Cheap Flights from Portland to Chicago
Browse current best options from Portland. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Portland
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Portland to Chicago
Explore current cheapest deals departing from Portland to Chicago
Round trip
Sort by: Cheapest
August 5 - August 11
PDX - Chicago
$233
$202
Round trip
September 16 - September 23
PDX - Chicago
$187
$202
Round trip
October 14 - October 21
PDX - Chicago
$263
$202
Round trip
October 13 - October 21
PDX - Chicago
$231
$202
Round trip
October 14 - October 20
PDX - Chicago
$237
$202
Round trip
October 7 - October 14
PDX - Chicago
$233
$202
Round trip
August 5 - August 10
PDX - Chicago
$240
$206
Round trip
August 4 - August 10
PDX - Chicago
$233
$206
Round trip
December 7 - December 9
PDX - Chicago
$266
$206
Round trip
September 30 - October 20
PDX - Chicago
$236
$211
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Portland to Chicago
How much is a round trip from Portland to Chicago
Regular price: $185 - $357
Prices for flights from Portland to Chicago are currently within the regular range.
The regular price range for flights from Portland to Chicago is typically between $185 and $357. The current lowest deal is $202 with Alaska Airlines, Inc. for travel from August 5 to August 11.
now $202
Low $185
High $357
The cheapest time to fly from Portland to Chicago
Flights from Portland to Chicago are generally lower priced from January to November. The cheapest month to fly is January, with a median price of $161. The most expensive month is March, with a median price of $442.
January
Flights from $161
March
Flights from $442
Direct flights from Portland to Chicago
Alaska Airlines, Inc.
Last-minute flights going from Portland to Chicago
Sat, Jun 20
PDX - Chicago
Portland (PDX) - Chicago (MDW)
$489
$399
One-way
Sat, Jun 20
PDX - Chicago
Portland (PDX) - Chicago (MDW)
$496
$441
One-way
Sat, Jun 20
PDX - Chicago
Portland (PDX) - Chicago (MDW)
$494
$441
One-way
Sat, Aug 1
PDX - Chicago
Portland (PDX) - Chicago (ORD)
American Airlines
$247
$259
One-way
Tue, Aug 4
PDX - Chicago
Portland (PDX) - Chicago (ORD)
Alaska Airlines, Inc.
$233
$206
One-way
Tue, Aug 4
PDX - Chicago
Portland (PDX) - Chicago (ORD)
Alaska Airlines, Inc.
$247
$215
One-way
Biggest price drops on these dates for flights from Portland to Chicago
Nov 4 - Nov 9
$397 → $242
39%
Aug 4 - Aug 11
$357 → $222
38%
Aug 6 - Aug 12
$360 → $243
32%
Aug 15 - Aug 22
$362 → $263
27%
Popular Airports to fly from Portland to Chicago
Portland - Chicago route insights
💸 Price insights
Recent fares are near the typical level.
Recent fares from Portland to Chicago are near the typical level of $325.
📅 Best time to fly
January is historically the cheapest month to fly.
Historically, January is the cheapest month to fly, with a median price of $161.
⏱️ Flight duration
Flights typically take 8h 57m.
The median flight duration from Portland to Chicago is 8 hours and 57 minutes.
✈️ Airlines & availability
41.6% of recent deals are direct.
Historically, 41.6% of deals for this route are direct, with connecting flights having 2 stopovers.
🏆 Airline highlight
Alaska Airlines, Inc. offers direct flights.
Alaska Airlines, Inc. has offered direct flights from Portland to Chicago in recent deals.
🎯 Booking tip
Deals appear frequently for this route.
Historically, deals for flights from Portland to Chicago appear frequently, averaging 1.03 per day.
Portland main airports to depart from
Portland International (PDX)
Portland International Airport is a great option for flights from Portland to Chicago.
📍 ~10 km from city center (reachable by car or public transport)
💸 Flights from ~$202
Chicago main airports to arrive at
Chicago Midway International (MDW)
Consider Chicago Midway International for flights to Chicago, offering a convenient arrival option.
