Cheap Flights from Chicago to Portland
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RatePunk searches hundreds of travel sites at once for deals on flights to Portland
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 Chicago to Portland
Explore current cheapest deals departing from Chicago to Portland
Round trip
Sort by: Cheapest
October 7 - October 14
ORD - Portland
$227
$202
Round trip
November 4 - November 10
ORD - Portland
$285
$202
Round trip
August 6 - August 12
ORD - Portland
$206
$212
Round trip
October 21 - November 6
ORD - Portland
$261
$212
Round trip
October 20 - November 6
ORD - Portland
$259
$212
Round trip
October 20 - October 29
ORD - Portland
$281
$219
Round trip
October 21 - October 29
ORD - Portland
$283
$219
Round trip
August 19 - August 24
ORD - Portland
$217
$223
Round trip
August 7 - August 11
ORD - Portland
$220
$228
Round trip
August 7 - August 12
ORD - Portland
$214
$229
Round trip
Unlock all 500+ flight deals to Portland and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Portland
How much is a round trip from Chicago to Portland
Regular price: $189 - $284
Prices for flights from Chicago to Portland are currently within the regular range.
The regular price range for flights from Chicago to Portland is between $189 and $284. The current lowest deal is $202 with American Airlines, for travel from Oct 7 to Oct 14.
now $202
Low $189
High $284
The cheapest time to fly from Chicago to Portland
The cheapest month to fly from Chicago to Portland is April, with a median price of $251. The most expensive month is March, with a median price of $416. Prices are generally lower from January to November.
April
Flights from $251
March
Flights from $416
Direct flights from Chicago to Portland
American Airlines
Last-minute flights going from Chicago to Portland
Sat, Jul 4
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$309
$264
One-way
Sat, Jul 18
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$315
$252
One-way
Sat, Jul 18
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$304
$268
One-way
Sat, Jul 18
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$318
$276
One-way
Sat, Jul 18
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$305
$276
One-way
Tue, Jul 21
ORD - Portland
Chicago (ORD) - Portland (PDX)
Frontier Airlines
$311
$276
One-way
Biggest price drops on these dates for flights from Chicago to Portland
Aug 20 - Aug 23
$565 → $312
45%
Aug 15 - Aug 17
$570 → $337
41%
Aug 10 - Aug 13
$419 → $262
37%
Aug 22 - Aug 29
$402 → $246
39%
Popular Airports to fly from Chicago to Portland
Chicago - Portland route insights
💸 Price insights
Recent fares near the typical level.
Recent fares for Chicago to Portland are near the typical level, with prices around $202.
📅 Best time to fly
April is historically the cheapest month.
Historically, April is the cheapest month to fly from Chicago to Portland, with a median price of $251.
⏱️ Flight duration
Median flight time is 8h 38m.
The median flight time from Chicago to Portland is 8 hours and 38 minutes.
✈️ Airlines & availability
Frequent deals are available.
Deals for flights from Chicago to Portland are frequent, with over 1 deal per day.
🏆 Airline highlight
American Airlines offers direct flights.
American Airlines provides direct flights from Chicago to Portland.
🎯 Booking tip
Good prices are available 7% of the time.
Historically, a good price for Chicago to Portland flights is available 7% of the time.
Chicago main airports to depart from
O Hare International (ORD)
Depart from O'Hare International for flights to Portland, often offering the cheapest fares.
📍 ~25 km from Chicago city center (reachable by car or train).
💸 Flights from ~$202
Chicago Midway International (MDW)
Consider Chicago Midway International for a convenient departure option to Portland.
📍 ~15 km from Chicago city center (reachable by car or train).
💸 Flights from ~$205
Chicago Rockford International (RFD)
Chicago Rockford International offers another departure point for your journey to Portland.
📍 ~100 km from Chicago city center (reachable by car).
💸 Flights from ~$323
Portland main airports to arrive at
Portland International (PDX)
Portland International Airport is a convenient arrival choice for flights from Chicago to Portland.
📍 ~10 km from Portland city center (reachable by car)
💸 Flights from ~$202
Airports nearby Portland used as alternative
Seattle–Tacoma International (SEA)
Seattle–Tacoma International offers significantly more direct flight options and competitive pricing for international routes.
📍 ~220 km from Portland (reachable by car or train)
💸 Flights from ~$189
Eugene (EUG)
Eugene provides a faster airport experience with easier security lines and reliable regional connections to West Coast hubs.
📍 ~170 km from Portland (reachable by car)
💸 Flights from ~$237
Paine Field Everett (PAE)
Paine Field Everett offers a premium, low-stress terminal experience, useful for travelers heading north of Seattle.
📍 ~300 km from Portland (reachable by car)
💸 Flights from ~$286
Roberts Field (RDM)
Roberts Field is the primary gateway for Central Oregon, useful if your travel plans involve the eastern side of the Cascades.
