Title: CA $193 Cheap Flights from Chicago (ORD) to Portland (PWM) - Expedia.ca ![Portland, Maine, USA downtown skyline](https://images.trvl-media.com/place/181420/ed709e29-68b6-43b1-967b-35a095561383.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/181420/ed709e29-68b6-43b1-967b-35a095561383.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $193 Cheap Flights from Chicago (ORD) to Portland (PWM) [View CA $193 flight on Tue, Oct 21, 2025](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:ORD,to:PWM,departure:21/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:192.20&airProductToken=AQpcCiwIwmwSAzkwNhiuHCCpUSi7-_oCMMv8-gI4TEAAWAFqAkROcghQSTdRQkVMMQosCMJsEgMzMDgYqVEgz2Uo2v76AjC4__oCOExAAVgBagJETnIIUEk0UVVFTDESCggBEAEYASoCQjYYASIECAEQASgCKAQoBjAB) - [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 Chicago O'Hare International Airport (ORD) to Portland Intl. Jetport Airport (PWM) - ![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:ord,to:pwm,departure:22/10/2025TANYT&leg2=from:pwm,to:ord,departure:29/10/2025TANYT&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.ca/Flights-Search?leg1=from:ord,to:pwm,departure:22/10/2025TANYT&leg2=from:pwm,to:ord,departure:29/10/2025TANYT&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.ca/Flights-Search?leg1=from:ord,to:pwm,departure:22/10/2025TANYT&leg2=from:pwm,to:ord,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}]) - ![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:ord,to:pwm,departure:22/10/2025TANYT&leg2=from:pwm,to:ord,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}]) - ![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:ord,to:pwm,departure:22/10/2025TANYT&leg2=from:pwm,to:ord,departure:29/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) ![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 Chicago (ORD) to Portland (PWM) Prices were available within the past 7 days and start at CA $193 for one-way flights and CA $339 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) Tue, Oct 21 - Sat, Oct 25 ORD Chicago PWM Portland CA $339 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:21/10/2025TANYT&leg2=from:PWM,to:ORD,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:338.80&airProductToken=AQpACh4IwmwSAzkwNhiuHCCpUSi7-_oCMMv8-gI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKNr--gIwuP_6AjhMQAFYAQpACh4IwmwSAzMwNxjPZSCpUSj9pPsCMM6l-wI4TEAAWAEKHgjCbBIDNDA1GKlRIK4cKK6p-wIw3ar7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Tue, Oct 21 - Thu, Oct 23 ORD Chicago PWM Portland CA $382 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:21/10/2025TANYT&leg2=from:PWM,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:381.80&airProductToken=AQpACh4IwmwSAzkwNhiuHCCpUSi7-_oCMMv8-gI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKNr--gIwuP_6AjhMQAFYAQpACh4IwmwSAzMwNxjPZSCpUSi9jvsCMI6P-wI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKIeQ-wIws5H7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Oct 18 - Sat, Oct 25 ORD Chicago PWM Portland CA $396 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:18/10/2025TANYT&leg2=from:PWM,to:ORD,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:395.70&airProductToken=AQpACh4IwmwSAzQwNhiuHCCpUSiu1_oCMMHY-gI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKPrc-gIw2N36AjhMQAFYAQpACh4IwmwSAzMwNxjPZSCpUSj9pPsCMM6l-wI4TEAAWAEKHgjCbBIDNDA1GKlRIK4cKK6p-wIw3ar7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Sat, Oct 18 - Thu, Oct 23 ORD Chicago PWM Portland CA $438 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:18/10/2025TANYT&leg2=from:PWM,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:437.70&airProductToken=AQpACh4IwmwSAzQwNhiuHCCpUSiu1_oCMMHY-gI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKPrc-gIw2N36AjhMQAFYAQpACh4IwmwSAzMwNxjPZSCpUSi9jvsCMI6P-wI4TEAAWAEKHgjCbBIDOTA1GKlRIK4cKIeQ-wIws5H7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Oct 21 - Wed, Oct 29 ORD Chicago PWM Portland CA $443 