>>>>
Cheap Flights from Portland to Chicago
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Convenient & reliable booking and payment system
Cheap Flights from Portland to Chicago starting at S$ 56
We've found these cheap flights for you. You can book one-way or return flight tickets.
- One way
- Round-trip
- PWM22:122h 46mDirectORD23:58Tue, May 21|Portland - Chicago|Frontier AirlinesS$ 56S$ 14261% OFF61% OFFS$ 142S$ 56
- PWM22:112h 46mDirectORD23:57Thu, Jul 4|Portland - Chicago|Frontier AirlinesS$ 65S$ 14254% OFF54% OFFS$ 142S$ 65
- PWM22:122h 46mDirectORD23:58Thu, May 30|Portland - Chicago|Frontier AirlinesS$ 76S$ 14247% OFF47% OFFS$ 142S$ 76
- PWM22:022h 46mDirectORD23:48Thu, Jun 13|Portland - Chicago|Frontier AirlinesS$ 82S$ 82
- PWM22:022h 46mDirectORD23:48Sun, Jun 9|Portland - Chicago|Frontier AirlinesS$ 91S$ 91
- PWM12:5611h 47m1 stopORD23:43Fri, May 10|Portland - Chicago|Frontier AirlinesS$ 92S$ 92
- PWM22:112h 46mDirectORD23:57Thu, Jun 6|Portland - Chicago|Frontier AirlinesS$ 92S$ 92
- PWM22:112h 46mDirectORD23:57Thu, Jul 11|Portland - Chicago|Frontier AirlinesS$ 111S$ 111
- PWM09:409h1 stopMDW17:40Sun, May 5|Portland - Chicago|Frontier AirlinesS$ 112S$ 112
- PWM12:5611h 47m1 stopORD23:43Fri, May 3|Portland - Chicago|Frontier AirlinesS$ 113S$ 113
- PWM13:003h 5mDirectCHI14:00Thu, May 2|Portland - Chicago|Frontier AirlinesFind More FlightsFind More Flights
Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Cheapest time to fly from Portland to Chicago
We monitor flight fares to help you find the best deals effortlessly
Displayed prices are calculated based on the lowest average weekly prices of the corresponding route on Trip.com.
Cheapest Airlines flying from Portland to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Frontier Airlines
From S$ 56
Breeze Airways
From S$ 143
Delta Air Lines
From S$ 154
American Airlines
From S$ 162
United Airlines
From S$ 198
Southwest Airlines
From S$ 227
ANA airlines
Find more flights and airlines
Alternative Routes from Portland to Chicago
Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Portland to Chicago.
- CheapestPWM22:112h 46mDirectORD23:57Portland International Jetport - O'Hare International AirportTue, Jun 18Frontier AirlinesS$ 55
- PWM11:4020h 14m1 transferMDW06:54Portland International Jetport - Midway International AirportTue, May 21Frontier AirlinesS$ 73
- PWM11:4020h 14m1 transferMDW06:54Portland International Jetport - Midway International AirportTue, May 21Frontier AirlinesS$ 73Find More Flights
Frequently Asked Questions
How to find a cheap flight from Portland to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Portland to Chicago. Book your flights at the right time and save more.
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
Compare Flight Prices
Compare prices on travel agency and airline websites.
Look Out for Deals
Check airline and travel agency websites for latest flight deals
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Find cheapest flight ticket from Portland to Chicago
Cheapest direct flight price | S$ 55 |
---|---|
Cheapest return ticket price | S$ 54 |
Cheapest month | May |
Peak season for travel | October |
Flight distance | 1,425.81km |
Average flight time | 2 hours 55 minutes |
Popular airline | Delta Air Lines |
Plan Your Trip Around Chicago
Find Cheap Flights & Deals on Trip.com
Popular Airlines to Chicago
- Alaska Airlines to Chicago
- Westjet Flights to Chicago
- Korean Air to Chicago
- Emirates Flights to Chicago
- Spirit Airlines Flights to Chicago
- Air Canada Flights to Chicago
- Allegiant Air Flights to Chicago
- Air India to Chicago
- United Airlines to Chicago
- Frontier Airlines Flights to Chicago
- ZIPAIR Flights to Chicago
- Egypt Air Flights to Chicago
- Southwest Airlines from Nashville to Chicago
Popular Flights to Chicago
Popular Flights from Portland
Travel Deals & Discounts
Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd. Travel License No. 02943
Site Operator: Trip.com Travel Singapore Pte. Ltd. Travel License No. 02943