Cheap Flights from Chicago, IL to Portland, ME from $66

One way Round trip

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On Cheapflightsplus.com you will find 7 direct and 494 connecting flights from Chicago to Portland. You can compare airfare deals from 10 airlines and multiple travel sites from $66, 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: $66 (one-way), $113 (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 $66. The fastest direct flight takes 2h 22m and the fastest connecting – 4h 2m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $211 Find flight	11:05 Chicago O'Hare International	14:35 Portland Portland Intl Jetport	2h 30m	United Airlines	UA3494
from $236 Find flight	18:00 Chicago O'Hare International	21:30 Portland Portland Intl Jetport	2h 30m	United Airlines	UA3525
from $239 Find flight	11:10 Chicago O'Hare International	14:42 Portland Portland Intl Jetport	2h 32m	United Airlines	UA5708
from $289 Find flight	18:00 Chicago O'Hare International	21:30 Portland Portland Intl Jetport	2h 30m	United Airlines	UA5761
from $456 Find flight	11:59 Chicago O'Hare International	15:21 Portland Portland Intl Jetport	2h 22m	United Airlines	UA3704
from $66 Find flight	11:33 Chicago Midway	20:14 Portland Portland Intl Jetport	7h 41m layover 1h 44m - Orlando	Frontier Airlines	F91458 F92622
from $66 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 $175 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 $199 Find flight	11:10 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	10h 40m layover 7h 21m - Newark	Spirit Airlines	NK857 UA2478
from $201 Find flight	07:49 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	14h 1m layover 10h 27m - Newark	Spirit Airlines	NK328 UA2478
from $213 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	11:41 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	10h 9m layover 6h 36m - Newark	American Airlines	AA532 UA2478
from $232 Find flight	09:48 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	12h 2m layover 8h 30m - Newark	JetBlue	B6906 UA2478
from $237 Find flight	14:00 Chicago O'Hare International	22:50 Portland Portland Intl Jetport	7h 50m layover 4h 19m - Newark	United Airlines	UA2182 UA2478
from $216 Find flight	11:10 Chicago O'Hare International	23:55 Portland Portland Intl Jetport	11h 45m layover 5h 51m - New York 0h 48m - Washington D.C.	Spirit Airlines	NK857 AA4492 AA5638
from $218 Find flight	07:49 Chicago O'Hare International	23:55 Portland Portland Intl Jetport	15h 6m layover 8h 57m - New York 0h 48m - Washington D.C.	Spirit Airlines	NK328 AA4492 AA5638

