Title: $26 Cheap Flights to Westchester, IL - Expedia.com ![Lodging Image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # $26 Cheap Flights to Westchester, IL [View $26 flight on Tue, Mar 10, 2026](https://expedia.com/Flights-Search?trip=oneway&leg1=from:EWR,to:ORD,departure:3/10/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:25.99&airProductToken=AQowCi4IzpYBEgMxMDgYxI0BIK4cKLmmhwMw1KeHAzhQQABYAWoCUlByCFAyMVNZQk5SEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) - [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 [Westchester Travel Guide](https://expedia.com/Westchester.dx7758)[Hotels in Westchester](https://expedia.com/Westchester-Hotels.d7758.Travel-Guide-Hotels)[Car Rentals in Westchester](https://expedia.com/Car-Rentals-In-Westchester.d7758.Car-Rental-Guide)[Westchester Vacation Packages](https://expedia.com/Westchester.d7758.Destination-Travel-Guides) ## Popular airlines to Westchester - ![](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:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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_DL.svg) Delta [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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_AA.svg) American Airlines [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&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_B6.svg) JetBlue Airways [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:Westchester, Illinois, United States of America,departure:2/26/2026TANYT&leg2=from:Westchester, Illinois, United States of America,to:CMH,departure:3/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![](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\* - ![](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\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our OneKeyCash [Learn about One Key](https://www.expedia.com/welcome-one-key) ## Today's featured flight deals to Westchester Nonstop Carry-on included Lower price than typical - Columbus (CMH)Chicago (ORD) Wed, Mar 4 Sun, Mar 8 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 11 hours ago 60% less than typical $97 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/4/2026TANYT&leg2=from:ORD,to:CMH,departure:3/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-ce5afdceaea443628f60415a8427627b-1873-1-st-v5-sos-ce5afdceaea443628f60415a8427627b-1870-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAaeYhFyQAQ-QAQCqAQcKA0NNSBAAsgEHCgNPUkQQAA~AQozCjEIwYIBEgQzNzc0GII7IK4cKIjdhgMw5d2GAzhCQABYAWoFQkFTSUNyCE9WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQozCjEIwYIBEgQzMzUzGK4cIII7KPCIhwMw0ImHAzhCQABYAWoFQkFTSUNyCFNWQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=340.00&displayPrice=96.80&src=dflp) - Columbus (CMH)Chicago (ORD) Tue, Mar 10 Sat, Mar 14 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 3-day trip found 14 hours ago 45% less than typical $134 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/10/2026TANYT&leg2=from:MDW,to:CMH,departure:3/14/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-8f8192a4f77942b996da12bd5ccec4ba-3749-1-st-v5-sos-8f8192a4f77942b996da12bd5ccec4ba-3647-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAdGwg1yqAQcKA0NNSBAAsgEHCgNDSEkQAA~AQozCjEIwYIBEgQzNTIwGII7IK4cKPOghwMw0KGHAzhCQABYAWoFQkFTSUNyCE9WQUlLU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw.AQoxCi8I15wBEgQxOTQwGOywASCCOyjizIcDMKjNhwM4VkAAWAFqA1dHQXIHVlpOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE&medianPrice=330.00&displayPrice=133.80&src=dflp) - Columbus (CMH)Chicago (ORD) Fri, Mar 6 Sun, Mar 15 ![American Airlines](https://a.travel-assets.com/air/airlines/aa_sq.svg)American Airlines • Nonstop --- 9-day trip found 8 hours ago 65% less than typical $97 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:3/6/2026TANYT&leg2=from:ORD,to:CMH,departure:3/15/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-7123085bac3e48c2a88bfc2c1413caca-2032-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcAB6A2Jmc4gBgu2EXKoBBwoDQ01IEACyAQcKA09SRBAA~AQozCjEIwYIBEgQzNDQ2GII7IK4cKJLyhgMw-PKGAzhCQABYAWoFQkFTSUNyCFNWQUlaTkJaCjMKMQjBggESBDMzNTMYrhwggjso0NeHAzCw2IcDOEJAAFgBagVCQVNJQ3IIU1dBSVpOQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL&medianPrice=362.00&displayPrice=96.80&src=dflp) - Columbus (CMH)Chicago (MDW) Thu, Mar 19 Sun, Mar 22 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 19 hours ago 20% less than typical $340 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/19/2026TANYT&leg2=from:MDW,to:CMH,departure:3/22/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-b447eb0c36ea4f5c95d3be20ee7c25cc-394-1-st-v5-sos-b447eb0c36ea4f5c95d3be20ee7c25cc-380-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAa6oglyQAQGQAQGqAQcKA0NNSBAAsgEHCgNNRFcQAA~AQoxCi8I15wBEgQxNjIzGII7IOywASigiogDMOuKiAM4VkAAWAFqA1dHQXIHVlpOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQpvCjYIxJgBEgQzNzk5GOywASDMfCiUrIgDMPisiAM4RUAAWAFqCU1BSU5CQVNJQ3IIVUFWT0EwQkMKNQjEmAESBDEzNTYYzHwggjsooK2IAzCJrogDOEVAAVgBaglNQUlOQkFTSUNyCFVBVk9BMEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ&medianPrice=565.00&displayPrice=339.61&src=dflp) - Columbus (CMH)Chicago (MDW) Sat, Mar 14 Fri, Mar 20 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 5-day trip found 6 hours ago 60% less than typical $134 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/14/2026TANYT&leg2=from:ORD,to:CMH,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-d0d8e4594fe94b338b373c5b690b3d82-3107-1-st-v5-sos-d0d8e4594fe94b338b373c5b690b3d82-3020-1~8.