Cheap Flight Tickets from Portland (PWM) to Chicago (ORD), Starting at $357

Good to Know: Cheapest and Fastest PWM - ORD Flights

Useful information for finding best airline tickets from Portland International Jetport to Chicago O'Hare International on your next trip.

Cheapest Round Trip Flight

$357

DL Delta Airlines • 1 stop • 10h 17m

Oct 02 – Oct 04

The cheapest round trip flight from Portland to Chicago (PWM-ORD-PWM) is currently $357

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Cheapest Direct Flight

$416

UA United Airlines • nonstop • 4h 17m

Oct 02

The cheapest nonstop flight from Portland to Chicago (PWM-ORD) is currently $416

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Fastest Flight

4h 17m

The fastest nonstop flight from Portland to Chicago (PWM-ORD) takes 4h 17m

Top Airlines Flying from Portland to Chicago

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Portland (PWM) to Chicago (ORD)

Compare and book low fare round-trip air tickets from Portland to Chicago. Ideal for travelers with confirmed return itineraries.

Oct 02 - Oct 04, Economy
DL
Portland → Chicago
10h 17m
4:20 PM - 9:37 PM • 1 stop
DL
Portland → Chicago
8h 44m
6:40 AM - 1:04 PM • 1 stop
$357
Delta Airlines
Oct 02 - Oct 04, Economy
DL
Portland → Chicago
7h 38m
6:30 AM - 10:28 AM • 1 stop
DL
Portland → Chicago
10h
8:55 AM - 3:55 PM • 1 stop
$357
Delta Airlines
Oct 02 - Oct 04, Economy
UA
Portland → Chicago
8h 27m
7:25 PM - 11:32 PM • 1 stop
UA
Portland → Chicago
4h 1m
6:59 AM - 10:40 AM • nonstop
$416
United Airlines
Oct 02 - Oct 04, Economy
AA
Portland → Chicago
7h 34m
12:24 PM - 4:18 PM • 1 stop
AA
Portland → Chicago
3h 56m
9:29 AM - 1:05 PM • nonstop
$469
American Airlines
Oct 02 - Oct 04, Economy
AA
Portland → Chicago
8h 30m
6:00 AM - 10:10 AM • 1 stop
AA
Portland → Chicago
3h 56m
9:29 AM - 1:05 PM • nonstop
$469
American Airlines
Oct 02 - Oct 04, Economy
AA
Portland → Chicago
5h 21m
5:38 PM - 7:59 PM • nonstop
AA
Portland → Chicago
4h 4m
1:10 PM - 4:54 PM • nonstop
$469
American Airlines

Fly from Portland to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Portland to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Portland to Chicago Flights

What are the airports in Portland?
PWM
What’s the most popular airline flying from PWM to ORD?
The most popular airline flying from Portland to Chicago are
Can I fly from PWM to ORD non-stop?
Yes, you can fly PWM to ORD non-stop on
Which airlines fly nonstop between Portland and Chicago?
The non-stop flights between Portland and Chicago are .
What’s the earliest departure time from PWM to ORD Airport?
The earliest flight leaves PWM at 6:00 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
Can I make changes to my Portland to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from PWM to ORD?
Read the fare rules of the Portland to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Portland and Chicago?
operate flights between Portland and Chicago
How long does a flight from Portland to Chicago take?
It takes approximately 2 hour to fly non-stop from PWM to ORD, which is 899.87 miles by air.
Which airlines provide the cheapest flights from Portland (PWM) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from PWM were found on DL : USD 357
Do I need a passport to fly between PWM and ORD?
No
What’s the latest departure time from PWM to ORD ?
The last flight leaves PWM at 7:25 pm

Hotels in Chicago (ORD)

5 hotels near Chicago O'Hare International — compare rates from top booking sites.

