Cheap Flights from Chicago, IL to Portland, ME from $59

One way Round trip

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On Cheapflightsplus.com you will find 5 direct and 120 connecting flights from Chicago to Portland. You can compare airfare deals from 5 airlines and multiple travel sites from $59, 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: $59 (one-way), $101 (round-trip).

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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 $59. The fastest direct flight takes 2h 22m and the fastest connecting – 4h 23m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $190 Find flight	11:05 Chicago O'Hare International	14:35 Portland Portland Intl Jetport	2h 30m	United Airlines	UA3494
from $214 Find flight	18:00 Chicago O'Hare International	21:30 Portland Portland Intl Jetport	2h 30m	United Airlines	UA3525
from $216 Find flight	11:10 Chicago O'Hare International	14:42 Portland Portland Intl Jetport	2h 32m	United Airlines	UA5708
from $216 Find flight	18:10 Chicago O'Hare International	21:42 Portland Portland Intl Jetport	2h 32m	United Airlines	UA3583
from $412 Find flight	11:59 Chicago O'Hare International	15:21 Portland Portland Intl Jetport	2h 22m	United Airlines	UA3704
from $59 Find flight	11:33 Chicago Midway	20:14 Portland Portland Intl Jetport	7h 41m layover 1h 44m - Orlando	Frontier Airlines	F91458 F92622
from $59 Find flight	10:59 Chicago O'Hare International	20:14 Portland Portland Intl Jetport	8h 15m layover 2h 15m - Orlando	Frontier Airlines	F93044 F92622
from $158 Find flight	06:05 Chicago O'Hare International	17:16 Portland Portland Intl Jetport	10h 11m layover 2h 31m - Fort Myers	Spirit Airlines	NK1839 MX744
from $192 Find flight	07:00 Chicago O'Hare International	17:34 Portland Portland Intl Jetport	9h 34m layover 2h 17m - Tampa	Spirit Airlines	NK138 MX100
from $225 Find flight	12:47 Chicago O'Hare International	18:24 Portland Portland Intl Jetport	4h 37m layover 0h 58m - Newark	United Airlines	UA2238 UA3619
from $225 Find flight	17:10 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	4h 40m layover 0h 56m - Newark	United Airlines	UA2419 UA2478
from $225 Find flight	08:48 Chicago O'Hare International	14:59 Portland Portland Intl Jetport	5h 11m layover 1h 31m - Washington D.C.	United Airlines	UA2415 UA3517
from $225 Find flight	15:50 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	6h 0m layover 2h 16m - Newark	United Airlines	UA2359 UA2478
from $225 Find flight	14:50 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	7h 0m layover 3h 16m - Newark	United Airlines	UA2436 UA2478
from $226 Find flight	08:50 Chicago O'Hare International	14:38 Portland Portland Intl Jetport	4h 48m layover 1h 7m - Washington D.C.	United Airlines	UA545 UA3627
from $226 Find flight	18:08 Chicago O'Hare International	23:59 Portland Portland Intl Jetport	4h 51m layover 1h 23m - Washington D.C.	United Airlines	UA444 UA408

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 21, 2024

Flight Schedule Chicago (Illinois) to Portland (Maine)

