Cheap Flights from San Jose to Chicago
Browse current best options from San Jose. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
San Jose
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 5 days ago
402 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated Jul 12, 2026.)
Today’s best flight deals from San Jose to Chicago
Explore current cheapest deals departing from San Jose to Chicago
Round trip
Sort by: Cheapest
September 7 - September 16
SJC - Chicago
$277
$192
Round trip
September 10 - September 28
SJC - Chicago
$258
$195
Round trip
September 10 - September 14
SJC - Chicago
$304
$195
Round trip
September 10 - October 5
SJC - Chicago
$256
$196
Round trip
September 15 - September 28
SJC - Chicago
$265
$206
Round trip
September 21 - September 28
SJC - Chicago
$293
$206
Round trip
September 14 - September 28
SJC - Chicago
$265
$206
Round trip
September 15 - October 5
SJC - Chicago
$258
$207
Round trip
September 14 - October 5
SJC - Chicago
$258
$207
Round trip
September 21 - October 5
SJC - Chicago
$265
$207
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
San Jose to Chicago: Overview
Insights for flights from San Jose to Chicago
How much is a round trip from San Jose to Chicago
Regular price: $256 - $390
Prices are currently below the regular range for flights from San Jose to Chicago.
The regular price range for flights from San Jose to Chicago is typically between $256 and $390. Currently, the lowest deal is $214 with Frontier Airlines, for travel from Sep 6-Sep 10.
now $214
Low $256
High $390
The cheapest time to fly from San Jose to Chicago
The cheapest month to fly from San Jose to Chicago is January, with a median price of $174. The most expensive month is October, with a median price of $573. Prices are generally lower from January to December.
January
Flights from $174
October
Flights from $573
Direct flights from San Jose to Chicago
Southwest Airlines
United Airlines
Last-minute flights going from San Jose to Chicago
Tue, Aug 4
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$331
$237
One-way
Tue, Aug 4
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$346
$237
One-way
Tue, Aug 4
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$347
$257
One-way
Tue, Aug 4
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$373
$268
One-way
Wed, Aug 5
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$346
$256
One-way
Wed, Aug 5
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$359
$256
One-way
Biggest price drops on these dates for flights from San Jose to Chicago
Oct 24 - Oct 28
$498 → $248
50%
Oct 24 - Oct 26
$500 → $301
40%
Oct 28 - Oct 31
$430 → $237
45%
Oct 3 - Oct 7
$447 → $257
42%
Popular Airports to fly from San Jose to Chicago
San Jose - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from San Jose to Chicago are below the typical level, with 21% good prices.
📅 Best time to fly
Fly in December for prices as low as $174
Historically, December, January, and February offer the lowest median prices for this route.
⏱️ Flight duration
Direct flights take 4h 22m
Direct flights typically take 4h 22m, while connecting flights average 11h 55m.
✈️ Airlines & availability
Connecting flights are dominant
Connecting flights make up 74% of recent deals, with a median of 2 stopovers.
🏆 Airline highlight
Southwest Airlines and United Airlines offer direct flights
Southwest Airlines and United Airlines have offered direct flights on this route recently.
🎯 Booking tip
Deals appear frequently
Deals for flights from San Jose to Chicago appear frequently, with many options in the last 30 days.
San Jose main airports to depart from
San Jose International (SJC)
San Jose International Airport is a convenient option for flights from San Jose to Chicago.
📍 ~5 km from San Jose (reachable by car or bus)
💸 Flights from ~$214
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago, offering many connections from San Jose.
📍 ~25 km from Chicago city center (reachable by car, train, or bus).
💸 Flights from ~$214
Chicago Midway International (MDW)
Chicago Midway International Airport is a convenient option for reaching Chicago from San Jose.
📍 ~14 km from Chicago city center (reachable by car, train, or bus).
💸 Flights from ~$237
Chicago Rockford International (RFD)
Chicago Rockford International Airport offers an alternative arrival point for flights to the Chicago area from San Jose.
📍 ~126 km from Chicago city center (reachable by car or bus).
