Cheap Flights from Portland, ME to Chicago, IL from $90
On Cheapflightsplus.com you will find 6 direct and 489 connecting flights from Portland to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $90, 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 $239 | 16:15 Portland Portland Intl Jetport | 18:27 Chicago O'Hare International | 3h 12m | United Airlines | UA3547 |
from $240 | 16:10 Portland Portland Intl Jetport | 18:24 Chicago O'Hare International | 3h 14m | United Airlines | UA5517 |
from $243 | 16:20 Portland Portland Intl Jetport | 18:26 Chicago O'Hare International | 3h 6m | United Airlines | UA3651 |
from $329 | 09:30 Portland Portland Intl Jetport | 11:29 Chicago O'Hare International | 2h 59m | United Airlines | UA5570 |
from $90 | 12:23 Portland Portland Intl Jetport | 18:48 Chicago Midway | 7h 25m layover 1h 9m - Tampa | Frontier Airlines | F92245 F91185 |
from $97 | 19:06 Portland Portland Intl Jetport | 09:52+1 день Chicago O'Hare International | 15h 46m layover 8h 47m - Orlando | Frontier Airlines | F92621 F93043 |
from $97 | 19:06 Portland Portland Intl Jetport | 10:28+1 день Chicago Midway | 16h 22m layover 9h 43m - Orlando | Frontier Airlines | F92621 F91457 |
from $205 | 06:00 Portland Portland Intl Jetport | 22:06 Chicago O'Hare International | 17h 6m layover 12h 55m - New York | United Airlines | UA2455 NK3386 |
from $226 | 12:01 Portland Portland Intl Jetport | 20:58 Chicago O'Hare International | 9h 57m layover 3h 20m - Orlando | Mexicana | MX739 NK1842 |
from $244 | 16:13 Portland Portland Intl Jetport | 08:03+1 день Chicago O'Hare International | 16h 50m layover 12h 26m - New York | United Airlines | UA3620 UA2389 |
from $249 | 13:43 Portland Portland Intl Jetport | 18:34 Chicago O'Hare International | 5h 51m layover 1h 35m - Washington D.C. | United Airlines | UA4291 UA2497 |
from $249 | 17:14 Portland Portland Intl Jetport | 23:00 Chicago O'Hare International | 6h 46m layover 2h 29m - Newark | United Airlines | UA3620 UA1308 |
from $250 | 19:27 Portland Portland Intl Jetport | 23:20 Chicago O'Hare International | 4h 53m layover 0h 51m - Washington D.C. | United Airlines | UA3582 UA1738 |
from $250 | 11:24 Portland Portland Intl Jetport | 15:54 Chicago O'Hare International | 5h 30m layover 1h 20m - Newark | United Airlines | UA3623 UA323 |
from $189 | 11:54 Portland Portland Intl Jetport | 00:24+1 день Chicago O'Hare International | 13h 30m layover 2h 11m - Tampa 2h 38m - Houston | Mexicana | MX139 NK3127 NK962 |
from $250 | 18:14 Portland Portland Intl Jetport | 15:16+1 день Chicago O'Hare International | 22h 2m layover 6h 38m - Tampa 6h 16m - Miami | Mexicana | MX101 NK2055 NK2 |
Flight Schedule Portland (Maine) to Chicago (Illinois)
Departure | Arrival | Flight Details | Flight Duration | Price |
---|---|---|---|---|
09:30 — 11:29
|
09:30 — 11:29
UA5570
United Airlines
Portland — Chicago
|
2h 59m |
Find flight
from$329 |
|
09:30 — 11:29
|
09:30 — 11:29
UA3635
United Airlines
Portland — Chicago
|
2h 59m |
Find flight
from$375 |
|
16:10 — 18:24
|
16:10 — 18:24
UA5517
United Airlines
Portland — Chicago
|
3h 14m |
Find flight
from$240 |
|
16:15 — 18:27
|
16:15 — 18:27
UA3547
United Airlines
Portland — Chicago
|
3h 12m |
Find flight
from$239 |
|
16:20 — 18:26
|
16:20 — 18:26
UA3651
United Airlines
Portland — Chicago
|
3h 6m |
Find flight
from$243 |
|
16:30 — 18:42
|
16:30 — 18:42
UA3678
United Airlines
Portland — Chicago
|
3h 12m |
Find flight
from$329 |
|
05:00 — 22:06
|
05:00 — 06:29
DL5610
Delta Air Lines Inc.
