Cheap Flights from Portland, ME to Chicago, IL from $105

One way Round trip

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On Cheapflightsplus.com you will find 10 direct and 388 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $105, book and save on cheap plane tickets and last minute offers. Also check out PWM-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip Portland to Chicago 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: $105 (one-way), $180 (round-trip).

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Best Flights from Portland to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Portland to Chicago with the lowest price of $105. The fastest direct flight takes 2h 51m and the fastest connecting – 4h 49m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $134 Find flight	06:00 Portland Portland Intl Jetport	07:53 Chicago O'Hare International	2h 53m	United Airlines	UA1834
from $134 Find flight	16:43 Portland Portland Intl Jetport	18:40 Chicago O'Hare International	2h 57m	United Airlines	UA1564
from $134 Find flight	11:43 Portland Portland Intl Jetport	13:46 Chicago O'Hare International	3h 3m	United Airlines	UA5697
from $149 Find flight	06:00 Portland Portland Intl Jetport	07:51 Chicago O'Hare International	2h 51m	United Airlines	UA1857
from $149 Find flight	16:56 Portland Portland Intl Jetport	18:47 Chicago O'Hare International	2h 51m	United Airlines	UA2466
from $307 Find flight	18:20 Portland Portland Intl Jetport	20:25 Chicago O'Hare International	3h 5m	United Airlines	UA5327
from $105 Find flight	16:57 Portland Portland Intl Jetport	00:04+1 день Chicago O'Hare International	8h 7m layover 1h 39m - Orlando	Frontier Airlines	F91929 F92791
from $118 Find flight	18:12 Portland Portland Intl Jetport	07:39+1 день Chicago Midway	14h 27m layover 8h 11m - Orlando	Frontier Airlines	F92621 F93853
from $119 Find flight	18:12 Portland Portland Intl Jetport	12:57+1 день Chicago O'Hare International	19h 45m layover 13h 14m - Orlando	Frontier Airlines	F92621 F93043
from $139 Find flight	12:15 Portland Portland Intl Jetport	16:48 Chicago O'Hare International	5h 33m layover 1h 9m - Washington D.C.	United Airlines	UA3699 UA1057
from $139 Find flight	09:30 Portland Portland Intl Jetport	14:33 Chicago O'Hare International	6h 3m layover 2h 0m - Washington D.C.	United Airlines	UA3683 UA2331
from $139 Find flight	16:04 Portland Portland Intl Jetport	22:12 Chicago O'Hare International	7h 8m layover 2h 43m - Newark	United Airlines	UA3620 UA546
from $140 Find flight	14:14 Portland Portland Intl Jetport	18:37 Chicago O'Hare International	5h 23m layover 0h 45m - Washington D.C.	United Airlines	UA3593 UA2497
from $140 Find flight	12:15 Portland Portland Intl Jetport	16:48 Chicago O'Hare International	5h 33m layover 1h 6m - Washington D.C.	United Airlines	UA4820 UA1057
from $140 Find flight	12:15 Portland Portland Intl Jetport	18:37 Chicago O'Hare International	7h 22m layover 2h 41m - Washington D.C.	United Airlines	UA4820 UA2497
from $164 Find flight	10:40 Portland Portland Intl Jetport	14:55 Chicago O'Hare International	5h 15m layover 1h 7m - Newark	United Airlines	UA3405 UA2053

