Title: CA $96 Cheap Flights from New York (JFK) to Chicago (ORD) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $96 Cheap Flights from New York (JFK) to Chicago (ORD) [View CA $96 flight on Mon, Nov 10, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:JFK,to:ORD,departure:10/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:95.60&airProductToken=AQozCjEIwYIBEgQyODQ4GKlRIK4cKPbb_AIwn938AjhCQABYAWoFQkFTSUNyCE9VQUpYU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) - [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 ## Popular airlines from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Sun Country Airlines](https://a.travel-assets.com/air/airlines/sy_sq.svg) Sun Country Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"SY"}}]) - ![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:jfk,to:ord,departure:10/11/2025TANYT&leg2=from:ord,to:jfk,departure:17/11/2025TANYT&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) ## Cheap flights from New York (JFK) to Chicago (ORD) Prices were available within the past 7 days and start at CA $96 for one-way flights and CA $162 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Dec 3 - Sun, Dec 7 JFK New York ORD Chicago CA $162 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:JFK,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:161.30&airProductToken=AQozCjEIwYIBEgQzMTYyGKlRIK4cKJzg_gIwyOH-AjhCQABYAWoFQkFTSUNyCE9WQUhVU0JYCjMKMQjBggESBDI4NDgYrhwgqVEonIr_AjCli_8COEJAAFgBagVCQVNJQ3IIT1ZBSlpTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Dec 3 - Sun, Dec 7 JFK New York ORD Chicago CA $163 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:JFK,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:162.40&airProductToken=AQozCjEIwYIBEgQyODE5GKlRIK4cKIjd_gIwsd7-AjhCQABYAWoFQkFTSUNyCE9WQUhVU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Nov 4 - Sat, Nov 8 JFK New York ORD Chicago CA $164 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:JFK,departure:08/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:163.20&airProductToken=AQohCh8IwmwSBDIxMDUYqVEgrhwowJv8AjDsnPwCOExAAFgBCiEKHwjCbBIEMjEwNhiuHCCpUSidw_wCMKPE_AI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Nov 1 - Thu, Nov 6 JFK New York ORD Chicago CA $165 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:01/11/2025TANYT&leg2=from:ORD,to:JFK,departure:06/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:164.50&airProductToken=AQovCi0IwmwSBDIxMDUYqVEgrhwolfn7AjDB-vsCOExAAFgBagJETnIIUEk3UVVTTDEKLwotCMJsEgQyMTA2GK4cIKlRKJmt_AIwoK78AjhMQABYAWoCRE5yCFBJN1FVU0wxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Dec 3 - Sun, Dec 7 JFK New York ORD Chicago CA $170 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:JFK,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:169.90&airProductToken=AQovCi0IwmwSBDIxMDUYqVEgrhwonOL-AjDI4_4COExAAFgBagJETnIIUEk3UVVTTDEKLwotCMJsEgQyMTA2GK4cIKlRKMyJ_wIw1Yr_AjhMQABYAWoCRE5yCFBJMlFCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Jan 22 - Thu, Jan 29 JFK New York ORD Chicago CA $176 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:JFK,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:175.20&airProductToken=AQozCjEIwYIBEgQzMTYyGKlRIK4cKNySgwMwjpSDAzhCQABYAWoFQkFTSUNyCE9WQUpaU0JYCjMKMQjBggESBDQ2ODAYrhwgqVEouN6DAzDH34MDOEJAAFgBagVCQVNJQ3IIT1ZBSlpTQlgSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Jan 22 - Thu, Jan 29 JFK New York ORD Chicago CA $177 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:22/01/2026TANYT&leg2=from:ORD,to:JFK,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:176.40&airProductToken=AQovCi0IwmwSBDIxMDUYqVEgrhwoz5CDAzD-kYMDOExAAFgBagJETnIIUEkyUUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Nov 15 - Wed, Dec 3 JFK New York ORD Chicago CA $184 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:JFK,departure:03/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:183.80&airProductToken=AQohCh8IwmwSBDIxMDUYqVEgrhwooJf9AjDMmP0COExAAFgBCiEKHwjCbBIEMjEwNhiuHCCpUSjM3P4CMNXd_gI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 3 - Sun, Dec 7 JFK New York ORD Chicago CA $198 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:JFK,departure:07/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:197.90&airProductToken=AQo3CjUIxJgBEgQ1MDE3GKlRIK4cKPjd_gIwo9_-AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSDNCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Sun Country Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/SY.GIF) Fri, Nov 28 - Sun, Nov 30 JFK New York ORD Chicago CA $837 Roundtrip found 16 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JFK,to:ORD,departure:28/11/2025TANYT&leg2=from:ORD,to:JFK,departure:30/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:836.63&airProductToken=AQpUCigI07IBEgM1NjgYqVEgzHwogKb-AjC-p_4COFFAAFgBcgdRNERBQ0FZCigI07IBEgMyNjMYzHwgrhwowKn-AjCkqv4COFFAAVgBcgdRNERBQ0FZClQKKAjTsgESAzI2MhiuHCDMfCjwwP4CMNbB_gI4UkAAWAFyB1IwREFDQVkKKAjTsgESAzU2NRjMfCCpUSiyxf4CMNfG_gI4UkABWAFyB1IwREFDQVkSCggBEAEYASoCU1kYASIECAEQASgCKAMoBDAN) ## Find the cheapest month to fly from New York (JFK) to Chicago (ORD) ### October is typically the cheapest month to fly From CA $122 - CA $384 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:JFK,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:JFK,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. Cheapest 23 min [Flights from CA $192](https://www.expedia.ca/Flights-Search?leg1=from:JFK,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:JFK,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from New York to Chicago (JFK - ORD) route information | Origin airport | John F. Kennedy Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, JetBlue Airways | | Roundtrip price | CA $161 | | Distance | 1180 km | | Average flight time | 1 hour 48 mins | ## New York to Chicago Flights **The easy way to book your flights from New York to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from New York whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.   Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from New York to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from John F. Kennedy Intl., JFK to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from New York to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from New York currently is just CA $162 rising to CA $837.   Here are more money-saving tips:  - Fly in December when flight prices are normally at their lowest  - Book about a month to 6 weeks before you travel for the best prices to Chicago   - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times  - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!  **Reasons to choose Expedia for your flight to Chicago from New York**  Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from JFK Airport to O'Hare Intl. Airport (ORD)? > Round-trip tickets between JFK and ORD start from CA $162. This price is based on fares listed within the last 7 days on Expedia for flights departing within the next year — book ASAP so you don't miss out. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD)? > We understand that things come up unexpectedly, so we've made it as easy as possible for you to cancel your flight online. Just visit the [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from JFK Airport to O'Hare Airport that have flexible change policies? > Flights from JFK Airport to O'Hare Intl. Airport (ORD) with flexible change policies are available with many carriers. Simply use our "No change fees" filter when searching. You'll only need to cover the cost difference between flights, with no additional fees to worry about. ### How many hours is the flight from JFK to ORD? > It takes just 2 hours and 51 minutes to travel from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) — perfect for a quick snooze. You'll be starting your descent into Chicago by the time you wake up. ### How far is the flight from John F. Kennedy Intl. Airport (JFK) to ORD? > You won't need a lengthy novel for this flight — it's only 1,200 kilometres from Jamaica to Chicago. Find your seat, order a snack and you'll be there in no time. ### Which airlines fly direct from JFK to O'Hare Intl. Airport (ORD)? > There are several airlines that fly directly from JFK to ORD. Delta (DL) is a popular choice, offering 117 flights on this route each month. Another carrier operating on this route is American Airlines (AA). You'll have 60 flights each month to take your pick of. ### Are JFK to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Booking your trip from John F. Kennedy Intl. Airport (JFK) to O'Hare Intl. Airport (ORD) last minute could be your ticket to a great deal. However, it could end up costing a good deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred carrier hasn't released tickets yet, check back regularly as deals are updated on Expedia all the time. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - [Flights from San Francisco to Evanston](https://www.expedia.ca/lp/flights/178305/8049/san-francisco-to-evanston) - [Flights from Seattle to Rosemont](https://www.expedia.ca/lp/flights/178307/7581/seattle-to-rosemont) - [Flights from Washington to Evanston](https://www.expedia.ca/lp/flights/178318/8049/washington-to-evanston) - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Winnipeg to Rosemont](https://www.expedia.ca/lp/flights/6141041/7581/winnipeg-to-rosemont) - [Flights from Ashland (AHM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ahm/chi/ashland-to-chicago) - [Flights from Ann Arbor (ARB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/arb/mdw/ann-arbor-to-chicago) - [Flights from Aspen (ASE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ase/mdw/aspen-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from León (BJX) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bjx/mdw/leon-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Belleville (BLV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/blv/chi/belleville-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Burlington (BTV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/btv/chi/burlington-to-chicago) - [Flights from Burlington (BTV) to Chicago (MDW)](https://www.expedia.ca/lp/flights/btv/mdw/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (CHI)](https://www.expedia.ca/lp/flights/buf/chi/buffalo-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bwi/mdw/baltimore-to-chicago) - [Flights from Blaine (BWS) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bws/chi/blaine-to-chicago) - [Flights from Belize City (BZE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bze/mdw/belize-city-to-chicago) - [Flights from Charleston (CHS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/chs/mdw/charleston-to-chicago) - [Flights from Cleveland (CLE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/cle/mdw/cleveland-to-chicago) - [Flights from Danville (DAN) to Chicago (CHI)](https://www.expedia.ca/lp/flights/dan/chi/danville-to-chicago) - [Flights from Delhi (DEL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/del/mdw/delhi-to-chicago) - [Flights from Des Moines (DSM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dsm/mdw/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/dtw/mdw/detroit-to-chicago) - [Flights from Detroit (DTW) to Chicago (PWK)](https://www.expedia.ca/lp/flights/dtw/pwk/detroit-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Fishers Island (FID) to Chicago (MDW)](https://www.expedia.ca/lp/flights/fid/mdw/fishers-island-to-chicago) - [Flights from Flint (FNT) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/fnt/ugn/flint-to-waukegan) - [Flights from Green