Cheap Flights from Chicago, IL to Portland, ME from $270

Return flight: Portland – Chicago
Page navigation
Price Calendar Cheap Flights Flights Schedule

On Cheapflightsplus.com you will find 1 direct and 7 connecting flights from Chicago to Portland. You can compare airfare deals from 1 airlines and multiple travel sites from $270, 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.

Find One-Way and Round-Trip Chicago to Portland Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $270 (one-way), $463 (round-trip).
Direct flights
  • Check to choose departure date Check to choose departure date
Check prices for return flight
Find flights

Best Flights from Chicago to Portland Today

Take a look at the list of non stop flights and flights with layovers from Chicago to Portland with the lowest price of $270. The fastest direct flight takes 2h 22m and the fastest connecting – 4h 23m.
Price Departure Arrival Flight Duration Airline Flight
from $456
Find flight
11:59
Chicago
O'Hare International
 15:21
Portland
Portland Intl Jetport
 2h 22m United Airlines
UA3704
from $270
Find flight
06:00
Chicago
O'Hare International
 11:23
Portland
Portland Intl Jetport
 4h 23m
layover
0h 45m - Newark
 United Airlines
UA2343
UA3716
from $508
Find flight
14:14
Chicago
O'Hare International
 23:15
Portland
Portland Intl Jetport
 8h 1m
layover
4h 32m - Newark
 United Airlines
UA1502
UA1082
from $643
Find flight
08:45
Chicago
O'Hare International
 14:42
Portland
Portland Intl Jetport
 4h 57m
layover
1h 19m - Washington D.C.
 United Airlines
UA545
UA3444
from $684
Find flight
11:53
Chicago
O'Hare International
 18:31
Portland
Portland Intl Jetport
 5h 38m
layover
1h 52m - Newark
 United Airlines
UA2488
UA3468
from $749
Find flight
09:03
Chicago
O'Hare International
 18:31
Portland
Portland Intl Jetport
 8h 28m
layover
4h 42m - Newark
 United Airlines
UA1213
UA3468
from $790
Find flight
12:55
Chicago
O'Hare International
 18:31
Portland
Portland Intl Jetport
 4h 36m
layover
0h 50m - Newark
 United Airlines
UA2238
UA3468
from $790
Find flight
10:53
Chicago
O'Hare International
 18:31
Portland
Portland Intl Jetport
 6h 38m
layover
2h 55m - Newark
 United Airlines
UA2091
UA3468
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 03, 2025
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 Arrival Flight Details Flight Duration Price
11:59 — 15:21
11:59 — 15:21 UA3704 United Airlines
Chicago — Portland
2h 22m
Find flight
from$456
06:00 — 11:23
06:00 — 09:11 UA2343 United Airlines
Chicago — Newark
45m stop
08:59 — 10:31 UA3716 United Airlines
Newark — Portland
4h 23m
including layover
Find flight
from$270
08:45 — 14:42
08:45 — 11:41 UA545 United Airlines
Chicago — Washington D.C.
1h 19m stop
13:00 — 14:42 UA3444 United Airlines
Washington D.C. — Portland
4h 57m
including layover
Find flight
from$643
09:03 — 18:31
09:03 — 12:18 UA1213 United Airlines
Chicago — Newark
4h 42m stop
17:00 — 18:31 UA3468 United Airlines
Newark — Portland
8h 28m
including layover
Find flight
from$749
10:53 — 18:31
10:53 — 14:05 UA2091 United Airlines
Chicago — Newark
2h 55m stop
17:00 — 18:31 UA3468 United Airlines
Newark — Portland
6h 38m
including layover
Find flight
from$790
11:53 — 18:31
11:53 — 15:08 UA2488 United Airlines
Chicago — Newark
1h 52m stop
17:00 — 18:31 UA3468 United Airlines
Newark — Portland
5h 38m
including layover
Find flight
from$684
12:55 — 18:31
12:55 — 16:10 UA2238 United Airlines
Chicago — Newark
50m stop
17:00 — 18:31 UA3468 United Airlines
Newark — Portland
4h 36m
including layover
Find flight
from$790
14:14 — 23:15
14:14 — 17:27 UA1502 United Airlines
Chicago — Newark
4h 32m stop
21:59 — 23:15 UA1082 United Airlines
Newark — Portland
8h 1m
including layover
Find flight
from$508
*Departure and arrival times - local. Updated on March 3, 2025

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 06:00 to 14:14 from 7 Chicago airports and arrive 06:00 to 14:14 to 1 Portland airport. Average flight time is 2h 22m.

  • The fastest flight 2h 22m
  • Average flight time 2h 22m
  • The earliest flight 06:00
  • The latest flight 14:14
  • Distance 886 ml

The cheapest months to travel to Portland are january (from 270 $), february (from 273 $).

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $270. This airfare is for economy class on one-way UA2343 flight by United Airlines for February 21, 2025 which leaves O'Hare International in Chicago at 06:00 am and arrives at Portland Portland Intl Jetport at 11:23.

Economy class
$270
Find
Business class
?
Find
First class
?
Find

Popular Airlines on the Route

The flight Chicago — Portland is served by 1 regular airline . Most of the flights on this route are operated by United Airlines - 8 departures per week at the price of from $ 270 . And the most expensive tickets are offered by United Airlines airline - from $ 790.

Direct flights

There are 1 nonstop flights on the route. The fastest direct flight is UA3704 by United Airlines takes 2h 22m and the cheapest is UA2343 by United Airlines for $456.

See more direct flights

Connecting Flights

There are 7 flights with layovers on the route. The fastest connecting flight is UA2343 by United Airlines takes 4h 23m and the cheapest is UA2343 by United Airlines for $270.

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 $270
    Find
  • Midway-MDW
    Find
  • Dupage County-DPA
    Find
  • Chicago FSS-CHI
    Find
  • Merrill C Meigs (closed)-CGX
    Find
  • Pal-Waukee-PWK
    Find
  • Chicago NAS-NOH
    Find

Portland airports

  • Portland Intl Jetport-PWM
    Find

Airplanes

There are flights to Portland from Chicago by 1 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Chicago

You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.

Top International Destinations from Chicago

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

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.

Back