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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
PWM CHI Sun, Feb 22 - Wed, Feb 25 $228
PWM CHI Sat, May 9 - Sat, May 16 $233
PWM CHI Mon, Jan 5 - Wed, Jan 7 $292
PWM CHI Sat, May 9 - Sat, May 16 $380
PWM CHI Sat, Feb 28 - Mon, Mar 2 $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
    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 PWM to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 US Airways, United Airlines
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Sun Mon Tue Wed Thu Fri Sat
1 2 3
4 5 6 7 8 9 10
11 12 13 14 15
$228
16 17
18 19 20 21 22 23 24
25 26 27 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 15 Portland (PWM) Chicago (ORD) US Airways $228
Earn $2.28
Return Mon, Jan 19 Chicago (ORD) Portland (PWM) US Airways

Lowest roundtrip airfare in January from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Jan 15 Portland (PWM) Chicago (ORD) US Airways $228
Earn $2.28
Return Mon, Jan 19 Chicago (ORD) Portland (PWM) US Airways
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February

Cheapest weekend flights in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Feb 28 Portland (PWM) Chicago (ORD) Delta Air Lines $406
Earn $4.06
Return Mon, Mar 2 Chicago (ORD) Portland (PWM) Delta Air Lines

Lowest roundtrip airfare in February from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Feb 7 Portland (PWM) Chicago (ORD) US Airways $228
Earn $2.28
Return Mon, Feb 16 Chicago (ORD) Portland (PWM) US Airways
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March

Lowest roundtrip airfare in March from Portland to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Mar 26 Portland (PWM) Chicago (ORD) jetBlue $290
Earn $2.90
Return Tue, Mar 31 Chicago (ORD) Portland (PWM) jetBlue
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Portland to Chicago Intro 3

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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 49m.
    • United Airlines flight 3714 (1:06 AM GMT, Canadair Regional Jet 700) is today's earliest available flight from Portland to Chicago.
    • United Airlines flight 3667 (11:27 AM GMT, Canadair Regional Jet 700) is today's latest available flight from Portland to Chicago.
    • Today's shortest direct flight from Portland to Chicago (United Airlines flight 3667, Canadair Regional Jet 700) takes 2h 48m.
    • Today's longest direct flight from Portland to Chicago (United Airlines flight 3714, Canadair Regional Jet 700) takes 2h 51m.
    • 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 Mon, Dec 22, 2014

Carrier Flight # Departing Arriving Aircraft Flight time
Airport Time Airport Time
United Airlines UA3714 PWM 7:06 AM ORD 8:57 AM CR7 2hr 51min
American Airlines/US Airways AA4643/US1409 PWM 5:45 AM ORD 9:40 AM E70/738 4hr 55min
US Airways/US Airways US5700/US1409 PWM 5:45 AM ORD 9:40 AM E70/738 4hr 55min
jetBlue/American Airlines B62807/AA190 PWM 5:35 AM ORD 9:55 AM E90/738 5hr 20min
jetBlue/US Airways B62807/US190 PWM 5:35 AM ORD 9:55 AM E90/738 5hr 20min
jetBlue/jetBlue B62807/B6905 PWM 5:35 AM ORD 10:19 AM E90/320 5hr 44min
Emirates/Emirates EK6756/EK6071 PWM 5:35 AM ORD 10:19 AM E90/320 5hr 44min
Delta Air Lines/Delta Air Lines DL6175/DL4501 PWM 6:45 AM ORD 10:48 AM ERJ/CR9 5hr 3min
American Airlines/United Airlines AA4643/UA3507 PWM 5:45 AM ORD 11:00 AM E70/E70 6hr 15min
US Airways/United Airlines US5700/UA3507 PWM 5:45 AM ORD 11:00 AM E70/E70 6hr 15min
American Airlines/US Airways AA4643/US40 PWM 5:45 AM ORD 11:05 AM E70/738 6hr 20min
US Airways/US Airways US5700/US40 PWM 5:45 AM ORD 11:05 AM E70/738 6hr 20min
American Airlines/American Airlines AA4554/AA1991 PWM 7:04 AM ORD 11:07 AM E75/320 5hr 3min