Title: CA $499 Cheap Flights from Waterloo (ALO) 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 $499 Cheap Flights from Waterloo (ALO) to Chicago (ORD) [View CA $499 flight on Wed, Jan 28, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ALO,to:ORD,departure:28/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:498.30&airProductToken=AQoyCjAIwYIBEgQ0MzI2GOByIK4cKMPWgwMwmNeDAzhTQABYAWoETUFJTnIIUzBBV1VOTjESCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) - [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 Waterloo, IA (ALO-Waterloo Regional) to Chicago O'Hare International Airport (ORD) - ![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:ALO,to:ORD,departure:18/01/2026TANYT&leg2=from:ORD,to:ALO,departure:25/01/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![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 Waterloo (ALO) to Chicago (ORD) Prices were available within the past 7 days and start at CA $499 for one-way flights and CA $522 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Mar 6 - Sun, Mar 8 ALO Waterloo ORD Chicago CA $522 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:06/03/2026TANYT&leg2=from:ORD,to:ALO,departure:08/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:521.50&airProductToken=AQozCjEIwYIBEgQ0MzI2GOByIK4cKNv2hgMwr_eGAzhCQABYAWoFQkFTSUNyCE5XRldaTkJaCjMKMQjBggESBDQzMjEYrhwg4HIolpCHAzDlkIcDOEJAAFgBagVCQVNJQ3IITldGV1pOQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Mar 5 - Mon, Mar 9 ALO Waterloo ORD Chicago CA $523 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:05/03/2026TANYT&leg2=from:ORD,to:ALO,departure:09/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:522.90&airProductToken=AQozCjEIwYIBEgQ0MzIyGOByIK4cKOjmhgMwveeGAzhCQABYAWoFQkFTSUNyCE5XRldaTkJaCjMKMQjBggESBDQzMjEYrhwg4HIotpuHAzCFnIcDOEJAAFgBagVCQVNJQ3IITldGV1pOQloSCggBEAEYASoCQUEYASIECAEQASgCKAMoBDAL) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Mar 4 - Tue, Mar 10 ALO Waterloo ORD Chicago CA $543 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:04/03/2026TANYT&leg2=from:ORD,to:ALO,departure:10/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:543.00&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKJvghgMw7-CGAzhOQABYAQoiCiAIwYIBEgQ0MzIxGK4cIOByKNamhwMwpaeHAzhOQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Mar 4 - Sun, Mar 8 ALO Waterloo ORD Chicago CA $574 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:04/03/2026TANYT&leg2=from:ORD,to:ALO,departure:08/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:573.10&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKJvghgMw7-CGAzhOQABYAQoiCiAIwYIBEgQ0MzI2GK4cIOByKO2LhwMwvIyHAzhOQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Jan 28 - Wed, Feb 4 ALO Waterloo ORD Chicago CA $582 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:28/01/2026TANYT&leg2=from:ORD,to:ALO,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:581.70&airProductToken=AQoyCjAIwYIBEgQ0MzI2GOByIK4cKMPWgwMwmNeDAzhTQABYAWoETUFJTnIIUzBGV1VOTjEKMgowCMGCARIENDMyMRiuHCDgcij7p4QDMMeohAM4TkAAWAFqBE1BSU5yCE5XRldVTk0xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Mar 4 - Sat, Mar 7 ALO Waterloo ORD Chicago CA $598 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:04/03/2026TANYT&leg2=from:ORD,to:ALO,departure:07/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:597.80&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKJvghgMw7-CGAzhOQABYAQoiCiAIwYIBEgQ0MzIxGK4cIOByKLKFhwMwgYaHAzhHQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Mar 6 - Sun, Mar 8 ALO Waterloo ORD Chicago CA $604 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:06/03/2026TANYT&leg2=from:ORD,to:ALO,departure:08/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:603.20&airProductToken=AQoyCjAIwYIBEgQ0MzI2GOByIK4cKNv2hgMwr_eGAzhOQABYAWoETUFJTnIITldGV1pOTTEKMgowCMGCARIENDMyMRiuHCDgciiWkIcDMOWQhwM4TkAAWAFqBE1BSU5yCE5XRldaTk0xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Mar 5 - Mon, Mar 9 ALO Waterloo ORD Chicago CA $605 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:05/03/2026TANYT&leg2=from:ORD,to:ALO,departure:09/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:604.60&airProductToken=AQoyCjAIwYIBEgQ0MzIyGOByIK4cKOjmhgMwveeGAzhOQABYAWoETUFJTnIITldGV1pOTTEKMgowCMGCARIENDMyMRiuHCDgcii2m4cDMIWchwM4TkAAWAFqBE1BSU5yCE5XRldaTk0xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Jan 14 - Tue, Jan 20 ALO Waterloo ORD Chicago CA $621 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:ALO,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:620.40&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKIO5ggMw2LmCAzhTQABYAQoiCiAIwYIBEgQ0MzIxGK4cIOByKJv_ggMw5_-CAzhTQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Mar 