Title: CA $132 Cheap Flights from Portland (PWM) 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 $132 Cheap Flights from Portland (PWM) to Chicago (CHI) [View CA $132 flight on Wed, Oct 22, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:PWM,to:ORD,departure:22/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:131.40&airProductToken=AQpcCiwIwmwSAzMwNxjPZSCpUSidg_sCMO6D-wI4TEAAWAFqAkROcghQQzJBVUVMMQosCMJsEgM5MDUYqVEgrhwo5oT7AjCShvsCOExAAVgBagJETnIIUEMyQVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) - [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 Portland Intl. Jetport Airport (PWM) to Chicago - ![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:pwm,to:chi,departure:02/10/2025TANYT&leg2=from:chi,to:pwm,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![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:pwm,to:chi,departure:02/10/2025TANYT&leg2=from:chi,to:pwm,departure:09/10/2025TANYT&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:pwm,to:chi,departure:02/10/2025TANYT&leg2=from:chi,to:pwm,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:pwm,to:chi,departure:02/10/2025TANYT&leg2=from:chi,to:pwm,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![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:pwm,to:chi,departure:02/10/2025TANYT&leg2=from:chi,to:pwm,departure:09/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ## Plan, book, fly with confidence - ### Be in the know Get alerts if flight prices drop or rise\* - ### Book smarter Save up to 30% on select hotels after you book a flight\* - ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Portland (PWM) to Chicago (CHI) Prices were available within the past 7 days and start at CA $132 for one-way flights and CA $296 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) Wed, Oct 22 - Fri, Oct 24 PWM Portland ORD Chicago CA $296 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:PWM,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:296.00&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSidg_sCMO6D-wI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKOaE-wIwkob7AjhMQAFYAQpACh4IwmwSAzkwNhiuHCCpUSibnfsCMKue-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKLqg-wIwmKH7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Wed, Oct 22 - Sat, Oct 25 PWM Portland ORD Chicago CA $315 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:PWM,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:314.30&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSidg_sCMO6D-wI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKOaE-wIwkob7AjhMQAFYAQpACh4IwmwSAzQwNhiuHCCpUSiOpvsCMKGn-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKNqr-wIws6z7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Oct 21 - Wed, Oct 22 PWM Portland ORD Chicago CA $328 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:21/10/2025TANYT&leg2=from:ORD,to:PWM,departure:22/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:327.20&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSj99_oCMM74-gI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKMb5-gIw8vr6AjhMQAFYAQpACh4IwmwSAzkwNhiuHCCpUSjchvsCMOyH-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKPqJ-wIw2Ir7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Oct 22 - Tue, Oct 28 PWM Portland ORD Chicago CA $347 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:PWM,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:346.60&airProductToken=AQpGCiEIxJgBEgQxODkxGM9lIOO0ASjthfsCMO-G-wI4RUAAWAEKIQjEmAESBDE2NjUY47QBIK4cKKaH-wIw94f7AjhFQAFYAQpGCiEIxJgBEgQyMDM5GK4cIOO0ASiax_sCMOnH-wI4RUAAWAEKIQjEmAESBDE4OTEY47QBIM9lKJLI-wIwgMn7AjhFQAFYARIKCAEQARgBKgJETBgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Oct 21 - Fri, Oct 24 PWM Portland ORD Chicago CA $360 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:21/10/2025TANYT&leg2=from:ORD,to:PWM,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:359.50&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSj99_oCMM74-gI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKMb5-gIw8vr6AjhMQAFYAQpACh4IwmwSAzkwNhiuHCCpUSibnfsCMKue-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKLqg-wIwmKH7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Oct 23 - Sat, Oct 25 PWM Portland ORD Chicago CA $367 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:23/10/2025TANYT&leg2=from:ORD,to:PWM,departure:25/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:367.00&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSi9jvsCMI6P-wI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKIeQ-wIws5H7AjhMQAFYAQpACh4IwmwSAzQwNhiuHCCpUSiOpvsCMKGn-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKNqr-wIws6z7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Oct 18 - Wed, Oct 22 PWM Portland ORD Chicago CA $377 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:18/10/2025TANYT&leg2=from:ORD,to:PWM,departure:22/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:376.70&airProductToken=AQpACh4IwmwSAzMwNxjPZSCpUSid1voCMO7W-gI4TEAAWAEKHgjCbBIDNDA1GKlRIK4cKM7a-gIw_dv6AjhMQAFYAQpACh4IwmwSAzkwNhiuHCCpUSjchvsCMOyH-wI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKPqJ-wIw2Ir7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Wed, Oct 22 - Mon, Oct 27 PWM Portland ORD Chicago CA $378 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:22/10/2025TANYT&leg2=from:ORD,to:PWM,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:377.70&airProductToken=AQpGCiEIxJgBEgQxODkxGM9lIOO0ASjthfsCMO-G-wI4RUAAWAEKIQjEmAESBDE2NjUY47QBIK4cKKaH-wIw94f7AjhFQAFYAQpECiAIxJgBEgQyNzYwGK4cIMsBKJXC-wIwoMP7AjhFQABYAQogCMSYARIENTc3NxjLASDPZSjbx_sCMLnI-wI4RUABWAESCggBEAEYASoCREwYASIECAEQASgEMAE) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Tue, Oct 21 - Tue, Oct 28 PWM Portland ORD Chicago CA $431 Roundtrip found 3 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:21/10/2025TANYT&leg2=from:ORD,to:PWM,departure:28/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:431.00&airProductToken=AQoiCiAI1YIBEgQxMzA0GM9lIK4cKMb3-gIw8fj6AjhLQABYAQpFCiEI1YIBEgQyMTMzGK4cIMSNASj3yvsCMIXM-wI4S0AAWAEKIAjVggESAzU1NRjEjQEgz2Uo1M37AjClzvsCOEtAAVgBEgoIARABGAEqAlVBGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Wed, Dec 31 - Thu, Jan 1 PWM Portland ORD Chicago CA $452 Roundtrip found 1 day ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PWM,to:ORD,departure:31/12/2025TANYT&leg2=from:ORD,to:PWM,departure:01/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:451.90&airProductToken=AQpGCiEIwYIBEgQyNTAxGM9lIOKaASihl4EDMMeYgQM4T0AAWAEKIQjBggESBDIyOTQY4poBIK4cKPuZgQMw_JqBAzhPQAFYAQpCCh8IwYIBEgQyMzQ1GK4cIEMouaKBAzCmo4EDOE9AAFgBCh8IwYIBEgQ1MDg4GEMgz2Uo6aOBAzDRpIEDOE9AAVgBEgoIARABGAEqAkFBGAEiBAgBEAEoCCgEMAE) ## Find the cheapest month to fly from Portland (PWM) to Chicago (CHI) ### October is typically the cheapest month to fly From CA $215 - CA $654 per traveller. ## Travel information | Origin airport | Portland Intl. Jetport | | --- | --- | | Destination airport | O'Hare Intl. | | Roundtrip price | CA $296 | | Distance | 1435 km | ## Book with confidence ### Portland to Illinois Flights **The easy way to book your flights from Portland to Chicago**  With Expedia, it’s simple to find and book flights to Chicago from Portland 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 Portland to Chicago today, tomorrow, or this week.   **Save dollars with cheap flights from Portland Intl. Jetport, PWM to CHI-All Airports, CHI**  Sort your search results by price to find great deals on your flight from Portland to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Portland currently is just CA $296 rising to CA $452.   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 Portland**  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. 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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.