Cheap Flights from Portland, ME to Chicago, IL from $87
On Cheapflightsplus.com you will find 7 direct and 259 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $87, 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
Best Flights from Portland to Chicago Today
Price | Departure | Arrival | Flight Duration | Airline | Flight |
---|---|---|---|---|---|
from $110 | 06:00 Portland Portland Intl Jetport | 07:51 Chicago O'Hare International | 2h 51m | United Airlines | UA1857 |
from $110 | 16:56 Portland Portland Intl Jetport | 18:47 Chicago O'Hare International | 2h 51m | United Airlines | UA2466 |
from $110 | 18:23 Portland Portland Intl Jetport | 20:23 Chicago O'Hare International | 3h 0m | United Airlines | UA4744 |
from $112 | 06:14 Portland Portland Intl Jetport | 08:05 Chicago O'Hare International | 2h 51m | United Airlines | UA1030 |
from $112 | 18:20 Portland Portland Intl Jetport | 20:25 Chicago O'Hare International | 3h 5m | United Airlines | UA5327 |
from $113 | 18:20 Portland Portland Intl Jetport | 20:25 Chicago O'Hare International | 3h 5m | United Airlines | UA3520 |
from $113 | 18:20 Portland Portland Intl Jetport | 20:25 Chicago O'Hare International | 3h 5m | United Airlines | UA3695 |
from $87 | 18:12 Portland Portland Intl Jetport | 07:39+1 день Chicago Midway | 14h 27m layover 8h 11m - Orlando | Frontier Airlines | F92621 F93853 |
from $102 | 10:05 Portland Portland Intl Jetport | 16:52 Chicago O'Hare International | 7h 47m layover 3h 44m - Washington D.C. | United Airlines | UA3438 UA1057 |
from $105 | 06:00 Portland Portland Intl Jetport | 10:39 Chicago O'Hare International | 5h 39m layover 1h 31m - Newark | United Airlines | UA2151 UA2337 |
from $113 | 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 $113 | 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 $113 | 08:00 Portland Portland Intl Jetport | 13:07 Chicago O'Hare International | 6h 7m layover 1h 58m - Newark | United Airlines | UA3639 UA1875 |
from $115 | 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 $115 | 10:50 Portland Portland Intl Jetport | 14:55 Chicago O'Hare International | 5h 5m layover 0h 57m - Newark | United Airlines | UA3623 UA2053 |
from $122 | 05:35 Portland Portland Intl Jetport | 09:43 Chicago O'Hare International | 5h 8m layover 1h 5m - Washington D.C. | United Airlines | UA3552 UA1909 |
Flight Schedule Portland (Maine) to Chicago (Illinois)
Departure | Arrival | Flight Details | Flight Duration | Price |
---|---|---|---|---|
06:00 — 07:51
|
06:00 — 07:51
UA1857
United Airlines
Portland — Chicago
|
2h 51m |
Find flight
from$110 |
|
06:14 — 08:05
|
06:14 — 08:05
UA1030
United Airlines
Portland — Chicago
|
2h 51m |
Find flight
from$112 |
|
16:56 — 18:47
|
16:56 — 18:47
UA2466
United Airlines
Portland — Chicago
|
2h 51m |
Find flight
from$110 |
|
18:20 — 20:25
|
18:20 — 20:25
UA5327
United Airlines
Portland — Chicago
|
3h 5m |
Find flight
from$112 |
|
18:20 — 20:25
|
18:20 — 20:25
UA3520
United Airlines
Portland — Chicago
|
3h 5m |
Find flight
from$113 |
|
18:20 — 20:25
|
18:20 — 20:25
UA3695
United Airlines
Portland — Chicago
|
3h 5m |
Find flight
from$113 |
|
18:23 — 20:23
|
18:23 — 20:23
UA4744
United Airlines
Portland — Chicago
|
3h |
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from$110 |
|
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$117 |
|
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$115 |
|
06:00 — 10:39
|
06:00 — 07:29
UA2151
United Airlines
Portland — Newark
1h 31m stop
09:00 — 10:39
UA2337
United Airlines
Newark — Chicago
|
5h 39m including layover |
Find flight
from$105 |
|
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$113 |
|
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$115 |
|
10:05 — 16:52
|
10:05 — 11:55
UA3438
United Airlines
Portland — Washington D.C.
3h 44m stop
15:39 — 16:52
UA1057
United Airlines
Washington D.C. — Chicago
|
7h 47m including layover |
Find flight
from$102 |
|
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$115 |
|
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$115 |
|
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$122 |
|
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$113 |
|
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$115 |
|
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$115 |
|
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$117 |
|
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$115 |
|
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$180 |
|
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$87 |
|
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$88 |
|
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$115 |
|
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$113 |
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 july (from 117 $), september (from 117 $), august (from 135 $).
The most expensive months are june (from 150 $), october (from 147 $), may (from 137 $).
What is the lowest airfare Portland to Chicago?
The cheapest plane ticket found by our users is $87. 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.
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 $ 87 . And the most expensive tickets are offered by United Airlines airline - from $ 593.
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 $110.
- UA - United Airlinesfrom $110Find
Connecting Flights
There are 259 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 $87.
- F9 - Frontier Airlinesfrom $87Find
- SY - Sun Country Airlinesfrom $129Find
- MX - Mexicanafrom $187Find
- UA - United Airlinesfrom $102Find
Airports
You can fly from Portland to Chicago from 1 airports (Portland Intl Jetport).
Portland airports
- Portland Intl Jetport-PWMfrom $87Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
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.
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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.
- from $73Find
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- from $68Find
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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