Title: $28 Cheap Flights to Crestwood, IL - Expedia.com ![Reflection on Lake at Dusk at Turtlehead Lake Nature Preserve in Orland Park, IL (Suburban Chicago)](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6960/240c7639-252c-425c-9300-8c5e47f6e396.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $28 Cheap Flights to Crestwood, IL [View $28 flight on Tue, Apr 14, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:LAX,to:ORD,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:27.98&airProductToken=AQoxCi8IxnISBDI0NDYYi7gBIK4cKOyxigMw6rOKAzhFQABYAWoEUENfMXIHSzIxRVhTMhIMCAEQARgBKgJGOTIAGAEiBAgBEAEoAigDMA0) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travelers 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 [Crestwood Travel Guide](https://expedia.com/Crestwood.dx6960)[Hotels in Crestwood](https://expedia.com/Crestwood-Hotels.d6960.Travel-Guide-Hotels)[Things to do in Crestwood](https://expedia.com/Things-To-Do-In-Crestwood.d6960.Travel-Guide-Activities)[Car Rentals in Crestwood](https://expedia.com/Car-Rentals-In-Crestwood.d6960.Car-Rental-Guide)[Crestwood Vacation Packages](https://expedia.com/Crestwood.d6960.Destination-Travel-Guides) ## Popular airlines to Crestwood - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Crestwood, Illinois, United States of America,departure:3/16/2026TANYT&leg2=from:Crestwood, Illinois, United States of America,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) ## How much is the cheapest flight to Crestwood? Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, Mar 24 - Wed, Mar 25 JFK New York ORD Chicago $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:3/24/2026TANYT&leg2=from:ORD,to:JFK,departure:3/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDEwNDMYqVEgrhwo7cCIAzChwogDOEVAAFgBagRQQ18xcgdLMjFFWFMyCjAKLgjGchIEMTA0NBiuHCCpUSjByogDMNHLiAM4RUAAWAFqBFBDXzFyB0syMVhYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Mon, Apr 13 - Tue, Apr 14 EWR New York ORD Chicago $58 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:ORD,departure:4/13/2026TANYT&leg2=from:ORD,to:EWR,departure:4/14/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:57.98&airProductToken=AQouCiwIzpYBEgMxMDgYxI0BIK4cKO6kigMwgqaKAzhQQABYAWoCUlByBlBBMjFOUgouCiwIzpYBEgMxMDcYrhwgxI0BKKWuigMwpa-KAzhQQABYAWoCUlByBlBBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Apr 15 - Fri, Apr 17 EWR New York RFD Rockford $145 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:RFD,departure:4/15/2026TANYT&leg2=from:RFD,to:EWR,departure:4/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:144.06&airProductToken=AQpnCjIIwYIBEgQzNTc2GMSNASCuHCiYt4oDML-4igM4QkAAWAFqBUJBU0lDcghPVkFJWVNCVgoxCMGCARIENjU3NxiuHCCxGSicuYoDMPu5igM4QkABWAFqBUJBU0lDcghPVkFJWVNCVgpnCjEIwYIBEgQ2NTc2GLEZIK4cKN_OigMwvs-KAzhCQABYAWoFQkFTSUNyCE9WQUlZU0JWCjIIwYIBEgQzMjM5GK4cIMSNASjF0IoDMNTRigM4QkABWAFqBUJBU0lDcghPVkFJWVNCVhIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Wed, Mar 25 - Wed, Apr 8 LGA New York MDW Chicago $146 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LGA,to:MDW,departure:3/25/2026TANYT&leg2=from:MDW,to:LGA,departure:4/8/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:146.00&airProductToken=AQoxCi8I15wBEgQxNDE0GMsBIOywASjKx4gDMODIiAM4REAAWAFqA1dHQXIHRExOVlQyRQoxCi8I15wBEgQyNTQzGOywASDLASjn5IkDMN_liQM4REAAWAFqA1dHQXIHRExOVlQyRRIKCAIQARgCKgJXThgBIgQIARABKAIoAygEMAE) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Wed, Apr 22 - Tue, Apr 28 LAX Los Angeles ORD Chicago $217 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:LAX,to:ORD,departure:4/22/2026TANYT&leg2=from:ORD,to:LAX,departure:4/28/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:216.40&airProductToken=AQplCjEIwaYBEgM3NDgYi7gBIJIBKOqGiwMwmoiLAzhYQABYAWoFU0FWRVJyCEdINU9YSkJOCjAIwaYBEgM1MzgYkgEgrhwoiomLAzCLi4sDOFhAAVgBagVTQVZFUnIIR0g1T1hKQk4KZgowCMGmARIDMzI5GK4cIJIBKIzNiwMwpc-LAzhYQABYAWoFU0FWRVJyCEdINU9YSkJOCjIIwaYBEgQxMzMzGJIBIIu4ASjF0osDMOrTiwM4WEABWAFqBVNBVkVScghHSDVPWEpCThIKCAEQARgBKgJBUxgBIgQIARABKAIoAygEMA0) ## Alternative airports near Crestwood Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/16/2026TANYT&leg2=from:ORD,to:CMH,departure:3/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 39 min [Flights from $260 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/16/2026TANYT&leg2=from:ORD,to:CMH,departure:3/26/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/16/2026TANYT&leg2=from:MDW,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. Closest 15 min [Flights from $323 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/16/2026TANYT&leg2=from:MDW,to:CMH,departure:3/23/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD) ### July is typically the cheapest month to fly From $77 - $303 per traveler. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=FTG_SPRING_PROMO_) ## Frequently asked questions ### What month is the cheapest to fly to Crestwood? ### Which US cities have the cheapest flights to Crestwood? > - Burlington (BRL, BTV) > - Quincy (UIN) > - Owensboro (OWB) > - Kirksville (IRK) > - Manistee (MBL) > > > with fares often starting from $39. ### Which US cities fly direct to Crestwood? > - New York (JFK, LGA) > - Newark (EWR) > - Los Angeles (LAX) > - Dallas (DAL, DFW) > - Houston (IAH) > > > To Midway Intl. (MDW) > - Atlanta (ATL) > - Dallas (DAL, DFW) > - Orlando (MCO) > - Phoenix (PHX) > - Los Angeles (LAX) > > > To General Mitchell Intl. (MKE) > - Chicago (MDW, ORD) > - Denver (DEN) > - New York (JFK, LGA) > - Newark (EWR) > - Phoenix (PHX) ### How to find a cheap flight to Crestwood? ### Which airlines fly to Crestwood? > - American Airlines > - Delta > - Frontier Airlines > - Spirit Airlines > - United > - United Airlines > - Volaris ### Where do you fly into Crestwood? > - The