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Save an average of $240 per person when bundling your flight and hotel together with Priceline
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Stops
- Nonstopfrom $370
- Up to 1 stop$194
- Up to 2 stops$413
Airlines
- Alaska Airlines$256
- American Airlines$334
- Delta Air Lines$318
- Frontier Airlines$243
- Hawaiian Airlines$269
- Southwest Airlines$411
- Spirit Airlines$194
- United Airlines$360
Cabin Class
- Economy$194
Departure Airports
- Norman Y. Mineta San Jose International Airport$194
Arrival Airports
- Chicago Midway Airport$318
- Chicago O Hare Airport$194
Layover Airports
- Baltimore/Washington International Thurgood Marshall Airport$411
- Bob Hope Airport$416
- Charlotte Douglas International Airport$365
- Dallas Fort Worth International Airport$301
- Dallas Love Field$416
- Denver International Airport$243
- Detroit Metropolitan Airport$318
- George Bush Intercontinental Houston Airport$451
- Harry Reid International Airport$194
- Hartsfield Jackson Atlanta International Airport$318
- Los Angeles International Airport$424
- Minneapolis-St Paul International/Wold-Chamberlain Airport$318
- Phoenix Sky Harbor International Airport$334
- Portland International Airport$256
- Salt Lake City International Airport$334
- San Diego International Airport$411
- Seattle Tacoma International Airport$256
Best Price. GUARANTEED.
Exclusively for Priceline Members
Tired of searching? Book now!
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BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
08/21/25
SJC
8h 16m
LAS
08/21/25
ORD
08/25/25
ORD
4h 53m
LAS
08/25/25
SJC
$194
08/15/25
SJC
8h 16m
LAS
08/15/25
ORD
08/18/25
ORD
4h 53m
LAS
08/18/25
SJC
$197
09/05/25
SJC
11h 36m
DEN
09/05/25
ORD
09/12/25
ORD
5h 32m
DEN
09/12/25
SJC
$243
09/09/25
SJC
10h 48m
SEA
09/09/25
ORD
09/13/25
ORD
5h 11m
PDX
09/13/25
SJC
$256
08/19/25
SJC
8h 34m
PDX
08/19/25
ORD
08/26/25
ORD
5h 36m
SEA
08/26/25
SJC
$262
08/14/25
SJC
10h 55m
SEA
08/14/25
ORD
08/18/25
ORD
2h 48m
Direct
08/18/25
SJC
$269
08/17/25
SJC
11h 52m
DEN
08/18/25
ORD
08/24/25
ORD
5h 16m
DEN
08/24/25
SJC
$270
08/16/25
SJC
11h 59m
PDX
08/16/25
ORD
08/23/25
ORD
5h 25m
PDX
08/23/25
SJC
$277
08/28/25
SJC
26h 23m
LAS
08/29/25
ORD
09/01/25
ORD
17h 30m
DFW
09/01/25
SJC
$301
09/03/25
SJC
9h 39m
DTW
09/04/25
MDW
09/10/25
MDW
5h 58m
ATL
09/10/25
SJC
$318
08/20/25
SJC
10h 10m
DTW
08/21/25
MDW
08/27/25
MDW
6h 13m
ATL
08/27/25
SJC
$318
08/13/25
SJC
10h 10m
DTW
08/14/25
MDW
08/20/25
MDW
6h 54m
MSP
08/20/25
SJC
$318
08/30/25
SJC
12h 49m
ATL
08/30/25
ORD
09/06/25
ORD
