Round-trip flight from Portland
PDX to CHI
The Chicago Hotel Collection Ambassador Gold Coast
Chicago, 1301 North State Parkway
8662 Reviews4-Star Hotel
22% Package Savings
$858/person
$2,212 $1,716 total
Incl. Flight + Hotel
Flight Deals from Portland to Chicago from $230
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Good to Know
Essential information to help you plan your flight from Portland to Chicago.
Cheapest Flight Round-trip
$275
Lowest round-trip price available on Priceline for this route right now.
This fare recently dropped from $368.
Nonstop · economyCheapest Flight One-way
$230
Lowest one-way price found on Priceline for this route in the last 16 days. Found 10 days ago.
The typical one-way fare on this route is $245.
Outbound · Nov 1
11:30 pmPDXPortland International Airport
5:15 amMDWChicago Midway Airport
3h 45m · Nonstop
Good deal price
$328
A round-trip at or under $328 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 $377 on this route, the lowest of any weekday.
$22 less than the average weekday, which is $399.
Best time to fly
Evenings
Evening departures average $320 on this route, the lowest of any time of day.
$58 less than the average departure, which is $378.
Low season
January
Fares average $279 in January, the cheapest month to fly this route.
$54 below the yearly average of $333.
When to book
4 weeks ahead
Fares on this route are lowest when booked about 4 weeks before departure.
Booking then averages $310, versus $373 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.
PDXORD
25% Price DropUnited Airlines
Depart Dec 12 · Return Dec 15
3-night trip · economy
$368now only$275Round-trip
PDXORD
24% Price DropAmerican Airlines
Depart Nov 16 · Return Nov 19
3-night trip · economy
$367now only$280Round-trip
PDXORD
21% Price DropUnited Airlines
Depart Nov 12 · Return Nov 17
5-night trip · economy
$359now only$283Round-trip
PDXORD
22% Price Drop
Frontier Airlines
Depart Dec 3 · Return Dec 7
4-night trip · economy
$366now only$285Round-trip
PDXORD
19% Price DropFrontier Airlines
Depart Dec 3 · Return Dec 6
3-night trip · economy
$368now only$297Round-trip
PDXORD
14% Price DropAmerican Airlines
Depart Dec 2 · Return Dec 6
4-night trip · economy
$366now only$314Round-trip
PDXORD
13% Price DropAmerican Airlines
Depart Dec 1 · Return Dec 6
5-night trip · economy
$366now only$319Round-trip
PDXORD
11% Price DropFrontier Airlines
Depart Nov 17 · Return Nov 20
3-night trip · economy
$365now only$325Round-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.
PDXORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestAmericanAlaskaUnitedDepart Nov 6 · Return Nov 9
3-night trip · economy
$309Round-trip
PDXORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestAmericanAlaskaUnitedDepart Oct 23 · Return Oct 26
3-night trip · economy
$497Round-trip
PDXORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestAmericanAlaskaUnitedDepart Nov 23
economy
$177One-way
PDXORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestAmericanAlaskaUnitedDepart Oct 27
economy
$231One-way
Southwest Airlinesfound Oct 1411/18/26
6:00 am
PDXPortland International Airport
11/18/26
11:50 am
MDWChicago Midway Airport
11/25/26
9:25 pm
MDWChicago Midway Airport
11/26/26
12:10 am
PDXPortland International Airport
$310
American Airlinesfound Oct 1411/18/26
11:03 pm
PDXPortland International Airport
11/19/26
5:07 am
ORDChicago O Hare Airport
11/25/26
5:42 pm
ORDChicago O Hare Airport
11/25/26
8:29 pm
PDXPortland International Airport
$318
Alaska Airlinesfound Oct 1411/18/26
7:01 am
PDXPortland International Airport
11/18/26
1:09 pm
ORDChicago O Hare Airport
11/25/26
3:19 pm
ORDChicago O Hare Airport
11/25/26
9:54 pm
PDXPortland International Airport
$330
American Airlinesfound Oct 1411/18/26
1:22 pm
PDXPortland International Airport
11/18/26
7:44 pm
ORDChicago O Hare Airport
11/25/26
5:42 pm
ORDChicago O Hare Airport
11/25/26
8:29 pm
PDXPortland International Airport
$318
BUNDLE + SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Southwest Airlinesfound Oct 1411/18/26
1:50 pm
PDXPortland International Airport
11/18/26
9:30 pm
MDWChicago Midway Airport
11/25/26
9:25 pm
MDWChicago Midway Airport
11/26/26
12:10 am
PDXPortland International Airport
$320
Alaska Airlinesfound Oct 1411/18/26
7:01 am
PDXPortland International Airport
11/18/26
1:09 pm
ORDChicago O Hare Airport
11/25/26
3:19 pm
ORDChicago O Hare Airport
11/25/26
10:58 pm
PDXPortland International Airport
$330
Southwest Airlinesfound Oct 1411/18/26
11:40 am
PDXPortland International Airport
11/18/26
7:35 pm
MDWChicago Midway Airport
11/25/26
9:25 pm
MDWChicago Midway Airport
11/26/26
12:10 am
PDXPortland International Airport
$320
American Airlinesfound Oct 1411/18/26
11:03 pm
PDXPortland International Airport
11/19/26
5:07 am
ORDChicago O Hare Airport
11/25/26
5:45 pm
ORDChicago O Hare Airport
11/25/26
11:16 pm
PDXPortland International Airport
$328
Southwest Airlinesfound Oct 1411/18/26
2:15 pm
PDXPortland International Airport
11/18/26
10:40 pm
MDWChicago Midway Airport
11/25/26
9:25 pm
MDWChicago Midway Airport
11/26/26
12:10 am
PDXPortland International Airport
$320
Alaska Airlinesfound Oct 1411/18/26
7:01 am
PDXPortland International Airport
11/18/26
1:09 pm
ORDChicago O Hare Airport
11/25/26
2:16 pm
ORDChicago O Hare Airport
11/25/26
11:27 pm
PDXPortland International Airport
$340
No flights match these filters.
