American Airlines Portland to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

Cheapflightsplus.com will find cheap American Airlines flights from Portland to Chicago. Compare airline ticket prices and book air tickets starting from $65 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of American Airlines, arrivals and departure details below.

Find Cheap Airfare Portland (ME) — Chicago (IL) by American Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in may: one-way - $65, two-way – $111.

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Cheap Flights from Portland to Chicago by American Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by American Airlines, their prices start from $65. The fastest nonstop flight takes 2h 40m. The fastest connecting flight — 4h 34m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $65 Find flight	12:32 pm Portland Portland Intl Jetport	2:12 pm Chicago O'Hare International	2h 40m	American Airlines	AA4133
from $65 Find flight	6:53 am Portland Portland Intl Jetport	8:34 am Chicago O'Hare International	2h 41m	American Airlines	AA3439
from $121 Find flight	1:45 pm Portland Portland Intl Jetport	3:35 pm Chicago O'Hare International	2h 50m	American Airlines	AA3892
from $67 Find flight	6:00 am Portland Portland Intl Jetport	12:13 pm Chicago O'Hare International	7h 13m layover 2h 52m - Charlotte	American Airlines	AA752 AA2408
from $68 Find flight	2:16 pm Portland Portland Intl Jetport	6:36 pm Chicago O'Hare International	5h 20m layover 1h 0m - Washington D.C.	American Airlines	AA4739 AA1486
from $68 Find flight	3:11 pm Portland Portland Intl Jetport	7:41 pm Chicago O'Hare International	5h 30m layover 1h 8m - Philadelphia	American Airlines	AA4353 AA490
from $68 Find flight	7:51 am Portland Portland Intl Jetport	12:32 pm Chicago O'Hare International	5h 41m layover 1h 31m - Philadelphia	American Airlines	AA4568 AA1755
from $68 Find flight	2:16 pm Portland Portland Intl Jetport	7:40 pm Chicago O'Hare International	6h 24m layover 2h 10m - Washington D.C.	American Airlines	AA4739 AA158
from $68 Find flight	7:51 am Portland Portland Intl Jetport	2:05 pm Chicago O'Hare International	7h 14m layover 3h 11m - Philadelphia	American Airlines	AA4568 AA2608
from $83 Find flight	2:26 pm Portland Portland Intl Jetport	7:11 pm Chicago O'Hare International	5h 45m layover 1h 15m - Charlotte	American Airlines	AA591 AA2488
from $106 Find flight	12:46 pm Portland Portland Intl Jetport	5:18 pm Chicago O'Hare International	5h 32m layover 1h 5m - Charlotte	American Airlines	AA591 AA1017
from $107 Find flight	6:10 pm Portland Portland Intl Jetport	10:15 pm Chicago O'Hare International	5h 5m layover 0h 55m - New York	American Airlines	AA3693 AA196

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/25/2024

American Airlines Flight Schedule Portland to Chicago

Below is a detailed 2024 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.

