Title: Cheap Flights to Oswego , IL from CA $144 - 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 $144 [View CA $144 flight on Mon, Apr 13, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:MDW,departure:13/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:143.79&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEo9qCKAzDkoYoDOFFAAFgBagNCR1RyCFEyTjBaUlpMEgoIARABGAEqAlRTGAEiBAgBEAEoAigDKAQwDQ) - [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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:19/10/2025TANYT&leg2=from:Oswego, Illinois, United States of America,to:CMH,departure:26/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ![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 $144 for one-way flights and CA $227 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) Mon, May 25 - Mon, Jun 1 YTZ Toronto MDW Chicago CA $227 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:25/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:01/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:226.31&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEoq_aNAzCZ940DOE1AAFgBagVCQVNJQ3IITTJOMFpSWkwKNQozCNCIARIEMjM5NBjssAEg-MwBKPzJjgMw4sqOAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ![Air Transat](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TS.gif) Fri, Mar 13 - Mon, Mar 16 YTZ Toronto MDW Chicago CA $227 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:13/03/2026TANYT&leg2=from:MDW,to:YTZ,departure:16/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:226.44&airProductToken=AQozCjEI1KYBEgQ3MzE0GPjMASDssAEolsSHAzCExYcDOFFAAFgBagNCR1RyCFEyTjBaUlpMCjMKMQjUpgESBDczMTUY7LABIPjMASib54cDMIHohwM4UUAAWAFqA0JHVHIIUTJOMFpSWkwSCggBEAEYASoCVFMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Feb 4 - Fri, Feb 6 YKF Kitchener ORD Chicago CA $236 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YKF,to:ORD,departure:04/02/2026TANYT&leg2=from:ORD,to:YKF,departure:06/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:235.48&airProductToken=AQpnCjIIwYYBEgQyNTA2GNgqIJjOASj3oYQDMLiihAM4R0AAWAFqBUJBU0lDcghHTkEyQTJCQQoxCMGGARIDNTA1GJjOASCuHCiho4QDMJWkhAM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQQpnCjEIwYYBEgM1MDYYrhwgmM4BKJC7hAMw87uEAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjIIwYYBEgQyNTEzGJjOASDYKijzvYQDMK--hAM4R0ABWAFqBUJBU0lDcghHTkEyQTJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Mar 31 - Fri, Apr 3 YYZ Toronto ORD Chicago CA $236 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:31/03/2026TANYT&leg2=from:ORD,to:YYZ,departure:03/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:235.62&airProductToken=AQojCiEI1YIBEgQzNjA1GJjOASCuHCi4jokDMK-PiQM4TkAAWAEKIwohCNWCARIEMzYwMRiuHCCYzgEo5K6JAzDNr4kDOE5AAFgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Mon, Mar 16 - Mon, Mar 23 YYC Calgary ORD Chicago CA $258 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:16/03/2026TANYT&leg2=from:ORD,to:YYC,departure:23/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.71&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKODkhwMwt-aHAzhFQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKMS1iAMwr7eIAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From CA $107 - CA $366 per traveller. ## Frequently asked questions ### What is the name of Oswego's airport? > O'Hare Intl. Airport (ORD) is the most frequently used airport in Oswego. ### How far is O'Hare Intl. Airport (ORD) from central Oswego? > O'Hare Intl. Airport (ORD) is 48 kilometres from downtown Oswego, so prepare yourself for a bit of a journey into the city centre. ### What airport is best to fly into Oswego? > Travellers flying into Oswego can land at two major airports. O'Hare Intl. Airport (ORD) is 48 kilometres away from the centre of town. Midway Intl. Airport (MDW) is 48 kilometres away. ### How many airlines fly to Oswego? > There are 51 air carriers that fly to Oswego from 237 airports around the world. ### Which airlines fly to Oswego? > Oswego receives most of its flights from United Airlines, American Airlines and Delta with United Airlines being the favourite choice of airline. New York is the most popular city for travellers to take off from. ### How many nonstop flights are there to Oswego? > Organizing an awesome Oswego vacation is child's play when there are 7,564 direct flights every week to choose from. ### Where are the most popular flights to Oswego departing from? > Flights to Oswego from New York, Washington and Dallas airports are very popular. ### How long is the flight to Oswego Airport? > Which airport you depart from determines how much of the in-flight entertainment you'll get to enjoy. From New York to Oswego, the average flight time is 2 hours and 44 minutes. From Washington it's roughly 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes. ### How