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Cheap flights from San Jose to Chicago (SJC - ORD)

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The best prices from San Jose to Chicago are usually found in February or January, booked 30 days in advance, depart on a Wednesday or Saturday and return on a Wednesday

SJC - CHI
Price
$238 - $406
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches
Popular in December High demand for flights, 20% potential price rise
Cheapest in February Best time to find cheap flights, 27% potential price drop
Round-trip from $238 From San Jose to Chicago
One-way from $216 One-way flight from San Jose to Chicago
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.

Cheap flights from San Jose to Chicago in June, July 2020

The best prices found for SJC to ORD flights for June, July
17 Jun - 6 Jul
$201pp
SJC
San Jose
$self.airline
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
SJC
San Jose
17 Jun - 24 Jun
$206pp
SJC
San Jose
$self.airline
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
SJC
San Jose
25 Jun - 30 Jun
$211pp
SJC
San Jose
$self.airline
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SJC
San Jose

San Jose to Chicago 2020 flight deals

Cheap flights to Chicago from San Jose found for this year
28 Jul - 11 Aug
$188pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
SJC
San Jose
23 Jul - 28 Jul
$196pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Alaska Airlines
 
1 STOP
SJC
San Jose
13 Jul - 14 Jul
$199pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
SJC
San Jose

Non-stop flights to Chicago from San Jose

Save time with San Jose to Chicago direct flight deals
21 Aug - 24 Aug
$277pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJC
San Jose
7 Aug - 9 Aug
$317pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
SJC
San Jose
16 Oct - 18 Oct
$417pp
SJC
San Jose
$self.airline
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
SJC
San Jose

Last minute flights from San Jose to Chicago

Late deals on round-trip flights to Chicago from San Jose, departing today and this week
26 May - 5 Jun
$338pp
SJC
San Jose
$self.airline
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SJC
San Jose
29 May - 1 Jun
$370pp
SJC
San Jose
$self.airline
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
SJC
San Jose
27 May - 9 Jun
$401pp
SJC
San Jose
Delta
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
SJC
San Jose

One-way flights to Chicago from San Jose

The cheapest one-way flights from San Jose to Chicago
5:29 pm - 10:15 am
JetBlue
1 Stop
14h 46m
SJC - ORD
JetBlue
$216
FlyFar
11:55 am - 11:49 am
Multiple Airlines
3 Stops
45h 54m
SJC - MDW
Multiple Airlines
$264
Kiwi.com
4:00 am - 4:55 pm
Delta
2 Stops
10h 55m
SJC - ORD
Delta
$307
Delta

Related info for your journey

Useful info, stats and facts about San Jose to Chicago flights.

Flight FAQs

From San Jose to Chicago

Are flight prices decreasing from San Jose to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both San Jose and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from San Jose to Chicago for under $200 on Cheapflights?

Yes, there are multiple flights from San Jose to Chicago for under $200. The cheapest flight booked recently is on Multiple Airlines for just $188, but on average you can expect to pay $220.

Are there nonstop flights from San Jose to Chicago for under $300 on Cheapflights?

Cheapflights has at least 3 direct flights from San Jose to Chicago under $300. A good price for a nonstop flight from San Jose to Chicago is less than $337.

Are there last-minute flights available from San Jose to Chicago for under $400?

There are currently 3+ open flights from San Jose to Chicago within the next 7 days for less than $400.

How popular is this flight route?

The San Jose to Chicago flight path was viewed by 62 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What is the cheapest airline for this route?

The cheapest airline for this route is American Airlines Inc.. When flying this airline from San Jose to Chicago on average you can expect to find 55 flights available for this route daily.

Is San Jose weather warmer or cooler than Chicago?

Our data indicates that the weather will be 84 °F on average in the month of July. The temperature in Chicago is typically hotter than in San Jose. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

Alternative routes for San Jose to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from San Jose to Chicago
Average temperature for June in Chicago
78.8 °F
Avg rainfall for June in Chicago
3.4 ″

Airports servicing San Jose

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from San Jose to Chicago

Morning 6 AM to noon 100% of SJC to ORD departures
Early morning Midnight to 6 AM 0% of SJC to ORD departures
Afternoon Noon to 6 PM 0% of SJC to ORD departures
Evening 6 PM to midnight 0% of SJC to ORD departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from San Jose to Chicago
Sunday
2 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
2 daily flights