Cheap flights from ORD to PWM (O'Hare Intl. to Portland Intl. Jetport)

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Cheap Flights from ORD to PWM starting at $144 One Way, $304 Round Trip

Prices starting at $304 for return flights and $144 for one-way flights to Portland Intl. Jetport were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jun 30 - Tue, Jul 7
ORD
Chicago
PWM
Portland
$304 Roundtrip, found 6 hours ago
$304
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Chicago to Portland, returning Tue, Jul 7, priced at $304 found 6 hours ago
Tue, Jun 30 - Tue, Jul 7
ORD
Chicago
PWM
Portland
$304 Roundtrip, found 6 hours ago
$304
Roundtrip
found 6 hours ago
Select United flight, departing Tue, Jun 30 from Chicago to Portland, returning Tue, Jul 7, priced at $304 found 6 hours ago
Wed, Aug 12 - Wed, Aug 19
ORD
Chicago
PWM
Portland
$307 Roundtrip, found 6 hours ago
$307
Roundtrip
found 6 hours ago
Select United flight, departing Wed, Aug 12 from Chicago to Portland, returning Wed, Aug 19, priced at $307 found 6 hours ago
Tue, Jun 23 - Tue, Jun 30
ORD
Chicago
PWM
Portland
$309 Roundtrip, found 2 hours ago
$309
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jun 23 from Chicago to Portland, returning Tue, Jun 30, priced at $309 found 2 hours ago
Sun, May 24 - Fri, May 29
ORD
Chicago
PWM
Portland
$313 Roundtrip, found 4 days ago
$313
Roundtrip
found 4 days ago
Select Delta flight, departing Sun, May 24 from Chicago to Portland, returning Fri, May 29, priced at $313 found 4 days ago

Hotel Ideas near Portland Intl. Jetport

Airport Hotels near Portland Intl. Jetport

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
$134 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9.4/10 Exceptional! (1,144 reviews)
"Made to order omelettes. Happy hour daily!"

Reviewed on May 21, 2026

Embassy Suites by Hilton Portland Maine
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
$88 nightly
The price is $98 total per night from May 28 to May 29
$98 total
May 28 - May 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,456 reviews)
"Stayed one night, traveling thru. The room was clean , the beds were comfortable. Only complaint was the restaurant for breakfast we went down at 7 and there was not anyone there. We sat down and waited for like ten minutes and left. Went elsewhere. Hotel was hard to find but it was dark when we ..."

Reviewed on May 21, 2026

Clarion Hotel Portland Airport ME
Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
145 Jetport Blvd Portland ME
$127 nightly
The price is $140 total per night from May 28 to May 29
$140 total
May 28 - May 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,000 reviews)
"All services have been excellent."

Reviewed on May 20, 2026

Hilton Garden Inn Portland Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Portland

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
$241 nightly
The price is $266 total per night from May 25 to May 26
$266 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
9.4/10 Exceptional! (1,780 reviews)
"Wonderful hotel with clean rooms, easy valet parking, and a great location. We loved the small area right off of the elevator on our floor which provided water, coffee, and pastries for use in the mornings."

Reviewed on May 21, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
$190 nightly
The price is $210 total per night from May 26 to May 27
$210 total
May 26 - May 27
Total with taxes and fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
9.4/10 Exceptional! (1,666 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."

Reviewed on May 20, 2026

Portland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
$187 nightly
The price is $206 total per night from May 27 to May 28
$206 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant ...
9.4/10 Exceptional! (1,227 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."

Reviewed on May 21, 2026

Cambria Hotel Portland Downtown-Old Port
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Portland Hotels With Airport Transportation

Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

2 out of 5
461 Maine Mall Rd South Portland ME
$80 nightly
The price is $87 total per night from May 27 to May 28
$87 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,508 reviews)
"Great place to stay. Clean and close to amenities."

