Title: Cheap Flights to Crestwood , IL from CA $155 - Expedia.ca ![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/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Cheap Flights to Crestwood , 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 Crestwood](https://expedia.ca/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Crestwood Car Rentals](https://expedia.ca/Car-Rentals-In-Crestwood.d6960.Car-Rental-Guide)[Crestwood Vacation Packages](https://expedia.ca/Crestwood.d6960.Destination-Travel-Guides) ## Popular airlines to Crestwood - ![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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&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:Crestwood, Illinois, United States of America,departure:02/12/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:09/12/2025TANYT&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 Crestwood? 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) Tue, Apr 7 - Tue, Apr 14 YTZ Toronto MDW Chicago CA $249 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:07/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.02&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEott2JAzCk3okDOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiAq4oDMOarigM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Wed, Jan 14 - Sun, Jan 18 YYZ Toronto ORD Chicago CA $258 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:YYZ,departure:18/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:257.06&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKIK6ggMw-rqCAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjMKMQjBhgESAzUxMBiuHCCYzgEotuiCAzCZ6YIDOEdAAFgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![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 7 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:31/03/2026TANYT&leg2=from:ORD,to:YYZ,departure:03/05/2026TANYT&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) Mon, Feb 2 - Fri, Feb 6 YYC Calgary ORD Chicago CA $263 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:02/02/2026TANYT&leg2=from:ORD,to:YYC,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:262.54&airProductToken=AQozCjEI16YBEgQxNjEwGJgWIK4cKKCMhAMw942EAzhBQABYAWoFQkFTSUNyCEFUVkQwWkJLCjMKMQjXpgESBDE2MTEYrhwgmBYopLuEAzCPvYQDOEFAAFgBagVCQVNJQ3IIQVRWRDBaQksSCggBEAEYASoCV1MYASIECAEQASgCKAMoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Jan 10 - Fri, Jan 16 YYZ Toronto ORD Chicago CA $264 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:10/01/2026TANYT&leg2=from:ORD,to:YYZ,departure:16/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:263.50&airProductToken=AQo0CjIIwYIBEgQzNjEwGJjOASCuHCikjYIDMJyOggM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAppCjIIwYIBEgQxNzg0GK4cIOKaASiVy4IDMJLMggM4QkAAWAFqBUJBU0lDcghPVkFDWlNCWAozCMGCARIENTAzMBjimgEgmM4BKKXOggMwos-CAzhCQAFYAWoFQkFTSUNyCE9WQUNaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ## 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. ## Alternative airports near Crestwood Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:ORD,departure:02/12/2025TANYT&leg2=from:ORD,to:CMH,departure:22/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 39 min [Flights from CA $429](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:ORD,departure:02/12/2025TANYT&leg2=from:ORD,to:CMH,departure:22/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:MDW,departure:02/12/2025TANYT&leg2=from:MDW,to:CMH,departure:25/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 15 min [Flights from CA $352](https://www.expedia.ca/Flights-Search?leg1=from:CMH,to:MDW,departure:02/12/2025TANYT&leg2=from:MDW,to:CMH,departure:25/12/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Expedia.ca gives you the best tools to secure great deals on flights to Crestwood. 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 Crestwood. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Crestwood. 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 Crestwood 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 Crestwood. Looking to save even more? Get additional savings by bundling your Crestwood 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 Crestwood trip! Flights to Crestwood information | Destination airport | Midway Intl. | | --- | --- | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | CA $248 | ## Need more than a Flight to Crestwood? Heading to Crestwood? Explore Crestwood with Expedia's Travel Guides to find the best hotels, vacation packages, car rental deals and more! [Crestwood Hotels](https://expedia.ca/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Crestwood Vacation Rentals](https://expedia.ca/Crestwood-Vacation-Rentals.d6960.Travel-Guide-VacationRentals) ## Trending flights to Crestwood 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) Tue, Apr 7 - Tue, Apr 14 YTZ Toronto MDW Chicago CA $249 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YTZ,to:MDW,departure:07/04/2026TANYT&leg2=from:MDW,to:YTZ,departure:14/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:248.02&airProductToken=AQokCiII0IgBEgQyMzkzGPjMASDssAEott2JAzCk3okDOE1AAFgBCiQKIgjQiAESBDIzODgY7LABIPjMASiAq4oDMOarigM4TUAAWAESCggBEAEYASoCUEQYASIECAEQASgEMAE) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other ### Lodging - [3 Star Hotels in Chicago Ridge](https://www.expedia.ca/3Star-Chicago-Ridge-Hotels.s30-0-d89160.