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

One way Round trip

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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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Best Flights from Portland to Chicago Today

Take a look at the list of non stop flights and flights with layovers from Portland to Chicago with the lowest price of $52. The fastest direct flight takes 2h 38m and the fastest connecting – 4h 20m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $52 Find flight	06:15 Portland Portland Intl Jetport	08:11 Chicago O'Hare International	2h 56m	United Airlines	UA3642
from $52 Find flight	16:45 Portland Portland Intl Jetport	18:23 Chicago O'Hare International	2h 38m	United Airlines	UA5539
from $65 Find flight	06:53 Portland Portland Intl Jetport	08:34 Chicago O'Hare International	2h 41m	American Airlines	AA3439
from $65 Find flight	12:32 Portland Portland Intl Jetport	14:12 Chicago O'Hare International	2h 40m	American Airlines	AA4133
from $67 Find flight	06:00 Portland Portland Intl Jetport	12:13 Chicago O'Hare International	7h 13m layover 2h 52m - Charlotte	American Airlines	AA752 AA2408
from $68 Find flight	14:16 Portland Portland Intl Jetport	18:36 Chicago O'Hare International	5h 20m layover 1h 0m - Washington D.C.	American Airlines	AA4739 AA1486
from $68 Find flight	15:11 Portland Portland Intl Jetport	19:41 Chicago O'Hare International	5h 30m layover 1h 8m - Philadelphia	American Airlines	AA4353 AA490
from $68 Find flight	07:51 Portland Portland Intl Jetport	12:32 Chicago O'Hare International	5h 41m layover 1h 31m - Philadelphia	American Airlines	AA4568 AA1755
from $68 Find flight	14:16 Portland Portland Intl Jetport	19:40 Chicago O'Hare International	6h 24m layover 2h 10m - Washington D.C.	American Airlines	AA4739 AA158
from $68 Find flight	07:51 Portland Portland Intl Jetport	14:05 Chicago O'Hare International	7h 14m layover 3h 11m - Philadelphia	American Airlines	AA4568 AA2608
from $83 Find flight	14:26 Portland Portland Intl Jetport	19:11 Chicago O'Hare International	5h 45m layover 1h 15m - Charlotte	American Airlines	AA591 AA2488
from $88 Find flight	17:55 Portland Portland Intl Jetport	23:15 Chicago O'Hare International	6h 20m layover 1h 41m - Atlanta	Delta Air Lines Inc.	DL466 DL1323

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 19, 2024

Flight Schedule Portland (Maine) to Chicago (Illinois)

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	Flight Details	Flight Duration	Price
06:15 — 08:11	06:15 — 08:11 UA3642 United Airlines Portland — Chicago	2h 56m	Find flight from$52
06:53 — 08:34	06:53 — 08:34 AA3439 American Airlines Portland — Chicago	2h 41m	Find flight from$65
12:32 — 14:12	12:32 — 14:12 AA4133 American Airlines Portland — Chicago	2h 40m	Find flight from$65
16:45 — 18:23	16:45 — 18:23 UA5539 United Airlines Portland — Chicago	2h 38m	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Find flight 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	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times - local. Updated on April 19, 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.

AA - American Airlines

from $65

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UA - United Airlines

from $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.

AA - American Airlines

from $67

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DL - Delta Air Lines Inc.

from $88

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UA - United Airlines

from $100

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WN - Southwest Airlines

from $93

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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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Airplanes

There are flights to Chicago from Portland by 4 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Embraer 175 (winglets)

from $52

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Embraer 175

from $65

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Airbus A319

from $67

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Embraer RJ145

from $68

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Airbus A320-100/200

from $88

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Bombardier CRJ 900

from $92

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Canadair Regional Jet 700

from $100

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Embraer RJ140

from $107

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Embraer 175 (short wing)

from $120

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Embraer 170

from $146

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Top Domestic Destinations from Portland

You may also consider searching for discounted plane tickets to some other popular places from Portland within United States.

Portland — Phoenix

from $69

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Portland — Cleveland

from $60

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Portland — Las Vegas

from $74

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Portland — Minneapolis

from $67

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Portland — New York

from $60

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Portland — Palm Springs

from $67

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Portland — Atlanta

from $64

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Portland — Columbus

from $61

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Portland — Houston

from $59

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Portland — Indianapolis

from $57

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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.

Portland — Frankfurt

from $54

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Portland — Dublin

from $68

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Portland — Guadalajara

from $68

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Portland — San Jose

from $58

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Portland — Vancouver

from $73

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Portland — Mexico City

from $58

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Portland — Berlin

from $60

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Portland — Toronto

from $71

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Portland — London

from $78

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Portland — Paris

from $80

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All flights from Portland | All flights to Chicago

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.
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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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