Title: CA $963 Cheap Flights from Sydney (SYD) 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 $963 Cheap Flights from Sydney (SYD) to Chicago (ORD) [View CA $963 flight on Wed, Oct 15, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:SYD,to:ORD,departure:15/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:962.20&airProductToken=AQpkCjEIxbIBEgM0NTEYkh4ggD0o9LH6AjDVuPoCOEVAAFgBagZZQkFTSUNyCEVOTjAwSDVUCi8IxbIBEgE5GIA9IK4cKP-5-gIw-cD6AjhFQAFYAWoGWUJBU0lDcghFTk4wMEg1VBIKCAEQARgBKgJFWRgBIgQIARABKAIoAygEMAE) - [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 Sydney Airport (SYD) to Chicago O'Hare International Airport (ORD) - ![Emirates](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_EK.svg) Emirates [](https://www.expedia.ca/Flights-Search?leg1=from:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"EK"}}]) - ![Air Canada](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AC.svg) Air Canada [](https://www.expedia.ca/Flights-Search?leg1=from:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AC"}}]) - ![Qantas Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QF.svg) Qantas Airways [](https://www.expedia.ca/Flights-Search?leg1=from:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QF"}}]) - ![Cathay Pacific](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_CX.svg) Cathay Pacific [](https://www.expedia.ca/Flights-Search?leg1=from:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"CX"}}]) - ![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:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&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:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Qatar Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_QR.svg) Qatar Airways [](https://www.expedia.ca/Flights-Search?leg1=from:syd,to:ord,departure:15/10/2025TANYT&leg2=from:ord,to:syd,departure:22/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"QR"}}]) ![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 Sydney (SYD) to Chicago (ORD) Prices were available within the past 7 days and start at CA $963 for one-way flights and CA $1,579 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) Sat, Nov 8 - Sat, Nov 22 SYD Sydney ORD Chicago CA $1,579 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:22/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1578.21&airProductToken=AQppCjIIwYIBEgI3MhiSHiCLuAEotL38AjDtw_wCOE9AAFgBagdNQUlOU0ZMcghPSkUwQ1NOMAozCMGCARIDNzkzGIu4ASCuHCi3xvwCMLHI_AI4T0ABWAFqB01BSU5TRkxyCE9KRTBDU04wCmoKNAjBggESBDI5MTcYrhwgi7gBKN7n_QIw9On9AjhPQABYAWoHTUFJTlNGTHIIT0pFMENTTjAKMgjBggESAjczGIu4ASCSHii19P0CMMj7_QI4T0ABWAFqB01BSU5TRkxyCE9KRTBDU04wEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Nov 8 - Sat, Nov 22 SYD Sydney ORD Chicago CA $1,600 Roundtrip found 6 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:08/11/2025TANYT&leg2=from:ORD,to:SYD,departure:22/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1599.51&airProductToken=AQppCjIIwYIBEgI3MhiSHiCLuAEotL38AjDtw_wCOE9AAFgBagdNQUlOU0ZMcghPSkUwQ1NOMAozCMGCARIDNzkzGIu4ASCuHCi3xvwCMLHI_AI4T0ABWAFqB01BSU5TRkxyCE9KRTBDU04wCpwBCjMIwYIBEgM4NjgYrhwgo7EBKMHl_QIw5eb9AjhPQABYAWoHTUFJTlNGTHIIT0pFMENTTjAKMQjBggESATcYo7EBIKEjKOHn_QIwzu_9AjhPQAFYAWoHTUFJTlNGTHIIT0pFMENTTjAKMgjKogESAzgyMRihIyCSHijR8_0CMLD0_QI4WkABWAFqB01BSU5TRkxyCE9KRTBDU04wEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwAQ) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $1,768 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1767.60&airProductToken=AQpmCjAIwYYBEgIzNBiSHiC4jQEotJD8AjCal_wCOEdAAFgBagVCQVNJQ3IIR0xYTzAzQkEKMgjBhgESBDEwNDgYuI0BIK4cKP6X_AIw-Zn8AjhHQAFYAWoFQkFTSUNyCEdOQTFBMEJBCmYKMgjBhgESBDEwNDkYrhwguI0BKJTp_AIwp-v8AjhHQABYAWoFQkFTSUNyCEdOQTFBMEJBCjAIwYYBEgIzMxi4jQEgkh4osO38AjDr9PwCOEdAAVgBagVCQVNJQ3IIR0xYTzAzQkESCggCEAEYAioCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $1,777 