Cheap Flights from Portland, OR to Chicago, IL from $74

One way Round trip

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On Cheapflightsplus.com you will find 5 direct and 142 connecting flights from Portland to Chicago. You can compare airfare deals from 6 airlines and multiple travel sites from $74, book and save on cheap plane tickets and last minute offers. Also check out PDX-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: $74 (one-way), $127 (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 $74. The fastest direct flight takes 3h 49m and the fastest connecting – 5h 51m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $141 Find flight	07:00 Portland Portland	13:02 Chicago O'Hare International	4h 2m	Alaska Airlines	AS324
from $163 Find flight	23:59 Portland Portland	05:48+1 день Chicago O'Hare International	3h 49m	United Airlines	UA1490
from $211 Find flight	07:00 Portland Portland	12:57 Chicago O'Hare International	3h 57m	United Airlines	UA1693
from $253 Find flight	11:00 Portland Portland	16:58 Chicago O'Hare International	3h 58m	United Airlines	UA1335
from $74 Find flight	12:03 Portland Portland	00:35+1 день Chicago O'Hare International	10h 32m layover 5h 27m - Denver	Frontier Airlines	F91790 F93172
from $76 Find flight	21:26 Portland Portland	10:42+1 день Chicago Midway	11h 16m layover 5h 16m - Phoenix	Frontier Airlines	F93160 F91736
from $84 Find flight	05:00 Portland Portland	14:26 Chicago O'Hare International	7h 26m layover 1h 40m - Las Vegas	Spirit Airlines	NK1722 NK2858
from $96 Find flight	16:30 Portland Portland	04:47+1 день Chicago O'Hare International	10h 17m layover 4h 1m - Las Vegas	Frontier Airlines	F91106 F92146
from $105 Find flight	18:37 Portland Portland	10:55+1 день Chicago O'Hare International	14h 18m layover 9h 15m - Minneapolis	Sun Country Airlines	SY296 SY259
from $125 Find flight	08:00 Portland Portland	16:58 Chicago O'Hare International	6h 58m layover 0h 56m - San Francisco	Alaska Airlines	AS1350 AS598
from $125 Find flight	13:51 Portland Portland	23:47 Chicago O'Hare International	7h 56m layover 2h 58m - Seattle	Alaska Airlines	AS1008 AS538
from $127 Find flight	06:05 Portland Portland	14:03 Chicago O'Hare International	5h 58m layover 0h 47m - Seattle	Alaska Airlines	AS124 AS408
from $127 Find flight	14:00 Portland Portland	23:42 Chicago O'Hare International	7h 42m layover 1h 39m - Las Vegas	Spirit Airlines	NK786 NK184
from $127 Find flight	19:59 Portland Portland	06:10+1 день Chicago O'Hare International	8h 11m layover 2h 18m - Las Vegas	Spirit Airlines	NK152 NK153
from $124 Find flight	19:16 Portland Portland	12:18+1 день Chicago O'Hare International	15h 2m layover 2h 26m - Las Vegas 4h 48m - Houston	Spirit Airlines	NK431 NK532 NK1145
from $165 Find flight	11:50 Portland Portland	23:59 Chicago O'Hare International	10h 9m layover 1h 5m - San Francisco 1h 4m - Seattle	Alaska Airlines	AS128 AS1059 AS538