📍 ~17 km from Chicago (reachable by car)
💸 Flights from ~$202
Chicago Rockford International (RFD)
Chicago Rockford International is an alternative arrival airport for flights to the Chicago area.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$298
O Hare International (ORD)
O Hare International is a major airport for flights to Chicago, providing extensive connectivity.
📍 ~40 km from Chicago (reachable by car)
💸 Flights from ~$202
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers high-frequency flight options and direct rail access to Chicago.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$317
South Bend International (SBN)
South Bend International is a close alternative to Chicago, connected by commuter rail.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$322
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, good for eastern Chicago metro travelers.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$205
Dane County Regional (MSN)
Dane County Regional is a reliable airport with less congestion than major Chicago hubs.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$285
Fort Wayne International (FWA)
Fort Wayne International is an alternative for travelers in Chicago's southeastern suburbs.
📍 ~220 km from Chicago (reachable by car)
💸 Flights from ~$348
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Portland to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From PDX
Elite
Aug 11
Chicago, United States
89% AI deal score
$1,537
$845
Save $692
From PDX
Elite
Aug 12
Chicago, United States
89% AI deal score
$1,537
$856
Save $681
From PDX
Elite
Aug 14
Chicago, United States
89% AI deal score
$1,537
$856
Save $681
From PDX
Elite
Aug 12
Chicago, United States
89% AI deal score
$1,487
$850
Save $637
From PDX
Elite
Aug 12
Chicago, United States
88% AI deal score
$1,492
$845
Save $647
From PDX
Elite
Aug 11
Chicago, United States
88% AI deal score
$1,449
$845
Save $604
From PDX
Elite
Aug 11
Chicago, United States
88% AI deal score
$1,522
$856
Save $666
From PDX
Elite
Aug 10
Chicago, United States
88% AI deal score
$1,515
$856
Save $659
From PDX
Elite
Aug 12
Chicago, United States
88% AI deal score
$1,522
$856
Save $666
From PDX
Elite
Aug 13
Chicago, United States
88% AI deal score
$1,522
$856
Save $666
From PDX
Elite
Aug 11
Chicago, United States
88% AI deal score
$1,492
$856
Save $636
From PDX
Elite
Aug 15
Chicago, United States
88% AI deal score
$1,522
$856
Save $666
From PDX
Elite
Aug 14
Chicago, United States
88% AI deal score
$1,492
$867
Save $625
From PDX
Elite
Aug 10
Chicago, United States
88% AI deal score
$1,486
$867
Save $619
From PDX
Elite
Aug 13
Chicago, United States
88% AI deal score
$1,537
$867
Save $670
From PDX
Elite
Aug 15
Chicago, United States
88% AI deal score
$1,537
$891
Save $646
From PDX
Elite
Nov 17
Chicago, United States
88% AI deal score
$1,384
$850
Save $534
From PDX
Elite
Aug 03
Chicago, United States
87% AI deal score
$1,398
$856
Save $542
From PDX
Elite
Aug 10
Chicago, United States
87% AI deal score
$1,412
$856
Save $556
From PDX
Elite
Aug 03
Chicago, United States
87% AI deal score
$1,387
$856
Save $531
From PDX
Elite
Aug 11
Chicago, United States
87% AI deal score
$1,407
$856
Save $551
From PDX
Elite
Aug 12
Chicago, United States
87% AI deal score
$1,418
$856
Save $562
From PDX