💸 Flights from ~$261
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International Airport is a major international airport with significant carrier presence and direct flight options.
📍 ~135 km from Chicago (reachable by car or train)
💸 Flights from ~$267
Gerald R. Ford International (GRR)
Gerald R. Ford International Airport is the second largest airport in Michigan with a robust domestic network.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$267
Dane County Regional (MSN)
Dane County Regional Airport is a reliable regional hub with efficient operations and good amenities.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$313
South Bend International (SBN)
South Bend International Airport is geographically the closest alternative airport to the Chicago metro area.
📍 ~120 km from Chicago (reachable by car or train)
💸 Flights from ~$296
Fort Wayne International (FWA)
Fort Wayne International Airport offers multiple cabin classes and solid connectivity for eastern domestic destinations.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$288
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from San Jose to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SJC
Elite
Nov 02
Chicago, United States
90% AI deal score
$2,000
$1,067
Save $933
From SJC
Elite
Nov 21
Chicago, United States
89% AI deal score
$1,834
$1,032
Save $802
From SJC
Elite
Oct 16
Chicago, United States
89% AI deal score
$1,898
$1,071
Save $827
From SJC
Elite
Dec 06
Chicago, United States
89% AI deal score
$1,978
$1,094
Save $884
From SJC
Elite
Aug 18
Chicago, United States
88% AI deal score
$1,638
$985
Save $653
From SJC
Elite
Aug 18
Chicago, United States
88% AI deal score
$1,666
$991
Save $675
From SJC
Elite
Aug 11
Chicago, United States
88% AI deal score
$1,833
$1,043
Save $790
From SJC
Elite
Oct 20
Chicago, United States
88% AI deal score
$1,628
$1,000
Save $628
From SJC
Elite
Sep 01
Chicago, United States
88% AI deal score
$1,792
$1,017
Save $775
From SJC
Elite
Nov 07
Chicago, United States
88% AI deal score
$1,636
$1,029
Save $607
From SJC
Elite
Sep 11
Chicago, United States
88% AI deal score
$1,791
$1,080
Save $711
From SJC
Elite
Aug 05
Chicago, United States
88% AI deal score
$2,035
$1,129
Save $906
From SJC
Elite
Aug 18
Chicago, United States
87% AI deal score
$1,636
$991
Save $645
From SJC
Elite
Aug 18
Chicago, United States
87% AI deal score
$1,606
$996
Save $610
From SJC
Elite
Aug 19
Chicago, United States
87% AI deal score
$1,638
$1,000
Save $638
From SJC
Elite
Jul 28
Chicago, United States
87% AI deal score
$1,676
$1,014
Save $662
From SJC
Elite
Aug 12
Chicago, United States
87% AI deal score
$1,642
$1,014
Save $628
From SJC
Elite
Aug 05
Chicago, United States
87% AI deal score
$1,604
$1,014
Save $590
From SJC
Elite
Aug 11
Chicago, United States
87% AI deal score
$1,640
$1,014
Save $626
From SJC
Elite
Aug 12
Chicago, United States
87% AI deal score
$1,610
$1,014
Save $596
From SJC
Elite
Aug 11
Chicago, United States
87% AI deal score
$1,610
$1,014
Save $596
From SJC
Elite
Aug 05
Chicago, United States
87% AI deal score
$1,604
$1,014
Save $590
From SJC
Elite
Aug 20
Chicago, United States
87% AI deal score
$1,654
$1,036
Save $618
From SJC
Elite
Aug 05
Chicago, United States
87% AI deal score
$1,670
$1,043
Save $627
From SJC