Top Deals on flights from Portland to Chicago
Portland, US (PDX) - Chicago, US (CHI)
Southwest AirlinesNov 1
11:30 pm
PDXPortland International Airport
Nov 2
5:15 am
MDWChicago Midway Airport
Search More
as low as
$230Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
12:02 am
PDXPortland International Airport
Nov 1
5:00 am
ORDChicago O Hare Airport
Search More
as low as
$233Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
11:09 pm
PDXPortland International Airport
Nov 2
5:07 am
ORDChicago O Hare Airport
Search More
as low as
$233Portland, US (PDX) - Chicago, US (CHI)
Alaska AirlinesNov 1
7:01 am
PDXPortland International Airport
Nov 1
1:09 pm
ORDChicago O Hare Airport
Search More
as low as
$235Portland, US (PDX) - Chicago, US (CHI)
Southwest AirlinesNov 1
9:25 pm
PDXPortland International Airport
Nov 2
5:55 am
MDWChicago Midway Airport
Search More
as low as
$240Portland, US (PDX) - Chicago, US (CHI)
Southwest AirlinesNov 1
7:00 pm
PDXPortland International Airport
Nov 2
5:45 am
MDWChicago Midway Airport
Search More
as low as
$240Portland, US (PDX) - Chicago, US (CHI)
Southwest AirlinesNov 1
7:35 am
PDXPortland International Airport
Nov 1
5:35 pm
MDWChicago Midway Airport
Search More
as low as
$241Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
11:49 pm
PDXPortland International Airport
Nov 2
8:48 am
ORDChicago O Hare Airport
Search More
as low as
$243Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
2:24 pm
PDXPortland International Airport
Nov 1
11:38 pm
ORDChicago O Hare Airport
Search More
as low as
$243Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
2:34 pm
PDXPortland International Airport
Nov 1
11:59 pm
ORDChicago O Hare Airport
Search More
as low as
$243Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
5:00 am
PDXPortland International Airport
Nov 1
2:43 pm
ORDChicago O Hare Airport
Search More
as low as
$243Portland, US (PDX) - Chicago, US (CHI)
American AirlinesNov 1
6:51 am
PDXPortland International Airport
Nov 1
4:57 pm
ORDChicago O Hare Airport
Search More
as low as
$243Best Chicago Hotel + Flight Packages
Portland - Chicago packages
Round-trip flight from Portland
PDX to CHI
Chicago South Loop Hotel
Chicago, 11 West 26th Street
6.24,224 Reviews2.5-Star Hotel
$1,035/person
$2,069 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
The Chicago Hotel Collection Magnificent Mile
Chicago, 166 East Superior Street
7.21,069 Reviews4-Star Hotel
14% Package Savings
$926/person
$2,151 $1,851 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
The Godfrey Hotel Chicago
Chicago, 127 West Huron Street
8.51,268 Reviews4.5-Star Hotel
13% Package Savings
$1,082/person
$2,493 $2,163 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
The Wade
Chicago, 644 N Lake Shore Dr
8.12,404 Reviews4.5-Star Hotel
21% Package Savings
$1,103/person
$2,803 $2,205 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
Congress Plaza Hotel
Chicago, 520 South Michigan Avenue
7.25,146 Reviews3-Star Hotel
10% Package Savings
$1,040/person
$2,318 $2,080 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
Kinzie Hotel
Chicago, 20 West Kinzie Street
8.71,289 Reviews4-Star Hotel
29% Package Savings
$1,120/person
$3,164 $2,240 total
Incl. Flight + Hotel
Round-trip flight from Portland
PDX to CHI
Sable at Navy Pier Chicago, Curio Collection by Hilton
Chicago, 900 E Grand Ave
91,135 Reviews4-Star Hotel
34% Package Savings
$1,155/person
$3,525 $2,309 total
Incl. Flight + Hotel
Best Chicago Hotel + Flight + Car Packages
Portland - Chicago packages
Round-trip flight from Portland
PDX to CHI
The Godfrey Hotel Chicago
Chicago, 127 West Huron Street
8.51,268 Reviews4.5-Star Hotel
Rental car included
Pick-up in CHI
15% Package Savings
$1,127/person
$2,639 $2,253 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
The Wade
Chicago, 644 N Lake Shore Dr
8.12,404 Reviews4.5-Star Hotel
Rental car included
Pick-up in CHI
22% Package Savings
$1,148/person
$2,950 $2,296 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
Congress Plaza Hotel
Chicago, 520 South Michigan Avenue
7.25,146 Reviews3-Star Hotel
Rental car included
