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 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 San Jose to Chicago
Explore current cheapest deals departing from San Jose to Chicago
Round trip
Sort by: Cheapest
July 21 - July 28
SJC - Chicago
$399
$264
Round trip
July 8 - July 22
SJC - Chicago
$384
$264
Round trip
July 15 - July 22
SJC - Chicago
$363
$274
Round trip
July 11 - July 15
SJC - Chicago
$380
$275
Round trip
July 9 - July 15
SJC - Chicago
$368
$275
Round trip
July 10 - July 15
SJC - Chicago
$373
$275
Round trip
August 12 - August 19
SJC - Chicago
$335
$276
Round trip
August 12 - August 25
SJC - Chicago
$307
$276
Round trip
July 16 - July 20
SJC - Chicago
$377
$288
Round trip
July 20 - July 23
SJC - Chicago
$367
$288
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 San Jose to Chicago
How much is a round trip from San Jose to Chicago
Regular price: $338 - $556
Prices for flights from San Jose to Chicago are currently below the regular range.
The regular price range for flights from San Jose to Chicago is between $338 and $556. The current lowest deal is $264 with Southwest Airlines for travel from Jul 21-Jul 28.
now $264
Low $338
High $556
The cheapest time to fly from San Jose to Chicago
The cheapest month to fly from SJC to CHI is January, with a median price of $174. The most expensive month is March, with a median price of $625. Generally, prices are lower from January to December.
January
Flights from $174
March
Flights from $625
Direct flights from San Jose to Chicago
Southwest Airlines
United Airlines
Last-minute flights going from San Jose to Chicago
Mon, Jul 6
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$386
$315
One-way
Tue, Jul 7
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$386
$311
One-way
Tue, Jul 7
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$358
$316
One-way
Wed, Jul 8
SJC - Chicago
San Jose (SJC) - Chicago (MDW)
Southwest Airlines
$384
$264
One-way
Wed, Jul 8
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Alaska Airlines, Inc.
$324
$312
One-way
Thu, Jul 9
SJC - Chicago
San Jose (SJC) - Chicago (ORD)
Frontier Airlines
$368
$275
One-way
Biggest price drops on these dates for flights from San Jose to Chicago
Oct 23 - Oct 25
$504 → $331
34%
Oct 10 - Oct 11
$501 → $329
34%
Oct 22 - Oct 25
$502 → $330
34%
Oct 16 - Oct 18
$504 → $332
34%
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 SJC to CHI are at $264, below the typical level of $347.
📅 Best time to fly
Fly in December, January, or February for the best prices
Historically, the cheapest flights to Chicago are in December, January, and February, at $174.
⏱️ Flight duration
Flights typically take 13h 25m
The median flight duration from San Jose to Chicago is 13 hours and 25 minutes.
✈️ Airlines & availability
Connecting flights are dominant for this route
Only 23.1% of deals are direct, with connecting flights typically having 2 stopovers.
🏆 Airline highlight
Southwest Airlines offers a $264 deal
A recent deal on Southwest Airlines to Chicago Midway International Airport is available for $264.
🎯 Booking tip
Deals appear frequently for this route
Historically, deals for flights from San Jose to Chicago appear frequently, averaging 1.03 per day.
San Jose main airports to depart from
San Jose International (SJC)
San Jose International Airport is a good choice for flights from San Jose to Chicago.
📍 ~5 km from San Jose city center (reachable by car)
💸 Flights from ~$264
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International Airport is a good option for flights from San Jose to Chicago, offering competitive prices.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$264
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves the Chicago area for travelers flying from San Jose.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$342
O Hare International (ORD)
O Hare International Airport is a major hub for flights from San Jose to Chicago.
📍 ~40 km from Chicago city center (reachable by car)
💸 Flights from ~$272
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~100 km from Chicago (reachable by rail)
💸 Flights from ~$368
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, with direct commuter rail connections.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$339
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$355
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service and less congestion.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$334
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and is an alternative for southeastern Chicago suburbs.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$354
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