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$156 Find Cheap Flights from Illinois to Portland - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 9/24. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Illinois to Portland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Illinois to Portland that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Illinois to Portland

Tue, Dec 1 - Wed, Dec 9
Delta Logo
12:15 pm - 7:29 pm
ORD
-
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6h 14m
1 stop
Delta Logo
6:00 am - 4:37 pm
PWM
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ORD
11h 37m
2 stops
$296Delta
Tue, Aug 4 - Wed, Aug 12
Delta Logo
12:46 pm - 12:59 am
MDW
-
PWM
11h 13m
2 stops
Delta Logo
6:05 am - 11:51 am
PWM
-
MDW
6h 46m
1 stop
$296Delta
Sat, Aug 15 - Mon, Aug 17
JetBlue Logo
6:00 am - 1:45 pm
ORD
-
PWM
6h 45m
1 stop
JetBlue Logo
6:00 am - 7:27 pm
PWM
-
ORD
14h 27m
2 stops
$297JetBlue
Wed, Oct 28 - Tue, Dec 1
United Airlines Logo
5:50 pm - 9:15 pm
ORD
-
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2h 25mnonstop
United Airlines Logo
4:48 pm - 6:45 pm
PWM
-
ORD
2h 57mnonstop
$298United Airlines
Tue, Aug 4 - Sat, Aug 8
American Airlines Logo
8:08 am - 11:45 am
ORD
-
PWM
2h 37mnonstop
American Airlines Logo
6:46 pm - 11:44 pm
PWM
-
ORD
5h 58m
1 stop
$299American Airlines
Sat, Sep 26 - Wed, Sep 30
Southwest Logo
3:45 pm - 9:00 pm
MDW
-
PWM
4h 15m
1 stop
Southwest Logo
7:45 am - 9:20 am
PWM
-
MDW
2h 35mnonstop
$299Southwest
Tue, Jul 28 - Thu, Aug 13
American Airlines Logo
3:18 pm - 6:52 pm
ORD
-
PWM
2h 34mnonstop
American Airlines Logo
6:46 pm - 11:44 pm
PWM
-
ORD
5h 58m
1 stop
$300American Airlines
Tue, Aug 11 - Thu, Aug 20
Southwest Logo
6:50 pm - 10:05 pm
MDW
-
PWM
2h 15mnonstop
Southwest Logo
5:55 am - 9:30 am
PWM
-
MDW
4h 35m
1 stop
$300Southwest
Fri, Sep 18 - Mon, Sep 21
JetBlue Logo
1:00 pm - 11:52 pm
ORD
-
PWM
9h 52m
1 stop
JetBlue Logo
6:00 am - 11:47 am
PWM
-
ORD
6h 47m
1 stop
$302JetBlue
Wed, Sep 30 - Wed, Oct 7
United Airlines Logo
2:28 pm - 9:54 pm
MLI
-
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6h 26m
1 stop
United Airlines Logo
7:58 am - 12:37 pm
PWM
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MLI
5h 39m
1 stop
$311United Airlines
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Good to know

Low seasonJanuary
Cheapest flight$156
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Chicago O'Hare Airport to Portland

FAQs for booking flights from Illinois to Portland

  • How does KAYAK find such low prices on flights from Illinois to Portland?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Illinois to Portland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Portland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Illinois to Portland?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Portland with an airline and back to Illinois with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Illinois to Portland?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Portland from Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Jackson
Freeport
Bartlett
Oxford
Intervale
Windham
Tamworth
Falmouth
Waterford
Durham

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

Portland (PWM)