Cheap Flights from Chicago, IL to Portland, ME from $51

One way Round trip

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On Cheapflightsplus.com you will find 17 direct and 596 connecting flights from Chicago to Portland. You can compare airfare deals from 8 airlines and multiple travel sites from $51, 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: $51 (one-way), $87 (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 $51. The fastest direct flight takes 2h 16m and the fastest connecting – 3h 42m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $51 Find flight	09:10 Chicago O'Hare International	12:30 Portland Portland Intl Jetport	2h 20m	United Airlines	UA4005
from $51 Find flight	11:30 Chicago O'Hare International	14:57 Portland Portland Intl Jetport	2h 27m	United Airlines	UA3447
from $51 Find flight	14:00 Chicago O'Hare International	17:33 Portland Portland Intl Jetport	2h 33m	United Airlines	UA4177
from $51 Find flight	18:00 Chicago O'Hare International	21:27 Portland Portland Intl Jetport	2h 27m	United Airlines	UA3991
from $51 Find flight	18:00 Chicago O'Hare International	21:32 Portland Portland Intl Jetport	2h 32m	United Airlines	UA5711
from $52 Find flight	11:15 Chicago O'Hare International	14:42 Portland Portland Intl Jetport	2h 27m	United Airlines	UA5501
from $52 Find flight	18:30 Chicago O'Hare International	21:56 Portland Portland Intl Jetport	2h 26m	United Airlines	UA3590
from $54 Find flight	08:45 Chicago O'Hare International	12:15 Portland Portland Intl Jetport	2h 30m	American Airlines	AA4148
from $54 Find flight	09:10 Chicago O'Hare International	12:30 Portland Portland Intl Jetport	2h 20m	United Airlines	UA2302
from $54 Find flight	18:00 Chicago O'Hare International	21:27 Portland Portland Intl Jetport	2h 27m	United Airlines	UA378
from $52 Find flight	07:19 Chicago O'Hare International	13:51 Portland Portland Intl Jetport	5h 32m layover 1h 14m - Charlotte	American Airlines	AA2052 AA591
from $52 Find flight	15:38 Chicago O'Hare International	22:40 Portland Portland Intl Jetport	6h 2m layover 1h 43m - Charlotte	American Airlines	AA612 AA2226

