Title: CA $220 Cheap Flights from Boston (BOS) to Chicago (MDW) - 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_flights_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $220 Cheap Flights from Boston (BOS) to Chicago (MDW) [View CA $220 flight on Thu, Dec 4, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:BOS,to:MDW,departure:04/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:219.10&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEo1eb-AjDj5_4COEVAAFgBaglNQUlOQkFTSUNyCFZBVlNYNUJDCjcIxJgBEgQ1Mjk4GOO0ASDssAEo6-n-AjC66v4COEVAAVgBaglNQUlOQkFTSUNyCFZBVlNYNEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 Logan International Airport (BOS) to Chicago Midway Airport (MDW) - ![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:bos,to:mdw,departure:24/10/2025TANYT&leg2=from:mdw,to:bos,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:bos,to:mdw,departure:24/10/2025TANYT&leg2=from:mdw,to:bos,departure:31/10/2025TANYT&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:bos,to:mdw,departure:24/10/2025TANYT&leg2=from:mdw,to:bos,departure:31/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ![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 Boston (BOS) to Chicago (MDW) Prices were available within the past 7 days and start at CA $220 for one-way flights and CA $419 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 22 - Thu, Nov 27 BOS Boston MDW Chicago CA $419 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:22/11/2025TANYT&leg2=from:MDW,to:BOS,departure:27/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:418.30&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEo1d_9AjDi4P0COEVAAFgBaglNQUlOQkFTSUNyCExBN05YMEJRCjcIxJgBEgQ0ODU4GOO0ASDssAEoiuH9AjDc4f0COEVAAVgBaglNQUlOQkFTSUNyCExBN05YMEJRCnIKNwjEmAESBDQ4NTgY7LABIOO0ASimmv4CMPGa_gI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU1g0QkMKNwjEmAESBDE3MDcY47QBIMGTASiFnf4CMPqd_gI4RUABWAFqCU1BSU5CQVNJQ3IIVkZWU0EwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Oct 30 - Mon, Nov 3 BOS Boston MDW Chicago CA $442 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:30/10/2025TANYT&leg2=from:MDW,to:BOS,departure:03/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:442.00&airProductToken=AQpyCjcIxJgBEgQxNzQ4GMGTASDjtAEojN77AjCY3_sCOEVAAFgBaglNQUlOQkFTSUNyCExBN05YMEJRCjcIxJgBEgQ1Mjk4GOO0ASDssAEoz9_7AjCY4PsCOEVAAVgBaglNQUlOQkFTSUNyCExBN05YMEJRCnIKNwjEmAESBDM1MDEY7LABIOO0ASi3kPwCMP-Q_AI4RUAAWAFqCU1BSU5CQVNJQ3IITEE3TlgwQlEKNwjEmAESBDExODcY47QBIMGTASjKkfwCMMGS_AI4RUABWAFqCU1BSU5CQVNJQ3IITEE3TlgwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Nov 22 - Fri, Nov 28 BOS Boston MDW Chicago CA $512 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:22/11/2025TANYT&leg2=from:MDW,to:BOS,departure:28/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:511.80&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEo1d_9AjDi4P0COEVAAFgBaglNQUlOQkFTSUNyCExBN05YMEJRCjcIxJgBEgQ0ODU4GOO0ASDssAEoiuH9AjDc4f0COEVAAVgBaglNQUlOQkFTSUNyCExBN05YMEJRCnAKNgjEmAESBDM3NzgY7LABIMx8KM2l_gIws6b-AjhFQABYAWoJTUFJTkJBU0lDcghLQVdHQTBCUQo2CMSYARIEMjU1OBjMfCDBkwEoqKf-AjDQqP4COEVAAVgBaglNQUlOQkFTSUNyCEtBV0dBMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $540 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:539.80&airProductToken=AQpvCjUIxJgBEgMzMjIYwZMBIOBcKK-hggMw5aKCAzhMQABYAWoJTUFJTkNMQVNDcghMQVZTWDBNRQo2CMSYARIEMTA3NhjgXCDssAEozqSCAzDCpYIDOExAAVgBaglNQUlOQ0xBU0NyCExBVlNYME1FCm8KNgjEmAESBDEwNjMY7LABIOBcKKP6ggMwm_uCAzhMQABYAWoJTUFJTkNMQVNDcghMQVZTWDNNTAo1CMSYARIDNTE4GOBcIMGTASjA_IIDMNz9ggM4TEABWAFqCU1BSU5DTEFTQ3IITEFWU1gzTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $582 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:581.70&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEotp2CAzDGnoIDOEVAAFgBaglNQUlOQkFTSUNyCEtBVlRYMEJDCjcIxJgBEgQzODU4GOO0ASDssAEo5Z6CAzC6n4IDOEVAAVgBaglNQUlOQkFTSUNyCEtBVlRYMEJDCm8KNgjEmAESBDEyODUY7LABIOBcKJD4ggMwivmCAzhFQABYAWoJTUFJTkJBU0lDcghLQVZUWDNCUQo1CMSYARIDODU1GOBcIMGTASjE-YIDMOL6ggM4RUABWAFqCU1BSU5CQVNJQ3IIS0FWVFgzQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $609 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:608.60&airProductToken=AQpyCjcIxJgBEgQxNzQ4GMGTASDjtAEokp-CAzCgoIIDOEtAAFgBaglNQUlOQ0xBU0NyCEtBVlRYME1FCjcIxJgBEgQzNTI3GOO0ASDssAEoy6CCAzCboYIDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVlRYME1FCnIKNwjEmAESBDM1MDEY7LABIOO0ASjf_YIDMKz-ggM4TEAAWAFqCU1BSU5DTEFTQ3IITEFWU1gzTUwKNwjEmAESBDExODcY47QBIMGTASj7_oIDMPb_ggM4TEABWAFqCU1BSU5DTEFTQ3IITEFWU1gzTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $639 