background

Business Class Flight Deals from San Jose to Chicago from $403

Bundle + Save

Bundle + Save

Top flight deals from leading airlines:

HA LogoQR LogoSQ LogoNH LogoEK LogoJL LogoTK Logo

... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

Bundle & Save

Save an average of $240 per person when bundling your flight and hotel together with Priceline

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Stops

  • Nonstop
    from $806
  • Up to 1 stop
    $887

Airlines

  • American Airlines
    $806

Cabin Class

  • First
    $806

Departure Airports

  • Norman Y. Mineta San Jose International Airport
    $1090
  • San Francisco International Airport
    $806

Arrival Airports

  • Chicago O Hare Airport
    $806

Layover Airports

  • Charlotte Douglas International Airport
    $887
  • Dallas Fort Worth International Airport
    $887
  • Los Angeles International Airport
    $985
  • Phoenix Sky Harbor International Airport
    $887

Best Price. GUARANTEED.

Exclusively for Priceline Members
Tired of searching? Book now!
We'll refund the difference if you find a lower price.

BUNDLE & SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$806
American Airlines Logo
American Airlines

07/25/25

SFO
9h 16m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$887
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$887
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$887
American Airlines Logo
American Airlines

07/25/25

SFO
8h 18m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$887
American Airlines Logo
American Airlines

07/25/25

SFO
4h 22m
Direct

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$896
American Airlines Logo
American Airlines

07/25/25

SFO
9h 16m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$968
American Airlines Logo
American Airlines

07/25/25

SFO
8h 18m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$968
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$968
American Airlines Logo
American Airlines

07/25/25

SFO
4h 22m
Direct

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$977
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
13h 51m
LAX

08/01/25

SFO
$985
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
11h 36m
LAX

08/01/25

SFO
$996
American Airlines Logo
American Airlines

07/25/25

SFO
4h 24m
Direct

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$1006
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 37m
Direct

08/01/25

SFO
$1020
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
10h 33m
LAX

08/01/25

SFO
$1036
American Airlines Logo
American Airlines

07/25/25

SFO
8h 18m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
13h 51m
LAX

08/01/25

SFO
$1066
American Airlines Logo
American Airlines

07/25/25

SFO
9h 16m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
13h 51m
LAX

08/01/25

SFO
$1066
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
13h 51m
LAX

08/01/25

SFO
$1066
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
11h 36m
LAX

08/01/25

SFO
$1077
American Airlines Logo
American Airlines

07/25/25

SFO
4h 24m
Direct

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 47m
PHX

08/01/25

SFO
$1087
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
8h 20m
PHX

08/01/25

SJC
$1090
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 37m
Direct

08/01/25

SFO
$1090
American Airlines Logo
American Airlines

07/25/25

SFO
4h 15m
Direct

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$1090
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 10m
PHX

08/01/25

SJC
$1090
American Airlines Logo
American Airlines

07/25/25

SFO
6h 55m
DFW

07/25/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 54m
Direct

08/01/25

SFO
$1100
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
4h 37m
Direct

08/01/25

SFO
$1101
American Airlines Logo
American Airlines

07/25/25

SFO
4h 18m
Direct

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 9m
PHX

08/01/25

SJC
$1143
American Airlines Logo
American Airlines

07/25/25

SFO
8h 18m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 10m
PHX

08/01/25

SJC
$1166
American Airlines Logo
American Airlines

07/25/25

SFO
6h 52m
DFW

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
6h 10m
PHX

08/01/25

SJC
$1166
American Airlines Logo
American Airlines

07/25/25

SFO
9h 16m
CLT

07/26/25

ORD
American Airlines Logo
American Airlines

08/01/25

ORD
8h 20m
PHX

08/01/25

SJC
$1166

Top Deals on flights Business Class from San Jose to Chicago

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 18m
Direct

Jul 26

ORD

as low as

$403

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
6h 52m
DFW

Jul 26

ORD

as low as

$484

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
10h 14m
CLT

Jul 25

ORD

as low as

$484

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 24m
Direct

Jul 25

ORD

as low as

$489

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 22m
Direct

Jul 25

ORD

as low as

$493

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
10h 24m
DFW

Jul 25

ORD

as low as

$683

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 15m
Direct

Jul 25

ORD

as low as

$687

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 23m
Direct

Jul 25

ORD

as low as

$687

San Francisco, US (SFO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 25

SFO
4h 25m
Direct

Jul 25

ORD

as low as

$687

San Francisco, US (SFO) - Chicago, US (CHI)

 Logo

Jul 25

SFO
4h 23m
Direct

Jul 25

ORD

as low as

$1638

San Francisco, US (SFO) - Chicago, US (CHI)

Hawaiian Airlines Logo
Hawaiian Airlines

Jul 25

SFO
4h 23m
Direct

Jul 25

ORD

as low as

$1638