Round-trip flight from Chicago
CHI to PDX
Holiday Inn Portland-Airport I-205 By IHG
Portland, 8439 Ne Columbia Blvd.
7.51,303 Reviews3-Star Hotel
11% Package Savings
$610/person
$1,369 $1,219 total
Incl. Flight + Hotel
Flight Deals from Chicago to Portland from $129
Bundle + Save
Top flight deals from leading airlines:
+100s more
+100s moreIncredible Deals
Save up to 50% on select flights with Priceline
Bundle & Save
Save an average of $240 per person when bundling your flight and hotel together with Priceline
Best Price Guarantee
If a VIP member finds a better price elsewhere, we’ll refund up to 200% of the difference
Help 24/7
We’re always here for you — reach us 24 hours a day, 7 days a week
Good to Know
Essential information to help you plan your flight from Chicago to Portland.
Cheapest Flight Round-trip
$275
Lowest round-trip price available on Priceline for this route right now.
This fare recently dropped from $372.
1 stop · economyCheapest Flight One-way
$129
Lowest one-way price found on Priceline for this route in the last 16 days. Found 12 days ago.
The typical one-way fare on this route is $179.
Outbound · Oct 29
4:59 pmORDChicago O Hare Airport
7:41 pmPDXPortland International Airport
4h 42m · Nonstop
Cheapest Nonstop
$303
Cheapest nonstop found on Priceline for this route in the last 16 days. Found 4 hours ago.
$28 more than the cheapest round-trip.
Outbound · Nov 14
5:00 pmORDChicago O Hare Airport
7:42 pmPDXPortland International Airport
4h 42m · Nonstop
Return · Nov 21
11:11 pmPDXPortland International Airport
5:15 amORDChicago O Hare Airport
4h 4m · Nonstop
Good deal price
$358
A round-trip at or under $358 is a good deal on this route right now.
75% of the fares we found on this route cost more; only a quarter cost less.
Timing Your Trip
The best day, time of day, season and booking window for this route.
Best day to fly
Saturdays
Saturday departures average $385 on this route, the lowest of any weekday.
$20 less than the average weekday, which is $405.
Best time to fly
Mornings
Morning departures average $385 on this route, the lowest of any time of day.
$29 less than the average departure, which is $414.
Low season
January
Fares average $325 in January, the cheapest month to fly this route, bottoming out near $314 in late January.
$47 below the yearly average of $372.
When to book
5 weeks ahead
Fares on this route are lowest when booked about 5 weeks before departure.
Booking then averages $318, versus $430 in the final days before the flight.
Price Drop Deals
Priceline is always monitoring flight prices on this route. When we spot an offer on a specific flight that’s significantly lower than what that flight usually sells for, we call it out here as a price drop.
ORDPDX
26% Price DropAmerican Airlines
Depart Nov 12 · Return Nov 17
5-night trip · economy
$372now only$275Round-trip
ORDPDX
25% Price DropFrontier Airlines
Depart Dec 3 · Return Dec 7
4-night trip · economy
$372now only$277Round-trip
MDWPDX
25% Price DropSouthwest Airlines
Depart Dec 5 · Return Dec 8
3-night trip · economy
$373now only$281Round-trip
ORDPDX
24% Price DropAlaska Airlines
Depart Jan 8 · Return Jan 12
4-night trip · economy
$371now only$281Round-trip
ORDPDX
24% Price DropUnited Airlines
Depart Nov 13 · Return Nov 16
3-night trip · economy
$372now only$283Round-trip
ORDPDX
23% Price DropAlaska Airlines
Depart Dec 2 · Return Dec 5
3-night trip · economy
$372now only$287Round-trip
ORDPDX
23% Price DropAlaska Airlines
Depart Dec 10 · Return Dec 14
4-night trip · economy
$372now only$287Round-trip
ORDPDX
23% Price DropAlaska Airlines
Depart Jan 14 · Return Jan 18
4-night trip · economy
$372now only$287Round-trip
ORDPDX
22% Price DropUnited Airlines
Depart Jan 12 · Return Jan 16
4-night trip · economy
$372now only$288Round-trip
ORDPDX
22% Price Drop
Delta Air Lines
Depart Nov 23 · Return Nov 26
3-night trip · economy
$372now only$291Round-trip
ORDPDX
22% Price DropAlaska Airlines
Depart Dec 4 · Return Dec 8
4-night trip · economy
$372now only$291Round-trip
ORDPDX
19% Price DropAlaska Airlines
Depart Nov 6 · Return Nov 9
3-night trip · economy
$371now only$299Round-trip
Express Deal
Express Deals® deliver Priceline’s biggest discounts on flights. Pick your route and dates and we’ll match you with a great offer from a trusted airline. These exclusive “mystery deals” reward flexibility with even deeper savings — your airline is revealed after you book.
