Best Flight From O'Hare Intl. To PWM

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Amazing ORD to PWM Flight Deals

The cheapest flights to Portland Intl. Jetport were $337 for round trip flights and $176 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
PWM
Portland
$337 Roundtrip, found 1 day ago
$337
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from Chicago to Portland, returning Sat, Oct 31, priced at $337 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
PWM
Portland
$342 Roundtrip, found 1 day ago
$342
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from Chicago to Portland, returning Sat, Oct 31, priced at $342 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
PWM
Portland
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from Chicago to Portland, returning Sat, Oct 31, priced at $347 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
PWM
Portland
$352 Roundtrip, found 1 day ago
$352
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from Chicago to Portland, returning Sat, Oct 31, priced at $352 found 1 day ago
Sat, Oct 24 - Sat, Oct 31
ORD
Chicago
PWM
Portland
$357 Roundtrip, found 1 day ago
$357
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Oct 24 from Chicago to Portland, returning Sat, Oct 31, priced at $357 found 1 day ago
Thu, Oct 15 - Tue, Oct 20
ORD
Chicago
PWM
Portland
$362 Roundtrip, found 1 day ago
$362
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 15 from Chicago to Portland, returning Tue, Oct 20, priced at $362 found 1 day ago

Hotels near Portland Intl. Jetport Airport (PWM)

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
$115 nightly
The price is $127 total per night from Sep 20 to Sep 21
$127 total
Sep 20 - Sep 21
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 clean rooms in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
8.2/10 Very Good! (1,678 reviews)
"All good"

Reviewed on Sep 11, 2026

Opens in a new windowClarion Hotel Portland Airport ME
Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
$214 nightly
The price is $237 total per night from Sep 13 to Sep 14
$237 total
Sep 13 - Sep 14
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 helpful staff in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
9.4/10 Exceptional! (1,168 reviews)
"Room was a very nice 2 room suite. The staff was very helpful. Breakfast was a nice bonus. Loved the happy hour as a way to start winding down."

Reviewed on Sep 10, 2026

Opens in a new windowEmbassy Suites by Hilton Portland Maine
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
$143 nightly
The price is $156 total per night from Sep 27 to Sep 28
$156 total
Sep 27 - Sep 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 breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Opens in a new windowCasco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
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Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
$132 nightly
The price is $144 total per night from Oct 12 to Oct 13
$144 total
Oct 12 - Oct 13
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
Opens in a new windowComfort Inn South Portland Airport
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
$98 nightly
The price is $106 total per night from Oct 4 to Oct 5
$106 total
Oct 4 - Oct 5
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 staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
6.4/10 (1,117 reviews)
"The property was very dirty, and there was too much noise at night. The room and the corridors smelled very bad. The receptionist at the front desk was also very rude. Overall, it was not a pleasant experience."

Reviewed on Sep 10, 2026

Opens in a new windowQuality Inn & Suites South Portland
La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
$151 nightly
The price is $167 total per night from Sep 20 to Sep 21
$167 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
8.4/10 Very Good! (2,238 reviews)
"Pink mold in the shower grout. Difficulty flushing the toilet. English muffin with mold on it in the buffet."

Reviewed on Sep 11, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
$54 nightly
The price is $59 total per night from Sep 20 to Sep 21
$59 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this business-friendly hotel in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Maine Mall and Thompson's Point are located nearby.
7.2/10 Good! (799 reviews)
"Check-in went well. The staff were friendly and helpful. The room was relatively clean although it did have a bit of an odd smell. More attention could be paid to sweeping along the baseboards and under the desk and furniture. There were some stains on the bedsheets which looked like spilled coffee. ..."

Reviewed on Sep 11, 2026

Opens in a new windowClarion Pointe South Portland
Moxy Portland Thompson's Point

Moxy Portland Thompson's Point

2.5 out of 5
220 THOMPSONS POINT ROAD Portland ME
$215 nightly
The price is $238 total per night from Oct 12 to Oct 13
$238 total
Oct 12 - Oct 13
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. Popular attractions Thompson's Point and Cross Insurance Arena are located nearby.
8.6/10 Excellent! (10 reviews)
"Perfect location if you’re going to an event at thompson’s Point while in Portland."

Reviewed on Sep 8, 2026

Opens in a new windowMoxy Portland Thompson's Point
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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.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.