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAZaohVyQAQCQAQKqAQcKA0NNSBAAsgEHCgNDSEkQAA~AQoxCi8I15wBEgQxOTQ2GII7IOywASiU0ocDMOTShwM4VkAAWAFqA1dHQXIHVlpOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQozCjEIwYIBEgQzMzUzGK4cIII7KPCPiAMw0JCIAzhCQABYAWoFQkFTSUNyCFNXQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=439.00&displayPrice=133.80&src=dflp) - Columbus (CMH)Chicago (MDW) Mon, Mar 16 Fri, Mar 20 ![Southwest Airlines](https://a.travel-assets.com/air/airlines/wn_sq.svg)Southwest Airlines • Nonstop --- 3-day trip found 11 hours ago 55% less than typical $134 [](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:3/16/2026TANYT&leg2=from:ORD,to:CMH,departure:3/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&airOfferToken=v5-sos-6cfdd43fb93c4251bfcffb719f485178-2871-1-st-v5-sos-6cfdd43fb93c4251bfcffb719f485178-2830-1~9.S.1~AQoCCAESBwjUBBABGAEoAlgCcABwAHoDYmZzegNiZnOIAemYhFyqAQcKA0NNSBACsgEHCgNDSEkQAA~AQoxCi8I15wBEgQxNjIzGII7IOywASjA6IcDMIvphwM4VkAAWAFqA1dHQXIHVlpOVk4yRBIKCAEQARgBKgJXThgBIgQIARABKAIoAygEMAE.AQozCjEIwYIBEgQzMzUzGK4cIII7KPCPiAMw0JCIAzhCQABYAWoFQkFTSUNyCFNXQUlaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw&medianPrice=407.00&displayPrice=133.80&src=dflp) ## How much is the cheapest flight to Westchester? Prices were available within the past 7 days and start at $26 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Mar 10 - Wed, Mar 11 EWR New York ORD Chicago $52 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:ORD,departure:3/10/2026TANYT&leg2=from:ORD,to:EWR,departure:3/11/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:51.98&airProductToken=AQowCi4IzpYBEgMxMDgYxI0BIK4cKLmmhwMw1KeHAzhQQABYAWoCUlByCFAyMVNZQk5SCjAKLgjOlgESAzEwNxiuHCDEjQEol7CHAzCYsYcDOFBAAFgBagJSUHIIUDIxU1lCTlISCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Frontier Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif) Tue, Apr 14 - Thu, Apr 30 EWR New York MDW Chicago $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:EWR,to:MDW,departure:4/14/2026TANYT&leg2=from:MDW,to:EWR,departure:4/30/2026TANYT&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=AQoyCjAIxnISBDE0MTMYxI0BIOywASjiqooDMPirigM4RUAAWAFqBFBDXzFyB0syMUVYUzIKMgowCMZyEgQxNDE0GOywASDEjQEort2LAzCu3osDOEVAAFgBagRQQ18xcgdLMjFSWFMyEgoIARABGAEqAkY5GAEiBAgBEAEoAigDMA0) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Oct 10 - Sat, Oct 17 ATL Atlanta ORD Chicago $115 Roundtrip found 3 days ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:ORD,departure:10/10/2026TANYT&leg2=from:ORD,to:ATL,departure:10/17/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:114.78&airProductToken=AQozCjEIwYIBEgQzNjIyGOBcIK4cKM2MmgMw1o2aAzhCQABYAWoFQkFTSUNyCE9XQUlKU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, May 9 - Tue, May 19 ATL Atlanta ORD Chicago $137 Roundtrip found 4 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:ORD,departure:5/9/2026TANYT&leg2=from:ORD,to:ATL,departure:5/19/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:136.80&airProductToken=AQo3CjUIxJgBEgQyODc5GOBcIK4cKOXGjAMw7ceMAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOWDNCRwo3CjUIxJgBEgQyNzM4GK4cIOBcKIO4jQMwhLmNAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOWDNCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Southwest Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/wn.gif) Tue, Apr 14 - Wed, Apr 15 ATL Atlanta MDW Chicago $137 Roundtrip found 22 hours ago [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:ATL,to:MDW,departure:4/14/2026TANYT&leg2=from:MDW,to:ATL,departure:4/15/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:136.80&airProductToken=AQowCi4I15wBEgMyNTgY4Fwg7LABKMCtigMws66KAzhWQABYAWoDV0dBcgdWRE5XUjJFCjEKLwjXnAESBDMyMTcY7LABIOBcKIm3igMw_LeKAzhWQABYAWoDV0dBcgdWRE5XUjJFEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ) ## Alternative airports near Westchester 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:2/26/2026TANYT&leg2=from:ORD,to:CMH,departure:3/8/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 19 min [Flights from $329 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:ORD,departure:2/26/2026TANYT&leg2=from:ORD,to:CMH,departure:3/8/2026TANYT&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:2/26/2026TANYT&leg2=from:MDW,to:CMH,departure:3/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) MDW Midway Intl. CheapestClosest 17 min [Flights from $294 ](https://www.expedia.com/Flights-Search?leg1=from:CMH,to:MDW,departure:2/26/2026TANYT&leg2=from:MDW,to:CMH,departure:3/5/2026TANYT&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_) ## Tips to find the cheapest flights to Westchester **The cheapest day to fly** Get started finding a cheap flight to Westchester 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 Westchester. 