Portland — New York
14h stop
20:29 — 22:06
NK3386
Spirit Airlines
New York — Chicago
|
18h 6m including layover |
Find flight
from$256 |
|
06:00 — 22:06
|
06:00 — 07:34
UA2455
United Airlines
Portland — New York
12h 55m stop
20:29 — 22:06
NK3386
Spirit Airlines
New York — Chicago
|
17h 6m including layover |
Find flight
from$205 |
|
06:00 — 13:44
|
06:00 — 07:34
UA2455
United Airlines
Portland — Newark
4h 34m stop
12:08 — 13:44
NK329
Spirit Airlines
Newark — Chicago
|
8h 44m including layover |
Find flight
from$218 |
|
11:24 — 15:54
|
11:24 — 13:00
UA3623
United Airlines
Portland — Newark
1h 20m stop
14:20 — 15:54
UA323
United Airlines
Newark — Chicago
|
5h 30m including layover |
Find flight
from$250 |
|
12:01 — 20:58
|
12:01 — 15:34
MX739
Mexicana
Portland — Orlando
3h 20m stop
18:54 — 20:58
NK1842
Spirit Airlines
Orlando — Chicago
|
9h 57m including layover |
Find flight
from$226 |
|
12:23 — 18:48
|
12:23 — 15:56
F92245
Frontier Airlines
Portland — Tampa
1h 9m stop
17:05 — 18:48
F91185
Frontier Airlines
Tampa — Chicago
|
7h 25m including layover |
Find flight
from$90 |
|
13:38 — 18:55
|
13:38 — 15:45
UA4313
United Airlines
Portland — Washington D.C.
1h 51m stop
17:36 — 18:55
UA1117
United Airlines
Washington D.C. — Chicago
|
6h 17m including layover |
Find flight
from$251 |
|
13:43 — 18:34
|
13:43 — 15:45
UA4291
United Airlines
Portland — Washington D.C.
1h 35m stop
17:20 — 18:34
UA2497
United Airlines
Washington D.C. — Chicago
|
5h 51m including layover |
Find flight
from$249 |
|
14:55 — 10:05
+1 day
|
14:55 — 16:25
DL5836
Delta Air Lines Inc.
Portland — New York
16h 10m stop
08:35 — 10:05
NK779
Spirit Airlines
New York — Chicago
|
20h 10m including layover |
Find flight
from$256 |
|
14:55 — 12:52
+1 day
|
14:55 — 16:25
DL5836
Delta Air Lines Inc.