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:21/10/2025TANYT&leg2=from:PWM,to:ORD,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:443.00&airProductToken=AQpECiAIxJgBEgQ1MjM4GK4cIKlRKKD7-gIws_z6AjhFQABYAQogCMSYARIENTQxMRipUSDPZSiW__oCMPX_-gI4RUABWAEKRAogCMSYARIENTY3MBjPZSDLASim0fsCMIPS-wI4RUAAWAEKIAjEmAESBDI4MTAYywEgrhwogtT7AjCi1fsCOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Tue, Oct 21 - Fri, Oct 24 ORD Chicago PWM Portland CA $479 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:21/10/2025TANYT&leg2=from:PWM,to:ORD,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:478.50&airProductToken=AQpECiAIxJgBEgQ1MjM4GK4cIKlRKKD7-gIws_z6AjhFQABYAQogCMSYARIENTQxMRipUSDPZSiW__oCMPX_-gI4RUABWAEKRAogCMSYARIENTY3MBjPZSDLASiGmfsCMOOZ-wI4RUAAWAEKIAjEmAESBDI3NjAYywEgrhwo1Z77AjD5n_sCOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![JetBlue Airways](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/b6.gif) Thu, Oct 16 - Sat, Oct 25 ORD Chicago PWM Portland CA $498 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:16/10/2025TANYT&leg2=from:PWM,to:ORD,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:497.90&airProductToken=AQpACh4IwmwSAzkwNhiuHCCpUSibw_oCMKvE-gI4TEAAWAEKHgjCbBIDMzA4GKlRIM9lKLrG-gIwmMf6AjhMQAFYAQpACh4IwmwSAzMwNxjPZSCpUSj9pPsCMM6l-wI4TEAAWAEKHgjCbBIDNDA1GKlRIK4cKK6p-wIw3ar7AjhMQAFYARIKCAEQARgBKgJCNhgBIgQIARABKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Sat, Oct 18 - Wed, Oct 29 ORD Chicago PWM Portland CA $499 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:18/10/2025TANYT&leg2=from:PWM,to:ORD,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:498.90&airProductToken=AQpECiAIxJgBEgQyOTk2GK4cIMsBKNDW-gIw09f6AjhFQABYAQogCMSYARIENTY3NxjLASDPZSiS2voCMOfa-gI4RUABWAEKRAogCMSYARIENTY3MBjPZSDLASim0fsCMIPS-wI4RUAAWAEKIAjEmAESBDI4MTAYywEgrhwogtT7AjCi1fsCOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![American Airlines](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/AA.gif) Sun, Oct 19 - Wed, Oct 29 ORD Chicago PWM Portland CA $640 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:19/10/2025TANYT&leg2=from:PWM,to:ORD,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:639.40&airProductToken=AQoiCiAIwYIBEgQ0OTY3GK4cIM9lKP7j-gIwkOX6AjhMQABYAQoiCiAIwYIBEgQ0MzkxGM9lIK4cKMbR-wIw9NL7AjhOQABYARIKCAEQARgBKgJBQRgBIgQIARABKAgoBDAB) ![United](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/UA.gif) Sun, Oct 19 - Sun, Oct 26 ORD Chicago PWM Portland CA $733 Roundtrip found 2 days ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:ORD,to:PWM,departure:19/10/2025TANYT&leg2=from:PWM,to:ORD,departure:26/10/2025TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:732.86&airProductToken=AQozCjEI1YIBEgQxOTc0GK4cIM9lKI7n-gIwqOj6AjhWQABYAWoFMl9lY29yCFZBQTRPS0VOEgoIARABGAEqAlVBGAEiBAgBEAEoAigDKAQwCw) ## Find the cheapest month to fly from Chicago (ORD) to Portland (PWM) ### September is typically the cheapest month to fly From CA $188 - CA $340 per traveller. ## Alternative airports near Portland Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:PWM,departure:22/10/2025TANYT&leg2=from:PWM,to:ORD,departure:25/10/2025TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) PWM Portland Intl. Jetport CheapestClosest 8 min [Flights from CA $339](https://www.expedia.ca/Flights-Search?leg1=from:ORD,to:PWM,departure:22/10/2025TANYT&leg2=from:PWM,to:ORD,departure:25/10/2025TANYT&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 O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM)? > Based on airfares available within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between ORD and PWM start from CA $339. Make your booking ASAP to get the best price for your adventure. Prices and availability are subject to change. Additional terms apply. ### Do I need to pay a cancellation fee if I cancel my flight from O'Hare Airport to Portland Intl. Jetport? > Each airline has a different set of terms and conditions. If you decide to cancel your getaway, head to our [Customer Service Portal](https://www.expedia.ca/helpcenter). ### How do I find cheap flights from ORD to Portland Intl. Jetport