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:638.70&airProductToken=AQpvCjUIxJgBEgM0NzYYwZMBIOBcKKeiggMw4aOCAzhMQABYAWoJTUFJTkNMQVNDcghMQVZTWDBNRQo2CMSYARIEMTA3NhjgXCDssAEozqSCAzDCpYIDOExAAVgBaglNQUlOQ0xBU0NyCExBVlNYME1FCnIKNwjEmAESBDM1MjcY7LABIOO0ASi0-4IDMP77ggM4UUAAWAFqCU1BSU5DTEFTQ3IIUUFVTlgwTUMKNwjEmAESBDExNzEY47QBIMGTASii_IIDMJr9ggM4UUABWAFqCU1BSU5DTEFTQ3IIUUFVTlgwTUMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $651 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:650.50&airProductToken=AQpvCjUIxJgBEgM0NzYYwZMBIOBcKKeiggMw4aOCAzhMQABYAWoJTUFJTkVYVFJBcghMQVYxWDBNRQo2CMSYARIEMTA3NhjgXCDssAEozqSCAzDCpYIDOExAAVgBaglNQUlORVhUUkFyCExBVjFYME1FCnAKNgjEmAESBDEwNjMY7LABIOBcKKP6ggMwm_uCAzhMQABYAWoJTUFJTkVYVFJBcghMQVYxWDNNTAo2CMSYARIEMjU5NRjgXCDBkwEo-vuCAzCX_YIDOExAAVgBaglNQUlORVhUUkFyCExBVjFYM01MEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Jan 12 - Tue, Jan 20 BOS Boston MDW Chicago CA $679 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:12/01/2026TANYT&leg2=from:MDW,to:BOS,departure:20/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:678.50&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEotp2CAzDGnoIDOEtAAFgBaglNQUlOQ0xBU0NyCEtBVlRYME1FCjcIxJgBEgQzODU4GOO0ASDssAEo5Z6CAzC6n4IDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVlRYME1FCm8KNgjEmAESBDEyODUY7LABIOBcKJD4ggMwivmCAzhLQABYAWoJTUFJTkNMQVNDcghLQVZUWDNNTAo1CMSYARIDODU1GOBcIMGTASjE-YIDMOL6ggM4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWVFgzTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Jun 26 - Fri, Jul 10 BOS Boston MDW Chicago CA $695 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:MDW,departure:26/06/2026TANYT&leg2=from:MDW,to:BOS,departure:10/07/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:694.60&airProductToken=AQpyCjcIxJgBEgQxMDE5GMGTASDjtAEomt2QAzCg3pADOFFAAFgBaglNQUlOQ0xBU0NyCFFBVU5YME1DCjcIxJgBEgQzODU4GOO0ASDssAEoyd6QAzCW35ADOFFAAVgBaglNQUlOQ0xBU0NyCFFBVU5YME1DCnIKNwjEmAESBDM1MDEY7LABIOO0ASiDgZIDMMuBkgM4TEAAWAFqCU1BSU5DTEFTQ3IITEE3TlgwTUwKNwjEmAESBDExODcY47QBIMGTASifgpIDMJSDkgM4TEABWAFqCU1BSU5DTEFTQ3IITEE3TlgwTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Find the cheapest month to fly from Boston (BOS) to Chicago (MDW) ### September is typically the cheapest month to fly From CA $106 - CA $417 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:BOS,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:BOS,departure:25/10/2025TANYT&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 $277](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:24/10/2025TANYT&leg2=from:ORD,to:BOS,departure:25/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Boston to Chicago (BOS - MDW) route information | Origin airport | Logan Intl. | | --- | --- | | Destination airport | Midway Intl. | | Airlines serving | Delta | | Roundtrip price | CA $418 | | Distance | 1371 km | | Average flight time | 1 hour 42 mins | ## Boston to Chicago Flights **The easy way to book your flights from Boston to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Boston 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 Southwest Airlines nonstop flights to Midway 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 Boston to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Logan Intl., BOS to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Boston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Boston currently is just CA $419 rising to CA $695.   Here are more money-saving tips:  - Fly in November 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 Boston**  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 BOS to Midway Intl. Airport (MDW)? > Round-trip tickets from BOS to Chicago Airport start from CA $419. This price is based on fares advertised 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 BOS to Midway Intl. Airport (MDW)? > The majority of flights can be cancelled online, but every air carrier has its own set of terms and conditions. If you do need to cancel your flight, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Logan Intl. Airport (BOS) to MDW that have flexible change policies? > Plenty of carriers will allow you to reschedule your flight without a change fee. All you pay is the difference in the ticket price. When searching for Logan Intl. Airport (BOS) to MDW