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$128 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 9/5. 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

Thu, Sep 3 - Tue, Sep 8
United Airlines Logo
5:50 pm - 9:23 pm
ORD
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2h 33mnonstop
United Airlines Logo
6:00 am - 7:57 am
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ORD
2h 57mnonstop
$279United Airlines
Sat, Aug 29 - Sat, Sep 5
Southwest Logo
5:55 am - 11:45 am
MDW
-
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4h 50m
1 stop
Southwest Logo
10:30 am - 4:40 pm
PWM
-
MDW
7h 10m
1 stop
$282Southwest
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
8:19 am - 2:21 pm
ORD
-
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5h 02m
1 stop
American Airlines Logo
7:28 am - 12:12 pm
PWM
-
ORD
5h 44m
1 stop
$282American Airlines
Sun, Sep 6 - Thu, Sep 10
American Airlines Logo
9:56 am - 4:33 pm
ORD
-
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5h 37m
1 stop
American Airlines Logo
12:24 pm - 5:28 pm
PWM
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ORD
6h 04m
1 stop
$282American Airlines
Sat, Aug 29 - Sat, Sep 5
Delta Logo
9:30 am - 3:58 pm
ORD
-
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5h 28m
1 stop
Delta Logo
12:10 pm - 7:13 pm
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ORD
8h 03m
1 stop
$282Delta
Wed, Sep 30 - Mon, Oct 5
United Airlines Logo
6:59 am - 10:40 am
ORD
-
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2h 41mnonstop
United Airlines Logo
6:00 am - 7:57 am
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ORD
2h 57mnonstop
$284United Airlines
Mon, Aug 24 - Sat, Aug 29
JetBlue Logo
6:00 am - 1:45 pm
ORD
-
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6h 45m
1 stop
JetBlue Logo
2:40 pm - 9:58 pm
PWM
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ORD
8h 18m
1 stop
$286JetBlue
Wed, Aug 26 - Sat, Aug 29
JetBlue Logo
6:00 am - 1:45 pm
ORD
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6h 45m
1 stop
JetBlue Logo
2:40 pm - 9:58 pm
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ORD
8h 18m
1 stop
$286JetBlue
Mon, Oct 19 - Mon, Oct 26
Southwest Logo
4:30 pm - 11:55 pm
MDW
-
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6h 25m
2 stops
Southwest Logo
5:20 am - 8:50 am
PWM
-
MDW
4h 30m
1 stop
$287Southwest
Tue, Dec 1 - Tue, Dec 15
Delta Logo
2:31 pm - 10:23 pm
STL
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6h 52m
1 stop
Delta Logo
12:50 pm - 5:00 pm
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STL
5h 10m
1 stop
$339Delta
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Good to know

Low season

January

Cheapest flight

$128
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 6% increase in price.
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)