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  1. Flights
  2. United States
  3. Chicago
  4. San Jose, CA - Chicago

Cheap Flights from San Jose, CA (SJC) to Chicago (CHI)

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Discover the cheapest flights from San Jose, CA to Chicago
Filter by
Thu, Dec 3 - Tue, Dec 8
AS
ASDirect
SJC - CHI
F9
F9Direct
CHI - SJC
187$
175$
Prime price per passenger
Wed, Dec 9 - Tue, Dec 15
AS
ASDirect
SJC - CHI
F9
F9Direct
CHI - SJC
192$
180$
Prime price per passenger
Tue, Nov 24 - Thu, Nov 26
AS
ASDirect
SJC - CHI
F9
F9Direct
CHI - SJC
198$
193$
Prime price per passenger
Mon, Jan 4 - Fri, Jan 8
AS
ASDirect
SJC - CHI
AS
ASDirect
CHI - SJC
256$
242$
Prime price per passenger
Thu, Jan 14 - Sat, Jan 23
AS
ASDirect
SJC - CHI
AS
ASDirect
CHI - SJC
256$
242$
Prime price per passenger
Wed, Dec 23 - Wed, Dec 30
AS
ASDirect
SJC - CHI
F9
F9Direct
CHI - SJC
277$
262$
Prime price per passenger
Tue, Dec 15
AS
ASDirect
SJC - CHI
101$
95$
Prime price per passenger
Tue, Nov 24
AS
ASDirect
SJC - CHI
101$
95$
Prime price per passenger
Thu, Dec 3
AS
ASDirect
SJC - CHI
101$
95$
Prime price per passenger
Tue, Dec 29
F9
F9Direct
SJC - CHI
-14 %
114$
98$
Prime price per passenger
Fri, Jan 22
AS
ASDirect
SJC - CHI
128$
117$
Prime price per passenger
Tue, Jan 5
AS
ASDirect
SJC - CHI
128$
121$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from San Jose, CA to Chicago

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the beginning of January. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.
Filter by
week: Jan 4 - Jan 10
Flights from just $147
$188
$157
$150
$162
$293
$198
$161
$274
$292
$212
$147
$158
OctoberNovemberDecemberJanuary
Flying Time5 h and 52 mWhen flying from San Jose, CA to Chicago, this can take around 5 h and 52 m in flying time, however this flight duration can vary due to other factors
Cheapest flight$95The best price for flights from San Jose, CA to Chicago offered by eDreams, which have been found by our customers in the last 3 days
Origin airportSan Jose Mineta International AirportWhen flying from San Jose, CA to Chicago
Destination airportsO'hare International Airport, Midway International AirportWhen traveling from San Jose, CA to Chicago
Peak seasonMarchMarch is the busiest time to fly from San Jose, CA to Chicago according to search data results from our customers
Airlines operating this routeAmerican AirlinesAirline(s) that fly from San Jose, CA to Chicago
One-way average Price$248A flight from San Jose, CA to Chicago at eDreams will cost around $248, this being based on prices of the previous 6 months of data
Best time to bookMarchMarch is one of the most frequent times to fly to Chicago from San Jose, CA according to real data from our customers
Airlines that fly from San Jose, CA to Chicago
American Airlines
American Airlines
300$
Distance: 1,833 mi
San Jose, CA airports
San Jose Mineta International Airport (SJC)How far from city center: 2 mi
Chicago airports
O'hare International Airport (ORD)How far from city center: 13 mi
Midway International Airport (MDW)How far from city center: 3 mi

Book a flight from San Jose, CA to Chicago

Compare fares, schedules and travel times for flights from San Jose, CA (SJC) to Chicago (CHI) on eDreams. Choose between nonstop and connecting flights, then sort the results by price, schedule or number of stops.

For reference, the lowest recent price for this route is $95. Your fare will vary depending on your travel date and how early you book.

  • Flight Duration: Nonstop flights from San Jose, CA to Chicago take about 5 h and 43 m, and connecting flights take longer.
  • Departure Airport: Most flights depart from San Jose Mineta International Airport (SJC), the main airport in San Jose, CA.
  • Arrival Airport: Flights land at O'hare International Airport (ORD), the main airport in Chicago.

Make your trip to Chicago easier by booking your flight, hotel and rental car together with eDreams. That way, everything is in one place and simple to keep track of.

Frequently asked questions about flights from San Jose, CA to Chicago

On average, how much is the price of a flight from San Jose, CA to Chicago?
When you fly from San Jose, CA to Chicago the average price is $248. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.
For flights from San Jose, CA to Chicago, how can I find the cheapest price?
The cheapest price for a flight from San Jose, CA to Chicago is $95. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.
When booking, when is the best time to get the best prices for flights from San Jose, CA to Chicago?
The most popular months to book a trip from San Jose, CA to Chicago are August, July and June, based on the searches of our customers.
When is the best time to travel from San Jose, CA to Chicago?
The best time of the year to visit Chicago depends on lots of personal preferences, especially the price. Regarding popularity, March is the best month to fly to Chicago from San Jose, CA in terms of searches from our customers, followed by December and June. If you prefer to avoid the busy season and get away from the crowds February, October and April are the months with fewer searches for San Jose, CA - Chicago.
How long does the flight from San Jose, CA to Chicago take?
Flight length from San Jose, CA to Chicago is around 5 h and 52 m on average, at an average distance of 1,833.04 mi, for flights for the route (which may have 1 or more stops in other cities in between).
Which airports have flights between San Jose, CA and Chicago?
The main route from San Jose, CA to Chicago is: San Jose Mineta International Airport (SJC) to O'hare International Airport(ORD). The following airlines fly this route:

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