Title: CA $323 Cheap Flights from Jackson Hole (JAC) 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 $323 Cheap Flights from Jackson Hole (JAC) to Chicago (ORD) [View CA $323 flight on Sun, Sep 27, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:JAC,to:ORD,departure:27/09/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:322.40&airProductToken=AQozCjEIwYIBEgQxNDYzGIkQIK4cKIz5mAMwzfqYAzhCQABYAWoFQkFTSUNyCFFWQVpaTkJaEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) - [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 Jackson Hole Airport (JAC) to Chicago O'Hare International Airport (ORD) - ![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:jac,to:ord,departure:18/11/2025TANYT&leg2=from:ord,to:jac,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:jac,to:ord,departure:18/11/2025TANYT&leg2=from:ord,to:jac,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:jac,to:ord,departure:18/11/2025TANYT&leg2=from:ord,to:jac,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Alaska Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AS.svg) Alaska Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:jac,to:ord,departure:18/11/2025TANYT&leg2=from:ord,to:jac,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}]) - ![Hawaiian Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_HA.svg) Hawaiian Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:jac,to:ord,departure:18/11/2025TANYT&leg2=from:ord,to:jac,departure:25/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"HA"}}]) - ![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 Jackson Hole (JAC) to Chicago (ORD) Prices were available within the past 7 days and start at CA $323 for one-way flights and CA $462 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) Wed, Jan 14 - Tue, Jan 27 JAC Jackson ORD Chicago CA $462 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:JAC,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:461.30&airProductToken=AQpECiAIxJgBEgQ0MDgyGIkQIPISKNy1ggMws7aCAzhFQABYAQogCMSYARIEMjI0NxjyEiCuHCjZtoIDMJq4ggM4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEijAx4MDMKvJgwM4RUAAWAEKIAjEmAESBDIyODIY8hIgiRAo0cmDAzCUyoMDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 13 - Tue, Jan 27 JAC Jackson ORD Chicago CA $469 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:JAC,departure:27/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:468.60&airProductToken=AQplCiAIxJgBEgQyMjgyGIkQIPISKI6tggMw262CAzhFQABYAQofCMSYARIDODc1GPISIOBcKKGuggMwh7CCAzhFQAFYAQogCMSYARIEMTE5ORjgXCCuHCjpsIIDMOWxggM4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEijAx4MDMKvJgwM4RUAAWAEKIAjEmAESBDIyODIY8hIgiRAo0cmDAzCUyoMDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Jan 14 - Wed, Jan 28 JAC Jackson ORD Chicago CA $489 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:JAC,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:488.20&airProductToken=AQpECiAIxJgBEgQ0MDgyGIkQIPISKNy1ggMws7aCAzhFQABYAQogCMSYARIEMjI0NxjyEiCuHCjZtoIDMJq4ggM4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEijg0oMDMMvUgwM4RUAAWAEKIAjEmAESBDIyODIY8hIgiRAo8dSDAzC01YMDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 13 - Wed, Jan 28 JAC Jackson ORD Chicago CA $496 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:JAC,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:495.50&airProductToken=AQplCiAIxJgBEgQyMjgyGIkQIPISKI6tggMw262CAzhFQABYAQofCMSYARIDODc1GPISIOBcKKGuggMwh7CCAzhFQAFYAQogCMSYARIEMTE5ORjgXCCuHCjpsIIDMOWxggM4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEijg0oMDMMvUgwM4RUAAWAEKIAjEmAESBDIyODIY8hIgiRAo8dSDAzC01YMDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Jan 14 - Thu, Jan 29 JAC Jackson ORD Chicago CA $501 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:14/01/2026TANYT&leg2=from:ORD,to:JAC,departure:29/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:500.90&airProductToken=AQpECiAIxJgBEgQ0MDgyGIkQIPISKNy1ggMws7aCAzhFQABYAQogCMSYARIEMjI0NxjyEiCuHCjZtoIDMJq4ggM4RUABWAEKZgogCMSYARIEMjA1NRiuHCCSASik4YMDMLzjgwM4RUAAWAEKIAjEmAESBDExMjgYkgEg8hIojOmDAzCI6oMDOEVAAVgBCiAIxJgBEgQyMjgyGPISIIkQKLHrgwMw9OuDAzhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Jan 13 - Thu, Jan 29 JAC Jackson ORD Chicago CA $509 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:13/01/2026TANYT&leg2=from:ORD,to:JAC,departure:29/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:508.20&airProductToken=AQplCiAIxJgBEgQyMjgyGIkQIPISKI6tggMw262CAzhFQABYAQofCMSYARIDODc1GPISIOBcKKGuggMwh7CCAzhFQAFYAQogCMSYARIEMTE5ORjgXCCuHCjpsIIDMOWxggM4RUABWAEKZgogCMSYARIEMjA1NRiuHCCSASik4YMDMLzjgwM4RUAAWAEKIAjEmAESBDExMjgYkgEg8hIojOmDAzCI6oMDOEVAAVgBCiAIxJgBEgQyMjgyGPISIIkQKLHrgwMw9OuDAzhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Nov 23 - Tue, Dec 9 