Search for flights

Flight type Round-trip One-way
Please type the date in the following format: M/d/yy . For example: January 3, 2013 would be entered as 1/3/13 .
Age categories
Age of children at time of trip

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

Additional search options

Portland to Chicago Flights

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.

Cheap flights from Portland to Chicago

Prices are for round-trip flights per adult (taxes and fees included)

Cheapest fares highlighted below

Sun Mon Tue Wed Thu Fri Sat
27 28 29 30 31 1 $278 2 $258
3 $268 4 $258 5 $258 6 $260 7 $258 8 $270 9 $251
10 $278 11 $258 12 $258 13 $258 14 $267 15 $268 16 $251
17 $316 18 19 $276 20 21 $258 22 $268 23
24 25 $268 26 27 $251 28 1 2

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 48 hours. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

February

Cheapest weekend flights in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Feb 9 Portland (PDX) Chicago (ORD) Alaska Airlines $251
Return Sun, Feb 10 Chicago (ORD) Portland (PDX) Alaska Airlines

Lowest roundtrip airfare in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Feb 27 Portland (PDX) Chicago (ORD) Alaska Airlines $251
Return Thu, Feb 28 Chicago (ORD) Portland (PDX) Alaska Airlines

Best one-week trip in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Mon, Feb 4 Portland (PDX) Chicago (ORD) Alaska Airlines $258
Return Mon, Feb 11 Chicago (ORD) Portland (PDX) Alaska Airlines
Back to menu Return to top

March

Cheapest weekend flights in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 14 Portland (PDX) Chicago (ORD) Alaska Airlines $276
Return Mon, Mar 18 Chicago (ORD) Portland (PDX) Alaska Airlines

Lowest roundtrip airfare in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Mar 2 Portland (PDX) Chicago (MDW) Frontier Airlines $260
Return Tue, Mar 5 Chicago (MDW) Portland (PDX) Frontier Airlines

Best one-week trip in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 7 Portland (PDX) Chicago (ORD) Alaska Airlines $267
Return Thu, Mar 14 Chicago (ORD) Portland (PDX) Alaska Airlines
Back to menu Return to top

April

Cheapest weekend flights in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Apr 11 Portland (PDX) Chicago (MDW) Frontier Airlines $333
Return Sun, Apr 14 Chicago (MDW) Portland (PDX) Frontier Airlines

Lowest roundtrip airfare in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Apr 9 Portland (PDX) Chicago (MDW) Frontier Airlines $286
Return Wed, Apr 10 Chicago (MDW) Portland (PDX) Frontier Airlines

Best one-week trip in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Apr 11 Portland (PDX) Chicago (MDW) Frontier Airlines $286
Return Thu, Apr 18 Chicago (MDW) Portland (PDX) Frontier Airlines
Back to menu Return to top

Flight facts

    • 4 direct flights are operating from Portland to Chicago today.
    • Today's average time for a direct flight is 3h 55m.
    • United Airlines flight 1525 (12:10 AM GMT, Boeing 737-900 Passenger) is today's earliest available flight from Portland to Chicago.
    • United Airlines flight 125 (8:04 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 (United Airlines flight 66, Boeing 737-800 Passenger) takes 3h 50m.
    • Today's longest direct flight from Portland to Chicago (United Airlines flight 1525, Boeing 737-900 Passenger) takes 4h 0m.

Lowest round trip fares by airline from Portland to Chicago

Airline Departure Arrival Travel dates Round-trip
airline logo Alaska Airlines PDX CHI Wed, Feb 27 - Thu, Feb 28 $250
airline logo United Airlines PDX CHI Thu, Feb 21 - Mon, Feb 25 $257
airline logo US Airways PDX CHI Tue, Jan 15 - Tue, Jan 22 $259
airline logo Frontier Airlines PDX CHI Sat, Mar 2 - Tue, Mar 5 $259
Delta Airlines Delta Air Lines PDX CHI Tue, Feb 5 - Wed, Feb 13 $279
airline logo American Airlines PDX CHI Tue, Feb 5 - Wed, Feb 13 $279
airline logo Virgin America PDX CHI Thu, Feb 14 - Sat, Mar 16 $337
Daily

Daily flight schedule for Fri, Jan 4, 2013

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
United Airlines UA360 PDX 6:10 AM ORD 12:08 PM 320 3hr 58min
US Airways US6862 PDX 6:10 AM ORD 12:08 PM 320 3hr 58min
United Airlines UA990 PDX 10:29 AM ORD 4:15 PM 752 3hr 46min
US Airways US6866 PDX 10:29 AM ORD 4:15 PM 752 3hr 46min
Alaska Airlines AS686 PDX 10:20 AM ORD 4:18 PM 73G 3hr 58min
United Airlines UA125 PDX 2:04 PM ORD 7:56 PM 738 3hr 52min
Back to menu Return to top

Weekly

Number of direct flights this week

Carrier Thu 3 Fri 4 Sat 5 Sun 6 Mon 7 Tue 8 Wed 9
airline logo Alaska Airlines 1 1 1 1 1 1 1
airline logo United Airlines 3 3 2 3 3 3 3
airline logo US Airways 0 2 1 2 2 0 1
Back to menu Return to top
Airports in Portland, OR, US
map of airports in Portland
  • 1

    Portland International Airport (PDX)

    Distance from City Center: 6.5 miles

Back to menu Return to top

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

Back to menu Return to top
0