Cheap Flights from Portland, ME to Chicago, IL from $98

One way Round trip

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On Cheapflightsplus.com you will find 6 direct and 489 connecting flights from Portland to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $98, 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: $98 (one-way), $168 (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 $98. The fastest direct flight takes 2h 59m and the fastest connecting – 4h 27m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $260 Find flight	16:15 Portland Portland Intl Jetport	18:27 Chicago O'Hare International	3h 12m	United Airlines	UA3547
from $260 Find flight	16:10 Portland Portland Intl Jetport	18:24 Chicago O'Hare International	3h 14m	United Airlines	UA5517
from $264 Find flight	16:20 Portland Portland Intl Jetport	18:26 Chicago O'Hare International	3h 6m	United Airlines	UA3651
from $357 Find flight	09:30 Portland Portland Intl Jetport	11:29 Chicago O'Hare International	2h 59m	United Airlines	UA5570
from $98 Find flight	12:23 Portland Portland Intl Jetport	18:48 Chicago Midway	7h 25m layover 1h 9m - Tampa	Frontier Airlines	F92245 F91185
from $105 Find flight	19:06 Portland Portland Intl Jetport	09:52+1 день Chicago O'Hare International	15h 46m layover 8h 47m - Orlando	Frontier Airlines	F92621 F93043
from $105 Find flight	19:06 Portland Portland Intl Jetport	10:28+1 день Chicago Midway	16h 22m layover 9h 43m - Orlando	Frontier Airlines	F92621 F91457
from $223 Find flight	06:00 Portland Portland Intl Jetport	22:06 Chicago O'Hare International	17h 6m layover 12h 55m - New York	United Airlines	UA2455 NK3386
from $245 Find flight	12:01 Portland Portland Intl Jetport	20:58 Chicago O'Hare International	9h 57m layover 3h 20m - Orlando	Mexicana	MX739 NK1842
from $265 Find flight	16:13 Portland Portland Intl Jetport	08:03+1 день Chicago O'Hare International	16h 50m layover 12h 26m - New York	United Airlines	UA3620 UA2389
from $270 Find flight	13:43 Portland Portland Intl Jetport	18:34 Chicago O'Hare International	5h 51m layover 1h 35m - Washington D.C.	United Airlines	UA4291 UA2497
from $270 Find flight	17:14 Portland Portland Intl Jetport	23:00 Chicago O'Hare International	6h 46m layover 2h 29m - Newark	United Airlines	UA3620 UA1308
from $271 Find flight	19:27 Portland Portland Intl Jetport	23:20 Chicago O'Hare International	4h 53m layover 0h 51m - Washington D.C.	United Airlines	UA3582 UA1738
from $271 Find flight	11:24 Portland Portland Intl Jetport	15:54 Chicago O'Hare International	5h 30m layover 1h 20m - Newark	United Airlines	UA3623 UA323
from $205 Find flight	11:54 Portland Portland Intl Jetport	00:24+1 день Chicago O'Hare International	13h 30m layover 2h 11m - Tampa 2h 38m - Houston	Mexicana	MX139 NK3127 NK962
from $272 Find flight	18:14 Portland Portland Intl Jetport	15:16+1 день Chicago O'Hare International	22h 2m layover 6h 38m - Tampa 6h 16m - Miami	Mexicana	MX101 NK2055 NK2

