Title: CA $137 Cheap Flights from Orlando (MCO) 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 $137 Cheap Flights from Orlando (MCO) to Chicago (MDW) [View CA $137 flight on Wed, Nov 12, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MCO,to:MDW,departure:12/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:136.90&airProductToken=AQpvCjUIxJgBEgQxNDk0GMxwIOBcKJbv_AIw9-_8AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSzhCRwo2CMSYARIEMTA2MxjgXCDssAEo4_D8AjDY8fwCOEVAAVgBaglNQUlOQkFTSUNyCFZBV05LOEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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 Orlando International Airport (MCO) to Chicago Midway Airport (MDW) - ![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:mco,to:mdw,departure:22/10/2025TANYT&leg2=from:mdw,to:mco,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) - ![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:mco,to:mdw,departure:22/10/2025TANYT&leg2=from:mdw,to:mco,departure:29/10/2025TANYT&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:mco,to:mdw,departure:22/10/2025TANYT&leg2=from:mdw,to:mco,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) ![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 Orlando (MCO) to Chicago (MDW) Prices were available within the past 7 days and start at CA $137 for one-way flights and CA $273 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) Thu, Dec 11 - Mon, Dec 15 MCO Orlando MDW Chicago CA $273 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:11/12/2025TANYT&leg2=from:MDW,to:MCO,departure:15/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:272.80&airProductToken=AQpvCjUIxJgBEgQxMjEzGMxwIOBcKIu4_wIw7rj_AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSzhCRwo2CMSYARIEMjA2MBjgXCDssAEoh7r_AjD6uv8COEVAAVgBaglNQUlOQkFTSUNyCFZBV05LOEJHCm8KNgjEmAESBDIwNjAY7LABIOBcKMro_wIwyOn_AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSzhCRwo1CMSYARIEMTA2NBjgXCDMcCjs6f8CMMbq_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTks4QkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Wed, Dec 10 MCO Orlando MDW Chicago CA $274 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:09/12/2025TANYT&leg2=from:MDW,to:MCO,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:273.90&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKKOf_wIwhqD_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEow6D_AjC6of8COEVAAVgBCkUKIQjEmAESBDI0MDAY7LABIOBcKPCq_wIw6Kv_AjhFQABYAQogCMSYARIEMTY1OBjgXCDMcCiLrP8CMOqs_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Oct 25 - Mon, Oct 27 MCO Orlando MDW Chicago CA $276 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:25/10/2025TANYT&leg2=from:MDW,to:MCO,departure:27/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:276.00&airProductToken=AQpxCjYIxJgBEgQxMjAxGMxwIOO0ASi9pPsCMNyl-wI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWTks4QkcKNwjEmAESBDUyOTgY47QBIOywASivp_sCMPan-wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTks4QkcKcAo3CMSYARIEMzYzMRjssAEg47QBKIu9-wIw0b37AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOSzhCRwo1CMSYARIDMzM3GOO0ASDMcCjovvsCMIPA-wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFWTks4QkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Thu, Dec 11 MCO Orlando MDW Chicago CA $287 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:09/12/2025TANYT&leg2=from:MDW,to:MCO,departure:11/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:286.80&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKKOf_wIwhqD_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEow6D_AjC6of8COEVAAVgBCkUKIQjEmAESBDEwNjMY7LABIOBcKLG4_wIwpbn_AjhFQABYAQogCMSYARIEMTE1MBjgXCDMcCjuuf8CMMe6_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 12 - Fri, Nov 14 MCO Orlando MDW Chicago CA $288 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:12/11/2025TANYT&leg2=from:MDW,to:MCO,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:287.80&airProductToken=AQpvCjUIxJgBEgQxNDk0GMxwIOBcKJbv_AIw9-_8AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOSzhCRwo2CMSYARIEMTA2MxjgXCDssAEo4_D8AjDY8fwCOEVAAVgBaglNQUlOQkFTSUNyCFZBV05LOEJHCm8KNgjEmAESBDIwNjAY7LABIOBcKOaL_QIw34z9AjhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTBCRwo1CMSYARIEMTA2NBjgXCDMcCiMjf0CMOaN_QI4RUABWAFqCU1BSU5CQVNJQ3IIVkFXTkEwQkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Dec 12 - Sun, Dec 14 MCO Orlando MDW Chicago CA $358 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:12/12/2025TANYT&leg2=from:MDW,to:MCO,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:357.70&airProductToken=AQpxCjYIxJgBEgQyODQ1GMxwIOO0ASj7wf8CMJvD_wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFXT0EwQkcKNwjEmAESBDUyOTgY47QBIOywASjrw_8CMLrE_wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFXT0EwQkcKbwo2CMSYARIEMjQwMBjssAEg4Fwo8Nf_AjDo2P8COEVAAFgBaglNQUlOQkFTSUNyCFZBV05LOEJHCjUIxJgBEgQxNjU4GOBcIMxwKIvZ_wIw6tn_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVdOSzhCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Oct 25 - Mon, Oct 27 MCO Orlando MDW Chicago CA $360 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:25/10/2025TANYT&leg2=from:MDW,to:MCO,departure:27/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:359.90&airProductToken=AQpxCjYIxJgBEgQyODQ1GMxwIOO0ASjJpfsCMOWm-wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFVT0s4QkcKNwjEmAESBDUyOTgY47QBIOywASivp_sCMPan-wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFVT0s4QkcKcQo3CMSYARIENTI5OBjssAEg47QBKOC--wIwp7_7AjhFQABYAWoJTUFJTkJBU0lDcghWQVZOSzhCRwo2CMSYARIEMTEzMxjjtAEgzHAo1b_7AjDwwPsCOEVAAVgBaglNQUlOQkFTSUNyCFZBVk5LOEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Dec 14 - Mon, Dec 22 MCO Orlando MDW Chicago CA $372 