📍 ~200 km from Portland (reachable by car)
💸 Flights from ~$343
Tri-Cities (PSC)
Tri-Cities serves as a viable backup for travelers in the Columbia River Gorge or Eastern Oregon.
📍 ~270 km from Portland (reachable by car)
💸 Flights from ~$290
Business & First Class Flight Deals to Portland
Discover luxury on the budget with premium cabin class on flights from Chicago to Portland.
Elite
Best Elite deals to Portland
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Oct 29
Portland, United States
90% AI deal score
$2,035
$769
Save $1,266
From ORD
Elite
Oct 07
Portland, United States
89% AI deal score
$2,028
$747
Save $1,281
From ORD
Elite
Aug 08
Portland, United States
86% AI deal score
$1,244
$845
Save $399
From ORD
Elite
Dec 12
Portland, United States
86% AI deal score
$1,271
$845
Save $426
From ORD
Elite
Aug 11
Portland, United States
86% AI deal score
$1,254
$850
Save $404
From ORD
Elite
Aug 11
Portland, United States
85% AI deal score
$1,219
$845
Save $374
From ORD
Elite
Dec 09
Portland, United States
85% AI deal score
$1,257
$845
Save $412
From ORD
Elite
Dec 08
Portland, United States
85% AI deal score
$1,253
$845
Save $408
From ORD
Elite
Dec 05
Portland, United States
85% AI deal score
$1,257
$845
Save $412
From ORD
Elite
Sep 08
Portland, United States
85% AI deal score
$1,248
$747
Save $501
From ORD
Elite
Aug 04
Portland, United States
84% AI deal score
$1,109
$845
Save $264
From ORD
Elite
Aug 05
Portland, United States
84% AI deal score
$1,088
$845
Save $243
From ORD
Elite
Aug 04
Portland, United States
84% AI deal score
$1,094
$845
Save $249
From ORD
Elite
Dec 09
Portland, United States
84% AI deal score
$1,138
$845
Save $293
From ORD
Elite
Dec 05
Portland, United States
84% AI deal score
$1,132
$845
Save $287
From ORD
Elite
Dec 08
Portland, United States
84% AI deal score
$1,132
$845
Save $287
From ORD
Elite
Dec 05
Portland, United States
84% AI deal score
$1,125
$845
Save $280
From ORD
Elite
Aug 04
Portland, United States
84% AI deal score
$1,103
$850
Save $253
From ORD
Elite
Aug 08
Portland, United States
83% AI deal score
$1,080
$845
Save $235
From ORD
Elite
Aug 05
Portland, United States
83% AI deal score
$1,072
$845
Save $227
From ORD
Elite
Nov 25
Portland, United States
83% AI deal score
$1,059
$845
Save $214
From ORD
Elite
Nov 24
Portland, United States
83% AI deal score
$1,057
$845
Save $212
From ORD
Elite
Nov 24
Portland, United States
83% AI deal score
$1,081
$845
Save $236
From ORD
Elite
Nov 25
Portland, United States
83% AI deal score
$1,081
$845
Save $236
From ORD
Elite
Jul 29
Portland, United States
82% AI deal score
$998
$845
Save $153
From ORD
Elite
Nov 24
Portland, United States
82% AI deal score
$1,015
$845
Save $170
From ORD
Elite
Nov 25
Portland, United States
82% AI deal score
$1,016
$845
Save $171
From ORD
Elite
Nov 25
Portland, United States
82% AI deal score
$1,015
$845
Save $170
From ORD
Elite
Oct 31
Portland, United States
82% AI deal score
$1,036
$845
Save $191
From ORD
Elite
Nov 17
Portland, United States
82% AI deal score
$1,018
$845
Save $173
From ORD
Elite
Aug 18
Portland, United States
82% AI deal score
$1,071
$747
Save $324
From ORD
Elite
Aug 12
Portland, United States
82% AI deal score
$1,096
$747
Save $349
From ORD
Elite
Jul 18
Portland, United States
82% AI deal score
$978
$747
Save $231
From ORD
Elite
Jul 18
Portland, United States
82% AI deal score
$970
$747
Save $223
From ORD
Elite
Aug 05
Portland, United States
82% AI deal score
$1,097
$747
Save $350
From ORD
Elite
Aug 08
Portland, United States
82% AI deal score
$1,088
$747
Save $341
From ORD
Elite
Nov 02
Portland, United States
82% AI deal score
$1,069
$769
Save $300
From ORD
Elite
Jul 29
Portland, United States
81% AI deal score
$972
$845
Save $127
From ORD
Elite
Nov 24
Portland, United States
81% AI deal score
$1,013
$845
Save $168
From ORD
Elite
Aug 18
Portland, United States
81% AI deal score
$1,059
$747
Save $312
From ORD
Elite
Aug 11
Portland, United States
81% AI deal score
$1,060
$747
Save $313
From ORD
Elite
Aug 15
Portland, United States
81% AI deal score
$1,059
$747
Save $312
From ORD
Elite
Aug 12
Portland, United States
81% AI deal score
$1,059
$747
Save $312
From ORD
Elite
Aug 08
Portland, United States
81% AI deal score
$1,061
$747
Save $314
From ORD
Elite
