Flights from Portland to Chicago

Selected fares from Portland to Chicago

Departure Arrival Travel dates Round-trip
PWM CHI Thu, May 7 - Wed, May 13 $250
PWM CHI Sat, May 9 - Tue, May 19 $270
PWM CHI Tue, May 12 - Sat, May 16 $272
PWM CHI Mon, Apr 13 - Tue, May 5 $457
PWM CHI Sat, May 9 - Tue, May 19 $490

Portland and Chicago airports and terminals

Airports in Portland ME, US

map of airports in Portland
  • 1

    Portland Airport (PWM)

    Distance from City Center: 2.9 miles

    Carriers for flights from PWM to CHI

    Carriers
    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 PWM to ORD

    Terminal Carriers
    Terminal 1 United Airlines
    Terminal 2 United Airlines
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$303
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$303
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$303
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $109

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 143 reviews

O'Hare International Airport Map

Rate Includes Breakfast

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Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 51 reviews

6500 South Cicero Avenue Map

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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

Hyatt Place Chicago Midway Airport

4 stars
Not yet reviewed

6550 S. Cicero Avenue Map

...Located just 1 mile south of Chicago International Airport, Hyatt offers a complementary 24 hour shuttle to and from the airport.... Midway Hotel Centers newest property is composed of 6 floors,... More

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Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The House 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

April

Cheapest weekend flights in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Apr 30 Portland (PWM) Chicago (ORD) US Airways $335
Earn $3.35
Return Sun, May 3 Chicago (ORD) Portland (PWM) US Airways

Lowest roundtrip airfare in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Apr 8 Portland (PWM) Chicago (ORD) US Airways $303
Earn $3.03
Return Tue, Apr 14 Chicago (ORD) Portland (PWM) US Airways
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May

Cheapest weekend flights in May from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, May 1 Portland (PWM) Chicago (ORD) US Airways $272
Earn $2.72
Return Mon, May 4 Chicago (ORD) Portland (PWM) US Airways

Lowest roundtrip airfare in May from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, May 7 Portland (PWM) Chicago (ORD) jetBlue $250
Earn $2.50
Return Wed, May 13 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in May from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, May 20 Portland (PWM) Chicago (ORD) jetBlue $268
Earn $2.68
Return Wed, May 27 Chicago (ORD) Portland (PWM) jetBlue
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June

Cheapest weekend flights in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jun 5 Portland (PWM) Chicago (ORD) American Airlines $292
Earn $2.92
Return Sun, Jun 7 Chicago (ORD) Portland (PWM) American Airlines

Lowest roundtrip airfare in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jun 23 Portland (PWM) Chicago (ORD) jetBlue $268
Earn $2.68
Return Wed, Jul 1 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jun 5 Portland (PWM) Chicago (ORD) jetBlue $290
Earn $2.90
Return Fri, Jun 12 Chicago (ORD) Portland (PWM) jetBlue
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Portland to Chicago Intro 12

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Interesting facts about flights from Portland to Chicago

    • 2 direct flights are operating from Portland to Chicago today.
    • Today's average time for a direct flight is 2h 57m.
    • United Airlines flight 5939 (6:05 AM GMT, Embraer RJ135/RJ140/RJ145) is today's earliest available flight from Portland to Chicago.
    • United Airlines flight 3528 (4:16 PM GMT, Embraer 170) is today's latest available flight from Portland to Chicago.
    • Today's shortest direct flight from Portland to Chicago (United Airlines flight 3528, Embraer 170) takes 2h 54m.
    • Today's longest direct flight from Portland to Chicago (United Airlines flight 5939, Embraer RJ135/RJ140/RJ145) takes 3h 0m.
    • Flights from Portland Airport (PWM) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Flight schedule for flights from Portland to Chicago on Wed, Apr 1, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
American Airlines/American Airlines AA4613/AA1579 PWM 5:45 AM ORD 9:36 AM E70/738 4hr 51min
American Airlines/US Airways AA4613/US1579 PWM 5:45 AM ORD 9:36 AM E70/738 4hr 51min
US Airways/American Airlines US4613/AA1579 PWM 5:45 AM ORD 9:36 AM E70/738 4hr 51min
US Airways/US Airways US4613/US1579 PWM 5:45 AM ORD 9:36 AM E70/738 4hr 51min
American Airlines/United Airlines AA4613/UA607 PWM 5:45 AM ORD 10:03 AM E70/319 5hr 18min
US Airways/United Airlines US4613/UA607 PWM 5:45 AM ORD 10:03 AM E70/319 5hr 18min
Delta Air Lines/American Airlines DL3778/AA317 PWM 6:00 AM ORD 10:10 AM CR9/738 5hr 10min
Delta Air Lines/US Airways DL3778/US317 PWM 6:00 AM ORD 10:10 AM CR9/738 5hr 10min
Emirates/Emirates EK6756/EK6749 PWM 6:00 AM ORD 10:50 AM E90/320 5hr 50min
jetBlue/jetBlue B62807/B6905 PWM 6:00 AM ORD 10:56 AM E90/320 5hr 56min
American Airlines/United Airlines AA4613/UA617 PWM 5:45 AM ORD 11:01 AM E70/320 6hr 16min
US Airways/United Airlines US4613/UA617 PWM 5:45 AM ORD 11:01 AM E70/320 6hr 16min
American Airlines/American Airlines AA4662/AA1991 PWM 7:07 AM ORD 11:05 AM E75/320 4hr 58min