Bluebird
Portland, Oregon

Private charter · MDW → PDX

Chicago to Portland

1,747 miles. One price for the whole airplane.

Photo: Spicypepper999 · CC0

Price your flight from Chicago to Portland

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Portland, door to door faster.

Trade about 37 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Portland International Airport in Portland, 1,747 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
1,747 mi
Flight
—
Driving
37 hours
Passengers
Up to 1
MDWChicagoPDXPortland
MDW → PDX1,747 miles direct

Departing Chicago

Airports in Chicago

  • MDW

    Major airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft

  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft

  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft

  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft

Arriving Portland

Airports in Portland

  • PDX

    Major airport

    Portland International Airport

    Portland · KPDX

    From downtown
    6 mi
    Longest runway
    11,000 ft

  • HIO

    Commercial airport

    Portland Hillsboro Airport

    Portland · KHIO

    From downtown
    13 mi
    Longest runway
    6,600 ft

  • TTD

    Commercial airport

    Portland Troutdale Airport

    Portland · KTTD

    From downtown
    14 mi
    Longest runway
    5,399 ft

  • KUAO

    Regional airport

    Aurora State Airport

    Aurora

    From downtown
    19 mi
    Longest runway
    5,003 ft

  • KSPB

    Regional airport

    Scappoose Industrial Airpark

    Scappoose

    From downtown
    19 mi
    Longest runway
    5,100 ft

When you land

Things to do in Portland

Portland is Oregon’s largest city and the business center of the state, set where the Willamette River meets the Columbia with Mount Hood on the eastern horizon. Nike’s world headquarters is in nearby Beaverton, adidas runs its North American operations from the city, Columbia Sportswear is based in the suburbs, and Intel’s largest operations sit to the west in Hillsboro. Oregon Health & Science University, a busy port, metals manufacturing and a strong design and creative economy round it out, and the city is famous for food carts, craft beer, coffee, bookstores and a dense network of parks.

  1. 01

    Portland Japanese Garden

    High in Washington Park, this serene garden of ponds, stone paths and moss is considered one of the finest Japanese gardens outside Japan, with a cultural village designed by Kengo Kuma.

  2. 02

    International Rose Test Garden

    Thousands of rose bushes bloom on terraces in Washington Park, with views of downtown and, on clear days, Mount Hood, giving Portland its City of Roses nickname.

  3. 03

    Powell’s City of Books

    Occupying an entire city block in the Pearl District, this landmark bookstore shelves new and used books together across color-coded rooms.

  4. 04

    Lan Su Chinese Garden

    In Old Town Chinatown, this walled garden built by artisans from Suzhou surrounds a lake with pavilions, bridges and a teahouse.

  5. 05

    Multnomah Falls

    About 30 miles east in the Columbia River Gorge, this tall, two-tiered waterfall is crossed by a footbridge and is one of Oregon’s most visited sights.

  6. 06

    Forest Park

    One of the largest urban forests in the country stretches along the hills northwest of downtown, laced with miles of trails including the Wildwood Trail.

Explore Portland charter

Questions

Chicago to Portland flights

How long is a private flight from Chicago to Portland?

About a short flight in a private jet, for 1,747 miles direct. Driving the same trip takes about 37 hours.

Which airports do flights from Chicago to Portland use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Portland International Airport (PDX), Portland Hillsboro Airport (HIO), or Portland Troutdale Airport (TTD). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Portland cost?

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Chicago and Portland?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Portland back to Chicago are priced the same way.

Return flight

Portland to Chicago

More flights from Chicago

More flights to Portland

Explore Chicago private charter and Portland private charter, airports and things to do. Arriving at Portland International Airport (PDX).

Chicago to Portland, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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