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	Flight Details	Flight Duration	Price
11:05 — 14:35	11:05 — 14:35 UA3494 United Airlines Chicago — Portland	2h 30m	Find flight from$190
11:10 — 14:42	11:10 — 14:42 UA5708 United Airlines Chicago — Portland	2h 32m	Find flight from$216
11:59 — 15:21	11:59 — 15:21 UA3704 United Airlines Chicago — Portland	2h 22m	Find flight from$412
18:00 — 21:30	18:00 — 21:30 UA3525 United Airlines Chicago — Portland	2h 30m	Find flight from$214
18:10 — 21:42	18:10 — 21:42 UA3583 United Airlines Chicago — Portland	2h 32m	Find flight from$216
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$244
06:05 — 17:16	06:05 — 10:04 NK1839 Spirit Airlines Chicago — Fort Myers 2h 31m stop 12:35 — 17:16 MX744 Mexicana Fort Myers — Portland	10h 11m including layover	Find flight from$158
07:00 — 17:34	07:00 — 10:48 NK138 Spirit Airlines Chicago — Tampa 2h 17m stop 13:05 — 17:34 MX100 Mexicana Tampa — Portland	9h 34m including layover	Find flight from$192
07:10 — 22:30	07:10 — 10:25 UA563 United Airlines Chicago — Newark 10h 43m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	14h 20m including layover	Find flight from$247
08:48 — 14:59	08:48 — 11:44 UA2415 United Airlines Chicago — Washington D.C. 1h 31m stop 13:15 — 14:59 UA3517 United Airlines Washington D.C. — Portland	5h 11m including layover	Find flight from$225
08:50 — 14:38	08:50 — 11:48 UA545 United Airlines Chicago — Washington D.C. 1h 7m stop 12:55 — 14:38 UA3627 United Airlines Washington D.C. — Portland	4h 48m including layover	Find flight from$226
09:10 — 16:52	09:10 — 12:28 UA2462 United Airlines Chicago — Newark 3h 1m stop 15:29 — 16:52 UA4401 United Airlines Newark — Portland	6h 42m including layover	Find flight from$227
09:10 — 22:30	09:10 — 12:28 UA2462 United Airlines Chicago — Newark 8h 40m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	12h 20m including layover	Find flight from$247
10:50 — 16:52	10:50 — 14:06 UA2091 United Airlines Chicago — Newark 1h 23m stop 15:29 — 16:52 UA4401 United Airlines Newark — Portland	5h 2m including layover	Find flight from$227
10:59 — 20:14	10:59 — 14:54 F93044 Frontier Airlines Chicago — Orlando 2h 15m stop 17:09 — 20:14 F92622 Frontier Airlines Orlando — Portland	8h 15m including layover	Find flight from$59
11:33 — 20:14	07:00 — 10:52 F91458 Frontier Airlines Chicago — Orlando 1h 44m stop 17:09 — 20:14 F92622 Frontier Airlines Orlando — Portland	7h 41m including layover	Find flight from$59
12:00 — 22:50	11:51 — 15:06 UA2133 United Airlines Chicago — Newark 6h 14m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	9h 50m including layover	Find flight from$248
12:47 — 18:24	12:45 — 16:00 UA2238 United Airlines Chicago — Newark 58m stop 17:17 — 18:46 UA3619 United Airlines Newark — Portland	4h 37m including layover	Find flight from$225
13:55 — 22:50	13:55 — 17:18 UA2654 United Airlines Chicago — Newark 4h 11m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	7h 55m including layover	Find flight from$248
13:55 — 10:17 +1 day	13:55 — 17:18 UA2654 United Airlines Chicago — Newark 15h 28m stop 08:46 — 10:17 UA3716 United Airlines Newark — Portland	19h 22m including layover	Find flight from$248
14:20 — 22:30	14:16 — 17:31 UA2115 United Airlines Chicago — Newark 3h 33m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	7h 10m including layover	Find flight from$230
14:50 — 22:50	14:50 — 18:13 UA2436 United Airlines Chicago — Newark 3h 16m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	7h including layover	Find flight from$225
15:42 — 23:20	15:42 — 19:00 UA1983 United Airlines Chicago — Newark 2h 59m stop 21:59 — 23:20 UA673 United Airlines Newark — Portland	6h 38m including layover	Find flight from$226
15:50 — 22:50	15:50 — 19:13 UA2359 United Airlines Chicago — Newark 2h 16m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	6h including layover	Find flight from$225
16:08 — 22:30	16:08 — 19:23 UA795 United Airlines Chicago — Newark 1h 45m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	5h 22m including layover	Find flight from$227
17:10 — 22:50	17:05 — 20:28 UA2419 United Airlines Chicago — Newark 56m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	4h 40m including layover	Find flight from$225
17:10 — 10:17 +1 day	17:05 — 20:28 UA2419 United Airlines Chicago — Newark 12h 13m stop 09:00 — 10:31 UA3716 United Airlines Newark — Portland	16h 7m including layover	Find flight from$248
19:47 — 22:30 +1 day	19:47 — 22:59 UA2362 United Airlines Chicago — Newark 22h 9m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	25h 43m including layover	Find flight from$247
19:50 — 10:17 +1 day	19:50 — 23:09 UA2362 United Airlines Chicago — Newark 9h 37m stop 08:46 — 10:17 UA3716 United Airlines Newark — Portland	13h 27m including layover	Find flight from$248
21:45 — 10:31 +1 day	21:45 — 00:58 UA2415 United Airlines Chicago — Newark 8h 1m stop 08:59 — 10:31 UA3716 United Airlines Newark — Portland	11h 46m including layover	Find flight from$244
21:45 — 22:30 +1 day	21:45 — 00:58 UA2415 United Airlines Chicago — Newark 20h 10m stop 21:08 — 22:30 UA539 United Airlines Newark — Portland	23h 45m including layover	Find flight from$244

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on November 21, 2024

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 21:45 from 7 Chicago airports and arrive 06:00 to 21:45 to 1 Portland airport. Average flight time is 2h 30m.

The fastest flight 2h 22m
Average flight time 2h 30m
The earliest flight 06:00
The latest flight 21:45
Distance 886 ml

The cheapest months to travel to Portland are december (from 59 $), january (from 158 $), february (from 219 $).

The most expensive months are november (from 247 $), february (from 219 $), january (from 158 $).

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $59. This airfare is for economy class on one-way F91458 flight by Frontier Airlines for December 9, 2024 which leaves Midway in Chicago at 11:33 am and arrives at Portland Portland Intl Jetport at 20:14.

Economy class

$59

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Business class

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First class

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Popular Airlines on the Route

The flight Chicago — Portland is served by 5 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 2 departures per week at the price of from $ 59 . And the most expensive tickets are offered by United Airlines airline - from $ 714.

Direct flights

There are 5 nonstop flights on the route. The fastest direct flight is UA3704 by United Airlines takes 2h 22m and the cheapest is F91458 by Frontier Airlines for $190.

UA - United Airlines

from $190

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Connecting Flights

There are 120 flights with layovers on the route. The fastest connecting flight is UA2343 by United Airlines takes 4h 23m and the cheapest is F91458 by Frontier Airlines for $59.

F9 - Frontier Airlines

from $59

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UA - United Airlines

from $225

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PD - Porter Airlines

from $369

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NK - Spirit Airlines

from $158

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TS - Air Transat

from $400

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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 $59
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Midway-MDW

from $59
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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

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Airplanes

There are flights to Portland from Chicago by 5 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.

Chicago — Las Vegas

from $508

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from $70

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from $59

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Chicago — Atlanta

from $76

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Chicago — Denver

from $61

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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.

Chicago — London

from $60

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Chicago — Manchester

from $58

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Chicago — Zurich

from $61

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Chicago — Cancun

from $72

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Chicago — Dublin

from $59

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Chicago — Madrid

from $72

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Chicago — Rome

from $79

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Chicago — Paris

from $61

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Chicago — Tel Aviv

from $628

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Chicago — Mumbai

from $74

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How to book a plane 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.
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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.
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