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Cheap Flights from Chicago to San Jose, CR, Costa Rica - CHI to SJO Last modified: May 29, 2016 12:55 PM

Popular flights from Chicago to San Jose Last modified: May 29, 2016 12:55 PM

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
Aug 30, 2016 Sep 10, 2016 $545
Sep 6, 2016 Sep 17, 2016 $545
American Airlines
Departure Date Return Date Lowest Price
Aug 10, 2016 Aug 17, 2016 $355
Lacsa Lineas Aereas Costarricenses
Departure Date Return Date Lowest Price
Jul 3, 2016 Jul 9, 2016 $539
JetBlue Airways
Departure Date Return Date Lowest Price
Aug 18, 2016 Sep 1, 2016 $449
Silver Airways
Departure Date Return Date Lowest Price
Jul 2, 2016 Jul 7, 2016 $1,219
Spirit Airlines
Departure Date Return Date Lowest Price
Jun 16, 2016 Jun 22, 2016 $319
Jun 16, 2016 Jun 20, 2016 $319
United Airlines
Departure Date Return Date Lowest Price
Jun 18, 2016 Jun 25, 2016 $335
Jul 1, 2016 Jul 9, 2016 $335
Jul 1, 2016 Jul 8, 2016 $335
Jul 2, 2016 Jul 9, 2016 $335
Jul 8, 2016 Jul 15, 2016 $335

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

We have collected flight cost data from across the web for travel from Chicago to San Jose, and have found the average flight price for this trip to be $345.

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

Airlines can adjust prices for plane tickets from Chicago to San Jose 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.

Cheapest Day To Fly from Chicago to San Jose

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$368 $340 $340 $319 $335 $335 $374

Lowest Fares Chart By Month from Chicago to San Jose

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

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago San Jose American 5/31/16 6/2/16 1 $522
June Chicago San Jose Spirit 6/16/16 6/20/16 1 $319
July Chicago San Jose United 7/1/16 7/8/16 0 $335
August Chicago San Jose United 8/5/16 8/13/16 0 $335
September Chicago San Jose United 9/14/16 9/30/16 1 $347
October Chicago San Jose United 10/8/16 10/15/16 1 $347
November Chicago San Jose Spirit 11/2/16 11/7/16 1 $359
December Chicago San Jose Spirit 12/1/16 12/5/16 1 $359

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

Your Chicago to San Jose 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 Chicago to San Jose is $457.

The average price for non-stop flights from Chicago to San Jose is $335.

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

Nonstop Flight Details from Chicago to San Jose
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
United 0 0 0 0 1 1 0 18:00 18:00

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

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 Chicago to San Jose. 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 Chicago to San Jose is $274.

The average price for round trip flights from Chicago to San Jose is $456.

Chicago to San Jose Flight Questions

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

Question: How long is a direct flight from Chicago to San Jose?
Answer: The average Chicago to San Jose flight time is 5 hours and 15 minutes.
Question: How many miles are there between Chicago and San Jose?
Answer: The distance from Chicago to San Jose is 2220 miles.
Question: How common are direct flights from Chicago to San Jose?
Answer: There are 2 direct flights from Chicago to San Jose.
Question: What is the most popular airline for non-stop flights from Chicago to San Jose?
Answer: United Airlines provides 100% of the non-stop flights between Chicago and San Jose.
Question: What are the most popular connecting cities when flying from Chicago to San Jose?
Answer: Atlanta, GA

Airlines Flying from Chicago to San Jose (CHI to SJO) Number of flights searched: 280Last modified: May 29, 2016 12:55 PM

Below are the different airlines that fly from Chicago to San Jose 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 Chicago to San Jose.

Chicago to San Jose
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American IND / MIA X X X X X
Air Canada YYZ X X
AeroMexico MEX X X X X X X X
AeroMexico GDL / MEX X X X X X X X
Avianca SAL X X X X X
Avianca SAL / GUA X X X X X
Copa PTY X X X X X X X
Delta ATL X X X X X X X
Delta MSP / ATL X X X X X X X
Spirit IAH X X X X X X X
United - X X
United EWR X X X X X X X
Southwest BWI X X X X X X X
Volaris GDL X X X
Volaris BJX / CUN X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and San Jose, 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 Chicago - CHI

FlightsAirlineLowest Price
Chicago to New York American, Alaska, JetBlue, Spirit, United $81
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $137
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $153
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $118
Chicago to Miami American, Alaska, Frontier, United $138
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $117
Chicago to Atlanta American, Spirit, United $97
Chicago to Houston American, Spirit, United $154
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $208
Chicago to Washington American, Alaska, Frontier, United $98
Chicago to Denver American, Alaska, Frontier, Spirit, United $117
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $168
Chicago to Ft Lauderdale American, JetBlue, Spirit, United $145
Chicago to Tampa American, Alaska, Spirit, United $157

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Liberia American, Alaska, JetBlue, Avianca LACSA, United $330
Chicago to Cancun Silver, Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris $338
Chicago to Quepos American, United $561

Cheap International Flights to San Jose - SJO

FlightsAirlineLowest Price
Milwaukee to San Jose American, Alaska, United $424
Indianapolis to San Jose American, Alaska, Avianca LACSA, United $414
Grand Rapids to San Jose American, Alaska, United $418
Madison to San Jose American, Alaska, United $572
Ft Wayne to San Jose American, Alaska, United $583
Appleton to San Jose Alaska, United $550
Peoria to San Jose American, Alaska, United Check Dates
Green Bay to San Jose American, Alaska, United $572
Moline to San Jose American, Alaska, United $572
South Bend to San Jose Alaska, United $654
Kalamazoo to San Jose American, Alaska, United $522
Bloomington - Normal to San Jose American, Alaska, United Check Dates
Champaign to San Jose American, United $568
Cheap Flights from Chicago to San Jose, CR, Costa Rica, from $319 Round trip from CHI to SJO