Flights from San Jose, California to Chicago, United States

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Did you mean flights from Chicago to San Jose, California?

San Jose, California to Chicago Last modified: Jul 19, 2019 2:10 -04:00

We've scanned 48,195,047,545 round trip itineraries and found the cheapest flights to Chicago. Frontier & Alaska frequently offer the best deals to Chicago flights, or select your preferred carrier below to see the cheapest days to fly.

Frontier
SJCCHI
Wed 8/28
1 stop
CHISJC
Sat 8/31
1 stop
$261
Alaska
SJCCHI
Wed 9/25
1 stop
CHISJC
Wed 10/2
1 stop
$269
United
SJCCHI
Thu 9/5
nonstop
CHISJC
Sat 9/7
nonstop
$277
American
SJCCHI
Tue 9/17
1 stop
CHISJC
Wed 9/25
1 stop
$279
Major Airlines
SJCCHI
Thu 9/5
1 stop
CHISJC
Sat 9/7
1 stop
$294
JetBlue
SJCCHI
Fri 9/13
1 stop
CHISJC
Tue 9/17
1 stop
$404

How Much is a Flight from San Jose, California to Chicago?

We have collected flight cost data from across the web for travel from San Jose, California to Chicago, and have found the average flight price for this trip to be $281.

Where To Buy Cheap Flights from San Jose, California to Chicago?

The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don't have to - which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from San Jose, California to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you'd like to learn more, read our article about the best time to buy airline tickets.

How far in advance should I book tickets from San Jose, California to Chicago?

The chart below shows up-to-date information regarding how far in advance to book your flight from San Jose, California to Chicago.

Non Stop versus Connecting
Advanced PurchaseNon StopConnecting
< 7 days $602 $488
7-14 days $396 $405
14-21 days $319 $328
21-30 days $319 $314
30-60 days $277 $261
60-90 days $307 $269
90+ days $284 $279

Cheapest Day To Fly from San Jose, California to Chicago

We've examined 57,595,778,181 itinerary searches that we've seen for departures in the next 90 days and found that the cheapest day to fly from San Jose, California to Chicago is Tuesday. See the chart below to compare prices for other days of the week.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$277$259$261$309$285$269$307

Compare Flight Prices from San Jose, California to Chicago by Month

Low priced flights are most commonly available by purchasing between one and three months in advance. International or holiday flights may need to be purchased even further in advance. The chart below shows the cheapest flight prices by month for San Jose, California to Chicago flights.

Month Origin Destination Carrier Depart Date Return Date Stops Price
July San Jose, California Chicago Frontier 7/24/19 8/3/19 1 $396
August San Jose, California Chicago Frontier 8/28/19 8/31/19 1 $261
September San Jose, California Chicago Alaska 9/24/19 10/8/19 1 $259
October San Jose, California Chicago Alaska 10/1/19 10/9/19 1 $269
November San Jose, California Chicago Alaska 11/6/19 11/13/19 1 $269
December San Jose, California Chicago American 12/6/19 12/12/19 2 $302
January San Jose, California Chicago American 1/14/20 1/22/20 1 $298
February San Jose, California Chicago American 2/15/20 2/22/20 1 $315

Cheap Last Minute Flights from San Jose, California to Chicago

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from San Jose, California to Chicago. The chart below shows the best last minute deals and cheap flights this weekend we could find.

Next 30 Days

SunMonTueWedThuFriSat
21 22 23 24 25 26 27
$526
28 29 30 31 1 2 3
$526 $451
4 5 6 7 8 9 10
$451 $337
11 12 13 14 15 16 17
$337 $322
18 19 20 21 22 23 24
$322 $318
25 26 27 28 29 30 31
$318

Connecting Flights vs Direct Flights from San Jose, California to Chicago

Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.

The average price for connecting flights from San Jose, California to Chicago is $305.

The average price for direct flights from San Jose, California to Chicago is $347.

The chart below shows up to date information regarding non-stop flights from San Jose, California to Chicago.

Weekly Direct Flights from San Jose, California to Chicago - By Carrier
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 3 3 3 3 3 2 3 02:38 17:49
United 1 1 1 1 1 1 1 01:46 01:46
Major Airlines 2 2 2 2 2 1 1 01:50 09:40

One Way Flights vs Round Trip Flights from San Jose, California to Chicago

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from San Jose, California to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from San Jose, California to Chicago is $155.

The average price for round trip flights from San Jose, California to Chicago is $305.

San Jose, California to Chicago Flight Questions

Below are some common questions that asked about this flight route:

Question: How long is the flight from San Jose, California to Chicago?
Answer: The average San Jose, California to Chicago flight time is 4 hours and 13 minutes.
Question: How far is Chicago from San Jose, California?
Answer: The distance from San Jose, California to Chicago is 1,824 miles (2,935 kilometers).
Question: How common are direct flights from San Jose, California to Chicago?
Answer: There are 39 direct flights from San Jose, California to Chicago.
Question: What are the most popular San Jose, California airlines for direct flights from San Jose, California to Chicago?
Answer: American Airlines provides 51% of the non-stop flights between San Jose, California and Chicago.
Question: What are the most popular connecting cities when flying from San Jose, California to Chicago?
Answer: Los Angeles, CA

Airlines in San Jose, California flying to Chicago Last modified: Jul 19, 2019 2:10 -04:00Number of routes searched: 266Number of itineraries searched: 223,609

Wondering which airlines fly out of San Jose, California to Chicago? We've gathered the average price of San Jose, California airlines with flights to Chicago. Different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary showing which days of the week individual carriers offer flights for the next 30 days.

San Jose, California to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
Alaska -
United -
American DFW
American LAX
American PDX
American PHX
Alaska PDX
Alaska SEA
Alaska LAX
Alaska SAN
JetBlue BOS
JetBlue JFK
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines JFK
Major Airlines SEA
Frontier DEN
Frontier LAS
United DEN
United IAH

San Jose, California to Chicago Airports

These are the major commercial airports we're currently monitoring in San Jose, California and Chicago. If your route includes a city with multiple airports, you may be able to find substantial savings by choosing an alternate airport.

Farecompare Research Tools

FareCompare's Flight Schedule Search Tool helps you find information about airline schedule filings, including flight numbers, depart times, and travel distance.

Cheap Domestic Flights from San Jose - SJC Last modified: Jul 19, 2019 2:10 -04:00

Cheap International Flights to Chicago - CHI Last modified: Jul 19, 2019 2:10 -04:00

FlightsLowest Price
San Francisco to Toronto$346

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Cheap Flights from San Jose, California to Chicago