Cheap Flights from Portland, ME to Chicago, IL from $117

One way Round trip

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On Cheapflightsplus.com you will find 7 direct and 169 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $117, 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: $117 (one-way), $201 (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 $117. The fastest direct flight takes 2h 51m and the fastest connecting – 4h 49m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $148 Find flight	06:00 Portland Portland Intl Jetport	07:51 Chicago O'Hare International	2h 51m	United Airlines	UA1857
from $148 Find flight	16:56 Portland Portland Intl Jetport	18:47 Chicago O'Hare International	2h 51m	United Airlines	UA2466
from $148 Find flight	18:23 Portland Portland Intl Jetport	20:23 Chicago O'Hare International	3h 0m	United Airlines	UA4744
from $151 Find flight	06:14 Portland Portland Intl Jetport	08:05 Chicago O'Hare International	2h 51m	United Airlines	UA1030
from $152 Find flight	18:20 Portland Portland Intl Jetport	20:25 Chicago O'Hare International	3h 5m	United Airlines	UA3520
from $152 Find flight	18:20 Portland Portland Intl Jetport	20:25 Chicago O'Hare International	3h 5m	United Airlines	UA3695
from $306 Find flight	18:20 Portland Portland Intl Jetport	20:25 Chicago O'Hare International	3h 5m	United Airlines	UA5327
from $117 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 $152 Find flight	19:26 Portland Portland Intl Jetport	23:15 Chicago O'Hare International	4h 49m layover 0h 55m - Washington D.C.	United Airlines	UA3582 UA1738
from $152 Find flight	14:22 Portland Portland Intl Jetport	18:30 Chicago O'Hare International	5h 8m layover 0h 55m - Washington D.C.	United Airlines	UA3624 UA2497
from $152 Find flight	08:00 Portland Portland Intl Jetport	13:07 Chicago O'Hare International	6h 7m layover 1h 58m - Newark	United Airlines	UA3639 UA1875
from $155 Find flight	05:45 Portland Portland Intl Jetport	09:36 Chicago O'Hare International	4h 51m layover 0h 47m - Washington D.C.	United Airlines	UA3415 UA1775
from $155 Find flight	10:50 Portland Portland Intl Jetport	14:55 Chicago O'Hare International	5h 5m layover 0h 57m - Newark	United Airlines	UA3623 UA2053
from $155 Find flight	10:05 Portland Portland Intl Jetport	14:29 Chicago O'Hare International	5h 24m layover 1h 22m - Washington D.C.	United Airlines	UA3438 UA2331
from $155 Find flight	06:00 Portland Portland Intl Jetport	10:38 Chicago O'Hare International	5h 38m layover 1h 28m - Newark	United Airlines	UA3472 UA2479
from $175 Find flight	12:42 Portland Portland Intl Jetport	11:32+1 день Chicago O'Hare International	23h 50m layover 19h 2m - Minneapolis	Sun Country Airlines	SY1822 SY1629

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 15, 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 — 07:51	06:00 — 07:51 UA1857 United Airlines Portland — Chicago	2h 51m	Find flight from$148
06:14 — 08:05	06:14 — 08:05 UA1030 United Airlines Portland — Chicago	2h 51m	Find flight from$151
16:56 — 18:47	16:56 — 18:47 UA2466 United Airlines Portland — Chicago	2h 51m	Find flight from$148
18:20 — 20:25	18:20 — 20:25 UA3520 United Airlines Portland — Chicago	3h 5m	Find flight from$152
18:20 — 20:25	18:20 — 20:25 UA3695 United Airlines Portland — Chicago	3h 5m	Find flight from$152
18:20 — 20:25	18:20 — 20:25 UA5327 United Airlines Portland — Chicago	3h 5m	Find flight from$306
18:23 — 20:23	18:23 — 20:23 UA4744 United Airlines Portland — Chicago	3h	Find flight from$148
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$157
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$155
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$152
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$155
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$155
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$155
12:11 — 17:00	12:10 — 13:59 UA3719 United Airlines Portland — Newark 1h 25m stop 15:25 — 17:00 UA2394 United Airlines Newark — Chicago	5h 49m including layover	Find flight from$155
12:11 — 18:29	12:10 — 13:59 UA3719 United Airlines Portland — Newark 2h 49m stop 16:49 — 18:29 UA661 United Airlines Newark — Chicago	7h 18m including layover	Find flight from$164
13:18 — 15:43 +1 day	13:18 — 17:09 MX789 Mexicana Portland — Fort Myers 20h 21m stop 13:30 — 15:43 NK2930 Spirit Airlines Fort Myers — Chicago	27h 25m including layover	Find flight from$251
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$152
14:22 — 19:55	14:14 — 16:12 UA3624 United Airlines Portland — Washington D.C. 2h 27m stop 18:40 — 19:48 UA2304 United Airlines Washington D.C. — Chicago	6h 33m including layover	Find flight from$155
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$155
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$157
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$155
17:35 — 07:38 +1 day	17:35 — 19:24 UA3616 United Airlines Portland — Newark 10h 36m stop 06:00 — 07:38 UA2164 United Airlines Newark — Chicago	15h 3m including layover	Find flight from$241
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$117
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$118
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$152

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

*Departure and arrival times - local. Updated on July 15, 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 3h.

The fastest flight 2h 51m
Average flight time 3h
The earliest flight 05:35
The latest flight 20:52
Distance 886 ml

The cheapest months to travel to Chicago are september (from 117 $), july (from 118 $), august (from 135 $).

The most expensive months are june (from 151 $), october (from 148 $), may (from 138 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $117. This airfare is for economy class on one-way F92621 flight by Frontier Airlines for September 27, 2025 which leaves Portland Intl Jetport in Portland at 18:12 am and arrives at Chicago Midway at 07:39.

Economy class

$117

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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 - 2 departures per week at the price of from $ 117 . And the most expensive tickets are offered by United Airlines airline - from $ 716.

Direct flights

There are 7 nonstop flights on the route. The fastest direct flight is UA1857 by United Airlines takes 2h 51m and the cheapest is F92621 by Frontier Airlines for $148.

UA - United Airlines

from $148

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Connecting Flights

There are 169 flights with layovers on the route. The fastest connecting flight is UA3582 by United Airlines takes 4h 49m and the cheapest is F92621 by Frontier Airlines for $117.

F9 - Frontier Airlines

from $117

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SY - Sun Country Airlines

from $175

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MX - Mexicana

from $251

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UA - United Airlines

from $152

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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 $117
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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.
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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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