Flights from Portland to Chicago Starting at NZD 140

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • Round-trip
  • One way

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

Find the best time to fly from Portland to Chicago

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  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

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.
United Airlines logo United Airlines

FAQ

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

    Airlines adjust prices for flights from Portland to Chicago 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 Portland (PWM) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around NZD 645.

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

    It takes around 5 hours 5 minutes to fly from Portland (PWM) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare Intl. Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

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

    Airlines with flights from Portland (PWM) to Chicago (CHI): United Airlines, Emirates and Air New Zealand.

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.
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 Portland to Chicago

Cheapest one-way flight price NZD 139
Cheapest round-trip ticket price NZD 415
Off-season for travel March
Peak season for travel June
Flight distance 1,425.81 km
Average flight time 5 hours 5 minutes
Popular airline United Airlines