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on November 21, 2024

Flight Schedule Portland (Oregon) 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
07:00 — 13:02	07:00 — 13:02 AS324 Alaska Airlines Portland — Chicago	4h 2m	Find flight from$141
07:00 — 12:57	07:00 — 12:57 UA1693 United Airlines Portland — Chicago	3h 57m	Find flight from$211
11:00 — 16:58	11:00 — 16:58 UA1335 United Airlines Portland — Chicago	3h 58m	Find flight from$253
23:59 — 05:48 +1 day	23:59 — 05:48 UA1490 United Airlines Portland — Chicago	3h 49m	Find flight from$163
23:59 — 06:00 +1 day	23:59 — 06:00 UA2646 United Airlines Portland — Chicago	4h 1m	Find flight from$181
00:48 — 11:52	06:05 — 09:34 F91790 Frontier Airlines Portland — Denver 4h 6m stop 08:50 — 12:13 F92210 Frontier Airlines Denver — Chicago	9h 4m including layover	Find flight from$76
05:00 — 14:26	05:00 — 07:11 NK1722 Spirit Airlines Portland — Las Vegas 1h 40m stop 08:51 — 14:26 NK2858 Spirit Airlines Las Vegas — Chicago	7h 26m including layover	Find flight from$84
05:00 — 18:18	05:00 — 06:03 AS1032 Alaska Airlines Portland — Seattle 6h 8m stop 12:11 — 18:18 AS410 Alaska Airlines Seattle — Chicago	11h 18m including layover	Find flight from$182
06:00 — 15:50	06:00 — 07:06 AS124 Alaska Airlines Portland — Seattle 2h 40m stop 10:50 — 16:58 AS352 Alaska Airlines Seattle — Chicago	7h 50m including layover	Find flight from$167
06:05 — 14:03	06:05 — 07:08 AS124 Alaska Airlines Portland — Seattle 47m stop 07:55 — 14:03 AS408 Alaska Airlines Seattle — Chicago	5h 58m including layover	Find flight from$127
07:00 — 16:58	07:00 — 08:52 AS3440 Alaska Airlines Portland — San Francisco 1h 54m stop 10:46 — 16:58 AS598 Alaska Airlines San Francisco — Chicago	7h 58m including layover	Find flight from$145
08:00 — 16:58	08:00 — 09:51 AS1350 Alaska Airlines Portland — San Francisco 56m stop 10:40 — 16:59 AS598 Alaska Airlines San Francisco — Chicago	6h 58m including layover	Find flight from$125
08:05 — 23:59	07:00 — 08:06 AS910 Alaska Airlines Portland — Seattle 8h 52m stop 18:06 — 23:59 AS538 Alaska Airlines Seattle — Chicago	13h 54m including layover	Find flight from$161
09:00 — 19:59	09:00 — 10:57 UA336 United Airlines Portland — San Francisco 2h 43m stop 13:40 — 19:59 UA2386 United Airlines San Francisco — Chicago	8h 59m including layover	Find flight from$174
09:31 — 17:59	09:31 — 10:29 AS2181 Alaska Airlines Portland — Seattle 1h 16m stop 11:45 — 17:59 AS352 Alaska Airlines Seattle — Chicago	6h 28m including layover	Find flight from$172
10:16 — 21:52	10:16 — 12:29 NK559 Spirit Airlines Portland — Las Vegas 3h 39m stop 16:08 — 21:52 NK714 Spirit Airlines Las Vegas — Chicago	9h 36m including layover	Find flight from$127
11:49 — 23:47	11:49 — 12:55 AS970 Alaska Airlines Portland — Seattle 4h 59m stop 18:06 — 23:59 AS538 Alaska Airlines Seattle — Chicago	9h 58m including layover	Find flight from$162
12:03 — 00:35 +1 day	12:03 — 15:32 F91790 Frontier Airlines Portland — Denver 5h 27m stop 20:59 — 00:35 F93172 Frontier Airlines Denver — Chicago	10h 32m including layover	Find flight from$74
13:06 — 21:25	12:55 — 16:26 UA616 United Airlines Portland — Denver 1h 18m stop 17:55 — 21:25 UA1898 United Airlines Denver — Chicago	6h 19m including layover	Find flight from$174
13:51 — 23:47	13:45 — 14:51 AS1008 Alaska Airlines Portland — Seattle 2h 58m stop 18:06 — 23:59 AS538 Alaska Airlines Seattle — Chicago	7h 56m including layover	Find flight from$125
14:00 — 23:42	14:00 — 16:16 NK786 Spirit Airlines Portland — Las Vegas 1h 39m stop 17:55 — 23:42 NK184 Spirit Airlines Las Vegas — Chicago	7h 42m including layover	Find flight from$127
14:40 — 16:27 +1 day	14:40 — 16:32 AS2054 Alaska Airlines Portland — San Francisco 17h 28m stop 10:00 — 16:27 AS598 Alaska Airlines San Francisco — Chicago	23h 47m including layover	Find flight from$191
15:00 — 14:40 +1 day	15:00 — 15:59 AS2355 Alaska Airlines Portland — Seattle 16h 26m stop 08:25 — 14:40 AS408 Alaska Airlines Seattle — Chicago	21h 40m including layover	Find flight from$186
16:30 — 06:33 +1 day	10:37 — 12:52 F91106 Frontier Airlines Portland — Las Vegas 6h 1m stop 06:11 — 11:48 F92330 Frontier Airlines Las Vegas — Chicago	12h 3m including layover	Find flight from$77
16:30 — 04:47 +1 day	16:30 — 18:58 F91106 Frontier Airlines Portland — Las Vegas 4h 1m stop 22:59 — 04:47 F92146 Frontier Airlines Las Vegas — Chicago	10h 17m including layover	Find flight from$96
18:37 — 10:55 +1 day	18:18 — 23:33 SY296 Sun Country Airlines Portland — Minneapolis 9h 15m stop 09:47 — 11:35 SY259 Sun Country Airlines Minneapolis — Chicago	14h 18m including layover	Find flight from$105
19:59 — 06:10 +1 day	19:59 — 22:12 NK152 Spirit Airlines Portland — Las Vegas 2h 18m stop 00:30 — 06:10 NK153 Spirit Airlines Las Vegas — Chicago	8h 11m including layover	Find flight from$127
20:22 — 16:27 +1 day	20:22 — 22:13 AS2038 Alaska Airlines Portland — San Francisco 11h 47m stop 10:00 — 16:27 AS598 Alaska Airlines San Francisco — Chicago	18h 5m including layover	Find flight from$186
20:50 — 16:59 +1 day	20:50 — 22:42 AS1295 Alaska Airlines Portland — San Francisco 11h 58m stop 10:40 — 16:59 AS598 Alaska Airlines San Francisco — Chicago	18h 9m including layover	Find flight from$197
21:26 — 10:42 +1 day	21:26 — 01:04 F93160 Frontier Airlines Portland — Phoenix 5h 16m stop 06:20 — 10:42 F91736 Frontier Airlines Phoenix — Chicago	11h 16m including layover	Find flight from$76
21:28 — 05:19 +1 day	21:28 — 22:29 AS2082 Alaska Airlines Portland — Seattle 53m stop 23:22 — 05:19 AS328 Alaska Airlines Seattle — Chicago	5h 51m including layover	Find flight from$167
10:41 — 23:47	10:41 — 12:52 AS3425 Alaska Airlines Portland — Boise 1h 55m stop 14:47 — 15:32 AS1019 Alaska Airlines Boise — Seattle 2h 19m stop 17:51 — 23:47 AS538 Alaska Airlines Seattle — Chicago	11h 6m including layover	Find flight from$204
11:50 — 23:59	11:00 — 12:52 AS128 Alaska Airlines Portland — San Francisco 1h 5m stop 14:43 — 16:59 AS1059 Alaska Airlines San Francisco — Seattle 1h 4m stop 18:00 — 23:59 AS538 Alaska Airlines Seattle — Chicago	10h 9m including layover	Find flight from$165
15:05 — 05:53 +1 day	15:05 — 16:54 AS836 Alaska Airlines Portland — San Francisco 56m stop 17:50 — 20:00 AS971 Alaska Airlines San Francisco — Seattle 3h 59m stop 23:59 — 05:53 AS461 Alaska Airlines Seattle — Chicago	12h 48m including layover	Find flight from$190
19:16 — 12:18 +1 day	19:16 — 21:29 NK431 Spirit Airlines Portland — Las Vegas 2h 26m stop 23:55 — 04:50 NK532 Spirit Airlines Las Vegas — Houston 4h 48m stop 09:38 — 12:18 NK1145 Spirit Airlines Houston — Chicago	15h 2m including layover	Find flight from$124