Elite
Oct 16
Chicago, United States
87% AI deal score
$1,604
$1,056
Save $548
From SJC
Elite
Nov 02
Chicago, United States
87% AI deal score
$1,649
$1,067
Save $582
From SJC
Elite
Jul 28
Chicago, United States
86% AI deal score
$1,682
$1,043
Save $639
From SJC
Elite
Aug 05
Chicago, United States
86% AI deal score
$1,667
$1,043
Save $624
From SJC
Elite
Jul 28
Chicago, United States
86% AI deal score
$1,679
$1,043
Save $636
From SJC
Elite
Aug 13
Chicago, United States
86% AI deal score
$1,659
$1,046
Save $613
From SJC
Elite
Aug 17
Chicago, United States
86% AI deal score
$1,636
$1,046
Save $590
From SJC
Elite
Aug 10
Chicago, United States
86% AI deal score
$1,633
$1,046
Save $587
From SJC
Elite
Aug 03
Chicago, United States
86% AI deal score
$1,605
$1,046
Save $559
From SJC
Elite
Jul 27
Chicago, United States
86% AI deal score
$1,679
$1,046
Save $633
From SJC
Elite
Aug 03
Chicago, United States
86% AI deal score
$1,610
$1,046
Save $564
From SJC
Elite
Aug 10
Chicago, United States
86% AI deal score
$1,604
$1,046
Save $558
From SJC
Elite
Aug 13
Chicago, United States
86% AI deal score
$1,610
$1,046
Save $564
From SJC
Elite
Sep 08
Chicago, United States
86% AI deal score
$1,503
$991
Save $512
From SJC
Elite
Sep 26
Chicago, United States
86% AI deal score
$1,518
$1,029
Save $489
From SJC
Elite
Sep 09
Chicago, United States
86% AI deal score
$1,764
$1,129
Save $635
From SJC
Elite
Jul 27
Chicago, United States
85% AI deal score
$1,679
$1,075
Save $604
From SJC
Elite
Jul 23
Chicago, United States
85% AI deal score
$1,444
$1,024
Save $420
From SJC
Elite
Aug 21
Chicago, United States
85% AI deal score
$1,528
$1,060
Save $468
From SJC
Elite
Oct 16
Chicago, United States
85% AI deal score
$1,547
$1,071
Save $476
From SJC
Elite
Oct 16
Chicago, United States
85% AI deal score
$1,554
$1,071
Save $483
From SJC
Elite
Nov 17
Chicago, United States
85% AI deal score
$1,634
$1,129
Save $505
From SJC
Elite
Nov 11
Chicago, United States
85% AI deal score
$1,634
$1,129
Save $505
From SJC
Elite
Oct 13
Chicago, United States
85% AI deal score
$1,617
$1,129
Save $488
From SJC
Elite
Nov 06
Chicago, United States
85% AI deal score
$1,636
$1,152
Save $484
From SJC
Elite
Aug 05
Chicago, United States
85% AI deal score
$2,296
$1,284
Save $1,012
From SJC
Elite
Sep 20
Chicago, United States
84% AI deal score
$1,373
$1,004
Save $369
From SJC
Elite
Aug 28
Chicago, United States
84% AI deal score
$2,234
$1,328
Save $906
From SJC
Elite
Sep 15
Chicago, United States
83% AI deal score
$1,493
$1,129
Save $364
From SJC
Elite
Jul 06
Chicago, United States
83% AI deal score
$1,849
$1,172
Save $677
From SJC
Elite
Sep 12
Chicago, United States
82% AI deal score
$1,275
$1,019
Save $256
From SJC
Elite
Sep 19
Chicago, United States
82% AI deal score
$1,283
$1,019
Save $264
From SJC
Elite
Aug 25
Chicago, United States
82% AI deal score
$1,370
$1,119
Save $251
From SJC
Elite
Dec 02
Chicago, United States
82% AI deal score
$1,968
$1,225
Save $743
From SJC
Elite
Jun 22
Chicago, United States
82% AI deal score
$1,994
$1,530
Save $464
From SJC
Elite
Aug 12
Chicago, United States
82% AI deal score
$1,173
$829
Save $344
From SJC
Elite
Aug 05
Chicago, United States
82% AI deal score
$1,201
$848
Save $353
From SJC
Elite
Aug 04
Chicago, United States
82% AI deal score
