Title: £96 Cheap Flights from Portland to Chicago (PDX to MDW) - 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) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # £96 Cheap Flights from Portland (PDX) to Chicago (MDW) [View £96 flight on Thu, 23 Apr 2026](https://expedia.co.uk/Flights-Search?trip=oneway&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:95.30&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4RUABWAFqCU1BSU5CQVNJQ3IIVkFWU0E1QkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ## Popular airlines from Portland International Airport (PDX) to Chicago Midway Airport (MDW) - ![](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:PDX,to:MDW,departure:13/04/2026TANYT&leg2=from:MDW,to:PDX,departure:20/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](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:PDX,to:MDW,departure:13/04/2026TANYT&leg2=from:MDW,to:PDX,departure:20/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](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\* - ![](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\* - ![](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 Portland (PDX) to Chicago (MDW) Prices were available within the past 7 days and start at £96 for one-way flights and £602 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Return ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £602 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:601.30&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4RUAAWAFqCU1BSU5CQVNJQ3IIWEFWTkEwQlEKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4RUABWAFqCU1BSU5CQVNJQ3IIWEFWTkEwQlESCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £639 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:638.90&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4WEAAWAFqCU1BSU5DTEFTQ3IIWEFWTkEwTUwKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4WEABWAFqCU1BSU5DTEFTQ3IIWEFWTkEwTUwKbwo2CMSYARIEMjQxNxjssAEg4Fwo8LKLAzDhs4sDOEhAAFgBaglNQUlOQ0xBU0NyCEhBVU9BME1DCjUIxJgBEgM1MDMY4Fwg77gBKKO0iwMw3baLAzhIQAFYAWoJTUFJTkNMQVNDcghIQVVPQTBNQxIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £669 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:669.00&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4WEAAWAFqCU1BSU5FWFRSQXIIWEFWUkEwTUwKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4WEABWAFqCU1BSU5FWFRSQXIIWEFWUkEwTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £704 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:703.40&airProductToken=AQpvCjUIxJgBEgM0NzIY77gBIMx8KKKMiwMw542LAzhLQABYAWoJTUFJTkNMQVNDcghLQVVPQTBNQwo2CMSYARIEMzc5NRjMfCDssAEosI6LAzCaj4sDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVU9BME1DCm8KNgjEmAESBDI0MTcY7LABIOBcKPCyiwMw4bOLAzhIQABYAWoJTUFJTkNMQVNDcghIQVVPQTBNQwo1CMSYARIDNTAzGOBcIO-4ASijtIsDMN22iwM4SEABWAFqCU1BSU5DTEFTQ3IISEFVT0EwTUMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £722 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:721.70&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4WEAAWAFqCU1BSU5DTEFTQ3IIWEFWTkEwTUwKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4WEABWAFqCU1BSU5DTEFTQ3IIWEFWTkEwTUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £752 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:751.80&airProductToken=AQpxCjYIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4WEAAWAFqCU1BSU5FWFRSQXIIWEFWUkEwTUwKNwjEmAESBDUyMTgY47QBIOywASjpmYsDMLuaiwM4WEABWAFqCU1BSU5FWFRSQXIIWEFWUkEwTUwKbwo2CMSYARIEMjQxNxjssAEg4Fwo8LKLAzDhs4sDOEhAAFgBaglNQUlORVhUUkFyCEhBVVpBME1FCjUIxJgBEgM1MDMY4Fwg77gBKKO0iwMw3baLAzhIQAFYAWoJTUFJTkVYVFJBcghIQVVaQTBNRRIKCAEQARgBKgJETBgBIgQIARABKAIoAygEMAE) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £767 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:766.80&airProductToken=AQpxCjYIxJgBEgM0NzIY77gBIMx8KKKMiwMw542LAzhTQABYAWoKQ09NRlRDTEFTQ3IIS0FVT0EwSUwKNwjEmAESBDM3OTUYzHwg7LABKLCOiwMwmo-LAzhLQAFYAWoKQ09NRlRDTEFTQ3IIS0FVT0EwSUwSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £787 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:786.20&airProductToken=AQpvCjUIxJgBEgM4NzkY77gBIOBcKMuRiwMw4pOLAzhRQABYAWoJTUFJTkNMQVNDcghRQVVPQTBNQwo2CMSYARIEMTA3NhjgXCDssAEo3pSLAzDQlYsDOFFAAVgBaglNQUlOQ0xBU0NyCFFBVU9BME1DCm8KNgjEmAESBDI0MTcY7LABIOBcKPCyiwMw4bOLAzhIQABYAWoJTUFJTkNMQVNDcghIQVVPQTBNQwo1CMSYARIDNTAzGOBcIO-4ASijtIsDMN22iwM4SEABWAFqCU1BSU5DTEFTQ3IISEFVT0EwTUMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £816 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:815.20&airProductToken=AQpzCjcIxJgBEgM1NzMY77gBIOO0ASj3losDMPSYiwM4U0AAWAFqCkNPTUZUQ0xBU0NyCFhBVk5BMElMCjgIxJgBEgQ1MjE4GOO0ASDssAEo6ZmLAzC7mosDOFNAAVgBagpDT01GVENMQVNDcghYQVZOQTBJTApxCjcIxJgBEgQyNDE3GOywASDgXCjwsosDMOGziwM4SEAAWAFqCkNPTUZUQ0xBU0NyCEhBVU9BMENFCjYIxJgBEgM1MDMY4Fwg77gBKKO0iwMw3baLAzhXQAFYAWoKQ09NRlRDTEFTQ3IISEFVT0EwQ0USCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Thu, 23 Apr - Sun, 26 Apr PDX Portland MDW Chicago £1,040 Return found 11 hours ago [](https://expedia.co.uk/Flights-Search?trip=roundtrip&leg1=from:PDX,to:MDW,departure:23/04/2026TANYT&leg2=from:MDW,to:PDX,departure:26/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1039.60&airProductToken=AQqjAQo0CNWCARIEMTc4NxjvuAEgg2ko05OLAzDylIsDOFFAAFgBagdFQ09OT01ZcghRQUE3T1FFTgozCNWCARIENTM2NhiDaSDMfCialYsDMKGWiwM4UUABWAFqB0VDT05PTVlyCFFBQTdPUUVOCjYIxJgBEgQzNzk1GMx8IOywASjQmYsDMLqaiwM4S0ABWAFqCU1BSU5DTEFTQ3IIS0FWR0EwTVEKbwo2CMSYARIEMjQxNxjssAEg4Fwo8LKLAzDhs4sDOEhAAFgBaglNQUlOQ0xBU0NyCEhBVU9BME1DCjUIxJgBEgM1MDMY4Fwg77gBKKO0iwMw3baLAzhIQAFYAWoJTUFJTkNMQVNDcghIQVVPQTBNQxIKCAEQARgBKgJVQRgBIgQIARABKAIoAygEMAE) ## 