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 $289 for round trip flights and $145 for one-way flights in the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$289 Roundtrip, found 3 days ago
$289
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $289 found 3 days ago
Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$299 Roundtrip, found 3 days ago
$299
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $299 found 3 days ago
Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $309 found 3 days ago
Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$334 Roundtrip, found 3 days ago
$334
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $334 found 3 days ago
Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$335 Roundtrip, found 3 days ago
$335
Roundtrip
found 3 days ago
Select American Airlines flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $335 found 3 days ago
Thu, Dec 3 - Tue, Dec 8
ORD
Chicago
PWM
Portland
$338 Roundtrip, found 3 days ago
$338
Roundtrip
found 3 days ago
Select United flight, departing Thu, Dec 3 from Chicago to Portland, returning Tue, Dec 8, priced at $338 found 3 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
$83 nightly
The price is $92 total per night from Nov 3 to Nov 4
$92 total
Nov 3 - Nov 4
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.
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
$119 nightly
The price is $132 total per night from Nov 2 to Nov 3
$132 total
Nov 2 - Nov 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! (1,205 reviews)
"Very clean property and friendly staff. Convenient location and not noisy, despite being right at the airport! The room phone was inoperable so we had trouble reaching the front desk with an issue that needed attention (refirgerator was not on). I was eventually able to text the front desk, a repair ..."

Reviewed on Oct 27, 2026

Opens in a new windowEmbassy Suites by Hilton Portland Maine
Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
738 Main Street South Portland ME
$72 nightly
The price is $79 total per night from Nov 11 to Nov 12
$79 total
Nov 11 - Nov 12
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 windowQuality Inn & Suites South Portland
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Hilton Garden Inn Portland Airport

Hilton Garden Inn Portland Airport

3 out of 5
145 Jetport Blvd Portland ME
$99 nightly
The price is $110 total per night from Nov 25 to Nov 26
$110 total
Nov 25 - Nov 26
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.
8.6/10 Excellent! (1,002 reviews)
"The toilet did not flush ! Ihad to remove the tank lid and lift the stopper. It was late and I neede to get to sleep rather than wait for a repairman. In the morning the room was cool and I attempted to adjust the thermostat and it was flashing a battery symbol. I reported it to the desk attendant ..."

Reviewed on Oct 27, 2026

Opens in a new windowHilton Garden Inn Portland Airport
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 Nov 17 to Nov 18
$92 total
Nov 17 - Nov 18
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
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
$108 nightly
The price is $119 total per night from Nov 18 to Nov 19
$119 total
Nov 18 - Nov 19
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.
Opens in a new windowThe Westin Portland Harborview
Inn at St John Portland In-Town

Inn at St John Portland In-Town

2.5 out of 5
939 Congress St Portland ME
$98 nightly
The price is $107 total per night from Nov 4 to Nov 5
$107 total
Nov 4 - Nov 5
Total with taxes and fees
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Thompson's Point and State Theatre are located nearby.
Opens in a new windowInn at St John Portland In-Town
Comfort Inn South Portland Airport

Comfort Inn South Portland Airport

2.5 out of 5
90 Maine Mall Rd South Portland ME
$73 nightly
The price is $79 total per night from Nov 22 to Nov 23
$79 total
Nov 22 - Nov 23
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
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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.