Title: CA $82 Cheap Flights from Boston (BOS) to Chicago (CHI) - 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 $82 Cheap Flights from Boston (BOS) to Chicago (CHI) [View CA $82 flight on Thu, Oct 23, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:BOS,to:ORD,departure:23/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:81.60&airProductToken=AQo0CjIIwYIBEgQyMzEyGMGTASCuHCiykPsCMOOR-wI4QkAAWAFqBUJBU0lDcghPN0FKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) - [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 Logan International Airport (BOS) to Chicago - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.ca/Flights-Search?leg1=from:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&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:bos,to:chi,departure:27/10/2025TANYT&leg2=from:chi,to:bos,departure:03/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}]) ![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 Boston (BOS) to Chicago (CHI) Prices were available within the past 7 days and start at CA $82 for one-way flights and CA $162 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Oct 30 - Wed, Nov 12 BOS Boston ORD Chicago CA $162 Roundtrip found 4 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:30/10/2025TANYT&leg2=from:ORD,to:BOS,departure:12/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:161.66&airProductToken=AQovCi0IwmwSAzMxMRjBkwEgrhwo7t37AjCn3_sCOExAAFgBagJETnIIUEk3UUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, Feb 8 - Tue, Feb 10 BOS Boston ORD Chicago CA $164 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:08/02/2026TANYT&leg2=from:ORD,to:BOS,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:163.20&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwo89GEAzCw04QDOExAAFgBagJETnIIUEk5UUJFTDEKLwotCMJsEgMzMTIYrhwgwZMBKM3mhAMw3eeEAzhMQABYAWoCRE5yCFBJOVFCRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sat, Nov 15 - Mon, Nov 17 BOS Boston ORD Chicago CA $165 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:15/11/2025TANYT&leg2=from:ORD,to:BOS,departure:17/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:164.32&airProductToken=AQo0CjIIwYIBEgQ0MzkyGMGTASCuHCjulf0CMLiX_QI4QkAAWAFqBUJBU0lDcghPN0FKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, Feb 8 - Tue, Feb 10 BOS Boston ORD Chicago CA $178 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:08/02/2026TANYT&leg2=from:ORD,to:BOS,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:177.20&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwo89GEAzCw04QDOExAAFgBagJETnIIUEk5UUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Thu, Oct 23 - Mon, Oct 27 BOS Boston ORD Chicago CA $179 Roundtrip found 4 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:BOS,departure:27/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:178.45&airProductToken=AQo0CjIIwYIBEgQyMzEyGMGTASCuHCiykPsCMOOR-wI4QkAAWAFqBUJBU0lDcghPN0FKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Dec 4 - Wed, Dec 10 BOS Boston ORD Chicago CA $180 Roundtrip found 5 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:04/12/2025TANYT&leg2=from:ORD,to:BOS,departure:10/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:179.83&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwopez-AjDn7f4COExAAFgBagJETnIIUEk5UUJFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Oct 25 - Wed, Oct 29 BOS Boston ORD Chicago CA $188 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:25/10/2025TANYT&leg2=from:ORD,to:BOS,departure:29/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:187.90&airProductToken=AQovCi0IwmwSAzMxMRjBkwEgrhwo_aT7AjC-pvsCOExAAFgBagJETnIIU0k0UVVFTDEKMAouCMJsEgQxMDEyGK4cIMGTASj71_sCMJPZ-wI4TEAAWAFqAkROcghQSTdRQkVMMRIKCAEQARgBKgJCNhgBIgQIARABKAIoBCgGMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sun, Feb 8 - Tue, Feb 10 BOS Boston ORD Chicago CA $192 Roundtrip just found [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:08/02/2026TANYT&leg2=from:ORD,to:BOS,departure:10/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:191.20&airProductToken=AQo4CjYIxJgBEgQ1NTk2GMGTASCuHCjKzoQDMIjQhAM4RUAAWAFqCU1BSU5CQVNJQ3IIWEFXTlgwQlEKOAo2CMSYARIENTU5NhiuHCDBkwEoquaEAzDA54QDOEVAAFgBaglNQUlOQkFTSUNyCFhBV05YMEJREgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Spirit Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif) Tue, Oct 28 - Sat, Nov 1 BOS Boston ORD Chicago CA $196 Roundtrip found 23 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:28/10/2025TANYT&leg2=from:ORD,to:BOS,departure:01/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:195.03&airProductToken=AQpaCi0IzpYBEgQxMzAxGMGTASDlWii0yvsCMIPM-wI4R0AAWAFqAlJQcgZHQTE0VjIKKQjOlgESATIY5Vogrhwoic77AjDLz_sCOEdAAVgBagJSUHIGR0ExNFYyEgoIARABGAEqAk5LGAEiBAgBEAEoAigDKAQwDQ) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, Oct 