We don’t use Express Deal prices when calculating this route’s lowest price or price averages, because these offers require extra flexibility from travelers.
ORDPDX
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
AmericanSouthwestFrontierUnitedDepart Oct 22 · Return Oct 25
3-night trip · economy
$489Round-trip
American Airlinesfound Oct 2011/14/26
5:00 pm
ORDChicago O Hare Airport
11/14/26
7:42 pm
PDXPortland International Airport
11/21/26
11:11 pm
PDXPortland International Airport
11/22/26
5:15 am
ORDChicago O Hare Airport
$303
American Airlinesfound Oct 2011/14/26
9:45 am
ORDChicago O Hare Airport
11/14/26
12:28 pm
PDXPortland International Airport
11/21/26
11:11 pm
PDXPortland International Airport
11/22/26
5:15 am
ORDChicago O Hare Airport
$303
Southwest Airlinesfound Oct 1011/02/26
9:15 pm
MDWChicago Midway Airport
11/02/26
11:55 pm
PDXPortland International Airport
11/09/26
11:30 pm
PDXPortland International Airport
11/10/26
5:15 am
MDWChicago Midway Airport
$343
Alaska Airlinesfound Oct 1211/10/26
2:07 pm
ORDChicago O Hare Airport
11/10/26
4:50 pm
PDXPortland International Airport
11/17/26
7:01 am
PDXPortland International Airport
11/17/26
1:09 pm
ORDChicago O Hare Airport
$343
BUNDLE + SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
American Airlinesfound Oct 1511/18/26
5:05 pm
ORDChicago O Hare Airport
11/18/26
7:47 pm
PDXPortland International Airport
11/25/26
2:24 pm
PDXPortland International Airport
11/25/26
11:34 pm
ORDChicago O Hare Airport
$318
Southwest Airlinesfound Oct 1211/10/26
8:40 pm
MDWChicago Midway Airport
11/10/26
11:25 pm
PDXPortland International Airport
11/17/26
11:20 am
PDXPortland International Airport
11/17/26
5:05 pm
MDWChicago Midway Airport
$343
American Airlinesfound Oct 1511/18/26
9:45 am
ORDChicago O Hare Airport
11/18/26
12:28 pm
PDXPortland International Airport
11/25/26
2:24 pm
PDXPortland International Airport
11/25/26
11:34 pm
ORDChicago O Hare Airport
$318
Southwest Airlinesfound Oct 1211/10/26
8:40 pm
MDWChicago Midway Airport
11/10/26
11:25 pm
PDXPortland International Airport
11/17/26
6:00 am
PDXPortland International Airport
11/17/26
11:50 am
MDWChicago Midway Airport
$343
American Airlinesfound Oct 1511/18/26
12:02 pm
ORDChicago O Hare Airport
11/18/26
5:48 pm
PDXPortland International Airport
11/25/26
2:24 pm
PDXPortland International Airport
11/25/26
11:34 pm
ORDChicago O Hare Airport
$328
Southwest Airlinesfound Oct 1011/02/26
9:15 pm
MDWChicago Midway Airport
11/02/26
11:55 pm
PDXPortland International Airport
11/09/26
9:25 pm
PDXPortland International Airport
11/10/26
5:55 am
MDWChicago Midway Airport
$353
No flights match these filters.