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on August 06, 2025

Flight Schedule Portland (Maine) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from Portland to Chicago. 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
06:00 — 07:53	06:00 — 07:53 UA1834 United Airlines Portland — Chicago	2h 53m	Find flight from$134
06:00 — 07:51	06:00 — 07:51 UA1857 United Airlines Portland — Chicago	2h 51m	Find flight from$149
06:14 — 08:05	06:14 — 08:05 UA1030 United Airlines Portland — Chicago	2h 51m	Find flight from$152
11:43 — 13:46	11:43 — 13:46 UA5697 United Airlines Portland — Chicago	3h 3m	Find flight from$134
16:43 — 18:40	16:43 — 18:40 UA1564 United Airlines Portland — Chicago	2h 57m	Find flight from$134
16:56 — 18:47	16:56 — 18:47 UA2466 United Airlines Portland — Chicago	2h 51m	Find flight from$149
18:20 — 20:25	18:20 — 20:25 UA3520 United Airlines Portland — Chicago	3h 5m	Find flight from$153
18:20 — 20:25	18:20 — 20:25 UA3695 United Airlines Portland — Chicago	3h 5m	Find flight from$153
18:20 — 20:25	18:20 — 20:25 UA5327 United Airlines Portland — Chicago	3h 5m	Find flight from$307
18:23 — 20:23	18:23 — 20:23 UA4744 United Airlines Portland — Chicago	3h	Find flight from$149
05:35 — 09:43	05:35 — 07:25 UA3552 United Airlines Portland — Washington D.C. 1h 5m stop 08:30 — 09:43 UA2440 United Airlines Washington D.C. — Chicago	5h 8m including layover	Find flight from$158
05:45 — 09:36	05:45 — 07:33 UA3415 United Airlines Portland — Washington D.C. 47m stop 08:20 — 09:36 UA1775 United Airlines Washington D.C. — Chicago	4h 51m including layover	Find flight from$156
08:00 — 13:07	08:00 — 09:31 UA3639 United Airlines Portland — Newark 1h 58m stop 11:29 — 13:07 UA1875 United Airlines Newark — Chicago	6h 7m including layover	Find flight from$153
08:00 — 13:07	08:00 — 09:31 UA3424 United Airlines Portland — Newark 1h 58m stop 11:29 — 13:07 UA1875 United Airlines Newark — Chicago	6h 7m including layover	Find flight from$156
09:30 — 14:33	09:30 — 11:20 UA3683 United Airlines Portland — Washington D.C. 2h stop 13:20 — 14:33 UA2331 United Airlines Washington D.C. — Chicago	6h 3m including layover	Find flight from$139
10:05 — 14:29	10:05 — 11:55 UA3438 United Airlines Portland — Washington D.C. 1h 22m stop 13:20 — 14:33 UA2331 United Airlines Washington D.C. — Chicago	5h 24m including layover	Find flight from$156
10:50 — 14:55	10:50 — 12:23 UA3623 United Airlines Portland — Newark 57m stop 13:20 — 14:55 UA2053 United Airlines Newark — Chicago	5h 5m including layover	Find flight from$156
12:15 — 16:48	12:15 — 14:26 UA3699 United Airlines Portland — Washington D.C. 1h 9m stop 15:35 — 16:48 UA1057 United Airlines Washington D.C. — Chicago	5h 33m including layover	Find flight from$139
12:15 — 18:37	12:15 — 14:26 UA3699 United Airlines Portland — Washington D.C. 2h 44m stop 17:10 — 18:37 UA2497 United Airlines Washington D.C. — Chicago	7h 22m including layover	Find flight from$139
14:14 — 18:37	14:05 — 16:16 UA3593 United Airlines Portland — Washington D.C. 45m stop 17:10 — 18:37 UA2497 United Airlines Washington D.C. — Chicago	5h 23m including layover	Find flight from$140
14:22 — 18:30	14:08 — 16:19 UA3624 United Airlines Portland — Washington D.C. 55m stop 17:18 — 18:45 UA2497 United Airlines Washington D.C. — Chicago	5h 8m including layover	Find flight from$153
15:04 — 19:57	15:04 — 16:44 UA3620 United Airlines Portland — Newark 1h 31m stop 18:15 — 19:57 UA254 United Airlines Newark — Chicago	5h 53m including layover	Find flight from$156
15:06 — 20:10	15:06 — 16:55 UA3620 United Airlines Portland — Newark 1h 34m stop 18:29 — 20:10 UA2310 United Airlines Newark — Chicago	6h 4m including layover	Find flight from$158
16:57 — 00:04 +1 day	16:57 — 20:18 F91929 Frontier Airlines Portland — Orlando 1h 39m stop 21:57 — 00:04 F92791 Frontier Airlines Orlando — Chicago	8h 7m including layover	Find flight from$105
16:57 — 08:22 +1 day	16:57 — 20:18 F91929 Frontier Airlines Portland — Orlando 9h 52m stop 06:10 — 08:22 F93043 Frontier Airlines Orlando — Chicago	16h 25m including layover	Find flight from$110
17:35 — 23:25	17:35 — 19:24 UA3616 United Airlines Portland — Newark 2h 20m stop 21:44 — 23:25 UA1308 United Airlines Newark — Chicago	6h 50m including layover	Find flight from$156
18:12 — 07:39 +1 day	18:58 — 22:30 F92621 Frontier Airlines Portland — Orlando 8h 11m stop 13:10 — 15:06 F93853 Frontier Airlines Orlando — Chicago	14h 27m including layover	Find flight from$118
18:12 — 12:57 +1 day	18:58 — 22:30 F92621 Frontier Airlines Portland — Orlando 13h 14m stop 13:06 — 15:27 F93043 Frontier Airlines Orlando — Chicago	19h 45m including layover	Find flight from$119
19:15 — 23:30	19:15 — 21:05 UA1429 United Airlines Portland — Washington D.C. 1h 14m stop 22:19 — 23:30 UA1738 United Airlines Washington D.C. — Chicago	5h 15m including layover	Find flight from$156
19:26 — 23:15	19:09 — 21:04 UA3582 United Airlines Portland — Washington D.C. 55m stop 22:18 — 23:30 UA1738 United Airlines Washington D.C. — Chicago	4h 49m including layover	Find flight from$153