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 24, 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
08:45 — 12:15	08:45 — 12:15 AA4148 American Airlines Chicago — Portland	2h 30m	Find flight from$54
08:45 — 12:15	08:45 — 12:15 AA4133 American Airlines Chicago — Portland	2h 30m	Find flight from$65
09:10 — 12:30	09:10 — 12:30 UA4005 United Airlines Chicago — Portland	2h 20m	Find flight from$51
09:10 — 12:30	09:10 — 12:30 UA2302 United Airlines Chicago — Portland	2h 20m	Find flight from$54
09:50 — 13:06	09:50 — 13:06 AA1540 American Airlines Chicago — Portland	2h 16m	Find flight from$193
10:40 — 14:04	10:40 — 14:04 UA1762 United Airlines Chicago — Portland	2h 24m	Find flight from$381
11:15 — 14:42	11:15 — 14:42 UA5501 United Airlines Chicago — Portland	2h 27m	Find flight from$52
11:30 — 14:57	11:30 — 14:57 UA3447 United Airlines Chicago — Portland	2h 27m	Find flight from$51
14:00 — 17:33	14:00 — 17:33 UA4177 United Airlines Chicago — Portland	2h 33m	Find flight from$51
14:00 — 17:24	14:00 — 17:24 UA3539 United Airlines Chicago — Portland	2h 24m	Find flight from$381
18:00 — 21:27	18:00 — 21:27 UA3991 United Airlines Chicago — Portland	2h 27m	Find flight from$51
18:00 — 21:32	18:00 — 21:32 UA5711 United Airlines Chicago — Portland	2h 32m	Find flight from$51
18:00 — 21:27	18:00 — 21:27 UA378 United Airlines Chicago — Portland	2h 27m	Find flight from$54
18:25 — 21:51	18:25 — 21:51 AA3438 American Airlines Chicago — Portland	2h 26m	Find flight from$54
18:30 — 21:56	18:30 — 21:56 UA3590 United Airlines Chicago — Portland	2h 26m	Find flight from$52
18:30 — 21:55	18:30 — 21:55 UA793 United Airlines Chicago — Portland	2h 25m	Find flight from$184
20:32 — 23:50	20:32 — 23:50 AA4953 American Airlines Chicago — Portland	2h 18m	Find flight from$193
05:20 — 13:51	05:20 — 08:21 AA1784 American Airlines Chicago — Charlotte 3h 14m stop 11:35 — 13:51 AA591 American Airlines Charlotte — Portland	7h 31m including layover	Find flight from$52
05:45 — 12:05	05:45 — 08:41 AA2527 American Airlines Chicago — Charlotte 1h 4m stop 09:45 — 12:05 AA1780 American Airlines Charlotte — Portland	5h 20m including layover	Find flight from$53
06:30 — 12:16	06:30 — 09:31 AA1033 American Airlines Chicago — Philadelphia 1h 4m stop 10:35 — 12:16 AA6158 American Airlines Philadelphia — Portland	4h 46m including layover	Find flight from$54
06:30 — 12:45	06:30 — 09:23 AA1466 American Airlines Chicago — Philadelphia 1h 44m stop 11:07 — 12:45 AA5044 American Airlines Philadelphia — Portland	5h 15m including layover	Find flight from$54
07:00 — 12:16	07:00 — 10:00 AA392 American Airlines Chicago — Philadelphia 35m stop 10:35 — 12:16 AA6158 American Airlines Philadelphia — Portland	4h 16m including layover	Find flight from$54
07:19 — 13:51	07:19 — 10:21 AA2052 American Airlines Chicago — Charlotte 1h 14m stop 11:35 — 13:51 AA591 American Airlines Charlotte — Portland	5h 32m including layover	Find flight from$52
08:20 — 16:42	08:20 — 11:13 AA1002 American Airlines Chicago — Washington D.C. 3h 46m stop 14:59 — 16:42 AA6062 American Airlines Washington D.C. — Portland	7h 22m including layover	Find flight from$53
08:20 — 13:52	08:20 — 11:00 AA985 American Airlines Chicago — Washington D.C. 1h 20m stop 12:20 — 13:52 AA5473 American Airlines Washington D.C. — Portland	4h 32m including layover	Find flight from$54
10:10 — 16:42	10:10 — 13:07 AA2499 American Airlines Chicago — Washington D.C. 1h 52m stop 14:59 — 16:42 AA6062 American Airlines Washington D.C. — Portland	5h 32m including layover	Find flight from$53
10:40 — 18:17	10:40 — 13:36 AA2328 American Airlines Chicago — Charlotte 2h 34m stop 16:10 — 18:17 AA2840 American Airlines Charlotte — Portland	6h 37m including layover	Find flight from$53
12:00 — 17:13	12:00 — 15:00 AA2095 American Airlines Chicago — Philadelphia 35m stop 15:35 — 17:13 AA2841 American Airlines Philadelphia — Portland	4h 13m including layover	Find flight from$54
12:35 — 18:17	12:35 — 15:34 AA511 American Airlines Chicago — Charlotte 36m stop 16:10 — 18:17 AA2840 American Airlines Charlotte — Portland	4h 42m including layover	Find flight from$53
13:30 — 21:16	13:30 — 16:28 AA1486 American Airlines Chicago — Washington D.C. 3h 2m stop 19:30 — 21:16 AA6042 American Airlines Washington D.C. — Portland	6h 46m including layover	Find flight from$54
13:45 — 22:09	13:45 — 16:46 AA2817 American Airlines Chicago — Charlotte 3h 9m stop 19:55 — 22:09 AA2375 American Airlines Charlotte — Portland	7h 24m including layover	Find flight from$53
14:03 — 22:40	14:03 — 17:05 AA2185 American Airlines Chicago — Charlotte 3h 20m stop 20:25 — 22:40 AA2226 American Airlines Charlotte — Portland	7h 37m including layover	Find flight from$52
15:05 — 20:35	15:05 — 18:06 AA1920 American Airlines Chicago — Philadelphia 59m stop 19:05 — 20:35 AA5029 American Airlines Philadelphia — Portland	4h 30m including layover	Find flight from$54
15:38 — 22:40	15:38 — 18:42 AA612 American Airlines Chicago — Charlotte 1h 43m stop 20:25 — 22:40 AA2226 American Airlines Charlotte — Portland	6h 2m including layover	Find flight from$52
16:00 — 22:09	16:00 — 18:57 AA433 American Airlines Chicago — Charlotte 58m stop 19:55 — 22:09 AA2375 American Airlines Charlotte — Portland	5h 9m including layover	Find flight from$53
16:30 — 22:39	16:30 — 19:32 AA2588 American Airlines Chicago — Philadelphia 1h 33m stop 21:05 — 22:39 AA1833 American Airlines Philadelphia — Portland	5h 9m including layover	Find flight from$54
17:05 — 23:45	17:05 — 19:45 AA2679 American Airlines Chicago — Washington D.C. 2h 25m stop 22:10 — 23:45 AA4615 American Airlines Washington D.C. — Portland	5h 40m including layover	Find flight from$54

