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Cheap Flights from San Jose to Chicago, IL, United States - SJC to CHI Last modified: May 30, 2016 7:50 AM

Popular flights from San Jose to Chicago Last modified: May 30, 2016 7:50 AM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

Alaska Airlines
Departure Date Return Date Lowest Price
Sep 26, 2016 Sep 28, 2016 $358
Sep 27, 2016 Oct 4, 2016 $358
American Airlines
Departure Date Return Date Lowest Price
Jun 8, 2016 Jun 11, 2016 $231
Jun 8, 2016 Jun 15, 2016 $231
Jun 9, 2016 Jun 10, 2016 $231
JetBlue Airways
Departure Date Return Date Lowest Price
Sep 3, 2016 Sep 7, 2016 $522
United Airlines
Departure Date Return Date Lowest Price
Sep 3, 2016 Sep 7, 2016 $299
Sep 6, 2016 Sep 13, 2016 $299
Sep 7, 2016 Sep 13, 2016 $299
Sep 26, 2016 Sep 28, 2016 $299

How Much Does it Cost to Fly from San Jose to Chicago (SJC to CHI)?

We have collected flight cost data from across the web for travel from San Jose to Chicago, and have found the average flight price for this trip to be $287.

When Can I Buy the Cheapest Flight from San Jose to Chicago (SJC to CHI)?

Airlines can adjust prices for plane tickets from San Jose to Chicago based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

How far in advance should you book flights from San Jose to Chicago

The chart below shows up-to-date information regarding how far in advance a flight from San Jose to Chicago should be booked.

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $609 $457
7-14 days $383 $231
14-21 days $357 $407
21-30 days $337 $345
30-60 days $337 $345
60-90 days $287 $295
90+ days $287 $295

Cheapest Day To Fly from San Jose to Chicago

The chart below shows up-to-date information regarding the cheapest days to fly from San Jose to Chicago.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$322 $287 $231 $231 $312 $312 $312

Cheapest Weekend Non-Stop Flights for the Next 30 Days from San Jose to Chicago

If you're ready to take a trip in the next 30 days and want to fly on the weekend, you might be wondering which weekend is the cheapest to fly. The chart below shows up-to-date data regarding weekend flight prices from San Jose to Chicago.

Next 30 Days

SunMonTueWedThuFriSat
29 30 31 1 2 3 4
$835
5 6 7 8 9 10 11
$835 $383
12 13 14 15 16 17 18
$383 $366
19 20 21 22 23 24 25
$366 $399
26 27 28 29 30 1 2
$399 $399
3 4 5 6 7 8 9
$399

Non-Stop vs Connecting Flights from San Jose to Chicago (SJC to CHI)

Your San Jose to Chicago flight can be significantly cheaper by choosing 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 to Chicago is $545.

The average price for non-stop flights from San Jose to Chicago is $378.

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

Nonstop Flight Details from San Jose to Chicago
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 3 3 3 3 3 3 3 06:20 14:25

Round Trip vs One Way Flights from San Jose to Chicago (SJC to CHI)

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 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 to Chicago is $205.

The average price for round trip flights from San Jose to Chicago is $543.

San Jose to Chicago Flight Questions

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

Question: How long is a direct flight from San Jose to Chicago?
Answer: The average San Jose to Chicago flight time is 4 hours and 19 minutes.
Question: How many miles are there between San Jose and Chicago?
Answer: The distance from San Jose to Chicago is 1824 miles.
Question: How common are direct flights from San Jose to Chicago?
Answer: There are 21 direct flights from San Jose to Chicago.
Question: What is the most popular airline for non-stop flights from San Jose to Chicago?
Answer: American Airlines provides 100% of the non-stop flights between San Jose and Chicago.
Question: What are the most popular connecting cities when flying from San Jose to Chicago?
Answer: Atlanta, GA

Airlines Flying from San Jose to Chicago (SJC to CHI) Number of flights searched: 240Last modified: May 30, 2016 7:50 AM

Below are the different airlines that fly from San Jose to Chicago with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from San Jose to Chicago.

San Jose to Chicago
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X X X X X X X
American PHX X X X X X X X
Alaska SEA X X X X X X X
Delta MSP X X X X X X X
Delta LAX / MSP X X X X X X X
United IAH X X X X X X X
Southwest - X X X X X X X
Southwest LAS X X X X X X X

Airports for Your Route

These pages contain information about the major airports in San Jose and Chicago, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from San Jose - SJC

FlightsAirlineLowest Price
San Jose to Milwaukee American, Alaska, United $396
San Jose to New York American, Alaska, JetBlue, United $324

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Chicago American, Alaska, JetBlue, Frontier, United, Virgin America $203
Oakland to Chicago American, Alaska, JetBlue, Spirit, United $204
Sacramento to Chicago American, Alaska, JetBlue, United $411
Fresno to Chicago American, Alaska, United $274
Reno to Chicago American, Alaska, United $361
Monterey to Chicago American, Alaska, United $412
San Luis Obispo to Chicago American, United $412
Modesto to ChicagoCheck Dates
Chico to ChicagoCheck Dates
Santa Rosa to Chicago American, Alaska $618
Santa Maria to Chicago United $362
San Francisco to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $344
San Francisco to Atlanta American, Alaska, Frontier, United $208
San Francisco to Milwaukee American, Alaska, Frontier, United $278
San Francisco to Detroit American, Alaska, Frontier, United $199
San Francisco to Indianapolis American, Alaska, Frontier, United $244
Sacramento to Milwaukee American, Alaska, United $364
San Francisco to Dallas - Ft Worth American, Alaska, Frontier, United, Virgin America $208
San Francisco to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $240
San Francisco to Los Angeles American, Alaska, United, Virgin America $132
San Francisco to Madison American, Alaska, Frontier, United $335
Oakland to Milwaukee American, Alaska, United $396
Oakland to New York American, Alaska, JetBlue, Spirit, United $369
Sacramento to Atlanta American, Alaska, United $199
San Francisco to St Louis American, Alaska, JetBlue, United $331
Sacramento to New York American, Alaska, JetBlue, United $320
San Francisco to Denver American, Alaska, Frontier, United, Virgin America $138

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Toronto American, Air Canada, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America, WestJet $399
Cheap Flights from San Jose to Chicago, IL, United States, from $231 Round trip from SJC to CHI