-waukegan) - [Flights from Paris (PAR) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/par/chi/paris-to-chicago) - [Flights from Portland (PDX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pdx/chi/portland-to-chicago) - [Flights from Portland (PDX) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/pdx/mdw/portland-to-chicago) - [Flights from Beijing (PEK) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pek/chi/beijing-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/phl/chi/philadelphia-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (PWK)](https://www.expedia.co.uk/lp/flights/phl/pwk/philadelphia-to-chicago) - [Flights from Phoenix (PHX) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/phx/mdw/phoenix-to-chicago) - [Flights from Port of Spain (POS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pos/chi/port-of-spain-to-chicago) - [Flights from Los Angeles (QLA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/qla/chi/los-angeles-to-chicago) - [Flights from Yangon (RGN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rgn/chi/yangon-to-chicago) - [Flights from Rishiri (RIS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ris/chi/rishiri-to-chicago) - [Flights from Rome (ROM) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rom/chi/rome-to-chicago) - [Flights from Rondon (RON) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ron/chi/rondon-to-chicago) - [Flights from Ruteng (RTG) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rtg/chi/ruteng-to-chicago) - [Flights from Louisville (SDF) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sdf/chi/louisville-to-chicago) - [Flights from Seattle (SEA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sea/chi/seattle-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/slc/chi/salt-lake-city-to-chicago) - [Flights from Sacramento (SMF) to Chicago (PWK)](https://www.expedia.co.uk/lp/flights/smf/pwk/sacramento-to-chicago) - [Flights from St. Cloud (STC) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/stc/mdw/st-cloud-to-chicago) - [Flights from Stockholm (STO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sto/chi/stockholm-to-chicago) - [Flights from Swansea (SWS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sws/chi/swansea-to-chicago) - [Flights from Sydney (SYD) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/syd/chi/sydney-to-chicago) - [Flights from Topeka (TOP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/top/chi/topeka-to-chicago) - [Flights from Winchester (WGO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/wgo/chi/winchester-to-chicago) - [Flights from Winton (WIN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/win/chi/winton-to-chicago) - [Flights from Tsiroanomandidy (WTS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/wts/chi/tsiroanomandidy-to-chicago) - [Flights from Fayetteville (XNA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/xna/mdw/fayetteville-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/yqg/mdw/windsor-to-chicago) - [Flights from Toronto (YTO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/yto/chi/toronto-to-chicago) \*Available to Expedia members.