closest major airport is Chicago, IL (ORD-O'Hare Intl.), about 24 miles from the city center, which is a hub for United, American Airlines, and Delta, with other airlines like Frontier Airlines, Air Canada also operating here. > - Milwaukee, WI (MKE-General Mitchell Intl.) is another option, about 90 miles away, serving as a hub for United, Delta, and WN, with American Airlines, Alaska Airlines also operating here. > - Chicago, IL (MDW-Midway Intl.), about 9 miles away, serving as a hub for WN, Delta, and Frontier Airlines, with Volaris, Porter Airlines also operating here. > - South Bend, IN (SBN-South Bend Intl.), about 100 miles away, serving as a hub for United, American Airlines, and Delta, with MX, OO also operating here. ### What is the cheapest airport to fly to in Crestwood? ### Which budget airlines fly to Crestwood? > - Southwest Airlines: serves Chicago (MDW), Chicago (ORD), Milwaukee (MKE) > - Spirit Airlines: serves Chicago (ORD), Milwaukee (MKE) > - Frontier Airlines: serves Chicago (MDW), Chicago (ORD), Milwaukee (MKE) > - Volaris: serves Chicago (MDW), Chicago (ORD) > - JetBlue Airways: serves Chicago (ORD), Milwaukee (MKE) > - Viva Aerobus: flies to Chicago (ORD) > - Sun Country Airlines: serves Chicago (ORD), Milwaukee (MKE) > - WestJet: serves Chicago (MDW), Chicago (ORD), South Bend (SBN), Milwaukee (MKE) > - Breeze: flies to South Bend (SBN) > - Arajet: flies to Chicago (ORD) ### What is the best month to visit Crestwood? ### How far in advance should I book a flight to Crestwood? ### What day of the week is cheapest day to buy a plane ticket to Crestwood? ### What is the most expensive month to fly to Crestwood? ### How far is the airport from central Crestwood? > - Chicago, IL (MDW-Midway Intl.): 10 miles southwest > - Chicago, IL (ORD-O'Hare Intl.): 20 miles west > > > These options give you flexibility when planning your trip. ### How can I track flight prices to Crestwood? ### How to get a cheap last-minute flight to Crestwood? ### Can I earn miles booking a flight to Crestwood with Expedia? ### Can I save money by booking a Crestwood trip package? ### Can I change or cancel my flight to Crestwood? \*Flight schedules are subject to change. ## Book with confidence # Tips to find the cheapest flights to Crestwood **The cheapest day to fly** Get started finding a cheap flight to Crestwood on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you. **The cheapest month to fly** March is the cheapest month to fly to Crestwood. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Crestwood. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute. **The most affordable time to book a flight** Typically, a Sunday can be the cheapest time to book a flight to Crestwood, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation. **The cheapest round-trip tickets to Crestwood** The lowest price for round-trip flights to Crestwood in 2026 starts from from $56, while one-way tickets start from from $28\. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Crestwood. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Crestwood** Frontier Airlines, Spirit Airlines, American Airlines, JetBlue Airways, Delta, Southwest Airlines, Alaska Airlines are just some of the airlines that can typically offer cheap tickets to Crestwood. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Crestwood and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Crestwood, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Crestwood. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia. **Save with a package** With Expedia's amazing [package deals](https://www.expedia.com/package-deals), you could save hundreds of dollars by booking your Crestwood plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving. **Date flexibility for the cheapest flights to Crestwood** If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Crestwood. **Stopover savings** The cheapest tickets to Crestwood are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Crestwood. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved. **Get Expedia's Price Drop Protection** Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference\*. This gives you peace of mind that you're getting one of the cheapest flights to Crestwood for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members. \*Terms apply. **Use our Price Tracking feature** Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Crestwood. Simply download the free Expedia app to your smart device and activate Crestwood flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices. **Book with Expedia** As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Crestwood. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too. Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages. ## Travel information | Destination airport | O'Hare Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | $56 | ## Trending flights to Crestwood Prices were available within the past 7 days and start at $28 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, Mar 24 - Wed, Mar 25 JFK New York ORD Chicago $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:3/24/2026TANYT&leg2=from:ORD,to:JFK,departure:3/25/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:55.96&airProductToken=AQowCi4IxnISBDEwNDMYqVEgrhwo7cCIAzChwogDOEVAAFgBagRQQ18xcgdLMjFFWFMyCjAKLgjGchIEMTA0NBiuHCCpUSjByogDMNHLiAM4RUAAWAFqBFBDXzFyB0syMVhYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Chicago Hotels ](https://www.expedia.com/Chicago-Hotels.d178248.Travel-Guide-Hotels) - [Hotels near Downtown Chicago ](https://www.expedia.com/Downtown-Chicago-Chicago-Hotels.0-n6350699-0.Travel-Guide-Filter-Hotels) - 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