Top Deals on flights from Chicago to Portland
Chicago, US (CHI) - Portland, US (PDX)
American AirlinesOct 29
4:59 pm
ORDChicago O Hare Airport
Oct 29
7:41 pm
PDXPortland International Airport
Search More
as low as
$129Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:45 pm
MDWChicago Midway Airport
Oct 30
12:15 am
PDXPortland International Airport
Search More
as low as
$131Chicago, US (CHI) - Portland, US (PDX)
Frontier AirlinesOct 29
5:15 pm
ORDChicago O Hare Airport
Oct 30
11:36 am
PDXPortland International Airport
Search More
as low as
$139Chicago, US (CHI) - Portland, US (PDX)
Frontier AirlinesOct 29
6:30 am
ORDChicago O Hare Airport
Oct 29
11:07 am
PDXPortland International Airport
Search More
as low as
$141Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
10:30 pm
MDWChicago Midway Airport
Oct 30
7:20 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:30 pm
MDWChicago Midway Airport
Oct 30
6:55 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
10:55 pm
MDWChicago Midway Airport
Oct 30
9:50 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:15 pm
MDWChicago Midway Airport
Oct 30
8:10 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:25 pm
MDWChicago Midway Airport
Oct 30
6:55 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:15 pm
MDWChicago Midway Airport
Oct 30
6:55 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
Southwest AirlinesOct 29
9:30 pm
MDWChicago Midway Airport
Oct 30
8:10 am
PDXPortland International Airport
Search More
as low as
$146Chicago, US (CHI) - Portland, US (PDX)
American AirlinesOct 29
9:45 am
ORDChicago O Hare Airport
Oct 29
12:22 pm
PDXPortland International Airport
Search More
as low as
$152Best Portland Hotel + Flight Packages
Chicago - Portland packages
Round-trip flight from Chicago
CHI to PDX
Hotel DeLuxe
Portland, 729 Sw 15th Avenue
8816 Reviews4-Star Hotel
25% Package Savings
$689/person
$1,844 $1,378 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
Evergreen Inn & Suites Portland Airport
Portland, 3828 Ne 82nd Avenue
3.5425 Reviews2-Star Hotel
9% Package Savings
$507/person
$1,119 $1,013 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
Holiday Inn - Portland - Columbia Riverfront By IHG
Portland, 909 N. Hayden Island Drive
8.2864 Reviews3-Star Hotel
13% Package Savings
$625/person
$1,431 $1,249 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
Comfort Suites Portland Airport
Portland, 12010 Northeast Airport Way
8.4585 Reviews2.5-Star Hotel
12% Package Savings
$637/person
$1,446 $1,274 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
The Mark Spencer Hotel
Portland, 409 Southwest 11th Avenue
8.72,433 Reviews3-Star Hotel
15% Package Savings
$667/person
$1,563 $1,333 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
The Royal Sonesta Portland Downtown
Portland, 506 Southwest Washington Street
8.8993 Reviews4.5-Star Hotel
9% Package Savings
$744/person
$1,628 $1,488 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to PDX
Country Inn & Suites By Radisson, Delta Park North Portland
Portland, 9930 North Whitaker Road
7.71,580 Reviews2.5-Star Hotel
7% Package Savings
$592/person
$1,276 $1,184 total
Incl. Flight + Hotel
Best Portland Hotel + Flight + Car Packages
Chicago - Portland packages
Round-trip flight from Chicago
CHI to PDX
Holiday Inn - Portland - Columbia Riverfront By IHG
Portland, 909 N. Hayden Island Drive
8.2864 Reviews3-Star Hotel
Rental car included
Pick-up in PDX
17% Package Savings
$767/person
$1,849 $1,533 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
The Royal Sonesta Portland Downtown
Portland, 506 Southwest Washington Street
8.8993 Reviews4.5-Star Hotel
Rental car included
Pick-up in PDX
13% Package Savings
$888/person
$2,045 $1,775 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
The Mark Spencer Hotel
Portland, 409 Southwest 11th Avenue
8.72,433 Reviews3-Star Hotel
Rental car included
Pick-up in PDX
18% Package Savings
$809/person
$1,982 $1,618 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
Red Lion Hotel Portland Airport
Portland, 7101 Ne 82nd Avenue
71,235 Reviews3-Star Hotel
Rental car included
Pick-up in PDX
12% Package Savings
$743/person
$1,684 $1,486 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
Country Inn & Suites By Radisson, Delta Park North Portland
Portland, 9930 North Whitaker Road
7.71,580 Reviews2.5-Star Hotel
Rental car included
Pick-up in PDX
13% Package Savings
$735/person
$1,696 $1,470 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
Holiday Inn Portland-Airport I-205 By IHG
Portland, 8439 Ne Columbia Blvd.