$1,246
$848
Save $398
From SJC
Elite
Aug 13
Chicago, United States
81% AI deal score
$1,375
$1,138
Save $237
From SJC
Elite
Aug 25
Chicago, United States
81% AI deal score
$1,184
$852
Save $332
From SJC
Elite
Aug 17
Chicago, United States
81% AI deal score
$1,208
$867
Save $341
From SJC
Elite
Aug 21
Chicago, United States
80% AI deal score
$1,915
$1,284
Save $631
From SJC
Elite
Aug 26
Chicago, United States
80% AI deal score
$1,958
$1,290
Save $668
From SJC
Elite
Oct 07
Chicago, United States
79% AI deal score
$1,624
$1,247
Save $377
From SJC
Elite
Aug 24
Chicago, United States
79% AI deal score
$1,821
$1,272
Save $549
From SJC
Elite
Sep 13
Chicago, United States
79% AI deal score
$1,751
$1,284
Save $467
From SJC
Elite
Sep 20
Chicago, United States
79% AI deal score
$1,739
$1,284
Save $455
From SJC
Elite
Jun 17
Chicago, United States
78% AI deal score
$2,172
$1,554
Save $618
From SJC
Elite
Jul 06
Chicago, United States
78% AI deal score
$2,008
$1,508
Save $500
From SJC
Elite
Jun 29
Chicago, United States
78% AI deal score
$2,059
$1,578
Save $481
From SJC
Elite
Aug 23
Chicago, United States
77% AI deal score
$1,366
$1,142
Save $224
From SJC
Elite
Aug 14
Chicago, United States
77% AI deal score
$1,197
$875
Save $322
From SJC
Elite
Oct 07
Chicago, United States
76% AI deal score
$1,101
$829
Save $272
From SJC
Elite
Sep 09
Chicago, United States
76% AI deal score
$1,086
$829
Save $257
From SJC
Elite
Sep 17
Chicago, United States
76% AI deal score
$1,124
$848
Save $276
From SJC
Elite
Sep 08
Chicago, United States
76% AI deal score
$1,166
$848
Save $318
From SJC
Elite
Sep 25
Chicago, United States
76% AI deal score
$1,113
$852
Save $261
From SJC
Elite
Sep 02
Chicago, United States
76% AI deal score
$1,116
$852
Save $264
From SJC
Elite
Sep 20
Chicago, United States
76% AI deal score
$1,149
$852
Save $297
From SJC
Elite
Aug 27
Chicago, United States
76% AI deal score
$1,178
$867
Save $311
From SJC
Elite
Aug 06
Chicago, United States
76% AI deal score
$1,201
$907
Save $294
From SJC
Elite
Aug 21
Chicago, United States
76% AI deal score
$1,236
$926
Save $310
From SJC
Elite
Aug 14
Chicago, United States
76% AI deal score
$1,243
$930
Save $313
From SJC
Elite
Jun 30
Chicago, United States
76% AI deal score
$1,088
$950
Save $138
From SJC
Elite
Sep 11
Chicago, United States
75% AI deal score
$1,361
$1,196
Save $165
From SJC
Elite
Sep 19
Chicago, United States
75% AI deal score
$1,111
$867
Save $244
From SJC
Elite
Sep 14
Chicago, United States
75% AI deal score
$1,139
$871
Save $268
From SJC
Elite
Aug 31
Chicago, United States
75% AI deal score
$1,166
$926
Save $240
From SJC
Elite
Aug 05
Chicago, United States
75% AI deal score
$1,175
$929
Save $246
From SJC
Elite
Aug 18
Chicago, United States
75% AI deal score
$1,173
$929
Save $244
From SJC
Elite
Sep 06
Chicago, United States
74% AI deal score
$1,271
$1,142
Save $129
From SJC
Elite
Jun 17
Chicago, United States
74% AI deal score
$1,692
$1,527
Save $165
From SJC
Elite
Nov 18
Chicago, United States
74% AI deal score
$969
$852
Save $117
From SJC
Elite
Sep 01
Chicago, United States
74% AI deal score
$1,071
$907
Save $164
From SJC
Elite
Oct 01
Chicago, United States
74% AI deal score
$1,125
$926
Save $199
From SJC
Elite
Sep 17
Chicago, United States
74% AI deal score
$1,139
$926
Save $213