4h 52m
SLC
09/06/25
SJC
$334
08/30/25
SJC
8h 29m
PHX
08/30/25
ORD
09/01/25
ORD
2h 33m
Direct
09/01/25
SJC
$334
08/14/25
SJC
8h 8m
DEN
08/14/25
ORD
08/18/25
ORD
2h 42m
Direct
08/18/25
SJC
$360
08/29/25
SJC
8h 14m
DEN
08/29/25
ORD
09/01/25
ORD
2h 46m
Direct
09/01/25
SJC
$361
08/30/25
SJC
8h 29m
PHX
08/30/25
ORD
09/01/25
ORD
6h 55m
CLT
09/01/25
SJC
$365
09/06/25
SJC
6h 25m
Direct
09/06/25
ORD
09/09/25
ORD
2h 46m
Direct
09/09/25
SJC
$370
08/28/25
SJC
9h 8m
DTW
08/29/25
ORD
09/04/25
ORD
5h 14m
SLC
09/04/25
SJC
$370
08/31/25
SJC
12h 49m
ATL
08/31/25
ORD
09/07/25
ORD
6h 11m
MSP
09/07/25
SJC
$382
08/28/25
SJC
14h 30m
SAN
08/29/25
MDW
09/01/25
MDW
10h 40m
BWI
09/01/25
SJC
$411
08/18/25
SJC
11h 29m
SEA
08/19/25
ORD
08/24/25
ORD
10h 4m
SEA
PDX
08/24/25
SJC
$413
08/28/25
SJC
14h 25m
DAL
08/29/25
MDW
09/01/25
MDW
8h 30m
DAL
BUR
09/01/25
SJC
$416
08/14/25
SJC
6h 22m
Direct
08/14/25
ORD
08/18/25
ORD
2h 50m
Direct
08/19/25
SJC
$417
08/21/25
SJC
13h 24m
LAX
SEA
08/21/25
ORD
08/24/25
ORD
8h 39m
SEA
08/24/25
SJC
$424
08/28/25
SJC
11h 10m
IAH
08/29/25
ORD
09/04/25
ORD
7h 20m
DEN
09/04/25
SJC
$451
08/20/25
SJC
11h 17m
DFW
08/20/25
ORD
08/27/25
ORD
6h 9m
DFW
08/27/25
SJC
$460
08/28/25
SJC
14h 30m
SAN
08/29/25
MDW
09/01/25
MDW
2h 30m
Direct
09/01/25
SJC
$464
08/21/25
SJC
13h 24m
LAX
SEA
08/21/25
ORD
08/24/25
ORD
9h 52m
PDX
LAX
08/24/25
SJC
$494
08/22/25
SJC
11h 10m
IAH
08/23/25
ORD
08/29/25
ORD
2h 45m
Direct
08/29/25
SJC
$508
Top Deals on flights from San Jose to Chicago
San Jose, US (SJC) - Chicago, US (CHI)
Aug 22
SJC
8h 16m
LAS
Aug 22
ORD
as low as
$92
San Jose, US (SJC) - Chicago, US (CHI)
Sep 5
SJC
10h 21m
DEN
Sep 5
MDW
as low as
$121
San Jose, US (SJC) - Chicago, US (CHI)
Sep 16
SJC
11h 7m
SEA
Sep 16
ORD
as low as
$127
San Jose, US (SJC) - Chicago, US (CHI)
Aug 19
SJC
8h 34m
PDX
Aug 19
ORD
as low as
$133
San Jose, US (SJC) - Chicago, US (CHI)
Oct 7
SJC
10h 29m
SAN
Oct 7
ORD
as low as
$133
San Jose, US (SJC) - Chicago, US (CHI)
Jul 30
SJC
24h 15m
LAS
Jul 31
MDW
as low as
$147
San Jose, US (SJC) - Chicago, US (CHI)
Sep 16
SJC
11h 31m
ATL
Sep 17
MDW
as low as
$159
San Jose, US (SJC) - Chicago, US (CHI)
Sep 23
SJC
12h 14m
SEA
Sep 23
ORD
as low as
$159
San Jose, US (SJC) - Chicago, US (CHI)
Aug 12
SJC
13h 27m
LAX
SEA
Aug 12
ORD
as low as
$180
San Jose, US (SJC) - Chicago, US (CHI)
Aug 28
SJC
14h 25m
DAL
Aug 29
MDW
as low as
$190
San Jose, US (SJC) - Chicago, US (CHI)
Aug 29
SJC
11h 24m
DTW
Aug 30
ORD
as low as
$191
San Jose, US (SJC) - Chicago, US (CHI)
Jul 23
SJC
8h 38m
SLC
Jul 23
ORD
as low as
$205
Flights to Chicago
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