Pick-up in CHI
12% Package Savings
$1,084/person
$2,463 $2,167 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
Kinzie Hotel
Chicago, 20 West Kinzie Street
8.71,289 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
29% Package Savings
$1,168/person
$3,309 $2,335 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
Sable at Navy Pier Chicago, Curio Collection by Hilton
Chicago, 900 E Grand Ave
91,135 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
34% Package Savings
$1,204/person
$3,671 $2,407 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
The Chicago Hotel Collection Ambassador Gold Coast
Chicago, 1301 North State Parkway
8662 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
23% Package Savings
$906/person
$2,357 $1,811 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
Chicago South Loop Hotel
Chicago, 11 West 26th Street
6.24,224 Reviews2.5-Star Hotel
Rental car included
Pick-up in CHI
2% Package Savings
$1,085/person
$2,221 $2,169 total
Incl. Flight + Hotel + Car
Round-trip flight from Portland
PDX to CHI
The Chicago Hotel Collection Magnificent Mile
Chicago, 166 East Superior Street
7.21,069 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
15% Package Savings
$971/person
$2,298 $1,942 total
Incl. Flight + Hotel + Car
When is the cheapest time to fly?
Cheapest in early January at about $279
Fares from Portland to Chicago are lowest in early January, around $279, and January is the cheapest month overall, averaging $279. They peak in late December at about $393, $114 more than the low. The yearly average is $333.
Show the data
| Month | Average fare | Early month | Late month |
|---|---|---|---|
| January | $279 | $279 | $279 |
| February | $301 | $294 | $309 |
| March | $349 | $331 | $366 |
| April | $342 | $347 | $336 |
| May | $332 | $331 | $332 |
| June | $362 | $352 | $372 |
| July | $349 | $356 | $342 |
| August | $326 | $333 | $320 |
| September | $318 | $310 | $325 |
| October | $328 | $338 | $319 |
| November | $336 | $325 | $347 |
| December | $371 | $348 | $393 |
How far in advance should I book?
Cheapest about 4 weeks out at $310
Book about 4 weeks before departure for the best fares from Portland to Chicago, around $310. Booking in the final days before the flight costs about $373, $63 more. Booking six months ahead runs about $407.
Show the data
| Days before departure | Average fare |
|---|---|
| 180 days | $407 |
| 172 days | $403 |
| 164 days | $403 |
| 156 days | $409 |
| 5mo | $415 |
| 148 days | $415 |
| 140 days | $412 |
| 132 days | $398 |
| 124 days | $377 |
| 116 days | $358 |
| 108 days | $342 |
| 100 days | $327 |
| 92 days | $320 |
| 84 days | $323 |
| 76 days | $333 |
| 68 days | $337 |
| 2mo | $331 |
| 52 days | $327 |
| 44 days | $320 |
| 36 days | $312 |
| 31 days | $310 |
| 28 days | $311 |
| 20 days | $322 |
| 12 days | $344 |
| 4 days | $363 |
| 0 days | $373 |
What's the cheapest day of the week to fly?
Saturday is the cheapest day of the week to fly from Portland to Chicago. At $377 it is 5% cheaper than the average day. Monday is the most expensive day, 11% above average.
Show the data
| Day | Average fare |
|---|---|
| Sun | $428 |
| Mon | $444 |
| Tue | $381 |
| Wed | $385 |
| Thu | $390 |
| Fri | $387 |
| Sat | $377 |
When is the best time of day to fly?
Evening (5pm - 9pm) is the cheapest time of day to fly from Portland to Chicago. At $320 it is 15% cheaper than the average time. Late night (9pm - 12am) is the most expensive time, 18% above average.
Show the data
| Time of day | Average fare |
|---|---|
| Morning | $383 |
| Midday | $355 |
| Afternoon | $389 |
| Evening | $320 |
| Late Night | $445 |
What do round-trip flights from Portland to Chicago cost?
Share of fares in each price range, adjusted to current prices.
Show the data
| Price range | Share of fares |
|---|---|
| $0 to $150 | 3% |
| $150 to $300 | 14% |
| $300 to $450 | 46% |
| $450 to $600 | 17% |
| $600 to $750 | 12% |
| $750 to $900 | 4% |
| $900 and up | 4% |
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 Portland to Chicago 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.