App
Help
NZD
Search Bookings
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Latest Flight Deals from Chicago to Portland

Book one-way or return flights from Chicago to Portland from as little as NZD 54. Choose from the popular airlines below and book your flight today!

  • One way
  • Round-trip
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Wed, May 8|Chicago - Portland|Spirit Airlines
        NZD 54NZD 143
        62% OFF
        62% OFF
        NZD 143NZD 54
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Wed, May 29|Chicago - Portland|Spirit Airlines
        NZD 55NZD 143
        62% OFF
        62% OFF
        NZD 143NZD 55
      • ORD20:26
        4h 27m
        Direct
        PDX22:53
        Wed, Jun 5|Chicago - Portland|Spirit Airlines
        NZD 57NZD 143
        61% OFF
        61% OFF
        NZD 143NZD 57
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Sat, May 25|Chicago - Portland|Spirit Airlines
        NZD 90
        NZD 90
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Sat, Jun 1|Chicago - Portland|Spirit Airlines
        NZD 90
        NZD 90
      • ORD20:26
        4h 27m
        Direct
        PDX22:53
        Wed, Jun 12|Chicago - Portland|Spirit Airlines
        NZD 90
        NZD 90
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Sat, May 11|Chicago - Portland|Spirit Airlines
        NZD 91
        NZD 91
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Wed, May 22|Chicago - Portland|Spirit Airlines
        NZD 94
        NZD 94
      • ORD20:00
        4h 30m
        Direct
        PDX22:30
        Wed, May 15|Chicago - Portland|Spirit Airlines
        NZD 97
        NZD 97
      • ORD18:27
        7h 32m
        1 stop
        PDX23:59
        Wed, May 8|Chicago - Portland|Frontier Airlines
        NZD 106
        NZD 106
      • CHI13:00
        3h 5m
        Direct
        PDX14:00
        Mon, May 6|Chicago - Portland|Spirit Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Searching for the best last minute flight from Chicago to Portland? Find one-way or return flights that are affordable and fit your itinerary.

Trip.com monitors the ticket fares of flights from Chicago to Portland. Stay updated on price trends and snag the best deals for your upcoming trip.

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to Portland

View airlines operating flights from Chicago to Portland. Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Spirit Airlines
From NZD 54
Alaska Airlines
From NZD 140
Frontier Airlines
From NZD 146
American Airlines
From NZD 148
Delta Air Lines
From NZD 174
Sun Country Airlines
From NZD 177
United Airlines
From NZD 202
Southwest Airlines
From NZD 320
Allegiant Air
From NZD 388
Jetblue Airways
From NZD 621
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Portland

Discover different routes, airlines, and transfers and find the best alternative flights for your journey from Chicago to Portland.

  • Cheapest
    Spirit Airlines
    ORD
    20:00
    4h 30m
    Direct
    PDX
    22:30
    O'Hare International Airport - Portland International Airport
    Wed, May 8Spirit Airlines
    NZD 54
  • Frontier Airlines
    MDW
    09:51
    9h 14m
    1 transfer
    PDX
    17:05
    Midway International Airport - Portland International Airport
    Tue, May 7Frontier Airlines
    NZD 104
  • Allegiant Air
    RFD
    21:58
    15h 16m
    1 transfer
    PDX
    11:14
    Chicago Rockford International Airport - Portland International Airport
    Thu, May 2Allegiant Air
    NZD 388
  • Allegiant Air
    RFD
    21:58
    15h 16m
    1 transfer
    PDX
    11:14
    Chicago Rockford International Airport - Portland International Airport
    Thu, May 2Allegiant Air
    NZD 388
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Chicago (CHI) to Portland (PDX) the cheapest?

    Airlines adjust prices for flights from Chicago to Portland based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Portland (PDX) cost?

    According to Trip.com's data, the lowest price is around NZD 511.

  • How long does it take to fly from Chicago (CHI) to Portland (PDX) and what is the distance?

    It takes around 4 hours 27 minutes to fly from Chicago (CHI) to Portland (PDX).

  • What are the most popular airlines that fly from Chicago (CHI) to Portland (PDX)?

    Airlines with flights from Chicago (CHI) to Portland (PDX): American Airlines, Air Canada, Brussels Airlines, United Airlines, Southwest Airlines, Lufthansa and Swiss Airlines.

How to find a cheap flight from Chicago to Portland

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 Chicago to Portland. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Information from Chicago to Portland

Cheapest nonstop flight price

NZD 54

Cheapest round-trip ticket price

NZD 113

Off-season for travel

May

Peak season for travel

October

Flight distance

2,816.22km

Average flight time

4 hours 27 minutes

Popular airline

American Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2024 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.