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Portland to Chicago Flights

Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from Portland to Chicago

Departure Arrival Travel dates Round-trip
PDX CHI Wed, Jun 3 - Sat, Jun 6 $207
PDX CHI Tue, Jan 27 - Tue, Feb 3 $277
PDX CHI Fri, Jan 2 - Thu, Jan 8 $366
PDX CHI Tue, Jan 27 - Mon, Feb 2 $369
PDX CHI Tue, Feb 17 - Wed, Feb 18 $369
PDX CHI Fri, Jan 30 - Tue, Feb 3 $375
PDX CHI Thu, Feb 19 - Tue, Feb 24 $383
PDX CHI Tue, Jan 20 - Fri, Jan 23 $394
PDX CHI Thu, May 7 - Wed, May 13 $570

Portland and Chicago airports and terminals

Airports in Portland OR, US
map of airports in Portland
  • 1

    Portland International Airport (PDX)

    Distance from City Center: 6.5 miles

    Carriers for flights from PDX to CHI

    Carriers
    Alaska Airlines, American Airlines, Malaysia Airlines, US Airways, United Airlines
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Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from PDX to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 3 Alaska Airlines, American Airlines, Malaysia Airlines, US Airways
Back to menu Return to top
Sun Mon Tue Wed Thu Fri Sat
1 2 3
4 5 6 7 8 9
$277
10
11 12 13 14 15 16 17
18 19 20 21 22 23 24
25 26 27
$277
28 29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $79

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 128 reviews

O'Hare International Airport Map

Rate Includes Breakfast

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $120

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 43 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $118

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.7 / 5 15 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $118

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $159

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

Perfect for business travel and weekend getaways, the renovated Marriott Chicago Midway is just two blocks from MDW airport and offers a free 24-hr shuttle.... More

Hotel only $87

Sheraton Chicago O'Hare Airport Hotel

4 stars
4.0 / 5 115 reviews

6501 North Mannheim Road Map

Save 15% on your stay, Breakfast Included

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

January

Cheapest weekend flights in January from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jan 29 Portland (PDX) Chicago (ORD) Frontier Airlines $278
Earn $2.78
Return Mon, Feb 2 Chicago (ORD) Portland (PDX) Frontier Airlines

Lowest roundtrip airfare in January from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 27 Portland (PDX) Chicago (ORD) Frontier Airlines $277
Earn $2.77
Return Tue, Feb 3 Chicago (ORD) Portland (PDX) Frontier Airlines

Best one-week trip in January from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jan 27 Portland (PDX) Chicago (ORD) Frontier Airlines $277
Earn $2.77
Return Tue, Feb 3 Chicago (ORD) Portland (PDX) Frontier Airlines
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February

Cheapest weekend flights in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 26 Portland (PDX) Chicago (ORD) Spirit Airlines $303
Earn $3.03
Return Mon, Mar 2 Chicago (ORD) Portland (PDX) Spirit Airlines

Lowest roundtrip airfare in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Feb 1 Portland (PDX) Chicago (ORD) Frontier Airlines $277
Earn $2.77
Return Wed, Feb 4 Chicago (ORD) Portland (PDX) Frontier Airlines

Best one-week trip in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Feb 5 Portland (PDX) Chicago (ORD) Spirit Airlines $353
Earn $3.53
Return Thu, Feb 12 Chicago (ORD) Portland (PDX) Spirit Airlines
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March

Cheapest weekend flights in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Mar 6 Portland (PDX) Chicago (ORD) Frontier Airlines $320
Earn $3.20
Return Sun, Mar 8 Chicago (ORD) Portland (PDX) Frontier Airlines

Lowest roundtrip airfare in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 3 Portland (PDX) Chicago (ORD) Spirit Airlines $283
Earn $2.83
Return Tue, Mar 10 Chicago (ORD) Portland (PDX) Spirit Airlines

Best one-week trip in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Mar 3 Portland (PDX) Chicago (ORD) Spirit Airlines $283
Earn $2.83
Return Tue, Mar 10 Chicago (ORD) Portland (PDX) Spirit Airlines
Back to menu Return to top

Plan Your Trip from Portland to Chicago

Portland International Airport

Flights from Portland depart from the Portland International Airport, located at 7000 NE Airport Way. The airport is approximately 22 miles south of downtown Portland and is serviced by 13 airlines, including Delta, Air Canada, Frontier and United. Orbitz.com makes it easy to book domestic and international flights from Portland. You don't have to scour the Internet to find cheap airline tickets. Orbitz.com searches all of the flights available to get you a ticket with a low fare.