Elite
Aug 10
Chicago, United States
87% AI deal score
$1,404
$867
Save $537
From PDX
Elite
Aug 10
Chicago, United States
87% AI deal score
$1,442
$867
Save $575
From PDX
Elite
Aug 03
Chicago, United States
87% AI deal score
$1,395
$867
Save $528
From PDX
Elite
Aug 13
Chicago, United States
87% AI deal score
$1,449
$867
Save $582
From PDX
Elite
Aug 12
Chicago, United States
87% AI deal score
$1,449
$891
Save $558
From PDX
Elite
Aug 14
Chicago, United States
87% AI deal score
$1,522
$902
Save $620
From PDX
Elite
Aug 13
Chicago, United States
87% AI deal score
$1,492
$902
Save $590
From PDX
Elite
Nov 17
Chicago, United States
87% AI deal score
$1,297
$845
Save $452
From PDX
Elite
Nov 17
Chicago, United States
87% AI deal score
$1,280
$845
Save $435
From PDX
Elite
Dec 12
Chicago, United States
87% AI deal score
$1,383
$845
Save $538
From PDX
Elite
Dec 08
Chicago, United States
87% AI deal score
$1,370
$845
Save $525
From PDX
Elite
Dec 05
Chicago, United States
87% AI deal score
$1,365
$845
Save $520
From PDX
Elite
Dec 08
Chicago, United States
87% AI deal score
$1,364
$845
Save $519
From PDX
Elite
Dec 05
Chicago, United States
87% AI deal score
$1,370
$845
Save $525
From PDX
Elite
Aug 15
Chicago, United States
87% AI deal score
$1,319
$850
Save $469
From PDX
Elite
Aug 11
Chicago, United States
87% AI deal score
$1,297
$850
Save $447
From PDX
Elite
Dec 09
Chicago, United States
87% AI deal score
$1,365
$850
Save $515
From PDX
Elite
Aug 03
Chicago, United States
86% AI deal score
$1,369
$867
Save $502
From PDX
Elite
Aug 03
Chicago, United States
86% AI deal score
$1,390
$867
Save $523
From PDX
Elite
Aug 11
Chicago, United States
86% AI deal score
$1,418
$891
Save $527
From PDX
Elite
Aug 10
Chicago, United States
86% AI deal score
$1,400
$902
Save $498
From PDX
Elite
Aug 15
Chicago, United States
86% AI deal score
$1,492
$934
Save $558
From PDX
Elite
Aug 15
Chicago, United States
86% AI deal score
$1,256
$845
Save $411
From PDX
Elite
Aug 11
Chicago, United States
86% AI deal score
$1,256
$845
Save $411
From PDX
Elite
Dec 05
Chicago, United States
86% AI deal score
$1,254
$845
Save $409
From PDX
Elite
Dec 08
Chicago, United States
86% AI deal score
$1,262
$845
Save $417
From PDX
Elite
Dec 05
Chicago, United States
86% AI deal score
$1,262
$845
Save $417
From PDX
Elite
Oct 31
Chicago, United States
86% AI deal score
$1,268
$849
Save $419
From PDX
Elite
Aug 12
Chicago, United States
86% AI deal score
$1,256
$850
Save $406
From PDX
Elite
Dec 09
Chicago, United States
86% AI deal score
$1,270
$850
Save $420
From PDX
Elite
Aug 01
Chicago, United States
86% AI deal score
$1,387
$935
Save $452
From PDX
Elite
Jul 13
Chicago, United States
85% AI deal score
$1,378
$753
Save $625
From PDX
Elite
Aug 15
Chicago, United States
85% AI deal score
$1,342
$890
Save $452
From PDX
Elite
Aug 12
Chicago, United States
85% AI deal score
$1,343
$890
Save $453
From PDX
Elite
Aug 11
Chicago, United States
85% AI deal score
$1,343
$890
Save $453
From PDX
Elite
Aug 13
Chicago, United States
85% AI deal score
$1,343
$901
Save $442
From PDX
Elite
Aug 14
Chicago, United States
85% AI deal score
$1,342
$901
Save $441
From PDX
Elite
Aug 10
Chicago, United States
85% AI deal score
$1,337
$901
Save $436
From PDX
Elite
Aug 03
Chicago, United States
85% AI deal score
$1,387
$902