that have flexible change policies? > Flights from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM) offering flexible change policies are available from several carriers. Simply use our "No change fees" filter when searching. You'll only need to pay the difference in ticket price, with no additional fees to worry about. ### How many hours is the flight from ORD to Portland Intl. Jetport Airport (PWM)? > It takes around 4 hours and 8 minutes to fly from ORD to PWM. But with a solid playlist and a good book, the hours will go by quicker. ### How far is the flight from O'Hare Airport to Portland Intl. Jetport Airport (PWM)? > A flight distance of just 1,450 kilometres separates Chicago and Portland. Once you're up in the skies, you won't get a chance to do much more than read the in-flight magazine. ### Which airlines fly direct from O'Hare Intl. Airport (ORD) to PWM? > If you want to fly directly from O'Hare Airport to Portland Intl. Jetport, United Airlines (UA) is an excellent choice. It operates 30 monthly flights between Chicago and Portland. ### Are O'Hare Intl. Airport (ORD) to PWM flight tickets cheaper when they're purchased at the last minute? > Booking your trip from ORD to Portland Intl. Jetport at the last minute could save you some serious cash. However, it could end up costing a good deal more! If you'd rather avoid the risk, book well ahead of your departure date. In fact, Expedia has some of the best bargains as far ahead as 12 months in advance. If your preferred carrier hasn't released tickets yet, check back frequently as deals are updated on Expedia all the time. ## Travel information | Origin airport | O'Hare Intl. | | --- | --- | | Destination airport | Portland Intl. Jetport | | Roundtrip price | CA $339 | | Distance | 1435 km | | Average flight time | 3 hours 33 mins | ## Book with confidence ### Chicago to Portland Flights **The easy way to book your flights from Chicago to Portland**  With Expedia, it’s simple to find and book flights to Portland from Chicago 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 American Airlines, Qatar Airways, Air New Zealand, United Airlines nonstop flights to Portland Intl. Jetport, 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 Chicago to Portland today, tomorrow, or this week.   **Save dollars with cheap flights from O'Hare Intl., ORD to Portland Intl. Jetport, PWM**  Sort your search results by price to find great deals on your flight from Chicago to Portland—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Portland from Chicago currently is just CA $339 rising to CA $733.   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 Portland   - 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 Portland from Chicago**  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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[Boutique Hotels in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Boutique-Hotel.0-n6336427-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Historic-Hotel.0-n6336427-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Hotel-With-Pool.0-n6336427-0-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Free Breakfast in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Hotels-With-Free-Breakfast.0-n6336427-0-tHotelswithFreeBreakfast.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Hotels-With-Kitchenettes.0-n6336427-0-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Mountain-Hotels.0-n6336427-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Portland Arts District](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels-Pet-Friendly-Hotel.0-n6336427-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Portland Arts District Hotels](https://www.expedia.ca/Portland-Arts-District-Portland-Hotels.0-n6336427-0.Travel-Guide-Filter-Hotels) - [Hotels near Portland Club](https://www.expedia.ca/Portland-Club-Hotels.0-l6077234-0.Travel-Guide-Filter-Hotels) - [Hotels near Portland Exposition