7.51,303 Reviews3-Star Hotel
Rental car included
Pick-up in PDX
16% Package Savings
$755/person
$1,796 $1,510 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
Hotel DeLuxe
Portland, 729 Sw 15th Avenue
8816 Reviews4-Star Hotel
Rental car included
Pick-up in PDX
27% Package Savings
$830/person
$2,264 $1,660 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to PDX
Evergreen Inn & Suites Portland Airport
Portland, 3828 Ne 82nd Avenue
3.5425 Reviews2-Star Hotel
Rental car included
Pick-up in PDX
16% Package Savings
$649/person
$1,539 $1,297 total
Incl. Flight + Hotel + Car
When is the cheapest time to fly?
Cheapest in late January at about $314
Fares from Chicago to Portland are lowest in late January, around $314, and January is the cheapest month overall, averaging $325. They peak in late December at about $430, $116 more than the low. The yearly average is $372.
Show the data
| Month | Average fare | Early month | Late month |
|---|---|---|---|
| January | $325 | $336 | $314 |
| February | $330 | $320 | $341 |
| March | $388 | $370 | $405 |
| April | $375 | $379 | $371 |
| May | $372 | $367 | $377 |
| June | $401 | $396 | $405 |
| July | $404 | $402 | $405 |
| August | $377 | $388 | $367 |
| September | $371 | $370 | $372 |
| October | $358 | $370 | $347 |
| November | $360 | $344 | $376 |
| December | $402 | $373 | $430 |
How far in advance should I book?
Cheapest about 5 weeks out at $318
Book about 5 weeks before departure for the best fares from Chicago to Portland, around $318. Booking in the final days before the flight costs about $430, $112 more. Booking six months ahead runs about $450.
Show the data
| Days before departure | Average fare |
|---|---|
| 180 days | $450 |
| 172 days | $444 |
| 164 days | $444 |
| 156 days | $441 |
| 148 days | $429 |
| 140 days | $414 |
| 132 days | $402 |
| 124 days | $396 |
| 116 days | $386 |
| 108 days | $370 |
| 100 days | $354 |
| 92 days | $341 |
| 84 days | $339 |
| 76 days | $343 |
| 68 days | $337 |
| 2mo | $336 |
| 52 days | $339 |
| 44 days | $332 |
| 36 days | $319 |
| 35 days | $318 |
| 28 days | $323 |
| 20 days | $343 |
| 12 days | $375 |
| 4 days | $411 |
| 0 days | $430 |
What's the cheapest day of the week to fly?
Saturday is the cheapest day of the week to fly from Chicago to Portland. At $385 it is 5% cheaper than the average day. Sunday is the most expensive day, 12% above average.
Show the data
| Day | Average fare |
|---|---|
| Sun | $452 |
| Mon | $406 |
| Tue | $393 |
| Wed | $387 |
| Thu | $408 |
| Fri | $405 |
| Sat | $385 |
When is the best time of day to fly?
Morning (5am - 12pm) is the cheapest time of day to fly from Chicago to Portland. At $385 it is 7% cheaper than the average time. Afternoon (2pm - 5pm) is the most expensive time, 8% above average.
Show the data
| Time of day | Average fare |
|---|---|
| Morning | $385 |
| Midday | $420 |
| Afternoon | $445 |
| Evening | $406 |
| Late Night | $412 |
What do round-trip flights from Chicago to Portland cost?
Share of fares in each price range, adjusted to current prices.
Show the data
| Price range | Share of fares |
|---|---|
| $150 to $300 | 19% |
| $300 to $450 | 30% |
| $450 to $600 | 26% |
| $600 to $750 | 16% |
| $750 to $900 | 5% |
| $900 to $1,050 | 3% |
| $1,050 and up | 2% |
Methodology: learn how we calculate these charts
The charts “When is the cheapest time to fly?”, “How far in advance should I book?”, “What's the cheapest day of the week to fly?” and “What do round-trip flights from Chicago to Portland cost?” are built from the prices Priceline customers actually paid for flights on this route over the past 12 months or more.
Where a route has too few bookings to fill every point in a chart, we borrow the shape of the curve from a group of routes with similar price behavior and fit it to the fares booked on this route.
Because past fares don’t reflect today’s market, we then adjust the historical prices for current conditions such as inflation and fuel costs, using the round-trip fares found in recent searches on this route.
The chart “When is the best time of day to fly?” is calculated directly from the fares found in recent searches, not from historical bookings.