Save $485
From PDX
Elite
Dec 16
Chicago, United States
85% AI deal score
$1,450
$921
Save $529
From PDX
Elite
Aug 04
Chicago, United States
85% AI deal score
$1,443
$934
Save $509
From PDX
Elite
Aug 11
Chicago, United States
85% AI deal score
$1,411
$934
Save $477
From PDX
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,222
$845
Save $377
From PDX
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,220
$845
Save $375
From PDX
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,216
$845
Save $371
From PDX
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,211
$845
Save $366
From PDX
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,211
$845
Save $366
From PDX
Elite
Jul 25
Chicago, United States
85% AI deal score
$1,301
$935
Save $366
From PDX
Elite
Nov 26
Chicago, United States
84% AI deal score
$1,277
$867
Save $410
From PDX
Elite
Jul 21
Chicago, United States
84% AI deal score
$1,389
$929
Save $460
From PDX
Elite
Oct 31
Chicago, United States
84% AI deal score
$1,194
$849
Save $345
From PDX
Elite
Oct 31
Chicago, United States
84% AI deal score
$1,194
$849
Save $345
From PDX
Elite
Jul 22
Chicago, United States
84% AI deal score
$1,214
$934
Save $280
From PDX
Elite
Jul 21
Chicago, United States
84% AI deal score
$1,203
$934
Save $269
From PDX
Elite
Nov 14
Chicago, United States
84% AI deal score
$1,297
$935
Save $362
From PDX
Elite
Oct 27
Chicago, United States
84% AI deal score
$1,272
$935
Save $337
From PDX
Elite
Jul 16
Chicago, United States
84% AI deal score
$1,775
$992
Save $783
From PDX
Elite
Jul 18
Chicago, United States
83% AI deal score
$1,184
$935
Save $249
From PDX
Elite
Nov 07
Chicago, United States
83% AI deal score
$1,594
$957
Save $637
From PDX
Elite
Aug 04
Chicago, United States
83% AI deal score
$1,349
$1,023
Save $326
From PDX
Elite
Aug 01
Chicago, United States
83% AI deal score
$1,333
$1,024
Save $309
From PDX
Elite
Aug 22
Chicago, United States
83% AI deal score
$1,166
$747
Save $419
From PDX
Elite
Aug 08
Chicago, United States
83% AI deal score
$1,157
$747
Save $410
From PDX
Elite
Jul 22
Chicago, United States
83% AI deal score
$966
$747
Save $219
From PDX
Elite
Aug 04
Chicago, United States
83% AI deal score
$1,144
$747
Save $397
From PDX
Elite
Jul 18
Chicago, United States
83% AI deal score
$947
$747
Save $200
From PDX
Elite
Jul 21
Chicago, United States
83% AI deal score
$970
$747
Save $223
From PDX
Elite
Nov 26
Chicago, United States
82% AI deal score
$1,264
$927
Save $337
From PDX
Elite
Jul 22
Chicago, United States
82% AI deal score
$1,209
$934
Save $275
From PDX
Elite
Jul 22
Chicago, United States
82% AI deal score
$1,209
$934
Save $275
From PDX
Elite
Jul 21
Chicago, United States
82% AI deal score
$1,140
$934
Save $206
From PDX
Elite
Oct 27
Chicago, United States
82% AI deal score
$1,073
$747
Save $326
From PDX
Elite
Aug 26
Chicago, United States
82% AI deal score
$1,111
$747
Save $364
From PDX
Elite
Aug 19
Chicago, United States
82% AI deal score
$1,115
$747
Save $368
From PDX
Elite
Aug 19
Chicago, United States
82% AI deal score
$1,139
$758
Save $381
From PDX
Elite
Aug 31
Chicago, United States
82% AI deal score
$1,108
$758
Save $350
From PDX
Elite
Aug 14
Chicago, United States
82% AI deal score
$1,144
$758
Save $386
From PDX
Elite
Aug 10
Chicago, United States
82% AI deal score
$1,140
$758
Save $382