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Flights from Chicago to Portland Starting at AU$ 93

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

  • One way
  • Return

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

Find the best time to fly from Chicago to Portland

We monitor flight fares to help you find the best deals effortlessly

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

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From AU$ 93
Spirit Airlines
From AU$ 116
Alaska Airlines
From AU$ 120
Delta Air Lines
From AU$ 160
American Airlines
From AU$ 167
United Airlines
From AU$ 185
Southwest Airlines
From AU$ 208
Sun Country Airlines
From AU$ 214
Allegiant Air
From AU$ 232
Jetblue Airways
From AU$ 440
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Portland

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Portland.

  • Cheapest
    Frontier Airlines
    MDW
    10:30
    15h 29m
    1 transfer
    PDX
    23:59
    Midway International Airport - Portland International Airport
    Sat, Apr 13Frontier Airlines
    AU$ 93
  • Frontier Airlines
    ORD
    18:27
    7h 32m
    1 transfer
    PDX
    23:59
    O'Hare International Airport - Portland International Airport
    Sat, Apr 13Frontier Airlines
    AU$ 93
  • Allegiant Air
    RFD
    20:56
    14h 19m
    1 transfer
    PDX
    09:15
    Chicago Rockford International Airport - Portland International Airport
    Thu, Apr 11Allegiant Air
    AU$ 232
  • Allegiant Air
    RFD
    20:56
    14h 19m
    1 transfer
    PDX
    09:15
    Chicago Rockford International Airport - Portland International Airport
    Thu, Apr 11Allegiant Air
    AU$ 232
    Find More Flights

How do I find the cheapest flights?

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

    Airlines adjust prices for flights from Chicago to Portland based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • How much are flights from Chicago (CHI) to Portland (PDX) cost?

    According to Trip.com's data, the lowest price is around AU$ 552.
  • How long is the flights from Chicago (CHI) to Portland (PDX)?

    It takes about 4 hours 33 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): Southwest Airlines, Air Canada, Brussels Airlines, United Airlines, American Airlines, Lufthansa and Swiss Airlines.
  • What's the most popular airline for direct flights from Chicago (CHI) to Portland (PDX)?

    United Airlines operates 1 direct flights from Chicago (CHI) to Portland (PDX).
  • How many airports in Portland (PDX)?

    There are 3 airport(s) in Portland (PDX): Hillsboro Airport, Portland International Airport and Portland-Troutdale Airport.

Flight Information from Chicago to Portland

Cheapest direct flight price

AU$ 92

Cheapest return ticket price

AU$ 227

Off-season for travel

December

Peak season for travel

June