JAC Jackson ORD Chicago CA $509 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:23/11/2025TANYT&leg2=from:ORD,to:JAC,departure:09/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:508.60&airProductToken=AQpECiAIxJgBEgQxNDY2GIkQIPISKK3v_QIw8-_9AjhFQABYAQogCMSYARIEMjQxMxjyEiCuHCi08f0CMO3y_QI4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEiigoP8CMIWi_wI4RUAAWAEKIAjEmAESBDE0NjYY8hIgiRAorqL_AjD0ov8COEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Dec 14 - Sun, Jan 4 JAC Jackson ORD Chicago CA $515 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:14/12/2025TANYT&leg2=from:ORD,to:JAC,departure:04/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:514.80&airProductToken=AQpmCiAIxJgBEgQzNjkzGIkQIPISKPLd_wIwv97_AjhFQABYAQogCMSYARIEMjk5OBjyEiCSASiZ4P8CMLTh_wI4RUABWAEKIAjEmAESBDIwNTUYkgEgrhwo2OT_AjDV5v8COEVAAVgBCkQKIAjEmAESBDIyMzEYrhwg8hIo5cSBAzDKxoEDOEVAAFgBCiAIxJgBEgQyMjgyGPISIIkQKOnGgQMwr8eBAzhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Mon, Dec 15 - Fri, Jan 2 JAC Jackson ORD Chicago CA $523 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:15/12/2025TANYT&leg2=from:ORD,to:JAC,departure:02/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:522.40&airProductToken=AQplCh8IxJgBEgM2OTEYiRAg8hIoiOT_AjDh5P8COEVAAFgBCiAIxJgBEgQyOTI0GPISIMx8KILm_wIwnOf_AjhFQAFYAQogCMSYARIEMTMwNhjMfCCuHCi85_8CMKHo_wI4RUABWAEKRAogCMSYARIEMjIzMRiuHCDyEiilroEDMIqwgQM4RUAAWAEKIAjEmAESBDIyODIY8hIgiRAoqbCBAzDvsIEDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Jan 6 - Tue, Jan 20 JAC Jackson ORD Chicago CA $560 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:06/01/2026TANYT&leg2=from:ORD,to:JAC,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:559.50&airProductToken=AQpDCiAI1YIBEgQxNzI3GIkQIINpKIHggQMw7eCBAzhMQABYAQofCNWCARIDMzc3GINpIK4cKO3hgQMwh-OBAzhMQAFYAQoiCiAI1YIBEgQyMjI1GK4cIIkQKMT5ggMwjvuCAzhMQABYARIKCAEQARgBKgJVQRgBIgQIARABKAQwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Dec 28 - Sun, Jan 11 JAC Jackson ORD Chicago CA $573 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:28/12/2025TANYT&leg2=from:ORD,to:JAC,departure:11/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:572.80&airProductToken=AQoiCiAIwYIBEgQxNTc4GIkQIK4cKK75gAMwi_uAAzhPQABYAQoiCiAIwYIBEgQxNjcyGK4cIIkQKN6UggMwqZaCAzhPQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Mon, Jan 19 - Wed, Feb 4 JAC Jackson ORD Chicago CA $580 Roundtrip found 6 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:JAC,to:ORD,departure:19/01/2026TANYT&leg2=from:ORD,to:JAC,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:579.60&airProductToken=AQpDCiAIwaYBEgQzNDU3GIkQIJIBKMfwggMw4_GCAzhYQABYAQofCMGmARIDNTM4GJIBIK4cKK7zggMwnvWCAzhYQAFYAQpECiAIwaYBEgQxNDQ3GK4cIJJoKL2lhAMw16eEAzhYQABYAQogCMGmARIEMzMxNxiSaCCJECiXroQDML-vhAM4WEABWAESCggBEAEYASoCQVMYASIECAEQASgEMAE) ## Find the cheapest month to fly from Jackson (JAC) to Chicago (ORD) ### September is typically the cheapest month to fly From CA $266 - CA $1,317 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:JAC,to:ORD,departure:18/11/2025TANYT&leg2=from:ORD,to:JAC,departure:07/12/2025TANYT&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 $509](https://www.expedia.ca/Flights-Search?leg1=from:JAC,to:ORD,departure:18/11/2025TANYT&leg2=from:ORD,to:JAC,departure:07/12/2025TANYT&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 JAC to ORD? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price advertised for a round-trip journey between Jackson Hole Airport and O'Hare Intl. Airport (ORD) was CA $462. Fares this good don't stick around for long, 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 Jackson Hole Airport (JAC) to ORD? > This can differ between air carriers, as each has its own terms and conditions. Head to the [Customer Service Portal](https://www.expedia.ca/helpcenter), where you'll find easy instructions on how to cancel online. ### How do I find cheap flights from JAC to ORD that have flexible change policies? > Use our "No change fees" filter to find flexible travel options for your flight from Jackson Hole Airport to O'Hare Intl. Airport (ORD). This allows you to snag a low rate in advance and still have the freedom to reschedule without any extra fees. Keep in mind that you'll need to cover the fare difference. ### How many hours is the flight from Jackson Hole Airport (JAC) to ORD? > Lasting around 5 hours and 52 minutes, the flight between JAC and ORD is a great opportunity to do some last-minute planning. How about using some of this time to work on your itinerary for Chicago? ### How far is the flight from JAC to O'Hare Intl. Airport (ORD)? > Around 1,850 kilometres separates Jackson and Chicago, so pack something to keep you busy for a couple of hours. That gripping