flights, you'll see a "No change fees" filter for you to pick. ### How many hours is the flight from BOS to Midway Airport? > It only takes an average of 5 hours and 23 minutes to jet from BOS to Midway Airport. Put your seat back and make yourself comfortable — but not too comfortable. You'll be touching down in Chicago in no time. ### How far is the flight from Logan Intl. Airport to Midway Airport? > It's only 1,400 kilometres from Logan Intl. Airport to Chicago Airport. It's quite possible that you'll spend more time travelling to and from the airport than actually flying! ### Which airlines fly direct from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW)? > A popular choice with many savvy travellers, Southwest Airlines (WN) offers 65 monthly flights from Logan Intl. Airport (BOS) to Midway Airport. Pick the one that fits in with your travel plans and book your seat today. ### Are Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute? > Late planners can occasionally find a bargain, with some of the cheapest fares from Logan Intl. Airport (BOS) to Midway Airport emerging a few weeks before the departure date. If you'd rather book ahead, Expedia compares and updates all the best flight deals frequently — as early as a year in advance in some cases. It depends on the carrier though, as not every airline releases prices that far in advance. ## Explore a world of travel with Expedia - Flights ### Flights - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Waterloo (ALO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/alo/ord/waterloo-to-chicago) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD)](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/buf/ord/buffalo-to-chicago) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Sault Ste. Marie (CIU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ciu/ord/sault-ste-marie-to-chicago) - [Flights from Charlotte (CLT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/clt/ord/charlotte-to-chicago) - [Flights from Columbus (CMH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cmh/ord/columbus-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dca/ord/washington-to-chicago) - [Flights from Delhi (DEL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/del/ord/delhi-to-chicago) - [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/den/ord/denver-to-chicago) - [Flights from Dallas (DFW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dfw/ord/dallas-to-chicago) - [Flights from Duluth (DLH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dlh/ord/duluth-to-chicago) - [Flights from Des Moines (DSM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dsm/ord/des-moines-to-chicago) - [Flights from Detroit (DTW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dtw/ord/detroit-to-chicago) - [Flights from Dubai (DXB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Fargo (FAR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/far/ord/fargo-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fll/ord/fort-lauderdale-to-chicago) - [Flights from Flint (FNT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fnt/ord/flint-to-chicago) - [Flights from Spokane (GEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/geg/ord/spokane-to-chicago) - [Flights from Grand Forks (GFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gfk/ord/grand-forks-to-chicago) - [Flights from Green Bay (GRB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grb/ord/green-bay-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grr/ord/grand-rapids-to-chicago) - [Flights from Great Falls (GTF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gtf/ord/great-falls-to-chicago) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hou/ord/houston-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hyd/ord/hyderabad-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/iag/ord/niagara-falls-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from Karachi (KHI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/khi/ord/karachi-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lax/ord/los-angeles-to-chicago) - [Flights from New York (LGA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lga/ord/new-york-to-chicago) - [Flights from London (LHR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lhr/ord/london-to-chicago) - [Flights from Kansas City (MCI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Orlando (MCO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mia/ord/miami-to-chicago) - [Flights from Milwaukee (MKE) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mke/ord/milwaukee-to-chicago) - [Flights from Minot (MOT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mot/ord/minot-to-chicago) - 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[Flights from Raleigh (RDU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rdu/ord/raleigh-to-chicago) - [Flights from Rockford (RFD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rfd/ord/rockford-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Seattle (SEA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sea/ord/seattle-to-chicago) - [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Syracuse (SYR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/syr/ord/syracuse-to-chicago) - [Flights from Sault Ste. Marie (YAM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yam/ord/sault-ste-marie-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycd/ord/nanaimo-to-chicago) - [Flights from St. Catharines (YCM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycm/ord/st-catharines-to-chicago) - [Flights from Edmonton (YEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yeg/ord/edmonton-to-chicago) - [Flights from Fredericton (YFC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yfc/ord/fredericton-to-chicago) - [Flights from Kingston (YGK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ygk/ord/kingston-to-chicago) - [Flights from Hamilton (YHM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhm/ord/hamilton-to-chicago) - [Flights from Halifax (YHZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yhz/ord/halifax-to-chicago) - [Flights from Kamloops (YKA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yka/ord/kamloops-to-chicago) - [Flights from Kitchener (YKF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ykf/ord/kitchener-to-chicago) - [Flights from Kelowna (YLW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ylw/ord/kelowna-to-chicago) - [Flights from Ottawa (YOW) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yow/ord/ottawa-to-chicago) - [Flights from Peterborough (YPQ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ypq/ord/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Flights from Windsor (YQG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqg/ord/windsor-to-chicago) - [Flights from Moncton (YQM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqm/ord/moncton-to-chicago) - [Flights from Regina (YQR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqr/ord/regina-to-chicago) - [Flights from Thunder Bay (YQT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqt/ord/thunder-bay-to-chicago) - [Flights from Sudbury (YSB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysb/ord/sudbury-to-chicago) - [Flights from Saint John (YSJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysj/ord/saint-john-to-chicago) - [Flights from Toronto (YTZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) - [Flights from Montreal (YUL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yul/ord/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yvr/ord/vancouver-to-chicago) - [Flights from Winnipeg (YWG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ywg/ord/winnipeg-to-chicago) - [Flights from Saskatoon (YXE) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxe/ord/saskatoon-to-chicago) - [Flights from London (YXU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxu/ord/london-to-chicago) - [Flights from Abbotsford (YXX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxx/ord/abbotsford-to-chicago) - [Flights from North Bay (YYB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyb/ord/north-bay-to-chicago) - [Flights from Calgary (YYC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyc/ord/calgary-to-chicago) - [Flights from Charlottetown (YYG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyg/ord/charlottetown-to-chicago) - [Flights from Victoria (YYJ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyj/ord/victoria-to-chicago) - [Flights from St. John's (YYT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyt/ord/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Flights from Sarnia (YZR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yzr/ord/sarnia-to-chicago) \*Available to Expedia members.