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

*Departure and arrival times - local. Updated on April 24, 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 05:00 to 23:55 from 7 Chicago airports and arrive 05:00 to 23:55 to 1 Portland airport. Average flight time is 2h 26m.

The fastest flight 2h 16m
Average flight time 2h 26m
The earliest flight 05:00
The latest flight 23:55
Distance 886 ml

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $51. This airfare is for economy class on one-way UA3447 flight by United Airlines for September 22, 2020 which leaves O'Hare International in Chicago at 11:30 am and arrives at Portland Portland Intl Jetport at 14:57.

Economy class

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First class

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Popular Airlines on the Route

The flight Chicago — Portland is served by 8 regular airlines and 5 low-cost airlines. Most of the flights on this route are operated by American Airlines - 221 departures per week at the price of from $ 52 . And the most expensive tickets are offered by United Airlines airline - from $ 1225.

Direct flights

There are 17 nonstop flights on the route. The fastest direct flight is AA1540 by American Airlines takes 2h 16m and the cheapest is UA3447 by United Airlines for $51.

AA - American Airlines

from $54

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UA - United Airlines

from $51

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Connecting Flights

There are 596 flights with layovers on the route. The fastest connecting flight is AA1002 by American Airlines takes 3h 42m and the cheapest is UA3447 by United Airlines for $52.

AA - American Airlines

from $52

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F9 - Frontier Airlines

from $93

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B6 - JetBlue

from $240

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DL - Delta Air Lines Inc.

from $79

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UA - United Airlines

from $78

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WN - Southwest Airlines

from $88

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VB - VivaAerobus

from $537

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NK - Spirit Airlines

from $65

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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 $51
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Midway-MDW

from $83
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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 8 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Embraer RJ135 / RJ140 / RJ145

from $51

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Embraer 175 (winglets)

from $52

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Boeing 737-800

from $52

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Airbus A321

from $52

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Airbus A320

from $52

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Airbus A321-100/200

from $53

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Boeing 787-8

from $54

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Embraer 175 (short wing)

from $54

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Airbus A319

from $54

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Airbus A320-100/200

from $54

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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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Chicago — Tampa

from $63

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Chicago — Los Angeles

from $181

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Chicago — Orlando

from $62

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Chicago — New York

from $74

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Chicago — Dallas

from $70

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Chicago — San Antonio

from $59

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Chicago — Atlanta

from $76

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Chicago — Miami

from $66

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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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All flights from Chicago | All flights to Portland

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»
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