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1776.64&airProductToken=AQpmCjAIwYYBEgIzNBiSHiC4jQEotJD8AjCal_wCOEtAAFgBagVCQVNJQ3IIS0xYTzAyQkEKMgjBhgESBDQ4NzYYuI0BIK4cKPaY_AIw9Jr8AjhLQAFYAWoFQkFTSUNyCEtMWE8wMkJBCmUKMQjBhgESAzUwNhiuHCCYzgEosOj8AjCT6fwCOEtAAFgBagVCQVNJQ3IIS0xYTzAyQkEKMAjBhgESAjMzGJjOASCSHiiM6vwCMOv0_AI4S0ABWAFqBUJBU0lDcghLTFhPMDJCQRIKCAEQARgBKgJBQxgBIgQIARABKAIoAygEMA0) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $1,786 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1785.68&airProductToken=AQpmCjAIwYYBEgIzNBiSHiCYzgEotJD8AjCamvwCOEtAAFgBagVCQVNJQ3IIS0xYTzAyQkEKMgjBhgESBDQ5OTAYmM4BIK4cKOaa_AIw55v8AjhLQAFYAWoFQkFTSUNyCEtMWE8wMkJBCmYKMgjBhgESBDQ0MDcYrhwgmM4BKIvn_AIw9ef8AjhLQABYAWoFQkFTSUNyCEtMWE8wMkJBCjAIwYYBEgIzMxiYzgEgkh4ojOr8AjDr9PwCOEtAAVgBagVCQVNJQ3IIS0xYTzAyQkESCggBEAEYASoCQUMYASIECAEQASgCKAMoBDAN) ![Air Canada](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AC.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $1,851 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1850.60&airProductToken=AQpsCjMIwYYBEgIzNBiSHiC4jQEotJD8AjCal_wCOEdAAFgBaghTVEFOREFSRHIIR0xYTzAzVEcKNQjBhgESBDQ4NzYYuI0BIK4cKPaY_AIw9Jr8AjhHQAFYAWoIU1RBTkRBUkRyCEdOQTFBMFRHCmwKNQjBhgESBDEwNDkYrhwguI0BKJTp_AIwp-v8AjhHQABYAWoIU1RBTkRBUkRyCEdOQTFBMFRHCjMIwYYBEgIzMxi4jQEgkh4osO38AjDr9PwCOEdAAVgBaghTVEFOREFSRHIIR0xYTzAzVEcSCggCEAEYAioCQUMYASIECAEQASgCKAMoBDAN) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, May 24 - Sun, Jun 7 SYD Sydney ORD Chicago CA $1,962 Roundtrip found 17 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:24/05/2026TANYT&leg2=from:ORD,to:SYD,departure:07/06/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1961.18&airProductToken=AQqlAQo0CMSYARICNDAYkh4gi7gBKJ3ljQMw0euNAzhFQABYAWoJTUFJTkJBU0lDcghUTFdHN0pCWgo2CMSYARIEMTE5NBiLuAEg8hIo-O2NAzDs7o0DOEVAAVgBaglNQUlOQkFTSUNyCFRMV0c3SkJaCjUIxJgBEgQyNDEzGPISIK4cKNHwjQMwkvKNAzhFQAFYAWoJTUFJTkJBU0lDcghUTFdHN0pCWgqkAQo1CMSYARIEMTE0NxiuHCDgXCjKio8DMMOLjwM4RUAAWAFqCU1BSU5CQVNJQ3IIWExYRzdKQloKNQjEmAESAzMwMRjgXCCLuAEoyYyPAzDujo8DOEVAAVgBaglNQUlOQkFTSUNyCFhMWEc3SkJaCjQIxJgBEgI0MRiLuAEgkh4o9JCPAzDzl48DOEVAAVgBaglNQUlOQkFTSUNyCFhMWEc3SkJaEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![All Nippon Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/NH.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $2,022 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:2021.56&airProductToken=AQpmCjEIzpABEgM4ODAYkh4gpxsopZX8AjDkmfwCOFNAAFgBagZFQ09WQUxyCFNGQTdUUVlTCjEIzpABEgMxMTIYpxsgrhwolZz8AjDgofwCOFNAAVgBagZFQ09WQUxyCFNGQTdUUVlTCmYKMQjOkAESAzExMRiuHCCnGyjB6fwCMPXv_AI4TEAAWAFqBkVDT1ZBTHIITEZBN1RRWUwKMQjOkAESAzg4ORinGyCSHiin9fwCMOv5_AI4TEABWAFqBkVDT1ZBTHIITEZBN1RRWUwSCggBEAEYASoCTkgYASIECAEQASgCKAMoBDAB) ![Cathay Pacific](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/CX.gif) Tue, Nov 4 - Tue, Nov 11 SYD Sydney ORD Chicago CA $2,039 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:04/11/2025TANYT&leg2=from:ORD,to:SYD,departure:11/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:2038.96&airProductToken=AQpsCjQIw7ABEgMxMzgYkh4gxzIoyJX8AjDkmfwCOE5AAFgBaglFQ09OTElHSFRyCE5SMjFBVUlSCjQIw7ABEgM4MDYYxzIgrhwo0538AjCvpPwCOE5AAVgBaglFQ09OTElHSFRyCE5SMjFBVUlSCmwKNAjDsAESAzgwNxiuHCDHMijT6PwCMI7w_AI4TkAAWAFqCUVDT05MSUdIVHIITlIyMUFVSVIKNAjDsAESAzE2MRjHMiCSHijA8PwCMOv0_AI4TkABWAFqCUVDT05MSUdIVHIITlIyMUFVSVISCggBEAEYASoCQ1gYASIECAEQASgCKAMoBDAB) ![Turkish Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/TK.gif) Fri, Nov 14 - Fri, Nov 28 SYD Sydney ORD Chicago CA $2,154 