Question 1

How long does it take to travel from Portland to Chicago?

Accepted Answer

A one-way nonstop (direct) flight between Portland and Chicago takes around 4.4 hours.

Question 2

What is the flight distance between Portland and Chicago?

Accepted Answer

The flight distance between Portland and Chicago is 2794 km.

Question 3

What airlines offer nonstop (direct) flights between Portland and Chicago?

Accepted Answer

Several carriers operate flights between Portland and Chicago. Airlines offering nonstop (direct) flights include United Airlines, Alaska Airlines.

Question 4

What are the most popular routes to and from Portland?

Accepted Answer

Travelers frequently search for route combinations, such as Portland and London, Guadalajara, Mexico City, Los Angeles, Las Vegas, Phoenix, San Francisco, Oaxaca, Manchester, Edinburgh, Denver, Kailua, New York, Ontario, Calgary, Puerto Escondido, Oaxaca, San Diego, Puerto Vallarta, San José del Cabo, Dallas.

Question 5

What are the most popular routes to and from Chicago?

Accepted Answer

Travelers frequently search for route combinations, such as Chicago and London, Mexico City, New York, Guadalajara, Edinburgh, Dallas, Manchester, Morelia, Atlanta, Los Angeles, Houston, León, Leeds, Orlando, San Francisco, Philadelphia, Tampa, Miami, Monterrey, Birmingham.

Question 6

What airports are near Portland?

Accepted Answer

The main airport in Portland is Portland International. It is also served by Seattle–Tacoma International, Portland International, Eugene, Roberts Field, Kenmore Air Harbor Seaplane Base.

Question 7

What airports are near Chicago?

Accepted Answer

The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, South Bend International, General Mitchell International, Dane County Regional, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard.

Question 8

Which airlines fly between Portland and Chicago?

Accepted Answer

Currently, you can fly between Portland and Chicago with Air Canada, Frontier Airlines, WestJet, Alaska Airlines, United Airlines.

Question 9

When’s the best time to travel between Portland and Chicago?

Accepted Answer

If you don’t have specific dates for your trip between Portland and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.

Question 10

What flights operate between Portland and Chicago?

Accepted Answer

Traveling between Portland and Chicago, you can choose between direct (nonstop) flights or flights with one or more stops. You can select the number of stops on your journey, including an overnight stopover, and the duration of the stopover. What’s more, you can also select where you want to have your stopover. Want to say "Hi" to a friend in another city en route to your destination? Or fancy a quick round of shopping? Go Multi-City or Nomad and add places to your search that you wish to visit.

Question 11

How many airports are there near Portland?

Accepted Answer

There are a number of airports in and around Portland. The main one is Portland International and other nearby airports include Seattle–Tacoma International, Portland International, Eugene, Roberts Field, Kenmore Air Harbor Seaplane Base

Question 12

How many airports are there near Chicago?

Accepted Answer

There are a number of airports in and around Chicago. The main one is O Hare International and other nearby airports include Gerald R. Ford International, South Bend International, General Mitchell International, Dane County Regional, Fort Wayne International, Quad City International, General Wayne A. Downing Peoria International, Central Illinois Regional, Muskegon County, University of Illinois Willard.

Question 13

What time do nonstop (direct) flights between Portland and Chicago depart?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Portland, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 14

What time do nonstop (direct) flights between Portland and Chicago arrive?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Question 15

What time do flights between Portland and Chicago depart?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred departure time when you search on our website or mobile app. Choose the time of day you wish to depart from Portland, such as morning, afternoon, evening, or night, or select the exact hours for departure.

Question 16

What time do flights between Portland and Chicago arrive?

Accepted Answer

This depends on the airline’s flight schedule. You can easily select your preferred arrival time when you search on our website or mobile app. Choose the time of day you wish to arrive at Chicago, such as morning, afternoon, evening, or night, or select the exact hours for arrival.

Cheapest one-way trip	£111
Cheapest nonstop round-trip	£283
Cheapest round-trip	£249
Average round-trip	£342
Nonstop flights in October	£194 – £605

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Blue Line to downtown	40-50 min	$5; standard fare	every 5–10 min (traffic dependent)	budget travelers to Loop
Pace Bus 250 to Metra	60-90 min	$2 – $5; combined bus and Metra fare	every 20–30 min (traffic dependent)	northwest suburbs connection
Taxi to downtown	35-70 min	$45 – $65; metered; varies by traffic	on-demand 24/7 (traffic dependent)	door-to-door with luggage
Ride-hailing (Uber/Lyft)	35-70 min	$35 – $75; surge pricing may apply	on-demand 24/7 (traffic dependent)	app-based convenience
Private transfer/shuttle	35-70 min	$60 – $120; pre-booked; fixed rate	by reservation (traffic dependent)	groups or business travel

Transport Option	Typical Time	Typical Cost	Frequency	Best For
CTA Orange Line to downtown	25-30 min	$5; standard fare	every 6–12 min (traffic dependent)	quick access to Loop
Taxi to downtown	20-45 min	$30 – $45; metered; varies by traffic	on-demand 24/7 (traffic dependent)	door-to-door convenience
Ride-hailing (Uber/Lyft)	20-45 min	$25 – $50; surge pricing may apply	on-demand 24/7 (traffic dependent)	flexible pickup location

Airline	Mon 28.09	Tue 29.09	Wed 30.09	Thu 01.10	Fri 02.10	Sat 03.10	Sun 04.10
United Airlines	---	---	---	1	6	6	6
Alaska Airlines	---	---	---	---	1	1	1
Weekly flights: 22 total	Daily flights: 3.14 average	Most flights: Friday 6 flights

Airline	Mon 05.10	Tue 06.10	Wed 07.10	Thu 08.10	Fri 09.10	Sat 10.10	Sun 11.10
United Airlines	6	6	6	6	6	6	5
Alaska Airlines	1	1	1	1	1	1	1
Weekly flights: 48 total	Daily flights: 6.86 average	Most flights: Monday 6 flights

Airline	Mon 12.10	Tue 13.10	Wed 14.10	Thu 15.10	Fri 16.10	Sat 17.10	Sun 18.10
United Airlines	5	5	5	5	5	5	5
Alaska Airlines	1	1	1	---	1	---	---
Weekly flights: 39 total	Daily flights: 5.57 average	Most flights: Monday 5 flights

Name	Carrier code	IATA Code	Passport needed during booking
Air Canada	ACA	AC	Yes
Frontier Airlines	FFT	F9	No
WestJet	WJA	WS	No
Alaska Airlines	ASA	AS	No
United Airlines	UAL	UA	No

Month	Average monthly max temperature	Average monthly min temperature
January	-1°C	-6°C
February	0°C	-5°C
March	6°C	0°C
April	11°C	5°C
May	17°C	10°C
June	22°C	16°C
July	26°C	20°C
August	25°C	19°C
September	22°C	16°C
October	15°C	10°C
November	8°C	3°C
December	2°C	-1°C

Cheap flights from Portland to Chicago from £111

Explore flight deals to Chicago

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

How much do flights to Chicago cost?

Cheapest one-way trip

Cheapest nonstop round-trip

Cheapest round-trip

Average round-trip

Nonstop flights in October

Getting from Chicago's airport to the city center

How to get from O'Hare International Airport (ORD) to Chicago?

How to get from Chicago Midway International Airport (MDW) to Chicago?

Key info about flying to Chicago

Weekly direct flights

Check-in for a flight from Portland to Chicago

Weather in Chicago

Average Weather

14 day forecast

Frequently asked questions