Cheap Flights from Chicago, IL to Portland, ME from $81

One way Round trip

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On Cheapflightsplus.com you will find 6 direct and 408 connecting flights from Chicago to Portland. You can compare airfare deals from 6 airlines and multiple travel sites from $81, 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: $81 (one-way), $139 (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 $81. The fastest direct flight takes 2h 26m and the fastest connecting – 4h 31m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $97 Find flight	18:30 Chicago O'Hare International	22:01 Portland Portland Intl Jetport	2h 31m	United Airlines	UA1974
from $97 Find flight	07:10 Chicago O'Hare International	10:49 Portland Portland Intl Jetport	2h 39m	United Airlines	UA5623
from $111 Find flight	10:58 Chicago O'Hare International	14:24 Portland Portland Intl Jetport	2h 26m	United Airlines	UA763
from $142 Find flight	13:55 Chicago O'Hare International	17:37 Portland Portland Intl Jetport	2h 42m	United Airlines	UA5849
from $167 Find flight	13:55 Chicago O'Hare International	17:37 Portland Portland Intl Jetport	2h 42m	United Airlines	UA3451
from $81 Find flight	21:12 Chicago Midway	16:02+1 день Portland Portland Intl Jetport	17h 50m layover 11h 47m - Orlando	Frontier Airlines	F93854 F92622
from $83 Find flight	17:14 Chicago O'Hare International	16:02+1 день Portland Portland Intl Jetport	21h 48m layover 15h 33m - Orlando	Frontier Airlines	F93044 F92622
from $84 Find flight	09:08 Chicago O'Hare International	18:13 Portland Portland Intl Jetport	8h 5m layover 1h 54m - Orlando	Frontier Airlines	F92792 F92622
from $101 Find flight	17:56 Chicago O'Hare International	23:59 Portland Portland Intl Jetport	5h 3m layover 1h 19m - Washington D.C.	United Airlines	UA2677 UA3674
from $111 Find flight	06:45 Chicago O'Hare International	11:11+1 день Portland Portland Intl Jetport	27h 26m layover 23h 5m - Minneapolis	Sun Country Airlines	SY1630 SY1821
from $113 Find flight	10:50 Chicago O'Hare International	19:27 Portland Portland Intl Jetport	7h 37m layover 3h 41m - Washington D.C.	United Airlines	UA758 UA3517
from $114 Find flight	07:15 Chicago O'Hare International	13:22 Portland Portland Intl Jetport	5h 7m layover 1h 25m - Newark	United Airlines	UA563 UA3685
from $114 Find flight	06:00 Chicago O'Hare International	13:18 Portland Portland Intl Jetport	6h 18m layover 2h 45m - Newark	United Airlines	UA1658 UA3512
from $114 Find flight	15:40 Chicago O'Hare International	23:14 Portland Portland Intl Jetport	6h 34m layover 2h 31m - Newark	United Airlines	UA2133 UA2127
from $116 Find flight	08:50 Chicago O'Hare International	14:25 Portland Portland Intl Jetport	4h 35m layover 0h 40m - Washington D.C.	United Airlines	UA2029 UA3529
from $116 Find flight	06:00 Chicago O'Hare International	13:22 Portland Portland Intl Jetport	6h 22m layover 2h 43m - Newark	United Airlines	UA1658 UA3685