Portland — Newark
18h 48m stop
11:13 — 12:52
NK329
Spirit Airlines
Newark — Chicago
|
22h 57m including layover |
Find flight
from$267 |
|
15:55 — 20:17
|
15:55 — 17:42
UA3620
United Airlines
Portland — Newark
48m stop
18:30 — 20:17
UA254
United Airlines
Newark — Chicago
|
5h 22m including layover |
Find flight
from$254 |
|
17:14 — 23:00
|
16:13 — 17:59
UA3620
United Airlines
Portland — Newark
2h 29m stop
21:29 — 23:00
UA1308
United Airlines
Newark — Chicago
|
6h 46m including layover |
Find flight
from$249 |
|
18:05 — 22:57
|
18:05 — 19:57
UA4507
United Airlines
Portland — Newark
1h 28m stop
21:25 — 22:57
UA1308
United Airlines
Newark — Chicago
|
5h 52m including layover |
Find flight
from$251 |
|
19:06 — 09:52
+1 day
|
19:06 — 22:43
F92621
Frontier Airlines
Portland — Orlando
8h 47m stop
07:30 — 09:52
F93043
Frontier Airlines
Orlando — Chicago
|
15h 46m including layover |
Find flight
from$97 |
|
19:06 — 10:28
+1 day
|
19:06 — 22:43
F92621
Frontier Airlines
Portland — Orlando
9h 43m stop
08:26 — 10:28
F91457
Frontier Airlines
Orlando — Chicago
|
16h 22m including layover |
Find flight
from$97 |
|
11:54 — 00:24
+1 day
|
11:54 — 15:24
MX139
Mexicana
Portland — Tampa
2h 11m stop
17:35 — 19:09
NK3127
Spirit Airlines
Tampa — Houston
2h 38m stop
21:47 — 00:24
NK962
Spirit Airlines
Houston — Chicago
|
13h 30m including layover |
Find flight
from$189 |
|
18:14 — 15:16
+1 day
|
18:14 — 22:58
MX101
Mexicana
Portland — Tampa
6h 38m stop
05:36 — 06:40
NK2055
Spirit Airlines
Tampa — Miami
6h 16m stop
12:56 — 15:16
NK2
Spirit Airlines
Miami — Chicago
|
22h 2m including layover |
Find flight
from$250 |
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 05:00 to 19:27 from 1 Portland airport and arrive 05:00 to 19:27 to 7 Chicago airports. Average flight time is 3h 9m.
- The fastest flight 2h 59m
- Average flight time 3h 9m
- The earliest flight 05:00
- The latest flight 19:27
- Distance 886 ml
The cheapest months to travel to Chicago are february (from 90 $), january (from 97 $), december (from 189 $).
The most expensive months are november (from 205 $), december (from 189 $), january (from 97 $).
What is the lowest airfare Portland to Chicago?
The cheapest plane ticket found by our users is $90. This airfare is for economy class on one-way F92245 flight by Frontier Airlines for February 21, 2025 which leaves Portland Intl Jetport in Portland at 12:23 am and arrives at Chicago Midway at 18:48.
Popular Airlines on the Route
The flight Portland — Chicago is served by 5 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 76 departures per week at the price of from $ 298 . And the most expensive tickets are offered by United Airlines airline - from $ 887.
Direct flights
There are 6 nonstop flights on the route. The fastest direct flight is UA5570 by United Airlines takes 2h 59m and the cheapest is F92245 by Frontier Airlines for $239.
- UA - United Airlinesfrom $239Find
Connecting Flights
There are 489 flights with layovers on the route. The fastest connecting flight is DL3632 by Delta Air Lines Inc. takes 4h 27m and the cheapest is F92245 by Frontier Airlines for $90.
- AA - American Airlinesfrom $298Find
- F9 - Frontier Airlinesfrom $90Find
- DL - Delta Air Lines Inc.from $256Find
- MX - Mexicanafrom $189Find
- UA - United Airlinesfrom $205Find
Airports
You can fly from Portland to Chicago from 1 airports (Portland Intl Jetport).
Portland airports
- Portland Intl Jetport-PWMfrom $90Find
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 5 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.
- Boeing 737 MAX 8from $205Find
- Canadair Regional Jet 900from $256Find
- Embraer 175 (short wing)from $256Find
- Airbus A319from $329Find
- Canadair Regional Jet 700from $334Find
- Airbus A321from $344Find
- Boeing 737-100/200from $363Find
- Canadair 900from $364Find
- Embraer 170from $404Find
- Embraer 175from $533Find
Top Domestic Destinations from Portland
You may also consider searching for discounted plane tickets to some other popular places from Portland within United States.
- from $74Find
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- from $68Find
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- from $64Find
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
- from $75Find
- from $59Find
- 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»
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- 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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