Flights from Portland to Chicago

Selected fares from Portland to Chicago

Departure Arrival Travel dates Round-trip
PWM CHI Sat, Apr 11 - Mon, Apr 13 $228
PWM CHI Mon, Apr 27 - Mon, May 4 $272
PWM CHI Mon, Apr 27 - Mon, May 4 $272
PWM CHI Tue, Apr 14 - Thu, Apr 16 $300
PWM CHI Wed, Apr 8 - Mon, Apr 13 $406

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
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$228
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$228
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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

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Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
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6500 South Cicero Avenue Map

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Hilton Garden Inn Chicago/Midway Airport

3 stars
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6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

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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

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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

April

Cheapest weekend flights in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Apr 11 Portland (PWM) Chicago (ORD) jetBlue $228
Earn $2.28
Return Mon, Apr 13 Chicago (ORD) Portland (PWM) jetBlue

Lowest roundtrip airfare in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Apr 8 Portland (PWM) Chicago (ORD) jetBlue $228
Earn $2.28
Return Sat, Apr 11 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in April from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Apr 30 Portland (PWM) Chicago (ORD) jetBlue $272
Earn $2.72
Return Thu, May 7 Chicago (ORD) Portland (PWM) jetBlue
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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 $298
Earn $2.98
Return Sat, May 2 Chicago (ORD) Portland (PWM) US Airways

Lowest roundtrip airfare in May from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, May 13 Portland (PWM) Chicago (ORD) American Airlines $272
Earn $2.72
Return Sat, May 16 Chicago (ORD) Portland (PWM) American Airlines

Best one-week trip in May from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, May 19 Portland (PWM) Chicago (ORD) US Airways $308
Earn $3.08
Return Tue, May 26 Chicago (ORD) Portland (PWM) US Airways
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June

Cheapest weekend flights in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Jun 26 Portland (PWM) Chicago (ORD) jetBlue $308
Earn $3.08
Return Mon, Jun 29 Chicago (ORD) Portland (PWM) jetBlue

Lowest roundtrip airfare in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sun, Jun 14 Portland (PWM) Chicago (ORD) jetBlue $272
Earn $2.72
Return Wed, Jun 17 Chicago (ORD) Portland (PWM) jetBlue

Best one-week trip in June from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jun 11 Portland (PWM) Chicago (ORD) jetBlue $346
Earn $3.46
Return Thu, Jun 18 Chicago (ORD) Portland (PWM) jetBlue
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Portland to Chicago Intro 7

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Flight Alerts Keep You Informed

Stay on top of the latest updates for flights from Portland to Chicago. We send you free email and mobile alerts to keep you informed about delays to Portland to Chicago flights.

Flight schedule for flights from Portland to Chicago on Fri, Mar 6, 2015

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
United Airlines UA5939 PWM 6:10 AM ORD 7:59 AM ERJ 2hr 49min
United Airlines/United Airlines UA3432/UA799 PWM 6:00 AM ORD 9:36 AM ER4/752 4hr 36min
United Airlines/United Airlines UA4905/UA312 PWM 6:03 AM ORD 9:36 AM DH4/320 4hr 33min
Delta Air Lines/American Airlines DL3778/AA317 PWM 6:00 AM ORD 10:05 AM CR9/738 5hr 5min
Delta Air Lines/US Airways DL3778/US317 PWM 6:00 AM ORD 10:05 AM CR9/738 5hr 5min
Emirates/Emirates EK6756/EK6071 PWM 6:00 AM ORD 10:17 AM E90/320 5hr 17min
jetBlue/jetBlue B62807/B6905 PWM 6:00 AM ORD 10:22 AM E90/320 5hr 22min
Delta Air Lines/United Airlines DL3778/UA711 PWM 6:00 AM ORD 10:29 AM CR9/319 5hr 29min
Delta Air Lines/Delta Air Lines DL6296/DL1284 PWM 7:00 AM ORD 10:36 AM CR7/73H 4hr 36min
American Airlines/United Airlines AA4541/UA609 PWM 5:55 AM ORD 10:55 AM E75/320 6hr 0min
American Airlines/US Airways AA4647/US4322 PWM 7:04 AM ORD 10:55 AM E75/E75 4hr 51min
American Airlines/American Airlines AA4647/AA4322 PWM 7:04 AM ORD 10:55 AM E75/E75 4hr 51min
US Airways/United Airlines US4541/UA609 PWM 5:55 AM ORD 10:55 AM E75/320 6hr 0min