$86 Cheap flight deals from Chicago (CHI) to Westbrook (PWM)

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This Weekend's Flight Deals from Chicago to Westbrook

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Jul 5 - Sun, Jul 12
ORD
O'Hare Intl.
PWM
Portland Intl. Jetport
$556 Roundtrip, found 1 day ago
$556
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jul 5 from O'Hare Intl. to Portland Intl. Jetport, returning Sun, Jul 12, priced at $556 found 1 day ago
Sun, Jul 5 - Sun, Jul 12
MDW
Midway Intl.
PWM
Portland Intl. Jetport
$556 Roundtrip, found 1 day ago
$556
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jul 5 from Midway Intl. to Portland Intl. Jetport, returning Sun, Jul 12, priced at $556 found 1 day ago
Sun, Jul 5 - Sun, Jul 12
RFD
Greater Rockford
PWM
Portland Intl. Jetport
$768 Roundtrip, found 1 day ago
$768
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jul 5 from Greater Rockford to Portland Intl. Jetport, returning Sun, Jul 12, priced at $768 found 1 day ago

Airfares from $86 One Way, $169 Round Trip from Chicago to Westbrook

Prices starting at $169 for return flights and $86 for one-way flights to Westbrook were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Sep 2 - Sat, Sep 5
ORD
Chicago
PWM
Portland
$169 Roundtrip, found 3 days ago
$169
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Sep 2 from Chicago to Portland, returning Sat, Sep 5, priced at $169 found 3 days ago
Tue, Aug 25 - Wed, Aug 26
ORD
Chicago
PWM
Portland
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Chicago to Portland, returning Wed, Aug 26, priced at $173 found 1 day ago
Sat, Aug 22 - Fri, Aug 28
ORD
Chicago
PWM
Portland
$181 Roundtrip, found 3 days ago
$181
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Aug 22 from Chicago to Portland, returning Fri, Aug 28, priced at $181 found 3 days ago
Tue, Sep 1 - Thu, Sep 10
ORD
Chicago
PWM
Portland
$185 Roundtrip, found 4 days ago
$185
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 1 from Chicago to Portland, returning Thu, Sep 10, priced at $185 found 4 days ago
Sat, Aug 8 - Tue, Aug 11
ORD
Chicago
PWM
Portland
$189 Roundtrip, found 3 hours ago
$189
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Aug 8 from Chicago to Portland, returning Tue, Aug 11, priced at $189 found 3 hours ago

Westbrook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites
3.0-star property

Ogunquit River Inn & Suites

9/10 Wonderful! (1,017 reviews)

Aug 11 - Aug 14

3 night stay

Chicago (CHI) to Portland (PWM)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $951, price is now $604 per person
$604
per person
found 23 hours ago
Excellent location and beautiful views

Reviewed on Sep 14, 2025

Inn at Diamond Cove
3.5-star property

Inn at Diamond Cove

8.8/10 Excellent! (196 reviews)

Jul 31 - Aug 4

4 night stay

Chicago (ORD) to Portland (PWM)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,527, price is now $1,016 per person
$1,016
per person
found 1 day ago
The Inn itself is gorgeous on a lovely quiet island for some exploring. The rooms are large and well maintained, and the staff while inexperienced does their best to help and answer questions. Our room was ready when we got there early, and they let us check-in a few hours ahead which was greatly appreciated. The pool is nice (a little chilly) and the hot tub was boiling, and we enjoyed relaxing by the pool. The beaches are nice to visit from a short walk but don't expect sandy beaches here. We walked around the island, even outside of the homeowner's association barrier and there is a nice gift shop where you can get ice cream, popsicles and some treats for ~1 a pop. Surprisingly reasonable for this island. The main issue with the island is food as one might expect, so just keep you expectations on the lower end (unlike the higher side prices) and you won't be too disappointed. The hotel restaurant is OK - the pancakes were at least good - but the two island restaurants left a lot to be desired. Would we return? I think if you are looking for a short getaway or are willing to go to portland for food, it can make an excellent relaxing trip.

Reviewed on Jul 26, 2024

Portland Harbor Hotel
4.0-star property

Portland Harbor Hotel

9.4/10 Exceptional! (1,786 reviews)

Aug 15 - Aug 21

6 night stay

Chicago (CHI) to Portland (PWM)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,422, price is now $1,655 per person
$1,655
per person
found 1 day ago
PHH was amazing! Clean, beautiful, easy, and elevated!

Reviewed on May 17, 2026

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More About Flying To Westbrook from Chicago

Route Information for Flights from Chicago to Westbrook

Origin Airport IATA Code
CHI
Destination Airport IATA Code
PWM
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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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.