Flights from San Jose, California to Chicago, United States

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

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 $792 $428
7-14 days $325 $348
14-21 days $325 $236
21-30 days $325 $206
30-60 days $257 $154
60-90 days $281 $166
90+ days $257 $160

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
February San Jose, California Chicago Frontier 2/29/20 3/4/20 1 $256
March San Jose, California Chicago Alaska 3/4/20 3/11/20 1 $229
April San Jose, California Chicago Alaska 4/27/20 5/5/20 1 $249
May San Jose, California Chicago Alaska 5/1/20 5/5/20 1 $253
June San Jose, California Chicago Major Airlines 6/9/20 6/24/20 2 $330
July San Jose, California Chicago Alaska 7/14/20 7/18/20 1 $341
August San Jose, California Chicago Alaska 8/27/20 8/31/20 1 $349
September San Jose, California Chicago American 9/29/20 10/4/20 1 $319

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
9 10 11 12 13 14 15
$393
16 17 18 19 20 21 22
$393 $337
23 24 25 26 27 28 29
$337 $261
1 2 3 4 5 6 7
$261 $253
8 9 10 11 12 13 14
$253 $295
15 16 17 18 19 20 21
$295

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 $229.

The average price for direct flights from San Jose, California to Chicago is $251.

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 02:25 17:49
United 1 1 1 1 1 1 1 17:45 17:45
Major Airlines 2 2 2 2 2 1 1 01:35 08:05

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 $124.

The average price for round trip flights from San Jose, California to Chicago is $229.

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 16 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 38 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 50% of the non-stop flights between San Jose, California and Chicago.

Airlines in San Jose, California flying to Chicago Last modified: Jun 1, 2020 5:56 -04:00Number of routes searched: 0Number of itineraries searched: 0

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.

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: Jun 1, 2020 5:56 -04:00

Cheap International Flights to Chicago - CHI Last modified: Jun 1, 2020 5:56 -04:00

FlightsLowest Price
San Francisco to Toronto$303

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Cheap Flights from San Jose, California to Chicago