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 04, 2025

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$211
11:05 — 14:35	11:05 — 14:35 UA3674 United Airlines Chicago — Portland	2h 30m	Find flight from$331
11:10 — 14:42	11:10 — 14:42 UA5708 United Airlines Chicago — Portland	2h 32m	Find flight from$239
11:59 — 15:21	11:59 — 15:21 UA3704 United Airlines Chicago — Portland	2h 22m	Find flight from$456
18:00 — 21:30	18:00 — 21:30 UA3525 United Airlines Chicago — Portland	2h 30m	Find flight from$236
18:00 — 21:30	18:00 — 21:30 UA5761 United Airlines Chicago — Portland	2h 30m	Find flight from$289
18:10 — 21:42	18:10 — 21:42 UA3583 United Airlines Chicago — Portland	2h 32m	Find flight from$239
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$175
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$213
07:49 — 22:50	07:49 — 11:02 NK328 Spirit Airlines Chicago — Newark 10h 27m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	14h 1m including layover	Find flight from$201
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$249
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$250
09:48 — 22:50	09:48 — 12:59 B6906 JetBlue Chicago — Newark 8h 30m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	12h 2m including layover	Find flight from$232
10:30 — 22:50	10:30 — 13:48 DL2434 Delta Air Lines Inc. Chicago — Newark 7h 41m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	11h 20m including layover	Find flight from$248
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$66
11:10 — 22:50	11:10 — 14:08 NK857 Spirit Airlines Chicago — Newark 7h 21m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	10h 40m including layover	Find flight from$199
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$66
12:00 — 22:50	12:00 — 15:09 UA303 United Airlines Chicago — Newark 6h 20m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	9h 50m including layover	Find flight from$239
12:45 — 22:50	12:45 — 15:56 DL2894 Delta Air Lines Inc. Chicago — Newark 5h 33m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	9h 5m including layover	Find flight from$248
13:06 — 22:50	13:06 — 16:14 UA1450 United Airlines Chicago — Newark 5h 15m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	8h 44m including layover	Find flight from$239
13:50 — 22:50	13:50 — 17:05 UA2329 United Airlines Chicago — Newark 4h 24m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	8h including layover	Find flight from$260
14:00 — 22:50	14:00 — 17:10 UA2182 United Airlines Chicago — Newark 4h 19m stop 21:29 — 22:50 UA2478 United Airlines Newark — Portland	7h 50m including layover	Find flight from$237
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$249
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$250
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$249
16:21 — 22:53	16:21 — 19:24 NK3385 Spirit Airlines Chicago — New York 2h 5m stop 21:29 — 22:53 DL5775 Delta Air Lines Inc. New York — Portland	5h 32m including layover	Find flight from$248
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$249
19:30 — 11:35 +1 day	19:30 — 22:47 DL1390 Delta Air Lines Inc. Chicago — New York 11h 18m stop 10:05 — 11:35 DL5774 Delta Air Lines Inc. New York — Portland	15h 5m including layover	Find flight from$268
19:30 — 15:51 +1 day	19:30 — 22:47 DL1390 Delta Air Lines Inc. Chicago — New York 15h 42m stop 14:29 — 15:51 DL5409 Delta Air Lines Inc. New York — Portland	19h 21m including layover	Find flight from$268
20:05 — 10:26 +1 day	20:05 — 23:24 UA2362 United Airlines Chicago — Newark 9h 31m stop 08:55 — 10:26 UA3609 United Airlines Newark — Portland	13h 21m including layover	Find flight from$261
21:35 — 10:26 +1 day	21:35 — 00:43 UA1791 United Airlines Chicago — Newark 8h 12m stop 08:55 — 10:26 UA3609 United Airlines Newark — Portland	11h 51m including layover	Find flight from$261
09:48 — 23:55	09:48 — 12:59 B6906 JetBlue Chicago — New York 7h stop 19:59 — 21:23 AA4492 American Airlines New York — Washington D.C. 48m stop 22:11 — 23:55 AA5638 American Airlines Washington D.C. — Portland	13h 7m including layover	Find flight from$249
16:21 — 12:00 +1 day	16:21 — 19:24 NK3385 Spirit Airlines Chicago — New York 12h 35m stop 07:59 — 09:23 AA4521 American Airlines New York — Washington D.C. 37m stop 10:00 — 12:00 AA5652 American Airlines Washington D.C. — Portland	18h 39m including layover	Find flight from$242

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

*Departure and arrival times - local. Updated on April 4, 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 03:45 to 21:45 from 7 Chicago airports and arrive 03:45 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 03:45
The latest flight 21:45
Distance 886 ml

The cheapest months to travel to Portland are december (from 66 $), january (from 175 $), november (from 199 $).

The most expensive months are february (from 243 $), november (from 199 $), january (from 175 $).

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $66. 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

$66

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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 10 regular airlines and 7 low-cost airlines. Most of the flights on this route are operated by United Airlines - 233 departures per week at the price of from $ 211 . And the most expensive tickets are offered by United Airlines airline - from $ 979.

Direct flights

There are 7 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 $211.

UA - United Airlines

from $211

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Connecting Flights

There are 494 flights with layovers on the route. The fastest connecting flight is AA2345 by American Airlines takes 4h 2m and the cheapest is F91458 by Frontier Airlines for $66.

UA - United Airlines

from $237

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AA - American Airlines

from $225

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F9 - Frontier Airlines

from $66

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B6 - JetBlue

from $232

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PD - Porter Airlines

from $408

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WN - Southwest Airlines

from $291

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DL - Delta Air Lines Inc.

from $248

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Y4 - Volaris

from $578

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NK - Spirit Airlines

from $175

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TS - Air Transat

from $443

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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 $66
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Midway-MDW

from $66
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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 10 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Airbus A321

from $216

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Boeing 737-800

from $225

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Airbus A320

from $232

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Boeing 737

from $237

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Boeing 737 MAX 8

from $239

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Airbus A319

from $257

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Boeing 717

from $279

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Boeing 737-900

from $281

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Embraer 175 (short wing)

from $281

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Boeing 757-200

from $283

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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 — New York

from $74

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Chicago — Atlanta

from $76

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Chicago — Orlando

from $62

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Chicago — Miami

from $66

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Chicago — Dallas

from $70

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Chicago — Houston

from $66

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Chicago — Boston

from $61

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Chicago — Phoenix

from $65

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Chicago — Denver

from $61

Find

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 — Cancun

from $72

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Chicago — Toronto

from $73

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Chicago — Paris

from $61

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Chicago — Rome

from $79

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Chicago — Hyderabad

from $73

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Chicago — Mexico City

from $76

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Chicago — Tokyo

from $60

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Chicago — Dublin

from $59

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Chicago — Mumbai

from $74

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How to book a plane ticket yourself?

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