Title: £44 Cheap Flights from Boston to Chicago (BOS to ORD) - Expedia.co.uk ![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) ## Popular airlines from Logan International Airport (BOS) to Chicago O'Hare International Airport (ORD) - ![JetBlue Airways](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_B6.svg) JetBlue Airways [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![American Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_AA.svg) American Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}]) - ![Delta](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&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.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![Spirit Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_NK.svg) Spirit Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"NK"}}]) - ![Southwest Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![Frontier Airlines](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_F9.svg) Frontier Airlines [](https://www.expedia.co.uk/Flights-Search?leg1=from:bos,to:ord,departure:11/11/2025TANYT&leg2=from:ord,to:bos,departure:18/11/2025TANYT&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 25% 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.co.uk/login) ## Cheap Flights from Boston (BOS) to Chicago (ORD) Prices were available within the past 7 days and start at £44 for one-way flights and £88 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sun, 18 Jan - Tue, 20 Jan BOS Boston ORD Chicago £88 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:18/01/2026TANYT&leg2=from:ORD,to:BOS,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:87.50&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwo0-WCAzCQ54IDOExAAFgBCiEKHwjCbBIDMzEyGK4cIMGTASit-oIDML37ggM4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, 17 Jan - Tue, 20 Jan BOS Boston ORD Chicago £88 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:17/01/2026TANYT&leg2=from:ORD,to:BOS,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:87.50&airProductToken=AQojCiEIxJgBEgQ1NjA3GMGTASCuHCiX24IDMNbcggM4RUAAWAEKIwohCMSYARIENTYzMxiuHCDBkwEo0fiCAzDs-YIDOEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, 11 Nov - Thu, 27 Nov BOS Boston ORD Chicago £92 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:BOS,departure:27/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:91.80&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwo5-j8AjCb6vwCOExAAFgBCiEKHwjCbBIDMzEyGK4cIMGTASjUm_4CMOac_gI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, 3 Dec - Thu, 18 Dec BOS Boston ORD Chicago £93 Return found 1 day ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:BOS,departure:18/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:92.90&airProductToken=AQojCiEIxJgBEgQyNjc2GMGTASCuHCiU4v4CMMPj_gI4RUAAWAEKIwohCMSYARIEMjU3MBiuHCDBkwEog4eAAzCTiIADOEVAAFgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, 3 Dec - Sat, 13 Dec BOS Boston ORD Chicago £94 Return found 3 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:03/12/2025TANYT&leg2=from:ORD,to:BOS,departure:13/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:93.70&airProductToken=AQpeCi0IwmwSAzcxNxjBkwEgqVEomOD-AjDl4P4COExAAFgBagJETnIIUEk5UUJPTDEKLQjCbBIEMjEwNRipUSCuHCic4v4CMMjj_gI4TEABWAFqAkROcghQSTlRQk9MMQovCi0IwmwSAzMxMhiuHCDBkwEolc__AjCl0P8COExAAFgBagJETnIIUEk3UVVTTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, 11 Nov - Sat, 15 Nov BOS Boston ORD Chicago £95 Return found 20 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:BOS,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:95.00&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwo5-j8AjCb6vwCOExAAFgBCiEKHwjCbBIDMzEyGK4cIMGTASjAk_0CMMyU_QI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, 10 Nov - Sat, 15 Nov BOS Boston ORD Chicago £98 Return found 20 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:BOS,departure:15/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:97.20&airProductToken=AQohCh8IwmwSAzgxMRjBkwEgrhwox938AjD73vwCOExAAFgBCiEKHwjCbBIDMzEyGK4cIMGTASjAk_0CMMyU_QI4TEAAWAESCggBEAEYASoCQjYYASIECAEQASgEMAE) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Mon, 10 Nov - Thu, 13 Nov BOS Boston ORD Chicago £99 Return found 20 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:BOS,departure:13/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:98.30&airProductToken=AQo0CjIIwYIBEgQyNTA0GMGTASCuHCiT3_wCMM3g_AI4QkAAWAFqBUJBU0lDcghPN0FKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Mon, 10 Nov - Thu, 13 Nov BOS Boston ORD Chicago £100 Return found 20 