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:PDX,to:ORD,departure:13/04/2026TANYT&leg2=from:ORD,to:PDX,departure:20/04/2026TANYT&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 £322 ](https://www.expedia.co.uk/Flights-Search?leg1=from:PDX,to:ORD,departure:13/04/2026TANYT&leg2=from:ORD,to:PDX,departure:20/04/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ## Find the cheapest month to fly from Portland (PDX) to Chicago (MDW) ### September is typically the cheapest month to fly From £99 - £292 per traveller. ## Frequently asked questions ### How much is a flight from Portland Intl. Airport (PDX) to Chicago Airport? ### Do I need to pay a cancellation fee if I cancel my flight from PDX to Midway Intl. Airport (MDW)? ### How do I find cheap flights from Portland Airport to Midway Airport that have flexible change policies? ### How far is the flight from Portland Airport to Midway Airport? ### Which airlines fly direct from Portland Intl. Airport (PDX) to MDW? ### Are Portland Airport to Chicago Airport flight tickets cheaper when they're purchased at the last minute? ## Travel information | Origin airport | Portland Intl. | | ------------------- | --------------- | | Destination airport | Midway Intl. | | Return price | £601 | | Distance | 2794 km | | Average flight time | 5 hours 52 mins | ## Book with confidence # Compare flights from Portland to Chicago easily and book with confidence For travelling on business or for pleasure, Expedia makes it easy to book your flights from Portland to Chicago. Operating between them flights per day, 20 airlines cover the route. And fly direct, getting you to Midway Intl. in just hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Portland Intl. to Midway 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 Portland Intl. (PDX) to Midway Intl. (MDW) The easiest way to view the best deals on flights from Portland 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 Portland Intl. to Midway Intl. start at just £602 and range up to £1,040\. To find an even better deal, try - being flexible on your dates – midweek flights can be cheaper - looking for other airports near Portland and Chicago - booking your flight during April, the cheapest month on this route - varying your flight times – early morning and late at night are sometimes cheaper Why you should book your Portland to Chicago flight with Expedia! We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Portland Intl. to Midway 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 Aberdeen (ABZ) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/abz/ord/aberdeen-to-chicago) - [Flights from Accra (ACC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/acc/ord/accra-to-chicago) - [Flights from Amman (AMM) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/amm/ord/amman-to-chicago) - [Flights from Amsterdam (AMS) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ams/ord/amsterdam-to-chicago) - [Flights from Athens (ATH) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ath/ord/athens-to-chicago) - [Flights from Atlanta (ATL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/atl/ord/atlanta-to-chicago) - [Flights from Austin (AUS) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/aus/ord/austin-to-chicago) - [Flights from Barcelona (BCN) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/bcn/ord/barcelona-to-chicago) - 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[Flights from Dubai (DXB) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/dxb/ord/dubai-to-chicago) - [Flights from Edinburgh (EDI) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/edi/ord/edinburgh-to-chicago) - [Flights from East Midlands (EMA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ema/ord/east-midlands-to-chicago) - [Flights from Fort Lauderdale (FLL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/fll/ord/fort-lauderdale-to-chicago) - [Flights from Frankfurt (FRA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/fra/ord/frankfurt-to-chicago) - [Flights from Fort Wayne (FWA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/fwa/ord/fort-wayne-to-chicago) - [Flights from Glasgow (GLA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/gla/ord/glasgow-to-chicago) - [Flights from Green Bay (GRB) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/grb/ord/green-bay-to-chicago) - [Flights from Grand Rapids (GRR) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/grr/ord/grand-rapids-to-chicago) - [Flights from Houston (HOU) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/hou/ord/houston-to-chicago) - [Flights from Hyderabad (HYD) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/hyd/ord/hyderabad-to-chicago) - [Flights from Washington (IAD) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/iad/ord/washington-to-chicago) - [Flights from Indianapolis (IND) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ind/ord/indianapolis-to-chicago) - [Flights from Inverness (INV) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/inv/ord/inverness-to-chicago) - [Flights from Istanbul (IST) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ist/ord/istanbul-to-chicago) - [Flights from New York (JFK) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/jfk/ord/new-york-to-chicago) - [Flights from Las Vegas (LAS) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/las/ord/las-vegas-to-chicago) - [Flights