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Cheap Flights from San Jose to Chicago, IL, United States - SJC to CHI

Popular flights from San Jose to Chicago

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
May 18, 2016 May 24, 2016 $240
American Airlines
Departure Date Return Date Lowest Price
May 11, 2016 May 18, 2016 $240
May 17, 2016 May 19, 2016 $240
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 3, 2016 Jun 7, 2016 $589
United Airlines
Departure Date Return Date Lowest Price
Jun 1, 2016 Jun 8, 2016 $262

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 $258.

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 $829 $341
7-14 days $287 $240
14-21 days $287 $240
21-30 days $287 $263
30-60 days $262 $263
60-90 days $435 $338
90+ days $277 $268

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
$263 $240 $240 $279 $278 $244 $263

Lowest Fares Chart By Month from San Jose to Chicago

The chart below shows the lowest fare by month when flying from San Jose to Chicago.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May San Jose Chicago American 5/11/16 5/18/16 1 $240
June San Jose Chicago United 6/1/16 6/8/16 0 $262
July San Jose Chicago United 7/31/16 8/11/16 1 $311
August San Jose Chicago Alaska 8/23/16 8/29/16 2 $272
September San Jose Chicago American 9/20/16 9/28/16 1 $272
October San Jose Chicago Alaska 10/27/16 11/2/16 2 $272
November San Jose Chicago Alaska 11/21/16 12/3/16 1 $268
December San Jose Chicago Alaska 12/13/16 12/17/16 1 $303

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
8 9 10 11 12 13 14
$380
15 16 17 18 19 20 21
$380 $361
22 23 24 25 26 27 28
$361 $405
29 30 31 1 2 3 4
$405 $287
5 6 7 8 9 10 11
$287

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 $368.

The average price for non-stop flights from San Jose to Chicago is $304.

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 2 3 3 3 3 3 07:05 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 $157.

The average price for round trip flights from San Jose to Chicago is $361.

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 21 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 17 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: Los Angeles, CA and Minneapolis - St Paul, MN

Airlines Flying from San Jose to Chicago (SJC to CHI)

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 ATL X X X X X X X
Delta LAX / MSP X X X X X X X
United DEN X X X X X X
Southwest - X X X X X X X
Southwest DEN 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 $392
San Jose to New York American, Alaska, JetBlue, United $309

Cheap Domestic Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Chicago American, Alaska, JetBlue, Frontier, United, Virgin America $187
Oakland to Chicago American, Alaska, JetBlue, Spirit, United $166
Sacramento to Chicago American, Alaska, JetBlue, United $280
Fresno to Chicago American, Alaska, United $326
Reno to Chicago American, Alaska, United $353
Monterey to Chicago American, Alaska, United $408
San Luis Obispo to Chicago American, United $472
Modesto to ChicagoCheck Dates
Chico to ChicagoCheck Dates
Santa Rosa to Chicago American, Alaska $558
Santa Maria to Chicago United $512
San Francisco to New York American, Alaska, JetBlue, Frontier, Sun Country, United, Virgin America $272
San Francisco to Atlanta American, Alaska, Frontier, United $198
San Francisco to Milwaukee American, Alaska, Frontier, United $261
San Francisco to Detroit American, Alaska, Frontier, United $278
San Francisco to Indianapolis American, Alaska, Frontier, United $265
Sacramento to Milwaukee American, Alaska, United $338
San Francisco to Dallas - Ft Worth American, Alaska, Frontier, United, Virgin America $197
San Francisco to Minneapolis - St Paul American, Alaska, Frontier, Sun Country, United $261
San Francisco to Los Angeles American, Alaska, United, Virgin America $134
San Francisco to Madison American, Alaska, Frontier, United $264
Oakland to Milwaukee American, Alaska, United $401
Oakland to New York American, Alaska, JetBlue, Spirit, United $331
Sacramento to Atlanta American, Alaska, United $350
San Francisco to St Louis American, Alaska, United $325
Sacramento to New York American, Alaska, JetBlue, United $284
San Francisco to Denver American, Alaska, Frontier, United, Virgin America $136

Cheap International Flights to Chicago - CHI

FlightsAirlineLowest Price
San Francisco to Toronto American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, WestJet, Great Lakes $432
Cheap Flights from San Jose to Chicago, IL, United States, from $240 Round trip from SJC to CHI