Bay (GRB) to Waukegan (UGN)](https://www.expedia.ca/lp/flights/grb/ugn/green-bay-to-waukegan) - [Flights from Grand Rapids (GRR) to Chicago (PWK)](https://www.expedia.ca/lp/flights/grr/pwk/grand-rapids-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/iag/chi/niagara-falls-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/iag/mdw/niagara-falls-to-chicago) - [Flights from Wilmington (ILM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ilm/chi/wilmington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ind/chi/indianapolis-to-chicago) - [Flights from Nakhon Phanom (KOP) to Chicago (MDW)](https://www.expedia.ca/lp/flights/kop/mdw/nakhon-phanom-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/las/mdw/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Montego Bay (MBJ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mbj/mdw/montego-bay-to-chicago) - [Flights from Orlando (MCO) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mco/mdw/orlando-to-chicago) - [Flights from Michigan City (MGC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/mgc/mdw/michigan-city-to-chicago) - [Flights from Muscle Shoals (MSL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/msl/mdw/muscle-shoals-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from New York (NYC) to Chicago (CHI)](https://www.expedia.ca/lp/flights/nyc/chi/new-york-to-chicago) - [Flights from Omaha (OMA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/oma/mdw/omaha-to-chicago) - [Flights from Chicago (ORD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ord/chi/chicago-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/phl/mdw/philadelphia-to-chicago) - [Flights from Pueblo (PUB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/pub/mdw/pueblo-to-chicago) - [Flights from Punta Cana (PUJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/puj/chi/punta-cana-to-chicago) - [Flights from Roanoke (ROA) to Chicago (MDW)](https://www.expedia.ca/lp/flights/roa/mdw/roanoke-to-chicago) - [Flights from Selinsgrove (SEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/seg/mdw/selinsgrove-to-chicago) - [Flights from Sacramento (SMF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/smf/mdw/sacramento-to-chicago) - [Flights from St. Louis (STL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/stl/mdw/st-louis-to-chicago) - [Flights from Newburgh (SWF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/swf/mdw/newburgh-to-chicago) - [Flights from Sydney (SYD) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syd/mdw/sydney-to-chicago) - [Flights from Syracuse (SYR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/syr/mdw/syracuse-to-chicago) - [Flights from Fort Leonard Wood (TBN) to Chicago (MDW)](https://www.expedia.ca/lp/flights/tbn/mdw/fort-leonard-wood-to-chicago) - [Flights from Ua Pou (UAP) to Chicago (CHI)](https://www.expedia.ca/lp/flights/uap/chi/ua-pou-to-chicago) - [Flights from Fort Frances (YAG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yag/chi/fort-frances-to-chicago) - [Flights from Brandon (YBR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ybr/mdw/brandon-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycd/chi/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ycm/chi/st-catharines-to-chicago) - [Flights from Edmonton (YEA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yea/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yeg/chi/edmonton-to-chicago) - [Flights from Edmonton (YEG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yeg/mdw/edmonton-to-chicago) - [Flights from Flin Flon (YFO) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yfo/chi/flin-flon-to-chicago) - [Flights from Hamilton (YHM) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yhm/mdw/hamilton-to-chicago) - [Flights from Kamloops (YKA) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yka/chi/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ylw/mdw/kelowna-to-chicago) - [Flights from Montreal (YMQ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ymq/chi/montreal-to-chicago) - [Flights from Ottawa (YOW) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yow/mdw/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ypq/mdw/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqb/mdw/quebec-to-chicago) - [Flights from Regina (YQR) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqr/chi/regina-to-chicago) - [Flights from Regina (YQR) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yqr/mdw/regina-to-chicago) - [Flights from Gander (YQX) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yqx/chi/gander-to-chicago) - [Flights from Sudbury (YSB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ysb/mdw/sudbury-to-chicago) - [Flights from Timmins (YTS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yts/mdw/timmins-to-chicago) - [Flights from Toronto (YTZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ytz/mdw/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yul/mdw/montreal-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ywg/mdw/winnipeg-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (PWK)](https://www.expedia.ca/lp/flights/ywg/pwk/winnipeg-to-chicago) - [Flights from Whitehorse (YXY) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yxy/chi/whitehorse-to-chicago) - [Flights from Calgary (YYC) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyc/mdw/calgary-to-chicago) - [Flights from Victoria (YYJ) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyj/chi/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (CHI)](https://www.expedia.ca/lp/flights/yyt/chi/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/yyz/mdw/toronto-to-chicago) - [Flights from Toronto (YYZ) to Chicago (PWK)](https://www.expedia.ca/lp/flights/yyz/pwk/toronto-to-chicago) \*Available to Expedia members.