Cheap Flights from Portland, ME to Chicago, IL from $76

Return flight: Chicago – Portland

On Cheapflightsplus.com you will find 9 direct and 352 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $76, 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: $76 (one-way), $130 (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
06:00 — 07:53
06:00 — 07:53 UA1834 United Airlines
Portland — Chicago
2h 53m
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from$97
06:14 — 08:05
06:14 — 08:05 UA1030 United Airlines
Portland — Chicago
2h 51m
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from$111
11:43 — 13:46
11:43 — 13:46 UA5697 United Airlines
Portland — Chicago
3h 3m
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from$97
16:43 — 18:40
16:43 — 18:40 UA1564 United Airlines
Portland — Chicago
2h 57m
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from$97
16:56 — 18:47
16:56 — 18:47 UA2466 United Airlines
Portland — Chicago
2h 51m
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from$111
18:20 — 20:25
18:20 — 20:25 UA5327 United Airlines
Portland — Chicago
3h 5m
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from$111
18:20 — 20:25
18:20 — 20:25 UA3520 United Airlines
Portland — Chicago
3h 5m
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from$111
18:20 — 20:25
18:20 — 20:25 UA3695 United Airlines
Portland — Chicago
3h 5m
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from$111
18:23 — 20:23
18:23 — 20:23 UA4744 United Airlines
Portland — Chicago
3h
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from$111
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
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from$115
05:35 — 09:43
05:35 — 07:25 UA3552 United Airlines
Portland — Washington D.C.
1h 5m stop
08:30 — 09:43 UA1909 United Airlines
Washington D.C. — Chicago
5h 8m
including layover
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from$120
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
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from$103
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
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from$114
08:00 — 14:55
08:00 — 09:31 UA3424 United Airlines
Portland — Newark
3h 49m stop
13:20 — 14:55 UA2053 United Airlines
Newark — Chicago
7h 55m
including layover
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from$115
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
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from$102
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
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from$101
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
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from$114
11:50 — 23:29
11:50 — 15:14 MX739 Mexicana
Portland — Orlando
6h 11m stop
21:25 — 23:29 NK2190 Spirit Airlines
Orlando — Chicago
12h 39m
including layover
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from$182
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
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from$101
12:15 — 16:48
12:15 — 14:29 UA4820 United Airlines
Portland — Washington D.C.
1h 6m stop
15:35 — 16:48 UA1057 United Airlines
Washington D.C. — Chicago
5h 33m
including layover
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from$102
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
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from$102
14:14 — 18:25
14:08 — 16:19 UA3624 United Airlines
Portland — Washington D.C.
58m stop
17:18 — 18:45 UA2497 United Airlines
Washington D.C. — Chicago
5h 11m
including layover
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from$114
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
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from$114
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
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from$115
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
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from$76
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
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from$81
18:58 — 15:06
+1 day
18:58 — 22:30 F92621 Frontier Airlines
Portland — Orlando
14h 34m stop
13:10 — 15:06 F93853 Frontier Airlines
Orlando — Chicago
21h 8m
including layover
Find flight
from$87
18:58 — 15:27
+1 day
18:58 — 22:30 F92621 Frontier Airlines
Portland — Orlando
14h 30m stop
13:06 — 15:27 F93043 Frontier Airlines
Orlando — Chicago
21h 29m
including layover
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from$87
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
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from$114
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$101
*Departure and arrival times - local. Updated on May 22, 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 may (from 102 $), july (from 116 $), august (from 133 $).

The most expensive months are june (from 148 $), august (from 133 $), july (from 116 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $76. 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
$76
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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 $ 76 . And the most expensive tickets are offered by United Airlines airline - from $ 627.

Direct flights

There are 9 nonstop flights on the route. The fastest direct flight is UA1030 by United Airlines takes 2h 51m and the cheapest is F91929 by Frontier Airlines for $97.

  • UA - United Airlines
    from $97
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Connecting Flights

There are 352 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 $76.

  • F9 - Frontier Airlines
    from $76
    Find
  • SY - Sun Country Airlines
    from $122
    Find
  • MX - Mexicana
    from $181
    Find
  • UA - United Airlines
    from $101
    Find
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 $76
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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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