novel you're eager to read will be just the ticket. ### Which airlines fly direct from Jackson Hole Airport (JAC) to O'Hare Intl. Airport (ORD)? > A leading airline that operates on the route from JAC to O'Hare Airport is United Airlines (UA). It offers 30 flights every month. After more options? Check out the ticket prices from American Airlines (AA). This carrier offers 26 flights a month between these destinations. ### Are Jackson Hole Airport (JAC) to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > Booking your trip from Jackson Hole Airport (JAC) to ORD at the last minute could be your ticket to a cheap deal. However, it could end up costing a good deal more! If you'd rather err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the biggest bargains as far ahead as 12 months in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time. ## Travel information | Origin airport | Jackson Hole | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $461 | | Distance | 1854 km | ## Book with confidence ### Jackson to Chicago Flights **The easy way to book your flights from Jackson Hole to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Jackson Hole 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 Jackson Hole to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Jackson Hole, JAC to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Jackson Hole to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Jackson Hole currently is just CA $462 rising to CA $1,684.   Here are more money-saving tips:  - Fly in January 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 Jackson Hole**  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 from Calgary to Rosemont](https://www.expedia.ca/lp/flights/178245/7581/calgary-to-rosemont) - [Flights from Denver to Northwest Chicago](https://www.expedia.ca/lp/flights/178254/6350697/denver-to-northwest-chicago) - [Flights from Los Angeles to Evanston](https://www.expedia.ca/lp/flights/178280/8049/los-angeles-to-evanston) - [Flights from Mexico City to Northwest Chicago](https://www.expedia.ca/lp/flights/178285/6350697/mexico-city-to-northwest-chicago) - [Flights from New York to Evanston](https://www.expedia.ca/lp/flights/178293/8049/new-york-to-evanston) - [Flights from Ottawa to Evanston](https://www.expedia.ca/lp/flights/178296/8049/ottawa-to-evanston) - [Flights from Philadelphia to Rosemont](https://www.expedia.ca/lp/flights/178297/7581/philadelphia-to-rosemont) - [Flights from Portland to Rosemont](https://www.expedia.ca/lp/flights/178299/7581/portland-to-rosemont) - [Flights from San Francisco to Evanston](https://www.expedia.ca/lp/flights/178305/8049/san-francisco-to-evanston) - [Flights from Seattle to Rosemont](https://www.expedia.ca/lp/flights/178307/7581/seattle-to-rosemont) - [Flights from Washington to Evanston](https://www.expedia.ca/lp/flights/178318/8049/washington-to-evanston) - [Flights from Lincoln to Rush Street](https://www.expedia.ca/lp/flights/602964/6175183/lincoln-to-rush-street) - [Flights from Winnipeg to Rosemont](https://www.expedia.ca/lp/flights/6141041/7581/winnipeg-to-rosemont) - [Flights from Ashland (AHM) to Chicago (CHI)](https://www.expedia.ca/lp/flights/ahm/chi/ashland-to-chicago) - [Flights from Ann Arbor (ARB) to Chicago (MDW)](https://www.expedia.ca/lp/flights/arb/mdw/ann-arbor-to-chicago) - [Flights from Aspen (ASE) to Chicago (MDW)](https://www.expedia.ca/lp/flights/ase/mdw/aspen-to-chicago) - [Flights from Atlanta (ATL) to Chicago (MDW)](https://www.expedia.ca/lp/flights/atl/mdw/atlanta-to-chicago) - [Flights from Aurora (AUZ) to Chicago (MDW)](https://www.expedia.ca/lp/flights/auz/mdw/aurora-to-chicago) - [Flights from Hartford (BDL) to Chicago (CHI)](https://www.expedia.ca/lp/flights/bdl/chi/hartford-to-chicago) - [Flights from León (BJX) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bjx/mdw/leon-to-chicago) - [Flights from Bellingham (BLI) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bli/mdw/bellingham-to-chicago) - [Flights from Belleville (BLV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/blv/chi/belleville-to-chicago) - [Flights from Boston (BOS) to Chicago (MDW)](https://www.expedia.ca/lp/flights/bos/mdw/boston-to-chicago) - [Flights from Burlington (BTV) to Chicago (CHI)](https://www.expedia.ca/lp/flights/btv/chi/burlington-to-chicago) - [Flights from Burlington (BTV) to Chicago (MDW)](https://www.expedia.ca/lp/flights/btv/mdw/burlington-to-chicago) - [Flights from Buffalo (BUF) to Chicago (CHI)](https://www.expedia.ca/lp/flights/buf/chi/buffalo-to-chicago) - [Flights from Buffalo (BUF) to Chicago (MDW)](https://www.expedia.ca/lp/flights/buf/mdw/buffalo-to-chicago) - [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.