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 $243 for round trip flights and $89 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Jul 15 - Tue, Jul 28
ORD
Chicago
PWM
Portland
$243 Roundtrip, found 1 day ago
$243
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jul 15 from Chicago to Portland, returning Tue, Jul 28, priced at $243 found 1 day ago
Wed, Jul 15 - Tue, Jul 28
ORD
Chicago
PWM
Portland
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jul 15 from Chicago to Portland, returning Tue, Jul 28, priced at $271 found 1 day ago
Wed, Jul 15 - Tue, Jul 28
ORD
Chicago
PWM
Portland
$291 Roundtrip, found 1 day ago
$291
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jul 15 from Chicago to Portland, returning Tue, Jul 28, priced at $291 found 1 day ago
Wed, Jul 15 - Tue, Jul 28
ORD
Chicago
PWM
Portland
$307 Roundtrip, found 1 day ago
$307
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 15 from Chicago to Portland, returning Tue, Jul 28, priced at $307 found 1 day ago
Wed, Jul 15 - Tue, Jul 28
ORD
Chicago
PWM
Portland
$317 Roundtrip, found 1 day ago
$317
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Jul 15 from Chicago to Portland, returning Tue, Jul 28, priced at $317 found 1 day ago
Tue, Jul 14 - Mon, Jul 27
ORD
Chicago
PWM
Portland
$320 Roundtrip, found 2 days ago
$320
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jul 14 from Chicago to Portland, returning Mon, Jul 27, priced at $320 found 2 days 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
$119 nightly
The price is $132 total per night from Jun 14 to Jun 15
$132 total
Jun 14 - Jun 15
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 State Theatre are located nearby.
8/10 Very Good! (1,492 reviews)
"Clean Property, rooms were spacious and comfortable. Easy 10 minute walk to Bissell Brewery and Thompson’s Point if you’re catching a show!"

Reviewed on Jun 10, 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
$189 nightly
The price is $209 total per night from Jun 14 to Jun 15
$209 total
Jun 14 - Jun 15
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! (1,157 reviews)
"Embassy Suites is a perfect spot near the PWM. Great breakfast with everything you could imagine! Airport shuttle literally takes minutes. Very convenient stay!"

Reviewed on Jun 9, 2026

Opens in a new windowEmbassy Suites by Hilton Portland Maine
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
$119 nightly
The price is $130 total per night from Jun 28 to Jun 29
$130 total
Jun 28 - Jun 29
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.
8.6/10 Excellent! (2,113 reviews)
"Friendly, helpful staff. Comfy bed. Water was clean tasting from faucet. Tv was excellent…but wifi was spoty. I will stay again. Close to transportation center and airport, and affordable."

Reviewed on Jun 12, 2026

Opens in a new windowComfort Inn South Portland Airport
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Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
145 Jetport Blvd Portland ME
$203 nightly
The price is $224 total per night from Jul 12 to Jul 13
$224 total
Jul 12 - Jul 13
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 and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
8.4/10 Very Good! (1,006 reviews)
"I DO NOT LIKE room cleaning/towel replacement every other day. Coffee pods in room were not refilled. I had to go to front desk and request cups/pods. I also don’t like having to pay $13.99 for a bagel, coffee, fruit (breakfast buffet). Do complementary continental breakfast instead. All that said, ..."

Reviewed on Jun 8, 2026

Opens in a new windowHilton Garden Inn Portland Airport
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
$139 nightly
The price is $154 total per night from Jun 14 to Jun 15
$154 total
Jun 14 - Jun 15
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 State Theatre are located nearby.
8.6/10 Excellent! (2,224 reviews)
"It was quiet."

Reviewed on Jun 12, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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
$104 nightly
The price is $113 total per night from Jun 15 to Jun 16
$113 total
Jun 15 - Jun 16
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.
8.4/10 Very Good! (2,938 reviews)
"Convenient location, amazing & friendly staff, nice spacious room. I wouldn't hesitate to stay again."

Reviewed on Jun 13, 2026

Opens in a new windowCasco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
$89 nightly
The price is $97 total per night from Jun 14 to Jun 15
$97 total
Jun 14 - Jun 15
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.
7.4/10 Good! (477 reviews)
"everything was gross, from the stained bedding with weird black flakes to the nasty odor coming from the AC. food smeared on the carpets in the hallways and dirt and debris piling in the elevator. Staff were pleasant."

Reviewed on Jun 12, 2026

Opens in a new windowClarion Pointe South Portland
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
363 Maine Mall Rd South Portland ME
$122 nightly
The price is $133 total per night from Jun 28 to Jun 29
$133 total
Jun 28 - Jun 29
Total with taxes and fees
Stay at this hotel in South Portland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Maine Mall and Thompson's Point are located nearby.
8/10 Very Good! (1,414 reviews)
"Room was clean and very spacious. Pool was clean and well maintained."

Reviewed on Jun 13, 2026

Opens in a new windowDoubleTree by Hilton Hotel Portland
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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.

Top Picks

*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.