Flights from Portland to Chicago

Selected fares from Portland to Chicago

Departure Arrival Travel dates Round-trip
PWM CHI Mon, Jun 29 - Wed, Jul 8 $308
PWM CHI Tue, Jun 9 - Tue, Jun 16 $330
PWM CHI Tue, Jun 16 - Tue, Jun 23 $332
PWM CHI Wed, May 27 - Sat, May 30 $359
PWM CHI Wed, May 27 - Sat, May 30 $374
PWM CHI Wed, May 27 - Sat, May 30 $441

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 International 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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$308
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Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $99

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 160 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 $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.2 / 5 55 reviews

6500 South Cicero Avenue Map

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

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Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 17 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

Hotel only $135

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

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 $359
Earn $3.59
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 Mon, Jun 29 Portland (PWM) Chicago (ORD) jetBlue $308
Earn $3.08
Return Wed, Jul 8 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Jun 9 Portland (PWM) Chicago (ORD) American Airlines $330
Earn $3.30
Return Tue, Jun 16 Chicago (ORD) Portland (PWM) American Airlines
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July

Cheapest weekend flights in July from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jul 16 Portland (PWM) Chicago (ORD) US Airways $402
Earn $4.02
Return Sun, Jul 19 Chicago (ORD) Portland (PWM) US Airways

Lowest roundtrip airfare in July from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jul 8 Portland (PWM) Chicago (ORD) jetBlue $308
Earn $3.08
Return Thu, Jul 9 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in July from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Jul 8 Portland (PWM) Chicago (ORD) US Airways $367
Earn $3.67
Return Wed, Jul 15 Chicago (ORD) Portland (PWM) US Airways
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Portland to Chicago Intro 25

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Interesting facts about flights from Portland to Chicago

    • 3 direct flights are operating from Portland to Chicago today.
    • Today's average time for a direct flight is 2h 42m.
    • United Airlines flight 3619 (6:40 AM GMT, Canadair Regional Jet 700) is today's earliest available flight from Portland to Chicago.
    • United Airlines flight 6129 (4:35 PM GMT, Embraer RJ135/RJ140/RJ145) is today's latest available flight from Portland to Chicago.
    • Today's shortest direct flight from Portland to Chicago (United Airlines flight 3619, Canadair Regional Jet 700) takes 2h 40m.
    • Today's longest direct flight from Portland to Chicago (United Airlines flight 3620, Canadair Regional Jet 700) takes 2h 44m.
    • Flights from Portland Airport (PWM) to Midway Airport (MDW), O'Hare International Airport (ORD) are available for this route.