Parking and Transportation

The Portland International Airport offers long-term parking for $19 per day. If you plan to leave your car at the airport for more than 90 days, you need to make prior arrangements with the airport's parking office. You can take a taxi from downtown Portland to the airport for approximately $32, so if you plan to leave your vehicle for more than two days, taking a taxi to the airport is a cheaper option. Streetcars also run from the downtown area to the airport, and streetcar tickets cost $2.40. If you need transportation when you arrive at your destination, Orbitz.com can reserve a rental car for you.

Dining at the Airport

If you want to grab a quick meal before your flight, the Portland International Airport has a variety of restaurant choices. You can stop in Starbucks or Coffee People for a quick snack. If you want a meal, you can eat at Wendy's, Sandoval's or Pizza Schmizza. Orbitz.com does more than book flights from Portland. The website has all of the tools you need to make sure your trip goes smoothly, giving you plenty of time to eat before your flight.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Interesting facts about flights from Portland to Chicago

    • 6 direct flights are operating from Portland to Chicago today.
    • Today's average time for a direct flight is 3h 56m.
    • United Airlines flight 646 (12:20 AM GMT, Airbus Industrie A320) is today's earliest available flight from Portland to Chicago.
    • United Airlines flight 1555 (7:56 AM GMT, Boeing 737-900 Passenger) is today's latest available flight from Portland to Chicago.
    • Today's shortest direct flight from Portland to Chicago (American Airlines flight 86, Boeing 737-800 Passenger) takes 3h 55m.
    • Today's longest direct flight from Portland to Chicago (Alaska Airlines flight 688, Boeing 737-700 Passenger) takes 4h 0m.
    • Flights from Portland International Airport (PDX) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Flight schedule for flights from Portland to Chicago on Sun, Dec 28, 2014

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
Alaska Airlines/United Airlines AS2470/UA1742 PDX 7:30 PM ORD 4:35 AM DH4/739 7hr 5min
American Airlines/American Airlines AA7612/AA1431 PDX 9:30 PM ORD 6:20 AM DH4/738 6hr 50min
Alaska Airlines/Alaska Airlines AS2174/AS1226 PDX 9:30 PM ORD 6:20 AM DH4/738 6hr 50min
Alaska Airlines/US Airways AS2174/US1431 PDX 9:30 PM ORD 6:20 AM DH4/738 6hr 50min
Alaska Airlines/American Airlines AS2174/AA1431 PDX 9:30 PM ORD 6:20 AM DH4/738 6hr 50min
Alaska Airlines/American Airlines AS5065/AA3148 PDX 10:55 PM ORD 7:25 AM 757/ER4 6hr 30min
Alaska Airlines/Alaska Airlines AS5065/AS4174 PDX 10:55 PM ORD 7:25 AM 757/ER4 6hr 30min
Alaska Airlines/US Airways AS5065/US8381 PDX 10:55 PM ORD 7:25 AM 757/ER4 6hr 30min
Delta Air Lines/United Airlines DL1670/UA3953 PDX 12:50 AM ORD 8:55 AM 763/ERJ 6hr 5min
Delta Air Lines/Delta Air Lines DL1670/DL5484 PDX 12:50 AM MDW 9:16 AM 763/CR7 6hr 26min
Delta Air Lines/US Airways DL1670/US4271 PDX 12:50 AM ORD 9:20 AM 763/E75 6hr 30min
Delta Air Lines/American Airlines DL1670/AA4271 PDX 12:50 AM ORD 9:20 AM 763/E75 6hr 30min
Delta Air Lines/Delta Air Lines DL1670/DL7304 PDX 12:50 AM ORD 10:26 AM 763/E75 7hr 36min