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Cheap Flights from Chicago to Portland

Prices were available within the past 7 days and starts at $103 for one-way flights and $205 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Aug 12
ORD
Chicago
to
PWM
Portland
$103

One way

found 4 hours ago

Open ORD to PWM flights search result page
Wed, Mar 4
ORD
Chicago
to
PWM
Portland
$122

One way

found 13 hours ago

Open ORD to PWM flights search result page
Tue, Sep 1
ORD
Chicago
to
PWM
Portland
$125

One way

found 10 hours ago

Open ORD to PWM flights search result page
Thu, May 14
ORD
Chicago
to
PWM
Portland
$146

One way

found 1 hour ago

Open ORD to PWM flights search result page
Wed, Mar 25
ORD
Chicago
to
PWM
Portland
$151

One way

found 8 hours ago

Open ORD to PWM flights search result page
Wed, Jul 8
ORD
Chicago
to
PWM
Portland
$157

One way

found 5 hours ago

Open ORD to PWM flights search result page
Wed, Aug 12
ORD
Chicago
to
PWM
Portland
$161

One way

found 4 hours ago

Open ORD to PWM flights search result page
Sun, Sep 6
ORD
Chicago
to
PWM
Portland
$162

One way

just found

Open ORD to PWM flights search result page
Sat, May 23
ORD
Chicago
to
PWM
Portland
$163

One way

found 1 day ago

Open ORD to PWM flights search result page
Sat, Jun 20
ORD
Chicago
to
PWM
Portland
$164

One way

found 2 hours ago

Open ORD to PWM flights search result page
Wed, Aug 12 - Wed, Aug 26
ORD
Chicago
to
PWM
Portland
$205

Roundtrip

found 4 days ago

Open ORD to PWM flights search result page
Tue, Apr 21 - Tue, Apr 28
ORD
Chicago
to
PWM
Portland
$221

Roundtrip

found 3 days ago

Open ORD to PWM flights search result page
Wed, Aug 19 - Wed, Aug 26
ORD
Chicago
to
PWM
Portland
$227

Roundtrip

found 2 days ago

Open ORD to PWM flights search result page
Tue, Mar 17 - Tue, Mar 17
ORD
Chicago
to
PWM
Portland
$228

Roundtrip

found 1 day ago

Open ORD to PWM flights search result page
Wed, Mar 11 - Wed, Mar 11
ORD
Chicago
to
PWM
Portland
$229

Roundtrip

found 3 days ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$232

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$233

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$235

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$235

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$237

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Wed, Aug 12
ORD
Chicago
to
PWM
Portland
$103

One way

found 4 hours ago

Open ORD to PWM flights search result page
Wed, Mar 4
ORD
Chicago
to
PWM
Portland
$122

One way

found 13 hours ago

Open ORD to PWM flights search result page
Tue, Sep 1
ORD
Chicago
to
PWM
Portland
$125

One way

found 10 hours ago

Open ORD to PWM flights search result page
Thu, May 14
ORD
Chicago
to
PWM
Portland
$146

One way

found 1 hour ago

Open ORD to PWM flights search result page
Wed, Mar 25
ORD
Chicago
to
PWM
Portland
$151

One way

found 8 hours ago

Open ORD to PWM flights search result page
Wed, Jul 8
ORD
Chicago
to
PWM
Portland
$157

One way

found 5 hours ago

Open ORD to PWM flights search result page
Wed, Aug 12
ORD
Chicago
to
PWM
Portland
$161

One way

found 4 hours ago

Open ORD to PWM flights search result page
Sun, Sep 6
ORD
Chicago
to
PWM
Portland
$162

One way

just found

Open ORD to PWM flights search result page
Sat, May 23
ORD
Chicago
to
PWM
Portland
$163

One way

found 1 day ago

Open ORD to PWM flights search result page
Sat, Jun 20
ORD
Chicago
to
PWM
Portland
$164

One way

found 2 hours ago

Open ORD to PWM flights search result page
Wed, Aug 12 - Wed, Aug 26
ORD
Chicago
to
PWM
Portland
$205

Roundtrip

found 4 days ago

Open ORD to PWM flights search result page
Tue, Apr 21 - Tue, Apr 28
ORD
Chicago
to
PWM
Portland
$221