Reviewed on May 21, 2026

Spark by Hilton Portland Airport Maine Mall
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
$134 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9.4/10 Exceptional! (1,144 reviews)
"Made to order omelettes. Happy hour daily!"

Reviewed on May 21, 2026

Embassy Suites by Hilton Portland Maine
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St Portland ME
$86 nightly
The price is $95 total per night from May 25 to May 26
$95 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful staff ...
7.8/10 Good! (1,012 reviews)
"Parking safe and efficient"

Reviewed on May 19, 2026

Ramada Plaza by Wyndham Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Portland Hotels

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
80 John Roberts Rd. South Portland ME
$84 nightly
The price is $92 total per night from May 31 to Jun 1
$92 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (2,919 reviews)
"Convenient location, good exercise facility, adequate breakfast."

Reviewed on May 21, 2026

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Spark by Hilton Portland Airport Maine Mall

Spark by Hilton Portland Airport Maine Mall

2 out of 5
461 Maine Mall Rd South Portland ME
$80 nightly
The price is $87 total per night from May 27 to May 28
$87 total
May 27 - May 28
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.8/10 Good! (1,508 reviews)
"Great place to stay. Clean and close to amenities."

Reviewed on May 21, 2026

Spark by Hilton Portland Airport Maine Mall
Super 8 by Wyndham Portland ME

Super 8 by Wyndham Portland ME

2 out of 5
208 Larrabee Rd Westbrook ME
$72 nightly
The price is $78 total per night from Jun 1 to Jun 2
$78 total
Jun 1 - Jun 2
Total with taxes and fees
Book a stay at this business-friendly motel in Westbrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Super 8 by Wyndham Portland ME
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Portland

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
$134 nightly
The price is $149 total per night from May 25 to May 26
$149 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the ...
9.4/10 Exceptional! (1,144 reviews)
"Made to order omelettes. Happy hour daily!"

Reviewed on May 21, 2026

Embassy Suites by Hilton Portland Maine
The Rhumb Line Resort

The Rhumb Line Resort

2.5 out of 5
41 Turbat's Creek off Ocean Avenue Kennebunkport ME
$162 nightly
The price is $176 total per night from May 25 to May 26
$176 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly motel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff ...
7.8/10 Good! (927 reviews)
"This hotel is very nice. free breakfast, great pool. It's just an outdated property and could use some sprucing up. Carpets, wallpaper, etc."

Reviewed on May 6, 2026

The Rhumb Line Resort
Dormir

Dormir

3 out of 5
965 Roosevelt Trail Windham ME
$163 nightly
The price is $177 total per night from May 26 to May 27
$177 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,002 reviews)
"Rooms were over priced, hot water for shower was limited, breakfast was average for this type of property."

Reviewed on May 19, 2026

Dormir
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

ORD to PWM Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
ORD Address & GPS
Address:
10000 West O'Hare
Chicago IL, 60666
United States
IATA Code:
ORD
Longitude:
-87.904876
Latitude:
41.976912
Time Zone:
America/Chicago
PWM Address & GPS
Address:
1001 Westbrook Street
Portland ME, 04102
United States
IATA Code:
PWM
Longitude:
-70.310307
Latitude:
43.647492
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from ORD to PWM?
United Airlines makes getting from Chicago to Portland a breeze. It has direct flights from ORD to Portland Intl. Jetport, so you won't have to bother with changing planes.
What is the shortest flight from O'Hare Intl. Airport (ORD) to PWM?
From Chicago, the exciting sights and sounds of Portland are 4 hours and 2 minutes away. Secure your favorite seat, or perhaps even one with a bit more legroom, and jet to your destination in pure comfort.
How many hours flight from O'Hare Airport to PWM?
The trip from ORD to Portland Intl. Jetport will take about 4 hours and 8 minutes. A couple of good movies, some audiobooks and a decent snooze will make the time zoom by.
What airlines have the most flights from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport?
With 58 flights each month between O'Hare Intl. Airport (ORD) and PWM, United Airlines will get you there comfortably and safely.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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