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Alsip](https://www.expedia.ca/Alsip-Hotels-Cheap-Hotels.0-0-d6302-tCheapHotels.Travel-Guide-Filter-Hotels) - 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[Luxury Hotels in Palos Park](https://www.expedia.ca/Palos-Park-Hotels-Luxury-Hotel.0-0-d6132161-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Palos Park Hotels](https://www.expedia.ca/Palos-Park-Hotels.d6132161.Travel-Guide-Hotels) - [Resorts in Palos Park](https://www.expedia.ca/Palos-Park-Resort-Hotels.d6132161-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Trinity Christian College](https://www.expedia.ca/Trinity-Christian-College-Hotels.0-l6143660-0.Travel-Guide-Filter-Hotels) - [B&B in Worth](https://www.expedia.ca/Worth-Bed-And-Breakfast.d176696-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Hostels in Worth](https://www.expedia.ca/Worth-Hostels.d176696-aaHostels.Travel-Guide-Accommodation) - [Cheap Hotels in Worth](https://www.expedia.ca/Worth-Hotels-Cheap-Hotels.0-0-d176696-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Worth](https://www.expedia.ca/Worth-Hotels-Hotels-With-Hot-Tubs.0-0-d176696-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Worth](https://www.expedia.ca/Worth-Hotels-LGBT-Friendly-Hotel.0-0-d176696-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Worth Hotels](https://www.expedia.ca/Worth-Hotels.d176696.Travel-Guide-Hotels) ### Flights - [Flights to Berwyn](https://www.expedia.ca/Cheap-Flights-To-Berwyn.d79328.Travel-Guide-Flights) - [Flights to Bolingbrook](https://www.expedia.ca/Cheap-Flights-To-Bolingbrook.d55064.Travel-Guide-Flights) - [Flights to Bridgeview](https://www.expedia.ca/Cheap-Flights-To-Bridgeview.d7045.Travel-Guide-Flights) - [Flights to Broadview](https://www.expedia.ca/Cheap-Flights-To-Broadview.d7064.Travel-Guide-Flights) - [Flights to Burbank](https://www.expedia.ca/Cheap-Flights-To-Burbank.d183178.Travel-Guide-Flights) - [Flights to Central Chicago](https://www.expedia.ca/Cheap-Flights-To-Central-Chicago.d553248635976475413.Travel-Guide-Flights) - [Flights to Chicago Ridge](https://www.expedia.ca/Cheap-Flights-To-Chicago-Ridge.d89160.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 Downers Grove](https://www.expedia.ca/Cheap-Flights-To-Downers-Grove.d181500.Travel-Guide-Flights) - [Flights to Equestrian Estates](https://www.expedia.ca/Cheap-Flights-To-Equestrian-Estates.d6132179.Travel-Guide-Flights) - [Flights to Far Southwest Side](https://www.expedia.ca/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights) - [Flights to Frankfort](https://www.expedia.ca/Cheap-Flights-To-Frankfort.d106055.Travel-Guide-Flights) - [Flights to Harvey](https://www.expedia.ca/Cheap-Flights-To-Harvey.d8292.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 Homewood](https://www.expedia.ca/Cheap-Flights-To-Homewood.d8374.Travel-Guide-Flights) - [Flights to La Grange](https://www.expedia.ca/Cheap-Flights-To-La-Grange.d178165.Travel-Guide-Flights) - [Flights to Lemont](https://www.expedia.ca/Cheap-Flights-To-Lemont.d125294.Travel-Guide-Flights) - [Flights to Lyons](https://www.expedia.ca/Cheap-Flights-To-Lyons.d183188.Travel-Guide-Flights) - [Flights to Markham](https://www.expedia.ca/Cheap-Flights-To-Markham.d177670.Travel-Guide-Flights) - [Flights to McCook](https://www.expedia.ca/Cheap-Flights-To-McCook.d6132272.Travel-Guide-Flights) - [Flights to Midway Intl.](https://www.expedia.ca/Cheap-Flights-To-Midway-Intl.d5719117.Travel-Guide-Flights) - [Flights to New Lenox](https://www.expedia.ca/Cheap-Flights-To-New-Lenox.d6215977.Travel-Guide-Flights) - [Flights to Oak Brook](https://www.expedia.ca/Cheap-Flights-To-Oak-Brook.d9218.Travel-Guide-Flights) - [Flights to Oak Park](https://www.expedia.ca/Cheap-Flights-To-Oak-Park.d9228.Travel-Guide-Flights) - [Flights to South Suburbs](https://www.expedia.ca/Cheap-Flights-To-South-Suburbs.d6264251.Travel-Guide-Flights) - [Flights to Southwest Side](https://www.expedia.ca/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights) - [Flights to Tinley Park](https://www.expedia.ca/Cheap-Flights-To-Tinley-Park.d55204.Travel-Guide-Flights) - [Flights to Worth](https://www.expedia.ca/Cheap-Flights-To-Worth.d176696.Travel-Guide-Flights) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) ### Packages - [Blue Island Vacations](https://www.expedia.ca/Blue-Island.d80954.Destination-Travel-Guides) - [Midlothian Vacations](https://www.expedia.ca/Midlothian.d133073.Destination-Travel-Guides) - [Visit Oak Forest](https://www.expedia.ca/Oak-Forest.dx140255) ### Cars - [Car rental Blue Island](https://www.expedia.ca/Car-Rentals-In-Blue-Island.d80954.Car-Rental-Guide) - [Car rental Chicago Ridge](https://www.expedia.ca/Car-Rentals-In-Chicago-Ridge.d89160.Car-Rental-Guide) - [Enterprise Rental Cars in Alsip](https://www.expedia.ca/Enterprise-Car-Rentals-In-Alsip.d6302-c15.Car-Rental-Guide-Suppliers) - [First-Car Rental Cars in Midlothian](https://www.expedia.ca/First-Car-Car-Rentals-In-Midlothian.d133073-c1019.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Oak Lawn](https://www.expedia.ca/Things-To-Do-In-Oak-Lawn.d9227.Travel-Guide-Activities) \*Available to Expedia members.