Title: CA $50 Cheap Flights from Miami (MIA) 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 $50 Cheap Flights from Miami (MIA) to Chicago (ORD) [View CA $50 flight on Wed, Jan 21, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:MIA,to:ORD,departure:21/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:49.48&airProductToken=AQouCiwIzpYBEgQxNzEwGIwCIK4cKO6CgwMwuoSDAzhXQABYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) - [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 Miami International Airport (MIA) to Chicago O'Hare International Airport (ORD) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![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:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![United](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_UA.svg) United [](https://www.expedia.ca/Flights-Search?leg1=from:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&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:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Sun Country Airlines](https://a.travel-assets.com/air/airlines/sy_sq.svg) Sun Country Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:13/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"SY"}}]) - ![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 Miami (MIA) to Chicago (ORD) Prices were available within the past 7 days and start at CA $50 for one-way flights and CA $70 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $70 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:69.69&airProductToken=AQouCiwIzpYBEgQxNzEwGIwCIK4cKNzJhQMwq8uFAzhQQABYAWoCUlByBlBBMjFZNAouCiwIzpYBEgQxNzEzGK4cIIwCKLawhgMw_LGGAzhQQABYAWoCUlByBlBBMjFZNBIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Sat, Jan 17 - Mon, Jan 19 MIA Miami ORD Chicago CA $85 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:MIA,departure:19/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:84.58&airProductToken=AQouCiwIzpYBEgQxNzEwGIwCIK4cKO7VggMwuteCAzhQQABYAWoCUlByBlBBMjFZNAouCiwIzpYBEgQxNzEzGK4cIIwCKPnyggMwvvSCAzhXQABYAWoCUlByBldBMjFOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $96 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:95.44&airProductToken=AQpcCiwIzpYBEgQxMjc0GIwCIIg4KM3QhQMwh9KFAzhQQABYAWoCUlByBlBBMjFZNAosCM6WARIEMTE1NhiIOCCuHCjD1IUDMOLVhQM4UEABWAFqAlJQcgZQQTIxWTQKLgosCM6WARIEMTcxMxiuHCCMAii2sIYDMPyxhgM4UEAAWAFqAlJQcgZQQTIxWTQSCggBEAEYASoCTksYASIECAEQASgCKAMoBDAN) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Wed, Jan 21 - Sat, Jan 24 MIA Miami ORD Chicago CA $110 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:21/01/2026TANYT&leg2=from:ORD,to:MIA,departure:24/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:109.42&airProductToken=AQouCiwIzpYBEgQxNzEwGIwCIK4cKO6CgwMwuoSDAzhQQABYAWoCUlByBlBBMjFZNAouCiwIzpYBEgQxNzEzGK4cIIwCKJmrgwMw3qyDAzhHQABYAWoCUlByBkdBMzBOUhIKCAEQARgBKgJOSxgBIgQIARABKAIoAygEMA0) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $120 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:119.82&airProductToken=AQpdCi0IzpYBEgQyODkzGIwCIMSNASiVzYUDMM7OhQM4V0AAWAFqAlJQcgZXQTIxTlIKLAjOlgESAzEwOBjEjQEgrhwoldGFAzCw0oUDOFdAAVgBagJSUHIGV0EyMU5SCi4KLAjOlgESBDE3MTMYrhwgjAIotrCGAzD8sYYDOFBAAFgBagJSUHIGUEEyMVk0EgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $122 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:121.19&airProductToken=AQpcCiwIzpYBEgQxMjc0GIwCIIg4KM3QhQMwh9KFAzhQQABYAWoCUlByBlBBMjFZNAosCM6WARIEMTE1NhiIOCCuHCjD1IUDMOLVhQM4UEABWAFqAlJQcgZQQTIxWTQKXAosCM6WARIEMTE1NxiuHCCIOCiksIYDMNixhgM4UEAAWAFqAlJQcgZQQTIxWTQKLAjOlgESBDEyNzMYiDggjAIonLSGAzCvtYYDOFBAAVgBagJSUHIGUEEyMVk0EgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $171 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:170.94&airProductToken=AQozCjEIwYIBEgQxMjA0GIwCIK4cKNTQhQMwqdKFAzhCQABYAWoFQkFTSUNyCFFXQVVJT0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 19 - Sat, Feb 28 MIA Miami ORD Chicago CA $185 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:19/02/2026TANYT&leg2=from:ORD,to:MIA,departure:28/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:184.34&airProductToken=AQpwCjYIxJgBEgQyNjM4GIwCIOO0ASiRyoUDMM3LhQM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFXTkEwQkcKNgjEmAESBDQ0ODEY47QBIK4cKLPMhQMwis2FAzhFQAFYAWoJTUFJTkJBU0lDcghWQVdOQTBCRxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Feb 5 - Thu, Feb 26 MIA Miami ORD Chicago CA $354 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:05/02/2026TANYT&leg2=from:ORD,to:MIA,departure:26/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:354.00&airProductToken=AQoiCiAI1YIBEgQyMjIzGIwCIK4cKIithAMw3q6EAzhHQABYAQoiCiAI1YIBEgQxMzU4GK4cIIwCKIqZhgMwz5qGAzhLQABYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Sun, Jan 4 - Thu, Jan 8 MIA Miami ORD Chicago CA $26,421 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:MIA,to:ORD,departure:04/01/2026TANYT&leg2=from:ORD,to:MIA,departure:08/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:26420.20&airProductToken=AQpoCjIIwaYBEgQ2NDA2GIwCIEMorMaBAzDMx4EDOFlAAFgBagJGTXIBWXoKCMGCARIEMjQ5NQoyCMGmARIENjE4MRhDIK4cKInIgQMwl8mBAzhZQAFYAWoCRk1yAVl6CgjBggESBDYxODEKnQEKMwjBpgESBDY1NDkYrhwg4iIokPKBAzDq8oEDOFlAAFgBagJGTXIBWXoKCMGCARIENjU0OQoyCMGmARIENjA1OBjiIiBDKNXzgQMwrPSBAzhZQAFYAWoCRk1yAVl6CgjBggESBDYwNTgKMgjBpgESBDQ1OTcYQyCMAijn9YEDMKD3gQM4WUABWAFqAkZNcgFZegoIwYIBEgQzMTgxEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Miami (MIA) to Chicago (ORD) ### February is typically the cheapest month to fly From CA $79 - CA $197 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:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:12/01/2026TANYT&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 $465 ](https://www.expedia.ca/Flights-Search?leg1=from:MIA,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:MIA,departure:12/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Frequently asked questions ### How much is a flight from MIA to O'Hare Intl. Airport (ORD)? ### Do I need to pay a cancellation fee if I cancel my flight from Miami Intl. Airport (MIA) to O'Hare Intl. Airport (ORD)? ### How do I find cheap flights from MIA to O'Hare Airport that have flexible change policies? ### How many hours is the flight from MIA to O'Hare Airport? ### How far is the flight from MIA to O'Hare Intl. Airport (ORD)? ### Which airlines fly direct from Miami Intl. Airport (MIA) to ORD? ### Are MIA to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Miami Intl. | | ------------------- | ----------------------------------------- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines, Delta, Spirit Airlines | | Roundtrip price | CA $70 | | Distance | 1918 km | | Average flight time | 2 hours 29 mins | ## Book with confidence # Miami to Chicago Flights **The easy way to book your flights from Miami to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Miami 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 Miami to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Miami Intl., MIA to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Miami to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Miami currently is just CA $70 rising to CA $26,421\. Here are more money-saving tips: - Fly in February 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 Miami** 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. 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[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.