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5.0-star hotel 5-star hotel

Fairmont Chicago at Millennium Park

📍 200 North Columbus Drive, Chicago, Illinois 60601

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5.0-star hotel 5-star hotel

InterContinental Chicago Magnificent Mile

📍 505 N Michigan Ave, Chicago, Illinois 60611

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5.0-star hotel 5-star hotel

JW Marriott Chicago

📍 151 West Adams Street, Chicago, Illinois 60603

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5.0-star hotel 5-star hotel

The Langham, Chicago

📍 330 North Wabash, Chicago, Illinois 60618

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5.0-star hotel 5-star hotel

The Ritz-Carlton, Chicago

📍 160 E Pearson Street, Chicago, Illinois 60611

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Hotel Deals in Chicago (IL)
Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts
Red Roof Inn

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

6.6/10
★★☆☆☆ Hotel 132.0 rooms
✓ Free WiFi

📍 22 West Algonquin Road, Chicago (IL)

Experience an abundance of unparalleled facilities and features at Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts. Maintain seamless communication using the complimentary Wi-Fi at hotel.For visit…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$74/night
View Deal
Motel 6 Chicago O'Hare - Schiller Park
Motel 6

Motel 6 Chicago O'Hare - Schiller Park

6.7/10
★★☆☆☆ Hotel

📍 9408 Lawrence Avenue, Chicago (IL), Illinois

Great care is taken to ensure guests experience comfort through top-notch services and amenities.Parking is accessible, supplied by the hotel for guests who arrive by car. The hotel is completely smo…

$94/night
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Baymont by Wyndham Glenview
Wyndham Hotels & Resorts

Baymont by Wyndham Glenview

8.1/10
★★★☆☆ Hotel 95.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1625 Milwaukee Ave, Chicago (IL), Illinois

At Baymont by Wyndham Glenview, exceptional service and top-notch amenities create a memorable experience for guests.Complimentary internet access is available in the hotel to ensure you stay connect…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$106/night
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Radisson Hotel Schaumburg
Choice Hotels

Radisson Hotel Schaumburg

7.0/10
★★★☆☆ Hotel 127.0 rooms
✓ Free WiFi ✓ Breakfast

📍 1550 N. Roselle Rd, Chicago (IL), Illinois

Radisson Hotel Schaumburg provides flawless service and all the necessary facilities for visitors. Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. W…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$111/night
View Deal
Quality Inn O'Hare Airport
Choice Hotels

Quality Inn O'Hare Airport

7.6/10
★★★☆☆ Hotel 144.0 rooms
✓ Free WiFi ✓ Breakfast

📍 3801 North Mannheim Road, Chicago (IL), Illinois

Quality Inn O'Hare Airport provides flawless service and all the necessary facilities for visitors.Stay connected with your associates, as complimentary Wi-Fi is available during your entire visit. T…

Check-in 02:00 PM  ·  Check-out 11:30 AM

$129/night
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Holiday Inn O'Hare Area By IHG
InterContinental Hotels Group

Holiday Inn O'Hare Area By IHG

7.9/10
★★★☆☆ Hotel 245.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5615 North Cumberland Avenue, Chicago (IL), Illinois

Holiday Inn O'Hare Area By IHG offers top-notch services and amenities, ensuring guests experience utmost comfort. Share your photos and respond to emails at your convenience, thanks to the free Wi-F…

Check-in 03:00 PM  ·  Check-out 12:00 PM

$179/night
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Chicago South Loop
No chain

Chicago South Loop

7.7/10
★★★☆☆ Hotel 232.0 rooms
✓ Free WiFi

📍 11 W 26th Street, Chicago (IL), Illinois

Chicago South Loop offers top-notch services and amenities, ensuring guests experience utmost comfort.Maintain seamless communication using the complimentary Wi-Fi at hotel. For visitors traveling by…

Check-in 03:00 PM  ·  Check-out 11:00 AM

$194/night
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Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
InterContinental Hotels Group

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

8.3/10
★★★★☆ Hotel 503.0 rooms
✓ Free WiFi ✓ Breakfast

📍 5440 North River Road, Chicago (IL), Illinois

Experience an abundance of unparalleled facilities and features at Crowne Plaza Chicago O'Hare Hotel & Conference Center By IHG.Share your photos and respond to emails at your convenience, thanks to …

Check-in 03:00 PM  ·  Check-out 12:00 PM

$194/night
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Freehand Chicago
No chain

Freehand Chicago

8.1/10
★★★★☆ Hotel 215.0 rooms
✓ Free WiFi

📍 19 East Ohio Street, Chicago (IL), Illinois

At Freehand Chicago, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the hotel to ensure you stay connected during …

Check-in 03:00 PM  ·  Check-out 12:00 PM

$216/night
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Portland (PWM) to Chicago (ORD): Airport Information

Origin Airport Portland International Jetport , Portland, US
Destination Airport Chicago O'Hare International , Chicago, US
Distance 900 miles

More Flight Options for Portland (PWM) and Chicago (ORD)

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