to book the cheapest flight to Oswego? > If you want to have some extra spending money on your trip to Oswego, listen up! As every experienced jet-setter will tell you, avoid booking at the last minute. Prices are often highest close to the departure date. Another terrific way to grab an unbeatable deal is to research all options. If where you're headed has more than one airport, don't forget to research the cost of flying into a smaller terminal. Lastly, another simple way to save some money is be ready to book at a moment's notice. If you spot an irresistible bargain, don't hesitate — grab it while you've got the chance. ### Do you have any tips for my flight to Oswego? > Wherever you're coming from, flying can be a pleasurable experience if you've prepared well enough. We've compiled a list of handy hints that will help get your Oswego escape started on the right foot. What to pack in your hand luggage: > > > > - Air travel can be a pleasure if you bring the right things. First of all you'll need toiletry items, such as a toothbrush and some deodorant, a fresh change of clothes and something to read. Next, find room in your carry-on bag for your electronic devices, chargers, any medications and maybe a blow-up neck pillow as well. Lastly, and most importantly, don't forget to bring your passport, travel papers and some money. > > > > Do not pack the following items in your hand luggage: > > > > - Squeeze all your full-sized bottles of shampoo and hairspray in your checked baggage. Any liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp objects, like your trusty Swiss Army knife, and dangerous products which are flammable or explosive, such as aerosol cans, spray paint and fireworks, are also restricted. > > > > What to wear on a flight: > > > > - Comfort should be your top priority when choosing what to wear on your flight. Loose, breathable clothing is a wise choice, as are flat, closed-toe shoes. > - The result of sustained periods of inactivity, deep vein thrombosis (DVT) is a blood clotting condition that can affect some passengers on long-haul flights. Reduce the risks by staying hydrated, keeping your legs and ankles moving and wearing compression tights or socks. ### How to get through airport security fast when flying to Oswego? > Being prepared before you get to the airport will help make your trip to Oswego a pleasure. Below you'll find some handy tips and tricks for a stress-free journey past security: > > > > - Be sure to keep your ID and travel documents at hand. They'll be the first things you'll be asked to show at airport security. > - The X-ray machine is up next. Empty your pockets and remove anything that is likely to set off the scanner's alarm. This includes things like earphones or headphones, as well as your coat or jacket. They'll need to be placed on the conveyor belt for screening. > - For just a few minutes, you'll have to unplug from the digital world. Your laptop, phone and any other electronic devices also need to go through the scanner. > - Any liquids or gels, such as perfume or hand cream, that you want to bring on board need to be in containers no larger than 3.4 ounces (100 millilitres). They must also all fit inside a quart-size (one litre), clear zip-lock bag. > - It's also possible you'll be required to remove your shoes for scanning, so wearing slip-on shoes is always a smart idea. > - Sharp or pointed objects (like knives and scissors) are not allowed in the cabin. They'll be seized at security, so pack them in your checked baggage. ## Book with confidence 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! ## Travel information | Destination airport | Midway Intl. | | --- | --- | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | CA $226 | ## Trending flights to Oswego Prices were available within the past 7 days and start at CA $144 for one-way flights and CA $227 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) Mon, May 25 - Mon, Jun 1 YTZ Toronto MDW Chicago CA $227 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:25/05/2026TANYT&leg2=from:MDW,to:YTZ,departure:01/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:226.31&airProductToken=AQo1CjMI0IgBEgQyMzg3GPjMASDssAEoq_aNAzCZ940DOE1AAFgBagVCQVNJQ3IITTJOMFpSWkwKNQozCNCIARIEMjM5NBjssAEg-MwBKPzJjgMw4sqOAzhNQABYAWoFQkFTSUNyCE0yTjBaUlpMEgoIARABGAEqAlBEGAEiBAgBEAEoAigDKAQwAQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - [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) - 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[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) - [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) - [Aurora Vacation Rentals](https://www.expedia.ca/Aurora-Vacation-Rentals.d6186.Travel-Guide-VacationRentals) \*Available to Expedia members.