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Cheap flights Chicago to Portland

1 passenger, economy

There are no nonstop flights from Chicago to Portland. With a connection, the trip takes from 4 hours 25 minutes. Distance: 1444 km. Tickets from $199 (departure 11 December).

Prices updated on 28 September at 09:21

See also: Flights from ChicagoFlights to Portland

Cheap flights Chicago to Portland

Compare prices, duration and stops

Southwest Airlines
WN 1776 Best price
14:05
Chicago Midway International Airport (MDW)
Fri, 11 Dec
4h 25min
1 stop
19:30
Portland (PWM)
Fri, 11 Dec
$199

Low price calendar

From
To
October 2026 — no data Thu, 22 Oct · One way

Prices as of 28 September, 09:33 Moscow time

Cheap flights Chicago to Portland

American Airlines
American Airlines
Price from
$170
United Airlines
United Airlines
Price from
$210

Popular destinations from Chicago

All →
CHI
Chicago — Philadelphia
United States → United States
PHL
from
$24
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
$29
CHI
Chicago — Baltimore
United States → United States
BWI
from
$33
CHI
Chicago — Denver
United States → United States
DEN
from
$36
CHI
Chicago — Washington
United States → United States
WAS
from
$46
CHI
Chicago — Burlington
United States → United States
BRL
from
$51
CHI
Chicago — Miami
United States → United States
MIA
from
$54
CHI
Chicago — Phoenix
United States → United States
PHX
from
$55

Popular destinations to Portland

All →
ORL
Orlando — Portland
United States → United States
PWM
from
$130
NYC
New York — Portland
United States → United States
PWM
from
$140
TLH
Tallahassee — Portland
United States → United States
PWM
from
$172
RIC
Richmond — Portland
United States → United States
PWM
from
$175
HRL
Harlingen — Portland
United States → United States
PWM
from
$191
ALB
Albany — Portland
United States → United States
PWM
from
$195
SJC
San Jose — Portland
United States → United States
PWM
from
$197
DEN
Denver — Portland
United States → United States
PWM
from
$203
MEM
Memphis — Portland
United States → United States
PWM
from
$206

Flights from Chicago to cities near Portland

Cheaper than Portland right now: Boston — from $90, $109 less. The cities are 153 km apart.

City Distance Direct Flights Airlines Price from
PortlandPWM — 011
BostonBOS 153 km 24266 $109 cheaper
ProvidencePVD 231 km 244 $43 cheaper

Distance is a straight line between the cities. Prices are the lowest one-way fares.

Cheap flights Chicago to Portland

Price from
$199
Average price
$204
Flight time
4 hours 25 minutes
Distance
1 444 km
Рейсов в неделю
1
Airlines
1
Most frequent flight
UA 3662

Prices as of 28 September, 09:21 Moscow time

Airports on the Chicago — Portland route

From → to Flights Direct Airlines Price from
Chicago Midway International AirportMDW PortlandPWM
101

Departure airports · Chicago

Arrival airports · Portland

  • PortlandPWM

Passenger reviews

No reviews for this route yet

Internet abroad

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Frequently Asked Questions

Based on the tickets found, there are no nonstop flights from Chicago to Portland — you will need to fly with a connection. Tickets with a connection start at $199. The journey takes from 4 hours 25 minutes.
The average ticket price Chicago Portland is $204. The cheapest ticket costs $199, operated by Southwest Airlines, flight WN 1776, departing Chicago on 11 December at 14:05, arriving Portland on 11 December at 19:30. Prices as of 28 September.
There are no nonstop flights. With a connection: from 4 hours 25 minutes.
Tickets from Chicago to Portland are sold by: Southwest Airlines. All flights have connections.
The distance from Chicago to Portland is 1444 km.
Yes, the time difference is 1 hour: Chicago — UTC−5, Portland — UTC−4. For example: Chicago 12:00 → Portland 13:00.