Cheap Flights from Portland, ME to Chicago, IL from $52

Return flight: Chicago – Portland

On Cheapflightsplus.com you will find 4 direct and 95 connecting flights from Portland to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $52, 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: $52 (one-way), $89 (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
06:15 — 08:11
06:15 — 08:11 UA3642 United Airlines
Portland — Chicago
2h 56m
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from$52
06:53 — 08:34
06:53 — 08:34 AA3439 American Airlines
Portland — Chicago
2h 41m
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from$65
12:32 — 14:12
12:32 — 14:12 AA4133 American Airlines
Portland — Chicago
2h 40m
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from$65
16:45 — 18:23
16:45 — 18:23 UA5539 United Airlines
Portland — Chicago
2h 38m
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from$52
07:51 — 12:32
07:51 — 09:29 AA4568 American Airlines
Portland — Philadelphia
1h 31m stop
11:00 — 12:32 AA1755 American Airlines
Philadelphia — Chicago
5h 41m
including layover
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from$68
07:51 — 14:05
07:51 — 09:29 AA4568 American Airlines
Portland — Philadelphia
3h 11m stop
12:40 — 14:05 AA2608 American Airlines
Philadelphia — Chicago
7h 14m
including layover
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from$68
08:40 — 14:00
08:40 — 10:15 WN3364 Southwest Airlines
Portland — Baltimore
2h 50m stop
13:05 — 14:00 WN1007 Southwest Airlines
Baltimore — Chicago
6h 20m
including layover
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from$97
10:30 — 14:00
10:30 — 12:00 WN291 Southwest Airlines
Portland — Baltimore
1h 5m stop
13:05 — 14:00 WN1007 Southwest Airlines
Baltimore — Chicago
4h 30m
including layover
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from$97
12:57 — 19:24
12:57 — 15:02 DL3862 Delta Air Lines Inc.
Portland — Detroit
4h 8m stop
19:10 — 19:24 DL3741 Delta Air Lines Inc.
Detroit — Chicago
7h 27m
including layover
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from$92
13:05 — 16:25
13:05 — 14:40 WN1339 Southwest Airlines
Portland — Baltimore
45m stop
15:25 — 16:25 WN1339 Southwest Airlines
Baltimore — Chicago
4h 20m
including layover
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from$93
14:16 — 18:36
14:16 — 16:10 AA4739 American Airlines
Portland — Washington D.C.
1h stop
17:10 — 18:36 AA1486 American Airlines
Washington D.C. — Chicago
5h 20m
including layover
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from$68
14:16 — 19:40
14:16 — 16:10 AA4739 American Airlines
Portland — Washington D.C.
2h 10m stop
18:20 — 19:40 AA158 American Airlines
Washington D.C. — Chicago
6h 24m
including layover
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from$68
15:11 — 19:41
15:11 — 16:52 AA4353 American Airlines
Portland — Philadelphia
1h 8m stop
18:00 — 19:41 AA490 American Airlines
Philadelphia — Chicago
5h 30m
including layover
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from$68
16:30 — 20:15
16:30 — 18:05 WN1813 Southwest Airlines
Portland — Baltimore
1h 10m stop
19:15 — 20:15 WN986 Southwest Airlines
Baltimore — Chicago
4h 45m
including layover
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from$97
17:55 — 23:15
17:55 — 20:39 DL466 Delta Air Lines Inc.
Portland — Atlanta
1h 41m stop
22:20 — 23:15 DL1323 Delta Air Lines Inc.
Atlanta — Chicago
6h 20m
including layover
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from$88
18:10 — 22:15
18:10 — 19:35 AA3693 American Airlines
Portland — New York
55m stop
20:30 — 22:15 AA196 American Airlines
New York — Chicago
5h 5m
including layover
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from$107
18:10 — 23:15
18:10 — 19:35 AA3693 American Airlines
Portland — New York
1h 55m stop
21:30 — 23:15 AA2461 American Airlines
New York — Chicago
6h 5m
including layover
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from$107
08:10 — 13:09
08:10 — 09:50 UA6161 United Airlines
Portland — Washington D.C.
50m stop
10:40 — 12:09 UA3531 United Airlines
Washington D.C. — Covington
36m stop
12:45 — 13:09 UA3454 United Airlines
Covington — Chicago
5h 59m
including layover
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from$100
10:30 — 23:55
10:30 — 12:00 WN291 Southwest Airlines
Portland — Baltimore
1h 20m stop
13:20 — 15:25 WN1122 Southwest Airlines
Baltimore — Dallas
6h 25m stop
21:50 — 23:55 WN1142 Southwest Airlines
Dallas — Chicago
14h 25m
including layover
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from$108
13:05 — 09:35
+1 day
13:05 — 14:40 WN1339 Southwest Airlines
Portland — Baltimore
2h 25m stop
17:05 — 19:40 WN854 Southwest Airlines
Baltimore — Miami
11h 33m stop
07:13 — 09:35 NK478 Spirit Airlines
Miami — Chicago
21h 30m
including layover
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from$120
15:11 — 07:44
+1 day
15:11 — 16:52 AA4353 American Airlines
Portland — Philadelphia
1h 43m stop
18:35 — 20:25 AA4711 American Airlines
Philadelphia — Columbus
11h stop
07:25 — 07:44 AA3476 American Airlines
Columbus — Chicago
17h 33m
including layover
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from$134
17:55 — 22:00
+1 day
17:55 — 20:39 DL466 Delta Air Lines Inc.
Portland — Atlanta
1h 16m stop
21:55 — 23:19 DL1788 Delta Air Lines Inc.
Atlanta — Minneapolis
21h 6m stop
20:25 — 22:00 WN1316 Southwest Airlines
Minneapolis — Chicago
29h 5m
including layover
Find flight
from$161
*Departure and arrival times - local. Updated on June 18, 2024

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 06:00 to 18:10 from 1 Portland airport and arrive 06:00 to 18:10 to 7 Chicago airports. Average flight time is 2h 41m.

  • The fastest flight 2h 38m
  • Average flight time 2h 41m
  • The earliest flight 06:00
  • The latest flight 18:10
  • Distance 886 ml

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $52. This airfare is for economy class on one-way UA5539 flight by United Airlines for August 26, 2020 which leaves Portland Intl Jetport in Portland at 16:45 am and arrives at Chicago O'Hare International at 18:23.

Economy class
$52
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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 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 42 departures per week at the price of from $ 65 . And the most expensive tickets are offered by Delta Air Lines Inc. airline - from $ 527.

Direct flights

There are 4 nonstop flights on the route. The fastest direct flight is UA5539 by United Airlines takes 2h 38m and the cheapest is UA5539 by United Airlines for $52.

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Connecting Flights

There are 95 flights with layovers on the route. The fastest connecting flight is WN1339 by Southwest Airlines takes 4h 20m and the cheapest is UA5539 by United Airlines for $67.

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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 $52
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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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