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:14/12/2025TANYT&leg2=from:MDW,to:MCO,departure:22/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:371.70&airProductToken=AQpFCiAIxJgBEgQxNDk0GMxwIOBcKJbX_wIw-Nf_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEo49j_AjDa2f8COEVAAVgBCkcKIgjEmAESBDUxNzYY7LABIOO0ASjIt4ADMJi4gAM4RUAAWAEKIQjEmAESBDE0OTIY47QBIMxwKMe4gAMw67mAAzhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Nov 12 - Fri, Nov 14 MCO Orlando MDW Chicago CA $385 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:12/11/2025TANYT&leg2=from:MDW,to:MCO,departure:14/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:384.60&airProductToken=AQpvCjUIxJgBEgQxNDk0GMxwIOBcKJbv_AIw9-_8AjhWQABYAWoJTUFJTkNMQVNDcghWQVdOSzhNRgo2CMSYARIEMTA2MxjgXCDssAEo4_D8AjDY8fwCOFZAAVgBaglNQUlOQ0xBU0NyCFZBV05LOE1GCm8KNgjEmAESBDIwNjAY7LABIOBcKOaL_QIw34z9AjhWQABYAWoJTUFJTkNMQVNDcghWQVdOQTBNRgo1CMSYARIEMTA2NBjgXCDMcCiMjf0CMOaN_QI4VkABWAFqCU1BSU5DTEFTQ3IIVkFXTkEwTUYSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Dec 12 - Sun, Dec 14 MCO Orlando MDW Chicago CA $388 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:12/12/2025TANYT&leg2=from:MDW,to:MCO,departure:14/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:387.10&airProductToken=AQpxCjYIxJgBEgQyODQ1GMxwIOO0ASj7wf8CMJvD_wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFVT0s4QkcKNwjEmAESBDUyOTgY47QBIOywASjrw_8CMLrE_wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFVT0s4QkcKbwo2CMSYARIEMjQwMBjssAEg4Fwo8Nf_AjDo2P8COEVAAFgBaglNQUlOQkFTSUNyCFZBV05LOEJHCjUIxJgBEgQxMDMwGOBcIMxwKI3a_wIw59r_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVdOSzhCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ## Find the cheapest month to fly from Orlando (MCO) to Chicago (MDW) ### February is typically the cheapest month to fly From CA $111 - CA $500 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:MCO,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:MCO,departure:29/10/2025TANYT&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 $340](https://www.expedia.ca/Flights-Search?leg1=from:MCO,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:MCO,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) Flight from Orlando to Chicago (MCO - MDW) route information | Origin airport | Orlando Intl. | | --- | --- | | Destination airport | Midway Intl. | | Roundtrip price | CA $273 | | Distance | 1585 km | | Average flight time | 1 hour 45 mins | ## Orlando to Chicago Flights **The easy way to book your flights from Orlando to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Orlando 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 Orlando to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Orlando Intl., MCO to Midway Intl., MDW**  Sort your search results by price to find great deals on your flight from Orlando to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Orlando currently is just CA $273 rising to CA $388.   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 Orlando**  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 Orlando Intl. Airport to Midway Intl. Airport (MDW)? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey from MCO to Chicago Airport was CA $273. Cheap tickets don't hang around forever, so make sure you book yours today. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Orlando Intl. Airport (MCO) to Midway Airport? > Each air carrier has its own terms and conditions. If you do decide to cancel, follow the easy instructions on our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from Orlando Intl. Airport to Midway Intl. Airport (MDW) that have flexible change policies? > Use our "No change fees" filter to find flexible ticketing options for your flight from Orlando Intl. Airport (MCO) to Chicago Airport. This allows you to snag a great price ahead of time and still have the freedom to reschedule without any extra fees. Fare adjustments may apply if your new flight is more expensive. ### How many hours is the flight from Orlando Intl. Airport (MCO) to Chicago Airport? > Sit back, choose a movie and 2 hours and 56 minutes will whiz by in the blink of an eye. That's how long it takes to travel to MDW from MCO. ### How far is the flight from MCO to Midway Airport? > Around 1,600 kilometres separates Orlando and Chicago, so pack some in-flight entertainment to help you fill in a couple of hours. That gripping novel you've yet to start will be just the ticket. ### Which airlines fly direct from Orlando Intl. Airport to Midway Airport? > There are several airlines that travel directly from MCO to Midway Airport. Southwest Airlines (WN) is a popular option, offering 182 flights on this route each month. You could also check out the fares available with Frontier Airlines (F9). This carrier operates 13 flights every month between Orlando and Chicago. ### Are MCO to Midway Airport flight tickets cheaper when they're purchased at the last minute? > Flight tickets from Orlando Intl. Airport (MCO) to MDW are available up to 12 months before departure on Expedia. And although you may pick up a great last-minute deal, it's never a sure thing. Also, booking your flights ahead of time means you'll have more choices — and you can avoid getting trapped in the dreaded middle seat! We're always updating our fares to bring you the biggest bargains, so check back often for all the latest specials. ## 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) - [Flights from Madison (MSN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msp/ord/minneapolis-to-chicago) - [Flights from Ogdensburg (OGS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ogs/ord/ogdensburg-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Ontario (ONT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Plattsburgh (PBG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pbg/ord/plattsburgh-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pit/ord/pittsburgh-to-chicago) - [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.