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

*Departure and arrival times - local. Updated on November 21, 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 2816 miles. Time difference between the cities is 2h. Airplanes depart 00:48 to 23:59 from 1 Portland airport and arrive 00:48 to 23:59 to 7 Chicago airports. Average flight time is 3h 58m.

The fastest flight 3h 49m
Average flight time 3h 58m
The earliest flight 00:48
The latest flight 23:59
Distance 1750 ml

The cheapest months to travel to Chicago are november (from 56 $), december (from 74 $), february (from 76 $).

The most expensive months are january (from 77 $), february (from 76 $), december (from 74 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $74. This airfare is for economy class on one-way F91790 flight by Frontier Airlines for December 13, 2024 which leaves Portland in Portland at 12:03 am and arrives at Chicago O'Hare International at 00:35.

Economy class

$74

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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 6 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 60 departures per week at the price of from $ 125 . And the most expensive tickets are offered by Volaris airline - from $ 493.

Direct flights

There are 5 nonstop flights on the route. The fastest direct flight is UA1490 by United Airlines takes 3h 49m and the cheapest is F91790 by Frontier Airlines for $141.

AS - Alaska Airlines

from $141

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UA - United Airlines

from $163

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Connecting Flights

There are 142 flights with layovers on the route. The fastest connecting flight is AS2082 by Alaska Airlines takes 5h 51m and the cheapest is F91790 by Frontier Airlines for $74.

AS - Alaska Airlines

from $125

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F9 - Frontier Airlines

from $74

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SY - Sun Country Airlines

from $105

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Y4 - Volaris

from $409

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UA - United Airlines

from $174

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NK - Spirit Airlines

from $84

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See more connecting flights

Airports

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

Portland airports

Portland-PDX

from $74
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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 6 airlines that use 4 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737-800

from $161

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Boeing 737-900

from $162

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Airbus A319

from $221

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Embraer 175 (short wing)

from $251

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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 $56

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Portland — Cleveland

from $74

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Portland — Las Vegas

from $71

Find
Portland — Minneapolis

from $55

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Portland — New York

from $79

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Portland — Palm Springs

from $68

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Portland — Columbus

from $74

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Portland — Atlanta

from $70

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Portland — Indianapolis

from $76

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Portland — Houston

from $79

Find

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 $70

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Portland — Dublin

from $78

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Portland — Guadalajara

from $73

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Portland — Vancouver

from $61

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Portland — Mexico City

from $55

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Portland — Berlin

from $69

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Portland — San Jose

from $79

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Portland — Toronto

from $79

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Portland — London

from $68

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Portland — Paris

from $69

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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.
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.
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