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 Westchester. 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 Westchester, 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 Westchester** The lowest price for round-trip flights to Westchester in 2026 starts from from $52, while one-way tickets start from from $26\. 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 Westchester. If you have a preferred departure time or airline, you can use the handy filters to customize your search. **The cheapest airlines flying to Westchester** Spirit Airlines, Frontier Airlines, Delta, American Airlines, Southwest Airlines are just some of the airlines that can typically offer cheap tickets to Westchester. 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 Westchester and countless more destinations worldwide. **The most affordable airports to fly into** To view the cheapest airports to fly into for Westchester, 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 Westchester. 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 Westchester 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 Westchester** 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 Westchester. **Stopover savings** The cheapest tickets to Westchester are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Westchester. 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 Westchester 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 Westchester. Simply download the free Expedia app to your smart device and activate Westchester 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 Westchester. 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. ## Frequently asked questions ### What month is the cheapest to fly to Westchester? ### Which US cities have the cheapest flights to Westchester? > - Burlington (BRL, BTV) > - Quincy (UIN) > - Owensboro (OWB) > - Kirksville (IRK) > - Manistee (MBL) > > > with fares often starting from $39. ### Which US cities fly direct to Westchester? > - 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 Westchester? ### Which airlines fly to Westchester? > - American Airlines > - Delta > - Frontier Airlines > - Spirit Airlines > - United > - United Airlines > - Volaris ### Where do you fly into Westchester? > - The closest major airport is Chicago, IL (ORD-O'Hare Intl.), about 9 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 76 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 11 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 109 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 Westchester? ### Which budget airlines fly to Westchester? > - 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), Milwaukee (MKE), South Bend (SBN) > - Breeze: flies to South Bend (SBN) > - Arajet: flies to Chicago (ORD) ### What is the best month to visit Westchester? ### How far in advance should I book a flight to Westchester? ### What day of the week is cheapest day to buy a plane ticket to Westchester? ### What is the most expensive month to fly to Westchester? ### How far is the airport from central Westchester? > - 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 Westchester? ### How to get a cheap last-minute flight to Westchester? ### Can I earn miles booking a flight to Westchester with Expedia? ### Can I save money by booking a Westchester trip package? ### Can I change or cancel my flight to Westchester? \*Flight schedules are subject to change. __Flights to Westchester information__ | Destination airport | O'Hare Intl. | | ----------------------------- | ------------ | | Destination airport IATA code | ORD | | Destination city name | Chicago | | Roundtrip price | $52 | ## Trending flights to Westchester Prices were available within the past 7 days and start at $26 for one-way flights and $52 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) Wed, Apr 22 - Sat, Apr 25 IAH Houston ORD Chicago $56 Roundtrip just found [](https://expedia.com/Flights-Search?trip=roundtrip&leg1=from:IAH,to:ORD,departure:4/22/2026TANYT&leg2=from:ORD,to:IAH,departure:4/25/2026TANYT&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=AQowCi4IxnISBDE4ODIYiDggrhwo14WLAzCBh4sDOEVAAFgBagRQQ18xcgdLMjFYWFMyCjAKLgjGchIEMzEzNRiuHCCIOCiOpYsDMMmmiwM4RUAAWAFqBFBDXzFyB0syMVNYUzISCggBEAEYASoCRjkYASIECAEQASgCKAMwDQ) ## 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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