Title: CA $138 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://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $138 Cheap Flights from Orlando (MCO) to Chicago (MDW) [View CA $138 flight on Fri, Jan 9, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MCO,to:MDW,departure:09/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:137.20&airProductToken=AQpvCjUIxJgBEgQxNTQ4GMxwIOBcKNb7gQMwuvyBAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTBCRwo2CMSYARIEMTA2MxjgXCDssAEoxv2BAzC7_oEDOEVAAVgBaglNQUlOQkFTSUNyCFZBV05BMEJHEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) - [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:07/12/2025TANYT&leg2=from:MDW,to:MCO,departure:14/12/2025TANYT&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:07/12/2025TANYT&leg2=from:MDW,to:MCO,departure:14/12/2025TANYT&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:07/12/2025TANYT&leg2=from:MDW,to:MCO,departure:14/12/2025TANYT&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 $138 for one-way flights and CA $277 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) Tue, Dec 9 - Tue, Dec 16 MCO Orlando MDW Chicago CA $277 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:09/12/2025TANYT&leg2=from:MDW,to:MCO,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:276.40&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKKOf_wIwhqD_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEow6D_AjC6of8COEVAAVgBCkUKIQjEmAESBDI0MDAY7LABIOBcKLDu_wIwqO__AjhFQABYAQogCMSYARIEMTY1OBjgXCDMcCjL7_8CMKrw_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Mon, Dec 15 MCO Orlando MDW Chicago CA $278 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:09/12/2025TANYT&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:277.50&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKKOf_wIwhqD_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEow6D_AjC6of8COEVAAVgBCkUKIQjEmAESBDI0MDAY7LABIOBcKJDj_wIwiOT_AjhFQABYAQogCMSYARIEMTY1OBjgXCDMcCir5P8CMIrl_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Dec 15 - Tue, Dec 16 MCO Orlando MDW Chicago CA $318 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:15/12/2025TANYT&leg2=from:MDW,to:MCO,departure:16/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:317.30&airProductToken=AQpFCiAIxJgBEgQxNDk3GMxwIOBcKJTp_wIwgOr_AjhFQABYAQohCMSYARIEMTA3NhjgXCDssAEoxer_AjC76_8COEVAAVgBCkUKIQjEmAESBDI0MDAY7LABIOBcKLDu_wIwqO__AjhFQABYAQogCMSYARIEMTY1OBjgXCDMcCjL7_8CMKrw_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Dec 9 - Fri, Dec 12 MCO Orlando MDW Chicago CA $319 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:09/12/2025TANYT&leg2=from:MDW,to:MCO,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:318.30&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKKOf_wIwhqD_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEow6D_AjC6of8COEVAAVgBCkUKIQjEmAESBDIwNjAY7LABIOBcKNHG_wIw0sf_AjhFQABYAQogCMSYARIEMTE2MhjgXCDMcCjIyP8CMJ_J_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Dec 3 - Fri, Dec 12 MCO Orlando MDW Chicago CA $368 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:03/12/2025TANYT&leg2=from:MDW,to:MCO,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:367.80&airProductToken=AQpuCjQIxJgBEgM2NjQYzHAg4Fwoh9_-AjDl3_4COEVAAFgBaglNQUlOQkFTSUNyCFZBVU5LOEJHCjYIxJgBEgQyMDYwGOBcIOywASiY4P4CMIrh_gI4RUABWAFqCU1BSU5CQVNJQ3IIVkFVTks4QkcKbwo2CMSYARIEMjA2MBjssAEg4Fwo0cb_AjDSx_8COEVAAFgBaglNQUlOQkFTSUNyCFZBVk5BMEJHCjUIxJgBEgQxMTYyGOBcIMxwKMjI_wIwn8n_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Dec 14 - Wed, Dec 17 MCO Orlando MDW Chicago CA $389 