5 - Sat, Mar 7 ALO Waterloo ORD Chicago CA $628 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:05/03/2026TANYT&leg2=from:ORD,to:ALO,departure:07/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:627.90&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKLvrhgMwj-yGAzhOQABYAQoiCiAIwYIBEgQ0MzIxGK4cIOByKLKFhwMwgYaHAzhHQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Mar 4 - Sun, Mar 15 ALO Waterloo ORD Chicago CA $642 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:04/03/2026TANYT&leg2=from:ORD,to:ALO,departure:15/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:641.90&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKJvghgMw7-CGAzhOQABYAQoiCiAIwYIBEgQ0MzI2GK4cIOByKM3ahwMwnNuHAzhOQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Fri, Mar 6 - Sun, Mar 8 ALO Waterloo ORD Chicago CA $664 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:06/03/2026TANYT&leg2=from:ORD,to:ALO,departure:08/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:663.40&airProductToken=AQoyCjAIwYIBEgQ0MzIyGOByIK4cKIjyhgMw3fKGAzhTQABYAWoETUFJTnIIUzBGV1pOTjEKMgowCMGCARIENDMyMRiuHCDgciiWkIcDMOWQhwM4TkAAWAFqBE1BSU5yCE5XRldaTk0xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Mar 5 - Sun, Mar 15 ALO Waterloo ORD Chicago CA $672 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:05/03/2026TANYT&leg2=from:ORD,to:ALO,departure:15/03/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:672.00&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKLvrhgMwj-yGAzhOQABYAQoiCiAIwYIBEgQ0MzI2GK4cIOByKM3ahwMwnNuHAzhOQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Jan 11 - Tue, Jan 20 ALO Waterloo ORD Chicago CA $708 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:11/01/2026TANYT&leg2=from:ORD,to:ALO,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:707.40&airProductToken=AQoiCiAIwYIBEgQ0MzI2GOByIK4cKKOXggMw-JeCAzhHQABYAQoiCiAIwYIBEgQ0MzIxGK4cIOByKJv_ggMw5_-CAzhTQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Jan 28 - Wed, Feb 4 ALO Waterloo ORD Chicago CA $719 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:28/01/2026TANYT&leg2=from:ORD,to:ALO,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:718.20&airProductToken=AQo0CjIIwYIBEgQ0MzI2GOByIK4cKMPWgwMwmNeDAzhTQABYAWoGTUFJTkZMcghTMEZXVVJVMQo0CjIIwYIBEgQ0MzIxGK4cIOByKPunhAMwx6iEAzhOQABYAWoGTUFJTkZMcghOV0ZXVVJVMRIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, Jan 12 - Mon, Jan 19 ALO Waterloo ORD Chicago CA $724 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ALO,to:ORD,departure:12/01/2026TANYT&leg2=from:ORD,to:ALO,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:723.60&airProductToken=AQoyCjAIwYIBEgQ0MzI2GOByIK4cKMOiggMwmKOCAzhTQABYAWoETUFJTnIIUzBGV1pOTjEKMgowCMGCARIENDMyMRiuHCDgcij784IDMMf0ggM4U0AAWAFqBE1BSU5yCFMwRldaTk4xEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Waterloo (ALO) to Chicago (ORD) ### January is typically the cheapest month to fly From CA $433 - CA $1,079 per traveller. __Flight from Waterloo to Chicago (ALO - ORD) route information__ | Origin airport | Waterloo Regional | | ------------------- | ----------------- | | Destination airport | O'Hare Intl. | | Airlines serving | American Airlines | | Roundtrip price | CA $522 | | Distance | 372 km | | Average flight time | 1 hour 30 mins | ## Waterloo to Chicago Flights **The easy way to book your flights from Waterloo to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Waterloo 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 Waterloo to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Waterloo Regional, ALO to O'Hare Intl., ORD** Sort your search results by price to find great deals on your flight from Waterloo to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Waterloo currently is just CA $522 rising to CA $724\. Here are more money-saving tips: - Fly in March 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 Waterloo** 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 Waterloo Regional Airport (ALO) to O'Hare Airport? ### Do I need to pay a cancellation fee if I cancel my flight from Waterloo Regional Airport to O'Hare Intl. Airport (ORD)? ### How do I find cheap flights from ALO to ORD that have flexible change policies? ### How many hours is the flight from Waterloo Regional Airport (ALO) to O'Hare Intl. Airport (ORD)? ### How far is the flight from Waterloo Regional Airport (ALO) to O'Hare Airport? ### Which airlines fly direct from Waterloo Regional Airport (ALO) to O'Hare Airport? ### Are Waterloo Regional Airport to O'Hare Intl. 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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.