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 28, 2025

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
09:30 — 11:29	09:30 — 11:29 UA5570 United Airlines Portland — Chicago	2h 59m	Find flight from$357
09:30 — 11:29	09:30 — 11:29 UA3635 United Airlines Portland — Chicago	2h 59m	Find flight from$407
16:10 — 18:24	16:10 — 18:24 UA5517 United Airlines Portland — Chicago	3h 14m	Find flight from$260
16:15 — 18:27	16:15 — 18:27 UA3547 United Airlines Portland — Chicago	3h 12m	Find flight from$260
16:20 — 18:26	16:20 — 18:26 UA3651 United Airlines Portland — Chicago	3h 6m	Find flight from$264
16:30 — 18:42	16:30 — 18:42 UA3678 United Airlines Portland — Chicago	3h 12m	Find flight from$357
05:00 — 22:06	05:00 — 06:29 DL5610 Delta Air Lines Inc. Portland — New York 14h stop 20:29 — 22:06 NK3386 Spirit Airlines New York — Chicago	18h 6m including layover	Find flight from$278
06:00 — 22:06	06:00 — 07:34 UA2455 United Airlines Portland — New York 12h 55m stop 20:29 — 22:06 NK3386 Spirit Airlines New York — Chicago	17h 6m including layover	Find flight from$223
06:00 — 13:44	06:00 — 07:34 UA2455 United Airlines Portland — Newark 4h 34m stop 12:08 — 13:44 NK329 Spirit Airlines Newark — Chicago	8h 44m including layover	Find flight from$236
11:24 — 15:54	11:24 — 13:00 UA3623 United Airlines Portland — Newark 1h 20m stop 14:20 — 15:54 UA323 United Airlines Newark — Chicago	5h 30m including layover	Find flight from$271
12:01 — 20:58	12:01 — 15:34 MX739 Mexicana Portland — Orlando 3h 20m stop 18:54 — 20:58 NK1842 Spirit Airlines Orlando — Chicago	9h 57m including layover	Find flight from$245
12:23 — 18:48	12:23 — 15:56 F92245 Frontier Airlines Portland — Tampa 1h 9m stop 17:05 — 18:48 F91185 Frontier Airlines Tampa — Chicago	7h 25m including layover	Find flight from$98
13:38 — 18:55	13:38 — 15:45 UA4313 United Airlines Portland — Washington D.C. 1h 51m stop 17:36 — 18:55 UA1117 United Airlines Washington D.C. — Chicago	6h 17m including layover	Find flight from$273
13:43 — 18:34	13:43 — 15:45 UA4291 United Airlines Portland — Washington D.C. 1h 35m stop 17:20 — 18:34 UA2497 United Airlines Washington D.C. — Chicago	5h 51m including layover	Find flight from$270
14:55 — 10:05 +1 day	14:55 — 16:25 DL5836 Delta Air Lines Inc. Portland — New York 16h 10m stop 08:35 — 10:05 NK779 Spirit Airlines New York — Chicago	20h 10m including layover	Find flight from$278
14:55 — 12:52 +1 day	14:55 — 16:25 DL5836 Delta Air Lines Inc. Portland — Newark 18h 48m stop 11:13 — 12:52 NK329 Spirit Airlines Newark — Chicago	22h 57m including layover	Find flight from$290
15:55 — 20:17	15:55 — 17:42 UA3620 United Airlines Portland — Newark 48m stop 18:30 — 20:17 UA254 United Airlines Newark — Chicago	5h 22m including layover	Find flight from$276
17:14 — 23:00	16:13 — 17:59 UA3620 United Airlines Portland — Newark 2h 29m stop 21:29 — 23:00 UA1308 United Airlines Newark — Chicago	6h 46m including layover	Find flight from$270
18:05 — 22:57	18:05 — 19:57 UA4507 United Airlines Portland — Newark 1h 28m stop 21:25 — 22:57 UA1308 United Airlines Newark — Chicago	5h 52m including layover	Find flight from$273
19:06 — 09:52 +1 day	19:06 — 22:43 F92621 Frontier Airlines Portland — Orlando 8h 47m stop 07:30 — 09:52 F93043 Frontier Airlines Orlando — Chicago	15h 46m including layover	Find flight from$105
19:06 — 10:28 +1 day	19:06 — 22:43 F92621 Frontier Airlines Portland — Orlando 9h 43m stop 08:26 — 10:28 F91457 Frontier Airlines Orlando — Chicago	16h 22m including layover	Find flight from$105
11:54 — 00:24 +1 day	11:54 — 15:24 MX139 Mexicana Portland — Tampa 2h 11m stop 17:35 — 19:09 NK3127 Spirit Airlines Tampa — Houston 2h 38m stop 21:47 — 00:24 NK962 Spirit Airlines Houston — Chicago	13h 30m including layover	Find flight from$205
18:14 — 15:16 +1 day	18:14 — 22:58 MX101 Mexicana Portland — Tampa 6h 38m stop 05:36 — 06:40 NK2055 Spirit Airlines Tampa — Miami 6h 16m stop 12:56 — 15:16 NK2 Spirit Airlines Miami — Chicago	22h 2m including layover	Find flight from$272

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

*Departure and arrival times - local. Updated on April 28, 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 05:00 to 19:27 from 1 Portland airport and arrive 05:00 to 19:27 to 7 Chicago airports. Average flight time is 3h 9m.

The fastest flight 2h 59m
Average flight time 3h 9m
The earliest flight 05:00
The latest flight 19:27
Distance 886 ml

The cheapest months to travel to Chicago are february (from 98 $), january (from 105 $), december (from 205 $).

The most expensive months are november (from 223 $), december (from 205 $), january (from 105 $).

What is the lowest airfare Portland to Chicago?

The cheapest plane ticket found by our users is $98. This airfare is for economy class on one-way F92245 flight by Frontier Airlines for February 21, 2025 which leaves Portland Intl Jetport in Portland at 12:23 am and arrives at Chicago Midway at 18:48.

Economy class

$98

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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 5 regular airlines and 1 low-cost airline. Most of the flights on this route are operated by American Airlines - 76 departures per week at the price of from $ 324 . And the most expensive tickets are offered by United Airlines airline - from $ 963.

Direct flights

There are 6 nonstop flights on the route. The fastest direct flight is UA5570 by United Airlines takes 2h 59m and the cheapest is F92245 by Frontier Airlines for $260.

UA - United Airlines

from $260

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Connecting Flights

There are 489 flights with layovers on the route. The fastest connecting flight is DL3632 by Delta Air Lines Inc. takes 4h 27m and the cheapest is F92245 by Frontier Airlines for $98.

AA - American Airlines

from $324

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F9 - Frontier Airlines

from $98

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DL - Delta Air Lines Inc.

from $278

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MX - Mexicana

from $205

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UA - United Airlines

from $223

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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 $98
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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 5 airlines that use 10 aircraft brands. They range from huge modern airplanes to small-sized.

Boeing 737 MAX 8

from $223

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Canadair Regional Jet 900

from $278

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Embraer 175 (short wing)

from $278

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Airbus A319

from $357

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Canadair Regional Jet 700

from $363

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Airbus A321

from $373

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Boeing 737-100/200

from $394

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Canadair 900

from $395

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Embraer 170

from $439

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Embraer 175

from $579

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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 — Las Vegas

from $74

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Portland — Seattle

from $80

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Portland — Chicago

from $60

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Portland — Denver

from $55

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Portland — San Diego

from $68

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Portland — Los Angeles

from $56

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Portland — Sacramento

from $58

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Portland — Austin

from $59

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Portland — Spokane

from $63

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Portland — Atlanta

from $64

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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 — Vancouver

from $73

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Portland — Calgary

from $75

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Portland — Amsterdam

from $59

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Portland — Guadalajara

from $68

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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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