Roundtrip

found 3 days ago

Open ORD to PWM flights search result page
Wed, Aug 19 - Wed, Aug 26
ORD
Chicago
to
PWM
Portland
$227

Roundtrip

found 2 days ago

Open ORD to PWM flights search result page
Tue, Mar 17 - Tue, Mar 17
ORD
Chicago
to
PWM
Portland
$228

Roundtrip

found 1 day ago

Open ORD to PWM flights search result page
Wed, Mar 11 - Wed, Mar 11
ORD
Chicago
to
PWM
Portland
$229

Roundtrip

found 3 days ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$232

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$233

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$235

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$235

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page
Tue, Mar 3 - Tue, Mar 10
ORD
Chicago
to
PWM
Portland
$237

Roundtrip

found 5 hours ago

Open ORD to PWM flights search result page

Chicago to Portland route information

Origin Airport O'Hare Intl.
Destination Airport Portland Intl. Jetport
Airlines Serving American Airlines, Delta, Frontier Airlines, JetBlue Airways, United
Flight Price $204
Distance 897 mi

Chicago

MDW-Midway Intl.

$234.40

Top Routes from Chicago

Top Routes to Portland

Cheap ORD to PWM Flights

  • How many flights are there per day from Chicago to Portland?

    The number of flight times varies by day, but on average, ORD to PWM sees seven different options. That is the same number of choices as the average route departing US.

  • What is the cheapest day to fly?

    The cheapest day to fly from Chicago to Portland is on Sunday. So, if you would like to save a bit of cash on your next business trip look for flights on Sunday.

  • Which airline has the least delays from Chicago to Portland?

    Booking with SkyWest Airlines means you will arrive to Portland approximately the time you were supposed to. In fact, this timely airline has an 82% on-time average.

  • Can I change the date of my flight?

    You sure can switch your departure date and you may save money by changing when you take off. The lowest-cost day to fly in March is Sunday. Being flexible with your travel days can provide you extra savings when booking.

  • How long does the average person stay in Portland?

    Of course, you're not an average person, but if you were, you'd stay about five days.

  • What is the cheapest airline flying from Chicago to Portland?

    Ticket costs are hitting highs of $644 over the next three months when flying to PWM from ORD. Check out Delta Air Lines, as customers have been booking flights at just $229.

  • How long is the flight from ORD to PWM?

    If you're able to take the direct flight (which is offered by United Airlines), you will be able to leave ORD at 9:13 AM CST and get to PWM at 12:29 PM EST (two hours and 16 minutes). Remember, there is a time change of one hour.

Chicago to Portland Flights

Whether you’re looking for a grand adventure or just want to get away for a last-minute break, flights from Chicago to Portland offer the perfect respite. Not only does exploring Portland provide the chance to make some magical memories, dip into delectable dishes, and tour the local landmarks, but the cheap airfare means you won’t bust your budget. So no matter whether your ideal itinerary involves flying one way, non-stop, or round trip, you’re bound to find flights that match your schedule on Expedia, and at prices that won’t shock your wallet.

Bagging a cheap flight from Chicago to Maine may mean more dollars to spend on for one-of-a-kind souvenirs when you arrive, but it doesn’t mean you have to skimp on your travel experience, as Expedia offers a sizzling selection of cheap airlines that’ll put you in your happy place on their planes, whether that’s getting lost in a hair-raising airport thriller, dreaming on the passing landscape over a glass of bubbly, or jotting down your vacation bucket list at 38,000 feet. There’s also bound to be plenty of opportunities to snap a few photos of the high life that will make your friends green with envy. After all, enjoying the journey is part of the fun.

With so many affordable flights and so many wonderful adventures awaiting you, there’s no reason to put off booking a fantastic flight from ORD to PWM today. So don’t leave it to the last minute to make your dream trip a reality: pack your bags with your go-to travel accessories, put together your list of must-see attractions and can’t-miss activities, and get ready to broaden your horizons – with Expedia, the wonders of Portland are only a plane trip away. Book your travel arrangements with us today!

If you would like to book flights to Portland more flexbily many prefers to purchase one-way tickets with options to take different airlines. One way ticket to Maine is $103 now!

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on Expedia.com of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.