Cheap Flights from Portland, ME to Chicago, IL from $90

Return flight: Chicago – Portland

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

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: $90 (one-way), $154 (round-trip).
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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 Arrival Flight Details Flight Duration Price
09:30 — 11:29
09:30 — 11:29 UA5570 United Airlines
Portland — Chicago
2h 59m
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from$329
09:30 — 11:29
09:30 — 11:29 UA3635 United Airlines
Portland — Chicago
2h 59m
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from$375
16:10 — 18:24
16:10 — 18:24 UA5517 United Airlines
Portland — Chicago
3h 14m
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from$240
16:15 — 18:27
16:15 — 18:27 UA3547 United Airlines
Portland — Chicago
3h 12m
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from$239
16:20 — 18:26
16:20 — 18:26 UA3651 United Airlines
Portland — Chicago
3h 6m
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from$243
16:30 — 18:42
16:30 — 18:42 UA3678 United Airlines
Portland — Chicago
3h 12m
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
*Departure and arrival times - local. Updated on April 4, 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 05:00 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.

Economy class
$90
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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 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 Airlines
    from $239
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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 Airlines
    from $298
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  • F9 - Frontier Airlines
    from $90
    Find
  • DL - Delta Air Lines Inc.
    from $256
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  • MX - Mexicana
    from $189
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  • UA - United Airlines
    from $205
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See more connecting flights

Airports

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

Portland airports

  • Portland Intl Jetport-PWM
    from $90
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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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How to book a plane ticket yourself?

How to book an air 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.

    To find a plane ticket, please select dates.

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