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:10/11/2025TANYT&leg2=from:ORD,to:BOS,departure:13/11/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:99.30&airProductToken=AQovCi0IwmwSAzgxMRjBkwEgrhwox938AjD73vwCOExAAFgBagJETnIIU0k0UVVFTDEKLwotCMJsEgMzMTIYrhwgwZMBKND9_AIw4P78AjhMQABYAWoCRE5yCFNJNFFVRUwxEgoIARABGAEqAkI2GAEiBAgBEAEoAigEKAYwAQ) ![Alaska Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AS.gif) Thu, 4 Dec - Thu, 11 Dec BOS Boston ORD Chicago £318 Return found 2 days ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:BOS,to:ORD,departure:04/12/2025TANYT&leg2=from:ORD,to:BOS,departure:11/12/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:317.10&airProductToken=AQpfCi4IwaYBEgMzMDYYwZMBIJIBKP_s_gIwhvD-AjhYQABYAWoCU1ZyCE9INE9DVkJOCi0IwaYBEgM1MzgYkgEgrhwo8vD-AjDl8v4COFhAAVgBagJTVnIIT0gyT0FWQk4KXwotCMGmARIDMzM3GK4cIJIBKNe7_wIw873_AjhYQABYAWoCU1ZyCE9IMk9BVkJOCi4IwaYBEgM1MzYYkgEgwZMBKI6__wIwzcH_AjhYQAFYAWoCU1ZyCE9INE9DVkJOEgoIARABGAEqAkFTGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Boston (BOS) to Chicago (ORD) ### September is typically the cheapest month to fly From £68 - £102 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.co.uk/Flights-Search?leg1=from:BOS,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:BOS,departure:14/11/2025TANYT&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 £95](https://www.expedia.co.uk/Flights-Search?leg1=from:BOS,to:ORD,departure:11/11/2025TANYT&leg2=from:ORD,to:BOS,departure:14/11/2025TANYT&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 to ORD? > If you're planning on travelling from BOS to O'Hare Airport, round-trip flights start from £88. This price is based on airfares advertised within the last 7 days on Expedia for flights departing within the next year, so don't hang about. Book now and save yourself both money and time. 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 (BOS) to ORD? > The majority of flights can be conveniently cancelled online, but whether or not you incur a fee varies between airlines. If you do have to cancel your trip, follow the easy instructions in the [Customer Service Portal](https://www.expedia.co.uk/service/?langid=1033). ### How do I find cheap flights from BOS to O'Hare Intl. Airport (ORD) 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 O'Hare Airport flights, you'll see a "no change fees" filter for you to select. ### How far is the flight from BOS to O'Hare Intl. Airport (ORD)? > Forget about a movie marathon on this flight — it's only 1,400 kilometres from Boston to Chicago. Sit down, buckle up and you'll be touching down before long. ### Which airlines fly direct from Logan Intl. Airport to ORD? > It's a breeze to fly directly from Logan Intl. Airport to ORD. Below are some of the top carriers that operate nonstop services on this route: > > > > - American Airlines - (AA) with 230 monthly flights > - United Airlines - (UA) with 178 monthly flights > - Delta Air Lines - (DL) with 139 monthly flights > - JetBlue Airways - (B6) with 30 monthly flights ### Are Logan Intl. Airport to O'Hare Intl. Airport (ORD) flight tickets cheaper when they're purchased at the last minute? > It is possible to get great last-minute deals from BOS to O'Hare Airport, but it's also possible to miss out entirely! As many airlines publish prices up to a year in advance, it's worth keeping an eye on fares early and being ready to pounce when you spot a good bargain. Expedia compares air carrier prices and updates flight deals frequently, so you can rest easy knowing you're always getting the latest offers. ## Book with confidence ### Compare flights from Boston to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Boston to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to O'Hare Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Logan Intl. to O'Hare Intl..   To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights.  Grab a great deal on your flight from Logan Intl. (BOS) to O'Hare Intl. (ORD) The easiest way to view the best deals on flights from Boston to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Logan Intl. to O'Hare Intl. start at just £88 and range up to £318.   To find an even better deal, try   - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Boston and Chicago - booking your flight during January, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper  Why you should book your Boston to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Logan Intl. to O'Hare Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.   Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.   ## Explore a world of travel with Expedia - Flights - [Flights from Lake Of The Ozarks (AIZ) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/aiz/chi/lake-of-the-ozarks-to-chicago) - [Flights from Amsterdam (AMS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ams/chi/amsterdam-to-chicago) - [Flights from Atlanta (ATL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/atl/chi/atlanta-to-chicago) - [Flights from Abu Dhabi (AUH) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/auh/mdw/abu-dhabi-to-chicago) - [Flights from Wilkes-Barre (AVP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/avp/chi/wilkes-barre-to-chicago) - [Flights from Beirut (BEY) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bey/chi/beirut-to-chicago) - [Flights from Birmingham (BHX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/bhx/chi/birmingham-to-chicago) - 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[Flights from Edinburgh (EDI) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/edi/chi/edinburgh-to-chicago) - [Flights from Edinburgh (EDI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/edi/mdw/edinburgh-to-chicago) - [Flights from Emden (EME) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/eme/chi/emden-to-chicago) - [Flights from Exeter (EXT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ext/chi/exeter-to-chicago) - [Flights from Frankfurt (FRA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/fra/chi/frankfurt-to-chicago) - [Flights from Galesburg (GBG) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gbg/mdw/galesburg-to-chicago) - [Flights from Glasgow (GLA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gla/mdw/glasgow-to-chicago) - [Flights from Geneva (GVA) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/gva/mdw/geneva-to-chicago) - [Flights from Gary (GYY) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/gyy/chi/gary-to-chicago) - [Flights from Hull (HUY) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/huy/mdw/hull-to-chicago) - [Flights from Washington (IAD) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/iad/mdw/washington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/ind/mdw/indianapolis-to-chicago) - [Flights from Isle of Man (IOM) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/iom/chi/isle-of-man-to-chicago) - [Flights from Iowa City (IOW) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/iow/mdw/iowa-city-to-chicago) - [Flights from Istanbul (IST) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ist/chi/istanbul-to-chicago) - [Flights from Jacksonville (JAX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/jax/chi/jacksonville-to-chicago) - [Flights from New York (JFK) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/jfk/mdw/new-york-to-chicago) - [Flights from Kigali (KGL) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/kgl/mdw/kigali-to-chicago) - [Flights from Karachi (KHI) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/khi/chi/karachi-to-chicago) - [Flights from Kaluga (KLF) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/klf/chi/kaluga-to-chicago) - [Flights from Kitadaito (KTD) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ktd/chi/kitadaito-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lax/chi/los-angeles-to-chicago) - [Flights from Le Havre (LEH) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/leh/chi/le-havre-to-chicago) - [Flights from London (LGW) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/lgw/mdw/london-to-chicago) - [Flights from London (LHR) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/lhr/mdw/london-to-chicago) - [Flights from Milan (LIN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lin/chi/milan-to-chicago) - [Flights from Little Rock (LIT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lit/chi/little-rock-to-chicago) - [Flights from Klamath Falls (LMT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lmt/chi/klamath-falls-to-chicago) - [Flights from London (LON) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/lon/ugn/london-to-waukegan) - [Flights from Liverpool (LPL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lpl/chi/liverpool-to-chicago) - [Flights from La Rochelle (LRH) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lrh/chi/la-rochelle-to-chicago) - [Flights from Lawrence (LWC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/lwc/chi/lawrence-to-chicago) - [Flights from Manchester (MAN) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/man/mdw/manchester-to-chicago) - [Flights from Kansas City (MCI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/mci/mdw/kansas-city-to-chicago) - [Flights from Memphis (MEM) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/mem/ugn/memphis-to-waukegan) - [Flights from Mexico City (MEX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mex/chi/mexico-city-to-chicago) - [Flights from Miami (MIA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mia/chi/miami-to-chicago) - [Flights from Malta (MLK) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mlk/chi/malta-to-chicago) - [Flights from Durham (MME) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/mme/mdw/durham-to-chicago) - [Flights from Manila (MNL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/mnl/chi/manila-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/msp/chi/minneapolis-to-chicago) - [Flights from Naples (NAP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/nap/chi/naples-to-chicago) - [Flights from Nottingham (NQT) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/nqt/chi/nottingham-to-chicago) - [Flights from Newcastle (NTL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ntl/chi/newcastle-to-chicago) - [Flights from Norwich (NWI) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/nwi/mdw/norwich-to-chicago) - [Flights from Obock (OBC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/obc/chi/obock-to-chicago) - [Flights from Chicago (ORD) to Waukegan (UGN)](https://www.expedia.co.uk/lp/flights/ord/ugn/chicago-to-waukegan) - [Flights from Paris (PAR) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/par/chi/paris-to-chicago) - [Flights from Portland (PDX) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pdx/chi/portland-to-chicago) - [Flights from Portland (PDX) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/pdx/mdw/portland-to-chicago) - [Flights from Beijing (PEK) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pek/chi/beijing-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/phl/chi/philadelphia-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (PWK)](https://www.expedia.co.uk/lp/flights/phl/pwk/philadelphia-to-chicago) - [Flights from Phoenix (PHX) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/phx/mdw/phoenix-to-chicago) - [Flights from Port of Spain (POS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/pos/chi/port-of-spain-to-chicago) - [Flights from Los Angeles (QLA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/qla/chi/los-angeles-to-chicago) - [Flights from Yangon (RGN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rgn/chi/yangon-to-chicago) - [Flights from Rishiri (RIS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ris/chi/rishiri-to-chicago) - [Flights from Rome (ROM) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rom/chi/rome-to-chicago) - [Flights from Rondon (RON) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/ron/chi/rondon-to-chicago) - [Flights from Ruteng (RTG) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/rtg/chi/ruteng-to-chicago) - [Flights from Louisville (SDF) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sdf/chi/louisville-to-chicago) - [Flights from Seattle (SEA) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sea/chi/seattle-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/slc/chi/salt-lake-city-to-chicago) - [Flights from Sacramento (SMF) to Chicago (PWK)](https://www.expedia.co.uk/lp/flights/smf/pwk/sacramento-to-chicago) - [Flights from St. Cloud (STC) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/stc/mdw/st-cloud-to-chicago) - [Flights from Stockholm (STO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sto/chi/stockholm-to-chicago) - [Flights from Swansea (SWS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/sws/chi/swansea-to-chicago) - [Flights from Sydney (SYD) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/syd/chi/sydney-to-chicago) - [Flights from Topeka (TOP) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/top/chi/topeka-to-chicago) - [Flights from Winchester (WGO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/wgo/chi/winchester-to-chicago) - [Flights from Winton (WIN) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/win/chi/winton-to-chicago) - [Flights from Tsiroanomandidy (WTS) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/wts/chi/tsiroanomandidy-to-chicago) - [Flights from Windsor (YQG) to Chicago (MDW)](https://www.expedia.co.uk/lp/flights/yqg/mdw/windsor-to-chicago) - [Flights from Toronto (YTO) to Chicago (CHI)](https://www.expedia.co.uk/lp/flights/yto/chi/toronto-to-chicago) \*Available to Expedia members.