from Los Angeles (LAX) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lax/ord/los-angeles-to-chicago) - [Flights from Leeds (LBA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lba/ord/leeds-to-chicago) - [Flights from London (LCY) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lcy/ord/london-to-chicago) - [Flights from New York (LGA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lga/ord/new-york-to-chicago) - [Flights from London (LGW) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lgw/ord/london-to-chicago) - [Flights from Lahore (LHE) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lhe/ord/lahore-to-chicago) - [Flights from London (LHR) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lhr/ord/london-to-chicago) - [Flights from Lagos (LOS) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/los/ord/lagos-to-chicago) - [Flights from Liverpool (LPL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/lpl/ord/liverpool-to-chicago) - [Flights from Manchester (MAN) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/man/ord/manchester-to-chicago) - [Flights from Kansas City (MCI) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mci/ord/kansas-city-to-chicago) - [Flights from Orlando (MCO) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mco/ord/orlando-to-chicago) - [Flights from Memphis (MEM) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mem/ord/memphis-to-chicago) - [Flights from Manchester (MHT) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mht/ord/manchester-to-chicago) - [Flights from Miami (MIA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mia/ord/miami-to-chicago) - [Flights from Milwaukee (MKE) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/mke/ord/milwaukee-to-chicago) - [Flights from Madison (MSN) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/msn/ord/madison-to-chicago) - [Flights from Minneapolis (MSP) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/msp/ord/minneapolis-to-chicago) - [Flights from New Orleans (MSY) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/msy/ord/new-orleans-to-chicago) - [Flights from Newcastle (NCL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/ncl/ord/newcastle-to-chicago) - [Flights from Norwich (NWI) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/nwi/ord/norwich-to-chicago) - [Flights from New York (NYC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/nyc/ord/new-york-to-chicago) - [Flights from Oklahoma City (OKC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/okc/ord/oklahoma-city-to-chicago) - [Flights from Omaha (OMA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/oma/ord/omaha-to-chicago) - [Flights from Portland (PDX) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/pdx/ord/portland-to-chicago) - [Flights from Philadelphia (PHL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/phl/ord/philadelphia-to-chicago) - [Flights from Peoria (PIA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/pia/ord/peoria-to-chicago) - [Flights from Pittsburgh (PIT) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/pit/ord/pittsburgh-to-chicago) - [Flights from Providenciales (PLS) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/pls/ord/providenciales-to-chicago) - [Flights from Providence (PVD) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/pvd/ord/providence-to-chicago) - [Flights from Raleigh (RDU) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/rdu/ord/raleigh-to-chicago) - [Flights from Rochester (ROC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/roc/ord/rochester-to-chicago) - [Flights from Rochester (RST) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/rst/ord/rochester-to-chicago) - [Flights from San Diego (SAN) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/san/ord/san-diego-to-chicago) - [Flights from Seattle (SEA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/sea/ord/seattle-to-chicago) - [Flights from San Francisco (SFO) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/sfo/ord/san-francisco-to-chicago) - [Flights from Springfield (SGF) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/sgf/ord/springfield-to-chicago) - [Flights from San Jose (SJC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/sjc/ord/san-jose-to-chicago) - [Flights from Salt Lake City (SLC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/slc/ord/salt-lake-city-to-chicago) - [Flights from Orange County (SNA) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/sna/ord/orange-county-to-chicago) - [Flights from St. Louis (STL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/stl/ord/st-louis-to-chicago) - [Flights from London (STN) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/stn/ord/london-to-chicago) - [Flights from Tulsa (TUL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/tul/ord/tulsa-to-chicago) - [Flights from Edmonton (YEG) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/yeg/ord/edmonton-to-chicago) - [Flights from Montreal (YUL) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/yul/ord/montreal-to-chicago) - [Flights from Vancouver (YVR) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/yvr/ord/vancouver-to-chicago) - [Flights from Calgary (YYC) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/yyc/ord/calgary-to-chicago) - [Flights from Toronto (YYZ) to Chicago (ORD) ](https://www.expedia.co.uk/lp/flights/yyz/ord/toronto-to-chicago) \*Available to Expedia members.