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 22, 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
07:10 — 10:49	07:10 — 10:49 UA5623 United Airlines Chicago — Portland	2h 39m	Find flight from$97
10:58 — 14:24	10:58 — 14:24 UA763 United Airlines Chicago — Portland	2h 26m	Find flight from$111
13:55 — 17:37	13:55 — 17:37 UA5849 United Airlines Chicago — Portland	2h 42m	Find flight from$142
13:55 — 17:37	13:55 — 17:37 UA3644 United Airlines Chicago — Portland	2h 42m	Find flight from$143
13:55 — 17:37	13:55 — 17:37 UA3451 United Airlines Chicago — Portland	2h 42m	Find flight from$167
18:30 — 22:01	18:30 — 22:01 UA1974 United Airlines Chicago — Portland	2h 31m	Find flight from$97
06:00 — 13:18	06:00 — 09:13 UA1658 United Airlines Chicago — Newark 2h 45m stop 12:13 — 13:33 UA3512 United Airlines Newark — Portland	6h 18m including layover	Find flight from$114
06:45 — 11:11 +1 day	06:45 — 08:25 SY1630 Sun Country Airlines Chicago — Minneapolis 23h 5m stop 07:30 — 11:11 SY1821 Sun Country Airlines Minneapolis — Portland	27h 26m including layover	Find flight from$111
07:15 — 13:22	07:15 — 10:33 UA563 United Airlines Chicago — Newark 1h 25m stop 11:58 — 13:22 UA3685 United Airlines Newark — Portland	5h 7m including layover	Find flight from$114
08:50 — 14:25	08:52 — 11:55 UA2029 United Airlines Chicago — Washington D.C. 40m stop 13:05 — 14:53 UA3529 United Airlines Washington D.C. — Portland	4h 35m including layover	Find flight from$116
08:52 — 14:23	08:52 — 11:55 UA1068 United Airlines Chicago — Washington D.C. 40m stop 12:35 — 14:23 UA3529 United Airlines Washington D.C. — Portland	4h 31m including layover	Find flight from$164
09:08 — 18:13	09:08 — 12:52 F92792 Frontier Airlines Chicago — Orlando 1h 54m stop 15:15 — 18:30 F92622 Frontier Airlines Orlando — Portland	8h 5m including layover	Find flight from$84
10:50 — 19:27	10:50 — 13:49 UA758 United Airlines Chicago — Washington D.C. 3h 41m stop 17:30 — 19:27 UA3517 United Airlines Washington D.C. — Portland	7h 37m including layover	Find flight from$113
11:23 — 17:43	11:23 — 14:28 UA1190 United Airlines Chicago — Washington D.C. 1h 27m stop 15:55 — 17:43 UA3715 United Airlines Washington D.C. — Portland	5h 20m including layover	Find flight from$158
11:46 — 18:26	11:46 — 15:12 UA1205 United Airlines Chicago — Newark 1h 47m stop 16:59 — 18:26 UA3599 United Airlines Newark — Portland	5h 40m including layover	Find flight from$148
12:22 — 18:13	12:22 — 15:48 UA1205 United Airlines Chicago — Newark 1h 1m stop 16:49 — 18:13 UA334 United Airlines Newark — Portland	4h 51m including layover	Find flight from$151
12:50 — 19:29	12:50 — 15:52 UA1377 United Airlines Chicago — Washington D.C. 1h 42m stop 17:34 — 19:29 UA3517 United Airlines Washington D.C. — Portland	5h 39m including layover	Find flight from$148
13:05 — 19:27	13:05 — 16:10 UA2337 United Airlines Chicago — Washington D.C. 1h 20m stop 17:30 — 19:27 UA3517 United Airlines Washington D.C. — Portland	5h 22m including layover	Find flight from$119
14:20 — 23:14	14:26 — 18:00 UA2649 United Airlines Chicago — Newark 3h 51m stop 21:59 — 23:27 UA1232 United Airlines Newark — Portland	7h 54m including layover	Find flight from$119
14:20 — 23:14	14:20 — 17:54 UA2649 United Airlines Chicago — Newark 3h 51m stop 21:45 — 23:14 UA2127 United Airlines Newark — Portland	7h 54m including layover	Find flight from$120
15:40 — 23:14	15:40 — 19:14 UA2133 United Airlines Chicago — Newark 2h 31m stop 21:45 — 23:14 UA2127 United Airlines Newark — Portland	6h 34m including layover	Find flight from$114
16:50 — 23:14	16:50 — 20:24 UA1785 United Airlines Chicago — Newark 1h 21m stop 21:45 — 23:14 UA1232 United Airlines Newark — Portland	5h 24m including layover	Find flight from$119
16:50 — 23:14	16:50 — 20:24 UA1785 United Airlines Chicago — Newark 1h 21m stop 21:45 — 23:14 UA2127 United Airlines Newark — Portland	5h 24m including layover	Find flight from$120
17:14 — 16:02 +1 day	17:14 — 21:11 F93044 Frontier Airlines Chicago — Orlando 15h 33m stop 12:44 — 16:02 F92622 Frontier Airlines Orlando — Portland	21h 48m including layover	Find flight from$83
17:56 — 23:59	17:53 — 20:52 UA2677 United Airlines Chicago — Washington D.C. 1h 19m stop 22:12 — 23:57 UA3674 United Airlines Washington D.C. — Portland	5h 3m including layover	Find flight from$101
20:17 — 11:23 +1 day	20:17 — 21:57 SY262 Sun Country Airlines Chicago — Minneapolis 9h 45m stop 07:42 — 11:23 SY1821 Sun Country Airlines Minneapolis — Portland	14h 6m including layover	Find flight from$139
20:30 — 23:59 +1 day	20:30 — 23:54 UA1311 United Airlines Chicago — Newark 22h 36m stop 22:30 — 23:59 UA3525 United Airlines Newark — Portland	26h 29m including layover	Find flight from$181
21:12 — 16:02 +1 day	21:12 — 00:57 F93854 Frontier Airlines Chicago — Orlando 11h 47m stop 12:44 — 16:02 F92622 Frontier Airlines Orlando — Portland	17h 50m including layover	Find flight from$81
21:25 — 09:24 +1 day	21:24 — 00:45 UA396 United Airlines Chicago — Newark 7h 19m stop 08:05 — 09:24 UA3514 United Airlines Newark — Portland	10h 59m including layover	Find flight from$174
22:15 — 11:11 +2 days	22:15 — 00:19 NK2179 Spirit Airlines Chicago — Las Vegas 23h 40m stop 23:59 — 05:06 SY778 Sun Country Airlines Las Vegas — Minneapolis 2h 24m stop 07:30 — 11:11 SY1821 Sun Country Airlines Minneapolis — Portland	35h 56m including layover	Find flight from$180

