Title: Cheap Flights to Crestwood , IL from CA $144 - 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 $144 [View CA $144 flight on Thu, Jan 29, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:YTZ,to:MDW,departure:29/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:143.71&airProductToken=AQozCjEI1KYBEgQ3MDYwGPjMASDssAEot96DAzCl34MDOFFAAFgBagNCR1RyCFEyTjBaUlpMEgoIARABGAEqAlRTGAEiBAgBEAEoAigDKAQwDQ) - [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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![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:18/10/2025TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:25/10/2025TANYT&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 Crestwood? 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 1 day 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 5 hours 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) Tue, Apr 7 - Tue, Apr 14 YYZ Toronto ORD Chicago CA $236 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:YYZ,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:235.35&airProductToken=AQozCjEIwYYBEgM1MDkYmM4BIK4cKKbfiQMwmeCJAzhHQABYAWoFQkFTSUNyCEdOQTJBMkJBCjMKMQjBhgESAzUwOBiuHCCYzgEou62KAzChrooDOEdAAFgBagVCQVNJQ3IIR05BMkEyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Apr 7 - Tue, Apr 14 YYZ Toronto ORD Chicago CA $236 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYZ,to:ORD,departure:07/04/2026TANYT&leg2=from:ORD,to:YYZ,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:235.35&airProductToken=AQo3CjUI1YIBEgQzNjQwGJjOASCuHCi84IkDMLPhiQM4TkAAWAFqCEVDT0JBU0lDcghHTkEyQTJCTgo3CjUI1YIBEgQzNTM4GK4cIJjOASjnr4oDMNmwigM4TkAAWAFqCEVDT0JBU0lDcghHTkEyQTJCThIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ![WestJet](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/WS.gif) Fri, Jan 23 - Fri, Jan 30 YYC Calgary ORD Chicago CA $248 Roundtrip found 8 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:YYC,to:ORD,departure:23/01/2026TANYT&leg2=from:ORD,to:YYC,departure:30/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:247.22&airProductToken=AQoiCiAI16YBEgQxNjEwGJgWIK4cKOCbgwMwt52DAzhBQABYAQoiCiAI16YBEgQxNjExGK4cIJgWKMTsgwMwr-6DAzhBQABYARIKCAEQARgBKgJXUxgBIgQIARABKAQwAQ) ## 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 Crestwood's airport? > O'Hare Intl. Airport (ORD) is the main airport in Crestwood. ### How far is ORD from central Crestwood? > Lengthy commutes don't have to be stressful if you plan ahead for them. Downtown Crestwood is 40 kilometres from ORD, so it's smart to know how to get to the city before you arrive. ### What airport is best to fly into Crestwood? > Flying to Crestwood means hopping off the plane at O'Hare Intl. Airport (ORD) or Midway Airport. The first is 40 kilometres away from the downtown area. The second one is 14 kilometres away. ### How many airlines fly to Crestwood? > There are 51 airlines connecting Crestwood to 237 airports from all over the globe. ### Which airlines fly to Crestwood? > United Airlines, American Airlines and Delta fly the most frequently to Crestwood. The majority of flights come from New York, with United Airlines having the most services on this route. ### How many nonstop flights are there to Crestwood? > Flying to a new place is much more fun when there aren't any lengthy stopovers. If you're making your way to Crestwood, the awesome news is that there are approximately 7,564 direct flights every week. ### Where are the most popular flights to Crestwood departing from? > Flights to Crestwood departing from New York, Washington and Dallas airports are the most sought after. ### How long is the flight to Crestwood Airport? > If it's New York you're departing, you'll be in the sky for around 2 hours and 44 minutes before you touchdown in Crestwood. Tarmac to tarmac from Washington takes about 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes. ### How to book the cheapest flight to Crestwood? > If you'd like to save some cash on your trip to Crestwood, then listen up! As every experienced traveller will tell you, don't leave booking until the last minute. Prices are usually more expensive just prior to the departure date. Also, shop around and compare your options. If your destination has more than one airport, you may be able to pick up a better deal by flying into one a little farther out. Last but not least, another simple way to save some money is be ready to book at a moment's notice. If you see an amazing deal, don't hold off — snap it up while you can. ### Do you have any tips for my flight to Crestwood? > If you're not prepared, air travel can be daunting. But there's no need to panic. Follow these handy tips and enjoy a comfortable start to your vacation in Crestwood. What to pack in your hand luggage: > > > > - Flying can be a great experience if you pack the right gear. First of all you'll need toiletry items, such as toothpaste, a toothbrush and some deodorant, a spare set of clothes and a few magazines. Secondly, find a spot in your carry-on bag for your laptop, a charger, your important medications and maybe a proper neck pillow too. Lastly, and most importantly, be sure to take your passport, travel papers and some cash. > > > > Do not pack the following items in your hand luggage: > > > > - Pack 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 by security. Sharp objects, like your pocket knife, and products which are flammable or explosive, such as flares, bleaching agents and fireworks, are also banned. > > > > What to wear on a flight: > > > > - Comfort should be your priority when choosing what to wear on board. Loose clothing is a smart choice, as are flat, enclosed shoes. > - The result of sustained periods of inactivity, deep vein thrombosis (DVT) is a blood clotting condition that can affect passengers during long-haul flights. Reduce the risks by drinking water, keeping your ankles and legs moving and wearing compression tights or socks. ### How to get through airport security fast when flying to Crestwood? > It's easy — be prepared. We've compiled some useful tips for a fuss-free trip through security. Look out Crestwood, here you come: > > > > - First things first. Your travel documents and passport will need to be shown to airport security. Have them easily accessible to avoid fumbling around for them. > - The X-ray machine comes next. Remove anything on you that is likely to set off the alarm. This includes items like earphones or headphones, as well as bulky coats or jackets. They'll all need to go on the X-ray conveyor belt. > - For just a few moments, you'll have to unplug from the digital world. Your phone, tablet and any other electronic gadgets must also be sent through the scanner. > - Any liquids or gels, such as toothpaste or perfume, that you want to take on board need to be in containers no larger than 3.4 ounces (100 millilitres). Also, they all must fit inside a quart-size (one litre), clear zip-lock bag. > - Slip-on shoes are a good footwear choice as you're less likely to be asked to remove them when going through security. Safety boots and heavier-style shoes are usually subjected to extra screening. > - Take all prohibited items out of your carry-on bag. If you have any sharp objects like a pocket knife or tools, pack them in your checked baggage. They won't be allowed on board. ## Book with confidence 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! ## Travel information | Destination airport | Midway Intl. | | --- | --- | | Destination airport IATA code | MDW | | Destination city name | Chicago | | Roundtrip price | CA $226 | ## Trending flights to Crestwood 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 1 day 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 - Other - [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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