Departure	Flight Details	Flight Time	Price
12:32 pm — 2:12 pm	12:32 pm — 2:12 pm AA4133 American Airlines Portland — Chicago	2h 40m	Find flight from$65
1:45 pm — 3:35 pm	1:45 pm — 3:35 pm AA3892 American Airlines Portland — Chicago	2h 50m	Find flight from$121
6:53 am — 8:34 am	6:53 am — 8:34 am AA3439 American Airlines Portland — Chicago	2h 41m	Find flight from$65
7:02 am — 8:55 am	7:02 am — 8:55 am AA3639 American Airlines Portland — Chicago	2h 53m	Find flight from$348
12:46 pm — 5:18 pm	12:46 pm — 3:15 pm AA591 American Airlines Portland — Charlotte 1h 5m stop 4:20 pm — 5:18 pm AA1017 American Airlines Charlotte — Chicago	5h 32m including layover	Find flight from$106
1:18 pm — 7:41 pm	1:18 pm — 2:56 pm AA4660 American Airlines Portland — Philadelphia 3h 4m stop 6:00 pm — 7:41 pm AA490 American Airlines Philadelphia — Chicago	7h 23m including layover	Find flight from$152
2:16 pm — 7:40 pm	2:16 pm — 4:10 pm AA4739 American Airlines Portland — Washington D.C. 2h 10m stop 6:20 pm — 7:40 pm AA158 American Airlines Washington D.C. — Chicago	6h 24m including layover	Find flight from$68
2:16 pm — 6:36 pm	2:16 pm — 4:10 pm AA4739 American Airlines Portland — Washington D.C. 1h stop 5:10 pm — 6:36 pm AA1486 American Airlines Washington D.C. — Chicago	5h 20m including layover	Find flight from$68
3:11 pm — 7:41 pm	3:11 pm — 4:52 pm AA4353 American Airlines Portland — Philadelphia 1h 8m stop 6:00 pm — 7:41 pm AA490 American Airlines Philadelphia — Chicago	5h 30m including layover	Find flight from$68
4:16 pm — 11:56 pm	4:16 pm — 7:00 pm AA5602 American Airlines Portland — Charlotte 3h 55m stop 10:55 pm — 11:56 pm AA483 American Airlines Charlotte — Chicago	8h 40m including layover	Find flight from$353
4:16 pm — 9:16 pm	4:16 pm — 7:00 pm AA5602 American Airlines Portland — Charlotte 1h 1m stop 8:01 pm — 9:16 pm AA2760 American Airlines Charlotte — Chicago	6h including layover	Find flight from$353
5:55 pm — 10:02 pm	5:55 pm — 7:18 pm AA3693 American Airlines Portland — New York 1h 11m stop 8:29 pm — 10:02 pm AA196 American Airlines New York — Chicago	5h 7m including layover	Find flight from$125
5:55 pm — 10:58 pm	5:55 pm — 7:18 pm AA3693 American Airlines Portland — New York 2h 12m stop 9:30 pm — 10:58 pm AA2461 American Airlines New York — Chicago	6h 3m including layover	Find flight from$125
6:00 am — 2:14 pm	6:00 am — 8:18 am AA752 American Airlines Portland — Charlotte 4h 48m stop 1:06 pm — 2:14 pm AA1650 American Airlines Charlotte — Chicago	9h 14m including layover	Find flight from$67
7:51 am — 12:32 pm	7:51 am — 9:29 am AA4568 American Airlines Portland — Philadelphia 1h 31m stop 11:00 am — 12:32 pm AA1755 American Airlines Philadelphia — Chicago	5h 41m including layover	Find flight from$68
7:51 am — 2:05 pm	7:51 am — 9:29 am AA4568 American Airlines Portland — Philadelphia 3h 11m stop 12:40 pm — 2:05 pm AA2608 American Airlines Philadelphia — Chicago	7h 14m including layover	Find flight from$68
8:10 am — 3:04 pm	8:10 am — 9:36 am AA3549 American Airlines Portland — New York 3h 54m stop 1:30 pm — 3:04 pm AA30 American Airlines New York — Chicago	7h 54m including layover	Find flight from$126
8:40 am — 3:15 pm	8:40 am — 10:06 am AA3549 American Airlines Portland — New York 3h 24m stop 1:30 pm — 3:15 pm AA30 American Airlines New York — Chicago	7h 35m including layover	Find flight from$107
10:40 am — 4:25 pm	10:40 am — 12:16 pm AA4867 American Airlines Portland — Philadelphia 38m stop 12:54 pm — 2:40 pm AA5379 American Airlines Philadelphia — Covington 1h 20m stop 4:00 pm — 4:25 pm AA3096 American Airlines Covington — Chicago	6h 45m including layover	Find flight from$283
10:45 am — 5:29 pm	10:45 am — 12:23 pm AA4867 American Airlines Portland — Philadelphia 1h 7m stop 1:30 pm — 3:20 pm AA528 American Airlines Philadelphia — Minneapolis 30m stop 3:50 pm — 5:29 pm AA122 American Airlines Minneapolis — Chicago	7h 44m including layover	Find flight from$316
3:11 pm — 12:22 pm +1 day	3:11 pm — 4:52 pm AA4353 American Airlines Portland — Philadelphia 1h 43m stop 6:35 pm — 8:25 pm AA4711 American Airlines Philadelphia — Columbus 15h 35m stop 12:00 pm — 12:22 pm AA3338 American Airlines Columbus — Chicago	22h 11m including layover	Find flight from$134

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 04/25/2024

Flight Information

There are 4 flights by American Airlines from Portland to Chicago every week with departures from Portland Intl Jetport. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:40 am to 8:40 am. Nonstop flight is 2h 40m. The time difference between Portland and Chicago is 1h.

The fastest flight 2h 40m
Average flight time 2h 46m
The earliest flight 10:40 am
The latest flight 8:40 am
Distance 886 ml

The cheapest flight by American Airlines that our users were able to find is $65. This airfare is economy class on one-way AA4133 flight for August 25, 2020 leaving Portland Intl Jetport in Portland at 12:32 pm, it includes all taxes and additional fees.

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American Airlines Airplanes on the Route

List of the most popular American Airlines airplanes flying from Portland to Chicago:

Embraer 175

from $65

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Airbus A319

from $67

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Embraer RJ145

from $68

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Embraer RJ140

from $107

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Embraer 175 (short wing)

from $120

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Canadair Regional Jet 700

from $121

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Canadair JET

from $126

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Canadair Regional Jet

from $314

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Canadair 900

from $353

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Canadair Regional Jet 900

from $353

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Other Popular Airlines on the Route

Besides American Airlines there are other 3 airline carriers between Portland and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Portland to Chicago.

Nonstop flights

There are 6 direct flights every day from Portland. Airlines and fares are below:

UA - United Airlines

from $52

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Connecting Flights

List of flights with layovers (1 and more stops):

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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See more connecting flights

How to book an air ticket yourself?

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