Building](https://www.expedia.ca/Portland-Exposition-Building-Hotels.0-l553248622845868665-0.Travel-Guide-Filter-Hotels) - [Portland Hotels](https://www.expedia.ca/Portland-Hotels.d181420.Travel-Guide-Hotels) - [Hotels near Portland Museum of Art](https://www.expedia.ca/Portland-Museum-Of-Art-Hotels.0-l6077214-0.Travel-Guide-Filter-Hotels) - [Hotels near Portland Transportation Center](https://www.expedia.ca/Portland-Transportation-Center-Hotels.d6329164.Travel-Guide-Hotels) - [Inns in Portland Transportation Center](https://www.expedia.ca/Portland-Transportation-Center-Inns.d6329164-aaInns.Travel-Guide-Accommodation) - [Rosemont Hotels](https://www.expedia.ca/Rosemont-Portland-Hotels.0-n553248635976472266-0.Travel-Guide-Filter-Hotels) - [Hotels near State Theatre](https://www.expedia.ca/State-Theatre-Hotels.0-l553248621532668181-0.Travel-Guide-Filter-Hotels) - [Stroudwater Hotels](https://www.expedia.ca/Stroudwater-Portland-Hotels.0-n553248635976473880-0.Travel-Guide-Filter-Hotels) - [Hotels near Thompson's Point](https://www.expedia.ca/Thompsons-Point-Hotels.0-l553248622839373742-0.Travel-Guide-Filter-Hotels) - [Hotels near University of Southern Maine](https://www.expedia.ca/University-Of-Southern-Maine-Hotels.0-l6077216-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Valley Street](https://www.expedia.ca/Valley-Street-Portland-Hotels-Cheap-Hotels.0-n553248635976480923-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Valley Street Hotels](https://www.expedia.ca/Valley-Street-Portland-Hotels.0-n553248635976480923-0.Travel-Guide-Filter-Hotels) - [Hotels near Victoria Mansion](https://www.expedia.ca/Victoria-Mansion-Hotels.0-l6077228-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in West End](https://www.expedia.ca/West-End-Portland-Hotels-Beach-Hotel.0-n553248635976481334-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in West End](https://www.expedia.ca/West-End-Portland-Hotels-Cheap-Hotels.0-n553248635976481334-0-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in West End](https://www.expedia.ca/West-End-Portland-Hotels-Family-Hotel.0-n553248635976481334-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in West End](https://www.expedia.ca/West-End-Portland-Hotels-Historic-Hotel.0-n553248635976481334-0-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in West End](https://www.expedia.ca/West-End-Portland-Hotels-Hotels-With-Balconies.0-n553248635976481334-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with Bar in West End](https://www.expedia.ca/West-End-Portland-Hotels-Hotels-With-Bar.0-n553248635976481334-0-tHotelswithBar.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in West End](https://www.expedia.ca/West-End-Portland-Hotels-Hotels-With-Hot-Tubs.0-n553248635976481334-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Romantic Hotels in West End](https://www.expedia.ca/West-End-Portland-Hotels-Romantic-Hotel.0-n553248635976481334-0-tRomanticHotel.Travel-Guide-Filter-Hotels) - [West End Hotels](https://www.expedia.ca/West-End-Portland-Hotels.0-n553248635976481334-0.Travel-Guide-Filter-Hotels) - [Flights to Portland](https://www.expedia.ca/Cheap-Flights-To-Portland.d181420.Travel-Guide-Flights) - [Flights from Atlanta to Frye Island](https://www.expedia.ca/lp/flights/178232/3000440292/atlanta-to-frye-island) - [Flights from Atlanta to Casco Bay Islands](https://www.expedia.ca/lp/flights/178232/553248621532668098/atlanta-to-casco-bay-islands) - [Flights from Atlanta to Hermit Island](https://www.expedia.ca/lp/flights/178232/6341836/atlanta-to-hermit-island) - [Flights from Boston to Kennebunkport](https://www.expedia.ca/lp/flights/178239/10869/boston-to-kennebunkport) - [Flights from Boston to Casco Bay Islands](https://www.expedia.ca/lp/flights/178239/553248621532668098/boston-to-casco-bay-islands) - [Flights from Boston to Hermit Island](https://www.expedia.ca/lp/flights/178239/6341836/boston-to-hermit-island) - [Flights from Boston to Old Orchard Beach](https://www.expedia.ca/lp/flights/178239/9256/boston-to-old-orchard-beach) - [Flights from Calgary to Casco Bay