23 - Fri, Oct 24 BOS Boston ORD Chicago CA $261 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:BOS,departure:24/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:261.00&airProductToken=AQozCjEI1YIBEgMzNjYYwZMBIK4cKPCO-wIwn5D7AjhHQABYAWoFMl9lY29yCEdBQTdBSEROCjQKMgjVggESBDE3NzkYrhwgwZMBKOyg-wIwgqL7AjhHQABYAWoFMl9lY29yCEdBQTdBSEROEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Boston (BOS) to Chicago (CHI) ### September is typically the cheapest month to fly From CA $115 - CA $235 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:BOS,to:ORD,departure:27/10/2025TANYT&leg2=from:ORD,to:BOS,departure:01/11/2025TANYT&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 $355](https://www.expedia.ca/Flights-Search?leg1=from:BOS,to:ORD,departure:27/10/2025TANYT&leg2=from:ORD,to:BOS,departure:01/11/2025TANYT&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 Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)? > Pack your bags, because round-trip journeys from Logan Intl. Airport to Chicago, IL (CHI-All Airports) start from CA $162. That's based on airfares listed within the last 7 days on Expedia for flights departing within the next year. Prices can increase quickly, so book now to get the best deal. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from Logan Intl. Airport to Chicago, IL (CHI-All Airports)? > Each air carrier has its own terms and conditions. If you decide to cancel your trip, visit our [Customer Service Portal](https://www.expedia.ca/service/?langid=1033). ### How do I find cheap flights from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports) that have flexible change policies? > Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Logan Intl. Airport to Chicago, IL (CHI-All Airports) flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from Logan Intl. Airport (BOS) to Chicago, IL (CHI-All Airports)? > The distance from Logan Intl. Airport (BOS) (BOS) to Chicago, IL (CHI-All Airports) (CHI) is 1,450 kilometers. You'll be stepping off the plane and collecting your baggage from the carousel in next to no time. ### Which airlines fly direct from BOS to Chicago, IL (CHI-All Airports)? > With so many airlines to choose from, you'll be able to find your perfect flight from Logan Intl. Airport to Chicago, IL (CHI-All Airports) in a few clicks. These are some of the most popular carriers that fly directly between these airports: > > > > - American Airlines - (AA) with 230 monthly flights > - United Airlines - (UA) with 178 monthly flights > - Delta Air Lines - (DL) with 139 monthly flights > - Southwest Airlines - (WN) with 121 monthly flights ### Are BOS to Chicago, IL (CHI-All Airports) flight tickets cheaper when they're purchased at the last minute? > It is possible to find a great last-minute deal from BOS to Chicago, IL (CHI-All Airports), but there's no guarantee. As many airlines release prices up to 12 months in advance, it's worth keeping an eye on fares early and being ready to book when you see a good bargain. Expedia compares carrier prices and updates flight deals often, so you can rest easy knowing you're always seeing the latest offers. ## Travel information | Origin airport | Logan Intl. | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $162 | | Distance | 1381 km | ## Book with confidence ### Boston to Illinois Flights **The easy way to book your flights from Boston to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Boston 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 CHI-All Airports, 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 Boston to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Logan Intl., BOS to CHI-All Airports, CHI**  Sort your search results by price to find great deals on your flight from Boston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Boston currently is just CA $162 rising to CA $261.   Here are more money-saving tips:  - Fly in October 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 Boston**  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 Allentown (ABE) to Rockford (RFD)](https://www.expedia.ca/lp/flights/abe/rfd/allentown-to-rockford) - [Flights from Ahmedabad (AMD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/amd/ord/ahmedabad-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/aus/ord/austin-to-chicago) - [Flights from Mesa (AZA) to Rockford (RFD)](https://www.expedia.ca/lp/flights/aza/rfd/mesa-to-rockford) - [Flights from Binghamton (BGM) to Rockford (RFD)](https://www.expedia.ca/lp/flights/bgm/rfd/binghamton-to-rockford) - [Flights from Bangor (BGR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bgr/ord/bangor-to-chicago) - [Flights from Bellingham (BLI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bli/ord/bellingham-to-chicago) - [Flights from Nashville (BNA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bna/ord/nashville-to-chicago) - [Flights from Mumbai (BOM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bom/ord/mumbai-to-chicago) - [Flights from Burlington (BTV) to Chicago (ORD)](https://www.expedia.ca/lp/flights/btv/ord/burlington-to-chicago) - [Flights from Buffalo (BUF) to Rockford (RFD)](https://www.expedia.ca/lp/flights/buf/rfd/buffalo-to-rockford) - [Flights from Baltimore (BWI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/bwi/ord/baltimore-to-chicago) - [Flights from Charlottesville (CHO) to Rockford (RFD)](https://www.expedia.ca/lp/flights/cho/rfd/charlottesville-to-rockford) - [Flights from Sault Ste. Marie (CIU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ciu/ord/sault-ste-marie-to-chicago) - [Flights from Charlotte (CLT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/clt/ord/charlotte-to-chicago) - [Flights from Columbus (CMH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cmh/ord/columbus-to-chicago) - [Flights from Cincinnati (CVG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/cvg/ord/cincinnati-to-chicago) - [Flights from Washington (DCA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dca/ord/washington-to-chicago) - [Flights from Denver (DEN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/den/ord/denver-to-chicago) - [Flights from Duluth (DLH) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dlh/ord/duluth-to-chicago) - [Flights from Detroit (DTW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/dtw/rfd/detroit-to-rockford) - [Flights from Dubai (DXB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fll/ord/fort-lauderdale-to-chicago) - [Flights from Flint (FNT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/fnt/ord/flint-to-chicago) - [Flights from Spokane (GEG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/geg/ord/spokane-to-chicago) - [Flights from Grand Forks (GFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/gfk/ord/grand-forks-to-chicago) - [Flights from Galveston (GLS) to Rockford (RFD)](https://www.expedia.ca/lp/flights/gls/rfd/galveston-to-rockford) - [Flights from Green Bay (GRB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grb/ord/green-bay-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/grr/ord/grand-rapids-to-chicago) - [Flights from Hot Springs (HOT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/hot/rfd/hot-springs-to-rockford) - [Flights from Houston (HOU) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hou/ord/houston-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/hyd/ord/hyderabad-to-chicago) - [Flights from Niagara Falls (IAG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/iag/ord/niagara-falls-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from New York (JFK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from New York (JFK) to Rockford (RFD)](https://www.expedia.ca/lp/flights/jfk/rfd/new-york-to-rockford) - [Flights from Lansing (LAN) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lan/rfd/lansing-to-rockford) - [Flights from Las Vegas (LAS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Larnaca (LCA) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lca/rfd/larnaca-to-rockford) - [Flights from London (LHR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/lhr/ord/london-to-chicago) - [Flights from London (LHR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/lhr/rfd/london-to-rockford) - [Flights from Mackinac Island (MCD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mcd/rfd/mackinac-island-to-rockford) - [Flights from Kansas City (MCI) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Kansas City (MCI) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mci/rfd/kansas-city-to-rockford) - [Flights from Orlando (MCO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Mexico City (MEX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mex/ord/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mia/ord/miami-to-chicago) - [Flights from Minot (MOT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/mot/ord/minot-to-chicago) - [Flights from Minot (MOT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/mot/rfd/minot-to-rockford) - [Flights from Muscle Shoals (MSL) to Rockford (RFD)](https://www.expedia.ca/lp/flights/msl/rfd/muscle-shoals-to-rockford) - [Flights from Madison (MSN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Rockford (RFD)](https://www.expedia.ca/lp/flights/msp/rfd/minneapolis-to-rockford) - [Flights from Tokyo (NRT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/nrt/rfd/tokyo-to-rockford) - [Flights from Ogdensburg (OGS) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ogs/ord/ogdensburg-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Ontario (ONT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ont/ord/ontario-to-chicago) - [Flights from Ontario (ONT) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ont/rfd/ontario-to-rockford) - [Flights from Chicago (ORD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ord/rfd/chicago-to-rockford) - [Flights from Paducah (PAH) to Rockford (RFD)](https://www.expedia.ca/lp/flights/pah/rfd/paducah-to-rockford) - [Flights from Plattsburgh (PBG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pbg/ord/plattsburgh-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD)](https://www.expedia.ca/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/pit/ord/pittsburgh-to-chicago) - [Flights from Redding (RDD) to Rockford (RFD)](https://www.expedia.ca/lp/flights/rdd/rfd/redding-to-rockford) - [Flights from Rockford (RFD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/rfd/ord/rockford-to-chicago) - [Flights from Roswell (ROW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/row/rfd/roswell-to-rockford) - [Flights from San Diego (SAN) to Chicago (ORD)](https://www.expedia.ca/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Louisville (SDF) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sdf/ord/louisville-to-chicago) - [Flights from Santander (SDR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/sdr/rfd/santander-to-rockford) - [Flights from San Francisco (SFO) to Chicago (ORD)](https://www.expedia.ca/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Syracuse (SYR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/syr/rfd/syracuse-to-rockford) - [Flights from Sault Ste. Marie (YAM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yam/ord/sault-ste-marie-to-chicago) - [Flights from Nanaimo (YCD) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ycd/ord/nanaimo-to-chicago) - [Flights from Edmonton (YEG) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yeg/rfd/edmonton-to-rockford) - [Flights from Fredericton (YFC) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yfc/ord/fredericton-to-chicago) - [Flights from Kingston (YGK) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ygk/ord/kingston-to-chicago) - [Flights from Hamilton (YHM) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yhm/rfd/hamilton-to-rockford) - [Flights from Halifax (YHZ) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yhz/rfd/halifax-to-rockford) - [Flights from Kamloops (YKA) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yka/ord/kamloops-to-chicago) - [Flights from Kelowna (YLW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ylw/rfd/kelowna-to-rockford) - [Flights from Ottawa (YOW) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yow/rfd/ottawa-to-rockford) - [Flights from Peterborough (YPQ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ypq/ord/peterborough-to-chicago) - [Flights from Québec (YQB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqb/ord/quebec-to-chicago) - [Flights from Moncton (YQM) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yqm/ord/moncton-to-chicago) - [Flights from Sudbury (YSB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ysb/ord/sudbury-to-chicago) - [Flights from Toronto (YTO) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yto/rfd/toronto-to-rockford) - [Flights from Toronto (YTZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/ytz/ord/toronto-to-chicago) - [Flights from Montreal (YUL) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yul/rfd/montreal-to-rockford) - [Flights from Vancouver (YVR) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yvr/rfd/vancouver-to-rockford) - [Flights from Winnipeg (YWG) to Rockford (RFD)](https://www.expedia.ca/lp/flights/ywg/rfd/winnipeg-to-rockford) - [Flights from Abbotsford (YXX) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yxx/ord/abbotsford-to-chicago) - [Flights from North Bay (YYB) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyb/ord/north-bay-to-chicago) - [Flights from Calgary (YYC) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yyc/rfd/calgary-to-rockford) - [Flights from Charlottetown (YYG) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyg/ord/charlottetown-to-chicago) - [Flights from St. John's (YYT) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyt/ord/st-johns-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yyz/ord/toronto-to-chicago) - [Flights from Toronto (YYZ) to Rockford (RFD)](https://www.expedia.ca/lp/flights/yyz/rfd/toronto-to-rockford) - [Flights from Sarnia (YZR) to Chicago (ORD)](https://www.expedia.ca/lp/flights/yzr/ord/sarnia-to-chicago) \*Available to Expedia members.