Aug 04
Portland, United States
81% AI deal score
$1,060
$747
Save $313
From ORD
Elite
Nov 27
Portland, United States
76% AI deal score
$1,060
$839
Save $221
From ORD
Elite
Jun 20
Portland, United States
75% AI deal score
$1,318
$1,045
Save $273
From ORD
Elite
Nov 06
Portland, United States
75% AI deal score
$1,125
$898
Save $227
From ORD
Elite
Aug 12
Portland, United States
74% AI deal score
$940
$845
Save $95
From ORD
Elite
Aug 12
Portland, United States
74% AI deal score
$965
$856
Save $109
From ORD
Elite
Aug 13
Portland, United States
74% AI deal score
$954
$856
Save $98
From ORD
Elite
Aug 12
Portland, United States
74% AI deal score
$954
$856
Save $98
From ORD
Elite
Aug 14
Portland, United States
74% AI deal score
$964
$856
Save $108
From ORD
Elite
Aug 13
Portland, United States
74% AI deal score
$965
$867
Save $98
From ORD
Elite
Aug 08
Portland, United States
73% AI deal score
$911
$845
Save $66
From ORD
Elite
Jul 30
Portland, United States
73% AI deal score
$932
$867
Save $65
From ORD
Elite
Aug 14
Portland, United States
73% AI deal score
$939
$867
Save $72
From ORD
Elite
Aug 07
Portland, United States
73% AI deal score
$936
$867
Save $69
From ORD
Elite
Jul 31
Portland, United States
73% AI deal score
$931
$867
Save $64
From ORD
Elite
Aug 06
Portland, United States
72% AI deal score
$891
$856
Save $35
From ORD
Elite
Aug 07
Portland, United States
72% AI deal score
$891
$857
Save $34
From ORD
Elite
Aug 07
Portland, United States
72% AI deal score
$911
$857
Save $54
From ORD
Elite
Aug 10
Portland, United States
72% AI deal score
$891
$858
Save $33
From ORD
Elite
Dec 11
Portland, United States
72% AI deal score
$923
$864
Save $59
From ORD
Elite
Aug 13
Portland, United States
72% AI deal score
$915
$867
Save $48
From ORD
Elite
Jul 30
Portland, United States
72% AI deal score
$912
$867
Save $45
From ORD
Elite
Jul 28
Portland, United States
71% AI deal score
$877
$856
Save $21
From ORD
Elite
Jul 31
Portland, United States
71% AI deal score
$866
$856
Save $10
From ORD
Elite
Aug 08
Portland, United States
71% AI deal score
$883
$856
Save $27
From ORD
Elite
Aug 07
Portland, United States
71% AI deal score
$874
$857
Save $17
From ORD
Elite
Aug 09
Portland, United States
71% AI deal score
$891
$867
Save $24
From ORD
Elite
Jul 27
Portland, United States
71% AI deal score
$877
$867
Save $10
From ORD
Elite
Aug 07
Portland, United States
71% AI deal score
$880
$868
Save $12
From ORD
Elite
Aug 07
Portland, United States
71% AI deal score
$883
$868
Save $15
From ORD
Elite
Jul 22
Portland, United States
71% AI deal score
$1,042
$1,023
Save $19
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$848
$845
Save $3
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$845
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$847
$846
Save $1
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$856
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$856
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$856
From ORD
Elite
Jul 31
Portland, United States
70% AI deal score
$856
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$856
From ORD
Elite
Jul 28
Portland, United States
70% AI deal score
$864
$856
Save $8
From ORD
Elite
Jul 31
Portland, United States
70% AI deal score
$865
$857
Save $8
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$857
From ORD
Elite
Nov 20
Portland, United States
70% AI deal score
$862
From ORD
Elite
Jul 31
Portland, United States
70% AI deal score
$867
From ORD
Elite
Jul 31
Portland, United States
70% AI deal score
$867
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$867
From ORD
Elite
Jul 31
Portland, United States
70% AI deal score
$869
$867
Save $2
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$867
From ORD
Elite
Jul 27
Portland, United States
70% AI deal score
$867
From ORD
Elite
Nov 04
Portland, United States
70% AI deal score
$892
From ORD
Elite
Nov 04
Portland, United States
70% AI deal score
$893
From ORD
Elite
Nov 20
Portland, United States
70% AI deal score
$902
From ORD
Elite
Nov 20
Portland, United States
70% AI deal score
$903
From ORD
Elite
Jul 29
Portland, United States
70% AI deal score
$934
From ORD
Elite
Jul 21
Portland, United States
70% AI deal score
$934
From ORD
Elite
Jul 21
Portland, United States
70% AI deal score
$934