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

*Departure and arrival times - local. Updated on August 6, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from Portland to Chicago depends on and how to choose the most interesting flight option for you.

Distance between Portland and Chicago is 1425 miles. Time difference between the cities is 1h. Airplanes depart 05:35 to 20:52 from 1 Portland airport and arrive 05:35 to 20:52 to 7 Chicago airports. Average flight time is 2h 59m.

The fastest flight 2h 51m
Average flight time 2h 59m
The earliest flight 05:35
The latest flight 20:52
Distance 886 ml

The cheapest months to travel to Chicago are may (from 105 $), september (from 118 $), july (from 119 $).

The most expensive months are june (from 152 $), october (from 149 $), august (from 136 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $105. This airfare is for economy class on one-way F91929 flight by Frontier Airlines for May 24, 2025 which leaves Portland Intl Jetport in Portland at 16:57 am and arrives at Chicago O'Hare International at 00:04.

Economy class

$105

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Business class

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First class

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Popular Airlines on the Route

The flight Portland — Chicago is served by 4 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 5 departures per week at the price of from $ 105 . And the most expensive tickets are offered by United Airlines airline - from $ 858.

Direct flights

There are 10 nonstop flights on the route. The fastest direct flight is UA1857 by United Airlines takes 2h 51m and the cheapest is F91929 by Frontier Airlines for $134.

UA - United Airlines

from $134

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Connecting Flights

There are 388 flights with layovers on the route. The fastest connecting flight is UA3582 by United Airlines takes 4h 49m and the cheapest is F91929 by Frontier Airlines for $105.

F9 - Frontier Airlines

from $105

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SY - Sun Country Airlines

from $167

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MX - Mexicana

from $248

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UA - United Airlines

from $139

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Airports

You can fly from Portland to Chicago from 1 airports (Portland Intl Jetport).

Portland airports

Portland Intl Jetport-PWM

from $105
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Chicago airports

O'Hare International-ORD

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Midway-MDW

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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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Airplanes

There are flights to Chicago from Portland by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from Portland

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

Portland — Las Vegas

from $74

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Portland — Seattle

from $80

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Portland — Chicago

from $60

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Portland — Denver

from $55

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Portland — San Diego

from $68

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Portland — Los Angeles

from $56

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Portland — Sacramento

from $58

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Portland — Austin

from $59

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Portland — Spokane

from $63

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Portland — Atlanta

from $64

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Top International Destinations from Portland

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.

Portland — Vancouver

from $73

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Portland — Calgary

from $75

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Portland — Amsterdam

from $59

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Portland — Guadalajara

from $68

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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.
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.
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