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 $302 for round trip flights and $119 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$302 Roundtrip, found 3 days ago
$302
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $302 found 3 days ago
Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $338 found 3 days ago
Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$342 Roundtrip, found 3 days ago
$342
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $342 found 3 days ago
Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$348 Roundtrip, found 3 days ago
$348
Roundtrip
found 3 days ago
Select United flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $348 found 3 days ago
Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$365 Roundtrip, found 3 days ago
$365
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $365 found 3 days ago
Thu, Oct 1 - Thu, Oct 8
ORD
Chicago
PWM
Portland
$369 Roundtrip, found 3 days ago
$369
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Oct 1 from Chicago to Portland, returning Thu, Oct 8, priced at $369 found 3 days ago

Hotels near Portland Intl. Jetport Airport (PWM)

Embassy Suites by Hilton Portland Maine

Embassy Suites by Hilton Portland Maine

3.5 out of 5
1050 Westbrook Street Portland ME
$246 nightly
The price is $272 total per night from Aug 2 to Aug 3
$272 total
Aug 2 - Aug 3
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! (1,167 reviews)
"The hallway was freezing along with AC on in the pool."

Reviewed on Jul 27, 2026

Opens in a new windowEmbassy 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
$153 nightly
The price is $170 total per night from Aug 23 to Aug 24
$170 total
Aug 23 - Aug 24
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.
8.2/10 Very Good! (1,581 reviews)
"Beds are super comfy - quiet. Close to airport"

Reviewed on Jul 27, 2026

Opens in a new windowClarion Hotel Portland Airport ME
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
$149 nightly
The price is $162 total per night from Aug 24 to Aug 25
$162 total
Aug 24 - Aug 25
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! (2,263 reviews)
"convenient location, great helpful staff."

Reviewed on Jul 28, 2026

Opens in a new windowComfort Inn South Portland Airport
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The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
$254 nightly
The price is $281 total per night from Aug 23 to Aug 24
$281 total
Aug 23 - Aug 24
Total with taxes and fees
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Cross Insurance Arena are located nearby.
9/10 Wonderful! (1,015 reviews)
"Comfy night's sleep at the Westin. Enjoyed that there is a shuttle to drop you off for dinner."

Reviewed on Jul 28, 2026

Opens in a new windowThe Westin Portland Harborview
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
$172 nightly
The price is $187 total per night from Aug 23 to Aug 24
$187 total
Aug 23 - Aug 24
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
Clarion Pointe South Portland

Clarion Pointe South Portland

2 out of 5
675 Main Street I-95 South Portland ME
$94 nightly
The price is $102 total per night from Aug 26 to Aug 27
$102 total
Aug 26 - Aug 27
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! (602 reviews)
"The staff were very friendly and the room was clean. The building and interior itself is a bit run down but absolutely correct for the price."

Reviewed on Jul 28, 2026

Opens in a new windowClarion Pointe 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
$169 nightly
The price is $187 total per night from Aug 23 to Aug 24
$187 total
Aug 23 - Aug 24
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.
8.4/10 Very Good! (2,194 reviews)
"Elevator was immediately next to our room, the ride was not smooth and it was a little noisy."

Reviewed on Jul 27, 2026

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

Fireside Inn & Suites Portland

3 out of 5
81 Riverside St Portland ME
$159 nightly
The price is $176 total per night from Aug 16 to Aug 17
$176 total
Aug 16 - Aug 17
Total with taxes and fees
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Thompson's Point and Maine Mall are located nearby.
Opens in a new windowFireside Inn & Suites 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.