Title: Cheap Flights to Oswego , IL from CA $155 - Expedia.ca ![Setting Sun](https://images.trvl-media.com/place/142441/b120e67f-cbdd-4376-a78c-263755ddd72d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Anthony Martinez ![](https://images.trvl-media.com/place/142441/b120e67f-cbdd-4376-a78c-263755ddd72d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Oswego , IL from CA $155 [View CA $155 flight on Tue, Jan 6, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:MDW,departure:06/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:154.60&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEo3NuBAzDK3IEDOE1AAFgBagVCQVNJQ3IITTJOMFpSWkwSCggBEAEYASoCUEQYASIECAEQASgCKAMoBDAB) - [Roundtrip](?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 [Hotels in Oswego](https://expedia.ca/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide)[Oswego Vacation Packages](https://expedia.ca/Oswego.d142441.Destination-Travel-Guides) ## Popular airlines to Oswego - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:Oswego, Illinois, United States of America,departure:05/12/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:12/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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 30% 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.ca/login) ## How much is the cheapest flight to Oswego? Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sat, May 2 - Thu, May 7 YTZ Toronto MDW Chicago CA $249 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:02/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:07/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.07&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEol_eLAzCE-IsDOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiQrYwDMPStjAM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Fri, Jan 23 - Sun, Jan 25 YHM Hamilton ORD Chicago CA $258 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YHM,to:ORD,departure:23/01/2026TANYT&leg2=from:ORD,to:YHM,departure:25/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.04&airProductToken=AQpnCjIIwYYBEgQyNDkyGPhhIJjOASjomoMDMKmbgwM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA1GJjOASCuHCihnIMDMJWdgwM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpoCjIIwYYBEgQ4OTAwGK4cIJjOASiosYMDMIyygwM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoyCMGGARIEMjQ5NRiYzgEg-GEop7ODAzDos4MDOEdAAVgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Mar 31 - Sun, May 3 YYZ Toronto ORD Chicago CA $258 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:31/03/2026TANYT&leg2=from:ORD,to:YYZ,departure:03/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.06&airProductToken=AQojCiEI1YIBEgQyMDY2GJjOASCuHCiHjIkDMP-MiQM4TkAAWAEKIwohCNWCARIEMzQ0MBiuHCCYzgEo-v6LAzDj_4sDOE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Feb 6 - Mon, Feb 9 YYC Calgary ORD Chicago CA $263 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:06/02/2026TANYT&leg2=from:ORD,to:YYC,departure:09/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:262.54&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKKC5hAMw97qEAzhBQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKITdhAMw796EAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Jan 23 - Mon, Jan 26 YYC Calgary ORD Chicago CA $263 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:23/01/2026TANYT&leg2=from:ORD,to:YYC,departure:26/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:262.64&airProductToken=AQozCjEIwYIBEgQ0MTYxGJgWIK4cKPidgwMw1J-DAzhCQABYAWoFQkFTSUNyCE9XQUNaTkJYCjMKMQjBggESBDQxNjEYrhwgmBYosb2DAzCkv4MDOEJAAFgBagVCQVNJQ3IIT1dBQ1pOQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From CA $109 - CA $409 per traveller. ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=FTG_BF_PROMO_) Expedia.ca gives you the best tools to secure great deals on flights to Oswego. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Oswego. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Oswego. Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Oswego flights with full confidence knowing that you've found the best deal online. Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Oswego. Looking to save even more? Get additional savings by bundling your Oswego flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Oswego trip! Flights to Oswego information | Destination airport | Midway Intl. | | --- | --- | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | CA $248 | ## Need more than a Flight to Oswego? Heading to Oswego? Explore Oswego with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Oswego Hotels](https://expedia.ca/Oswego-Hotels.d142441.Travel-Guide-Hotels)[Oswego Car Rentals](https://expedia.ca/Car-Rentals-In-Oswego.d142441.Car-Rental-Guide)[Oswego Vacations](https://expedia.ca/Oswego.d142441.Destination-Travel-Guides) ## Trending flights to Oswego Prices were available within the past 7 days and start at CA $155 for one-way flights and CA $249 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Porter Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/PD.gif) Sat, May 2 - Thu, May 7 YTZ Toronto MDW Chicago CA $249 Roundtrip found 3 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:02/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:07/05/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.07&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEol_eLAzCE-IsDOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiQrYwDMPStjAM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental ### Lodging - [Farmstay in Aurora](https://www.expedia.ca/Aurora-Agritourism.d6186-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Aurora](https://www.expedia.ca/Aurora-Apart-Hotels.d6186-aaApartHotels.Travel-Guide-Accommodation) - 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[Chicago Hotels](https://www.expedia.ca/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Hotels.0-l6260166-0.Travel-Guide-Filter-Hotels) - [Hotels near Hollywood Casino](https://www.expedia.ca/Hollywood-Casino-Hotels.0-l6065135-0.Travel-Guide-Filter-Hotels) - [Farmstay in Montgomery](https://www.expedia.ca/Montgomery-Agritourism.d6156952-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Montgomery](https://www.expedia.ca/Montgomery-Bed-And-Breakfast.d6156952-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Montgomery](https://www.expedia.ca/Montgomery-Chalets.d6156952-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Montgomery](https://www.expedia.ca/Montgomery-Guest-Houses.d6156952-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Montgomery](https://www.expedia.ca/Montgomery-Hotels-Cheap-Hotels.0-0-d6156952-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Montgomery](https://www.expedia.ca/Montgomery-Hotels-Luxury-Hotel.0-0-d6156952-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Montgomery](https://www.expedia.ca/Montgomery-Hotels-Waterpark-Hotels.0-0-d6156952-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Montgomery Hotels](https://www.expedia.ca/Montgomery-Hotels.d6156952.Travel-Guide-Hotels) - [Inns in Montgomery](https://www.expedia.ca/Montgomery-Inns.d6156952-aaInns.Travel-Guide-Accommodation) - [Motels in Montgomery](https://www.expedia.ca/Montgomery-Motels.d6156952-aaMotels.Travel-Guide-Accommodation) - [Hotels near Paramount Theater](https://www.expedia.ca/Paramount-Theater-Hotels.0-l6129536-0.Travel-Guide-Filter-Hotels) - [Hotels near Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Hotels.0-l553248621532658485-0.Travel-Guide-Filter-Hotels) - [Yorkville Hotels](https://www.expedia.ca/Yorkville-Hotels.d602761.Travel-Guide-Hotels) ### Flights - [Flights to Aurora](https://www.expedia.ca/Cheap-Flights-To-Aurora.d6186.Travel-Guide-Flights) - [Flights to Bolingbrook](https://www.expedia.ca/Cheap-Flights-To-Bolingbrook.d55064.Travel-Guide-Flights) - [Flights to Chicago](https://www.expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights) - [Flights to Darien](https://www.expedia.ca/Cheap-Flights-To-Darien.d181404.Travel-Guide-Flights) - [Flights to DeKalb](https://www.expedia.ca/Cheap-Flights-To-DeKalb.d7588.Travel-Guide-Flights) - [Flights to Downers Grove](https://www.expedia.ca/Cheap-Flights-To-Downers-Grove.d181500.Travel-Guide-Flights) - [Flights to Elmhurst](https://www.expedia.ca/Cheap-Flights-To-Elmhurst.d7836.Travel-Guide-Flights) - [Flights to Equestrian Estates](https://www.expedia.ca/Cheap-Flights-To-Equestrian-Estates.d6132179.Travel-Guide-Flights) - [Flights to Geneva](https://www.expedia.ca/Cheap-Flights-To-Geneva.d55721.Travel-Guide-Flights) - [Flights to Hickory Hills](https://www.expedia.ca/Cheap-Flights-To-Hickory-Hills.d6132128.Travel-Guide-Flights) - [Flights to Hillside](https://www.expedia.ca/Cheap-Flights-To-Hillside.d8353.Travel-Guide-Flights) - [Flights to Itasca](https://www.expedia.ca/Cheap-Flights-To-Itasca.d8201.Travel-Guide-Flights) - 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[Flights to Northwest Chicago](https://www.expedia.ca/Cheap-Flights-To-Northwest-Chicago.d6350697.Travel-Guide-Flights) - [Flights to Oak Brook](https://www.expedia.ca/Cheap-Flights-To-Oak-Brook.d9218.Travel-Guide-Flights) - [Flights to Plainfield](https://www.expedia.ca/Cheap-Flights-To-Plainfield.d601963.Travel-Guide-Flights) - [Flights to Romeoville](https://www.expedia.ca/Cheap-Flights-To-Romeoville.d9605.Travel-Guide-Flights) - [Flights to Sandwich](https://www.expedia.ca/Cheap-Flights-To-Sandwich.d6085096.Travel-Guide-Flights) - [Flights to St. Charles](https://www.expedia.ca/Cheap-Flights-To-St-Charles.d9747.Travel-Guide-Flights) - [Flights to Western Suburbs](https://www.expedia.ca/Cheap-Flights-To-Western-Suburbs.d6059325.Travel-Guide-Flights) - [Flights to Yorkville](https://www.expedia.ca/Cheap-Flights-To-Yorkville.d602761.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [Fox Valley Winery](https://www.expedia.ca/Fox-Valley-Winery-Oswego.d553248621532658490.Vacation-Attraction) - [Hollywood Casino Aurora](https://www.expedia.ca/Hollywood-Casino-Aurora-Aurora.d6260166.Vacation-Attraction) - [Hollywood Casino](https://www.expedia.ca/Hollywood-Casino-Aurora.d6065135.Vacation-Attraction) - [Hudson Crossing Park](https://www.expedia.ca/Hudson-Crossing-Park-Oswego.d553248621532658491.Vacation-Attraction) - [Raging Waves Waterpark](https://www.expedia.ca/Raging-Waves-Waterpark-Yorkville.d553248621532658485.Vacation-Attraction) ### Cars - [Car rentals in Budget 1426 State Route 66 Ste 101](https://www.expedia.ca/Budget-at-1426-State-Route-66-Ste-101-Flagstaff-Arizona-USA.v6186.Car-Rental-Guide-Location) - [Car rental Aurora](https://www.expedia.ca/Car-Rentals-In-Aurora.d6186.Car-Rental-Guide) - [Hertz Rental Cars in Aurora](https://www.expedia.ca/Hertz-Car-Rentals-In-Aurora.d6186-c40.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Aurora Vacation Rentals](https://www.expedia.ca/Aurora-Vacation-Rentals.d6186.Travel-Guide-VacationRentals) \*Available to Expedia members.