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

*Departure and arrival times - local. Updated on May 22, 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 05:02 to 22:15 from 7 Chicago airports and arrive 05:02 to 22:15 to 1 Portland airport. Average flight time is 2h 41m.

The fastest flight 2h 26m
Average flight time 2h 41m
The earliest flight 05:02
The latest flight 22:15
Distance 886 ml

The cheapest months to travel to Portland are may (from 109 $), july (from 113 $), june (from 118 $).

The most expensive months are august (from 127 $), june (from 118 $), july (from 113 $).

What is the lowest airfare Chicago to Portland?

The cheapest plane ticket found by our users is $81. This airfare is for economy class on one-way F93854 flight by Frontier Airlines for May 30, 2025 which leaves Midway in Chicago at 21:12 am and arrives at Portland Portland Intl Jetport at 16:02.

Economy class

$81

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First class

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Popular Airlines on the Route

The flight Chicago — Portland is served by 6 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 270 departures per week at the price of from $ 97 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 961.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is UA763 by United Airlines takes 2h 26m and the cheapest is F93854 by Frontier Airlines for $97.

UA - United Airlines

from $97

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Connecting Flights

There are 408 flights with layovers on the route. The fastest connecting flight is UA1068 by United Airlines takes 4h 31m and the cheapest is F93854 by Frontier Airlines for $81.

UA - United Airlines

from $101

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AS - Alaska Airlines

from $961

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F9 - Frontier Airlines

from $81

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SY - Sun Country Airlines

from $111

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NK - Spirit Airlines

from $180

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G4 - Allegiant Air

from $201

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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 $83
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Midway-MDW

from $81
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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 6 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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Chicago — New York

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Chicago — Atlanta

from $76

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from $62

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from $70

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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

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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 — 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?

Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
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