Cheap Flights from Chicago, IL to Portland, ME from $142

Return flight: Portland – Chicago

On Cheapflightsplus.com you will find 6 direct and 487 connecting flights from Chicago to Portland. You can compare airfare deals from 9 airlines and multiple travel sites from $142, book and save on cheap plane tickets and last minute offers. Also check out CHI-PWM flight schedule to find best flight time, convenient departure and arrival airports.

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Portland depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Portland is 1425 miles. Time difference between the cities is 1h. Airplanes depart 05:00 to 21:36 from 7 Chicago airports and arrive 05:00 to 21:36 to 1 Portland airport. Average flight time is 2h 29m.

  • The fastest flight 2h 10m
  • Average flight time 2h 29m
  • The earliest flight 05:00
  • The latest flight 21:36
  • Distance 886 ml

The cheapest months to travel to Portland are november (from 142 $), july (from 142 $), august (from 145 $).

The most expensive months are september (from 148 $), october (from 148 $), august (from 145 $).

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $142. This airfare is for economy class on one-way UA1974 flight by United Airlines for November 1, 2025 which leaves O'Hare International in Chicago at 18:10 am and arrives at Portland Portland Intl Jetport at 21:44.

Economy class
$142
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Business class
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First class
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Flight Schedule Chicago (Illinois) to Portland (Maine)

06:00 — 13:53
6h 53m flight time
Find flight
from$150
06:00 — 09:15 Chicago — Newark
UA1658 United Airlines
3h 15m stop
11:58 — 13:22 Newark — Portland
UA3685 United Airlines
06:00 — 16:44
9h 44m flight time
Find flight
from$230
06:00 — 09:15 Chicago — Newark
UA1658 United Airlines
6h 1m stop
15:25 — 16:52 Newark — Portland
UA3651 United Airlines
07:10 — 13:53
5h 43m flight time
Find flight
from$148
07:15 — 10:33 Chicago — Newark
UA563 United Airlines
2h 3m stop
11:58 — 13:22 Newark — Portland
UA3685 United Airlines
07:10 — 16:44
8h 34m flight time
Find flight
from$230
07:10 — 10:27 Chicago — Newark
UA563 United Airlines
4h 49m stop
15:25 — 16:52 Newark — Portland
UA3651 United Airlines
07:58 — 11:28
2h 30m flight time
Find flight
from$849
Chicago — Portland
AA4741 American Airlines
08:50 — 14:33
4h 43m flight time
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from$150
08:52 — 11:55 Chicago — Washington D.C.
UA2029 United Airlines
47m stop
13:05 — 14:53 Washington D.C. — Portland
UA3529 United Airlines
10:40 — 16:44
5h 4m flight time
Find flight
from$148
10:55 — 14:13 Chicago — Newark
UA1126 United Airlines
1h 18m stop
15:25 — 16:52 Newark — Portland
UA3651 United Airlines
10:45 — 19:41
7h 56m flight time
Find flight
from$148
10:43 — 13:49 Chicago — Washington D.C.
UA1030 United Airlines
3h 54m stop
17:34 — 19:29 Washington D.C. — Portland
UA3517 United Airlines
11:05 — 14:33
2h 28m flight time
Find flight
from$144
Chicago — Portland
UA763 United Airlines
11:30 — 14:56
2h 26m flight time
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from$849
Chicago — Portland
AA4967 American Airlines
12:55 — 19:41
5h 46m flight time
Find flight
from$155
13:05 — 16:10 Chicago — Washington D.C.
UA2337 United Airlines
1h 48m stop
17:30 — 19:27 Washington D.C. — Portland
UA3517 United Airlines
13:40 — 16:50
2h 10m flight time
Find flight
from$705
Chicago — Portland
WN447 Southwest Airlines
17:55 — 23:59
5h 4m flight time
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from$148
17:55 — 20:55 Chicago — Washington D.C.
UA2677 United Airlines
1h 14m stop
22:05 — 23:54 Washington D.C. — Portland
UA3611 United Airlines
18:10 — 21:44
2h 34m flight time
Find flight
from$142
Chicago — Portland
UA1974 United Airlines
19:10 — 22:45
2h 35m flight time
Find flight
from$675
Chicago — Portland
AA4403 American Airlines
Full flight schedule will help you in detecting at what time planes fly from Chicago to Portland. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
*Departure and arrival times - local. Updated on October 29, 2025.

Popular Airlines on the Route

The flight Chicago — Portland is served by 9 regular airlines and 6 low-cost airlines. Most of the flights on this route are operated by American Airlines - 157 departures per week at the price of from $ 365 . And the most expensive tickets are offered by American Airlines airline - from $ 2526.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is WN447 by Southwest Airlines takes 2h 10m and the cheapest is UA1974 by United Airlines for $142.

  • AA - American Airlines
    from $675
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  • WN - Southwest Airlines
    from $705
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  • UA - United Airlines
    from $142
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See more direct flights

Connecting Flights

There are 487 flights with layovers on the route. The fastest connecting flight is DL2039 by Delta Air Lines Inc. takes 3h 50m and the cheapest is UA1974 by United Airlines for $148.

  • AA - American Airlines
    from $365
    Find
  • F9 - Frontier Airlines
    from $282
    Find
  • B6 - JetBlue
    from $294
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  • PD - Porter Airlines
    from $1272
    Find
  • SY - Sun Country Airlines
    from $761
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  • WN - Southwest Airlines
    from $552
    Find
  • DL - Delta Air Lines Inc.
    from $353
    Find
  • UA - United Airlines
    from $148
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  • NK - Spirit Airlines
    from $301
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See more connecting flights

Airports

You can fly from Chicago to Portland from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $142
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  • Midway-MDW
    from $552
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Portland airports

  • Portland Intl Jetport-PWM
    Find

How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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