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:14/12/2025TANYT&leg2=from:MDW,to:MCO,departure:17/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:388.20&airProductToken=AQpFCiAIxJgBEgQxMTkyGMxwIOBcKMPX_wIwptj_AjhFQABYAQohCMSYARIEMTA2MxjgXCDssAEo49j_AjDa2f8COEVAAVgBCkUKIQjEmAESBDI0MDAY7LABIOBcKND5_wIwyPr_AjhFQABYAQogCMSYARIEMTY1OBjgXCDMcCjr-v8CMMr7_wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Feb 1 - Wed, Feb 4 MCO Orlando MDW Chicago CA $391 Roundtrip found 2 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:01/02/2026TANYT&leg2=from:MDW,to:MCO,departure:04/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:390.60&airProductToken=AQpvCjUIxJgBEgQxNTQ4GMxwIOBcKLb-gwMwmP-DAzhFQABYAWoJTUFJTkJBU0lDcghWQVdOQTBCRwo2CMSYARIEMTA2MxjgXCDssAEohICEAzD5gIQDOEVAAVgBaglNQUlOQkFTSUNyCFZBV05BMEJHCm8KNgjEmAESBDIwNjAY7LABIOBcKM6mhAMw16eEAzhFQABYAWoJTUFJTkJBU0lDcghYQVdPQTBCRwo1CMSYARIEMTE2MhjgXCDMcCiXqIQDMO-ohAM4RUABWAFqCU1BSU5CQVNJQ3IIWEFXT0EwQkcSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Dec 6 - Fri, Dec 12 MCO Orlando MDW Chicago CA $432 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:06/12/2025TANYT&leg2=from:MDW,to:MCO,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:431.40&airProductToken=AQpxCjYIxJgBEgQxNDU1GMxwIOO0ASjfgP8CMISC_wI4RUAAWAFqCU1BSU5CQVNJQ3IIWEFVT0EwQkcKNwjEmAESBDQ4NjkY47QBIOywASj2gv8CMMaD_wI4RUABWAFqCU1BSU5CQVNJQ3IIWEFVT0EwQkcKbwo2CMSYARIEMjA2MBjssAEg4Fwo0cb_AjDSx_8COEVAAFgBaglNQUlOQkFTSUNyCFZBVk5BMEJHCjUIxJgBEgQxNzIyGOBcIMxwKITJ_wIw3sn_AjhFQAFYAWoJTUFJTkJBU0lDcghWQVZOQTBCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Dec 6 - Fri, Dec 12 MCO Orlando MDW Chicago CA $440 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:06/12/2025TANYT&leg2=from:MDW,to:MCO,departure:12/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:440.00&airProductToken=AQpxCjYIxJgBEgQyODQ1GMxwIOO0ASi7_v4CMNv__gI4RUAAWAFqCU1BSU5CQVNJQ3IIVkFVTks4QkcKNwjEmAESBDUyOTgY47QBIOywASiwgP8CMPqA_wI4RUABWAFqCU1BSU5CQVNJQ3IIVkFVTks4QkcKbwo2CMSYARIEMjA2MBjssAEg4Fwo0cb_AjDSx_8COEVAAFgBaglNQUlOQkFTSUNyCFhBVk9BMEJHCjUIxJgBEgQxMTYyGOBcIMxwKMjI_wIwn8n_AjhFQAFYAWoJTUFJTkJBU0lDcghYQVZPQTBCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Dec 25 - Mon, Dec 29 MCO Orlando MDW Chicago CA $444 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MCO,to:MDW,departure:25/12/2025TANYT&leg2=from:MDW,to:MCO,departure:29/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:443.20&airProductToken=AQpvCjUIxJgBEgQxMzcyGMxwIOBcKIDYgAMw5NiAAzhFQABYAWoJTUFJTkJBU0lDcghWQTdTQTBCUQo2CMSYARIEMTA3NhjgXCDssAEosdqAAzCm24ADOEVAAVgBaglNQUlOQkFTSUNyCFZBN1NBMEJRCnEKNwjEmAESBDUxNzYY7LABIOO0ASiohoEDMPiGgQM4RUAAWAFqCU1BSU5CQVNJQ3IIWEFXTkEwQkMKNgjEmAESBDE0OTIY47QBIMxwKKeHgQMwy4iBAzhFQAFYAWoJTUFJTkJBU0lDcghYQVdOQTBCQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=FTG_BF_PROMO_) ## Find the cheapest month to fly from Orlando (MCO) to Chicago (MDW) ### November is typically the cheapest month to fly From CA $99 - CA $533 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:07/12/2025TANYT&leg2=from:ORD,to:MCO,departure:11/12/2025TANYT&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 $269](https://www.expedia.ca/Flights-Search?leg1=from:MCO,to:ORD,departure:07/12/2025TANYT&leg2=from:ORD,to:MCO,departure:11/12/2025TANYT&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. | | Airlines serving | Delta | | Roundtrip price | CA $270 | | Distance | 1585 km | | Average flight time | 1 hour 49 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 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 $277 rising to CA $444.   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. ## 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. 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