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:SYD,to:ORD,departure:14/11/2025TANYT&leg2=from:ORD,to:SYD,departure:28/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:2153.16&airProductToken=AQpaCiwI1JYBEgMxNzUYkh4gyJwBKMeF_QIw0Y_9AjhQQABYAWoCUlNyBlBGM1hQWAoqCNSWARIBNRjInAEgrhwo85H9AjC5l_0COFBAAVgBagJSU3IGUEYzWFBYClwKLAjUlgESAzE4NhiuHCDInAEozqb-AjC6q_4COFdAAFgBagJQU3IGV0YzWFBDCiwI1JYBEgMxNzQYyJwBIJIeKJWv_gIw1Lj-AjhXQAFYAWoCUFNyBldGM1hQQxIKCAEQARgBKgJUSxgBIgQIARABKAIoAygEMAE) ## Frequently asked questions ### How much is a flight from Mascot Airport to ORD? > Within the past 7 days on Expedia, for flights departing within the next year, the lowest price quoted for a round-trip flight between Kingsford Smith Intl. Airport (SYD) and ORD was CA $1,579. Cheap fares don't hang around, so make sure you book yours ASAP. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from SYD to O'Hare Intl. Airport (ORD)? > The majority of flights can be cancelled online, but each air carrier has its own terms and conditions. If you do have to cancel your flight, visit our [Customer Service Portal](https://www.expedia.ca/helpcenter) and follow the instructions. ### How do I find cheap flights from Mascot Airport to O'Hare Intl. Airport (ORD) that have flexible change policies? > Select our "No change fees" filter to find flexible ticketing options for your flight from Mascot Airport to ORD. This allows you to snag a good price in advance and still have the freedom to reschedule without any additional fees. Just keep in mind that fare differences may still apply. ### How many hours is the flight from Kingsford Smith Intl. Airport (SYD) to O'Hare Airport? > Averaging 22 hours and 16 minutes, the flight from SYD to O'Hare Airport is a long one. To make your journey more enjoyable, pack a neck pillow and some noise-cancelling earphones. ### How far is the flight from Mascot Airport to O'Hare Intl. Airport (ORD)? > With a flight distance of 14,900 kilometres from SYD to O'Hare Airport, this is a long flight. Make sure you stay hydrated and get up to stretch your legs from time to time. ### Which airlines fly direct from SYD to O'Hare Airport? > There are no direct flights, so you'll have to make at least one stop between Sydney Airport and O'Hare Airport. Use the layover time to stretch your legs and enjoy some personal space. ### Are SYD to O'Hare Airport flight tickets cheaper when they're purchased at the last minute? > Booking your trip from Sydney Airport to ORD at the last minute could be your ticket to an awesome deal. However, it could end up costing you a whole lot more! If you'd prefer to err on the side of caution, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to a year in advance. If your preferred air carrier hasn't released tickets yet, check back frequently as deals are updated all the time on Expedia. ## Travel information | Origin airport | Kingsford Smith Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $1,578 | | Distance | 14775 km | ## Book with confidence ### Sydney to Chicago Flights **The easy way to book your flights from Sydney to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Sydney 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 Sydney to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Kingsford Smith Intl., SYD to O'Hare Intl., ORD**  Sort your search results by price to find great deals on your flight from Sydney to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Sydney currently is just CA $1,579 rising to CA $2,154.   Here are more money-saving tips:  - Fly in November 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 Sydney**  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.