Islands](https://www.expedia.ca/lp/flights/178245/553248621532668098/calgary-to-casco-bay-islands) - [Flights from Denver to Kennebunkport](https://www.expedia.ca/lp/flights/178254/10869/denver-to-kennebunkport) - [Flights from Denver to Casco Bay Islands](https://www.expedia.ca/lp/flights/178254/553248621532668098/denver-to-casco-bay-islands) - [Flights from Denver to Hermit Island](https://www.expedia.ca/lp/flights/178254/6341836/denver-to-hermit-island) - [Flights from Denver to Old Orchard Beach](https://www.expedia.ca/lp/flights/178254/9256/denver-to-old-orchard-beach) - [Flights from London to Kennebunkport](https://www.expedia.ca/lp/flights/178279/10869/london-to-kennebunkport) - [Flights from London to Casco Bay Islands](https://www.expedia.ca/lp/flights/178279/553248621532668098/london-to-casco-bay-islands) - [Flights from Los Angeles to Kennebunkport](https://www.expedia.ca/lp/flights/178280/10869/los-angeles-to-kennebunkport) - [Flights from Los Angeles to Old Orchard Beach](https://www.expedia.ca/lp/flights/178280/9256/los-angeles-to-old-orchard-beach) - [Flights from Montreal to Casco Bay Islands](https://www.expedia.ca/lp/flights/178288/553248621532668098/montreal-to-casco-bay-islands) - [Flights from Nashville to Kennebunkport](https://www.expedia.ca/lp/flights/178291/10869/nashville-to-kennebunkport) - [Flights from New York to Kennebunkport](https://www.expedia.ca/lp/flights/178293/10869/new-york-to-kennebunkport) - [Flights from San Antonio to Kennebunkport](https://www.expedia.ca/lp/flights/178303/10869/san-antonio-to-kennebunkport) - [Flights from Seattle to Casco Bay Islands](https://www.expedia.ca/lp/flights/178307/553248621532668098/seattle-to-casco-bay-islands) - [Flights from Seattle to Hermit Island](https://www.expedia.ca/lp/flights/178307/6341836/seattle-to-hermit-island) - [Flights from Washington to Casco Bay Islands](https://www.expedia.ca/lp/flights/178318/553248621532668098/washington-to-casco-bay-islands) - [Flights from Edmonton to Casco Bay Islands](https://www.expedia.ca/lp/flights/180002/553248621532668098/edmonton-to-casco-bay-islands) - [Flights from Birmingham to South Coast](https://www.expedia.ca/lp/flights/6023342/6057321/birmingham-to-south-coast) - [Flights from Buffalo to Casco Bay Islands](https://www.expedia.ca/lp/flights/602674/553248621532668098/buffalo-to-casco-bay-islands) - [Flights from Buffalo to Hermit Island](https://www.expedia.ca/lp/flights/602674/6341836/buffalo-to-hermit-island) - [Flights from Tucson to Old Orchard Beach](https://www.expedia.ca/lp/flights/602986/9256/tucson-to-old-orchard-beach) - [Flights from Louisville to Old Orchard Beach](https://www.expedia.ca/lp/flights/603002/9256/louisville-to-old-orchard-beach) - [Flights from Albany (ALB) to Sanford (SFM)](https://www.expedia.ca/lp/flights/alb/sfm/albany-to-sanford) - [Flights from Cincinnati (CVG) to Sanford (SFM)](https://www.expedia.ca/lp/flights/cvg/sfm/cincinnati-to-sanford) - [Flights from Lome (LFW) to Sanford (SFM)](https://www.expedia.ca/lp/flights/lfw/sfm/lome-to-sanford) - [Flights from Kansas City (MCI) to Brunswick (NHZ)](https://www.expedia.ca/lp/flights/mci/nhz/kansas-city-to-brunswick) - [Flights from Philadelphia (PHL) to Fryeburg (FRY)](https://www.expedia.ca/lp/flights/phl/fry/philadelphia-to-fryeburg) - [Flights from Portsmouth (PSM) to Sanford (SFM)](https://www.expedia.ca/lp/flights/psm/sfm/portsmouth-to-sanford) - [Maine Mall](https://www.expedia.ca/Maine-Mall-South-Portland.d6077232.Vacation-Attraction) - [Mclellan-Sweat Mansion](https://www.expedia.ca/McLellan-Sweat-Mansion-Downtown-Portland.d6327527.Vacation-Attraction) - [Portland Museum of Art](https://www.expedia.ca/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction) - [Visit Old Port](https://www.expedia.ca/Portland-Old-Port.dx6172121) - [State Theatre](https://www.expedia.ca/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction) - [Things to do in Portland](https://www.expedia.ca/Things-To-Do-In-Portland.d181420.Travel-Guide-Activities) \*Available to Expedia members.