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Cheap Flights from Chicago to San Jose, CR, Costa Rica - CHI to SJO

Popular flights from Chicago to San Jose

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 27, 2016 May 31, 2016 $611
May 27, 2016 May 31, 2016 $611
American Airlines
Departure Date Return Date Lowest Price
Jun 3, 2016 Jun 9, 2016 $339
Jun 3, 2016 Jun 9, 2016 $339
JetBlue Airways
Departure Date Return Date Lowest Price
May 23, 2016 May 26, 2016 $535
Spirit Airlines
Departure Date Return Date Lowest Price
May 16, 2016 May 19, 2016 $319
May 18, 2016 May 25, 2016 $319
United Airlines
Departure Date Return Date Lowest Price
Jun 10, 2016 Jun 17, 2016 $335
Jun 10, 2016 Jun 18, 2016 $335
Jun 11, 2016 Jun 17, 2016 $335
Jun 11, 2016 Jun 18, 2016 $335
Jun 17, 2016 Jun 25, 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 $332.

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
$319 $334 $319 $340 $335 $335 $342

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 Spirit 5/16/16 5/19/16 1 $319
June Chicago San Jose United 6/10/16 6/17/16 0 $335
July Chicago San Jose American 7/6/16 7/13/16 1 $341
August Chicago San Jose American 8/4/16 8/9/16 2 $345
September Chicago San Jose American 9/28/16 10/5/16 1 $341
October Chicago San Jose American 10/12/16 10/18/16 1 $341
November Chicago San Jose Spirit 11/1/16 11/8/16 1 $359
December Chicago San Jose Spirit 12/1/16 12/4/16 1 $359

TIPSave $15 by flying into Liberia instead of San Jose from Chicago

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 $265.

The average price for round trip flights from Chicago to San Jose is $442.

Chicago to San Jose Flight Questions

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

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)

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 MCO / 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
Delta ATL X X X X X X X
Delta MSP / ATL X X X X X X X
Spirit FLL X X X X X 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 GDL / 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 $99
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $131
Chicago to Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $162
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $97
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $87
Chicago to Atlanta American, Spirit, United $71
Chicago to Houston American, Spirit, United $117
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $187
Chicago to Washington American, Alaska, Frontier, United $107
Chicago to Denver American, Alaska, Frontier, Spirit, United $81
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $127
Chicago to Ft Lauderdale American, Alaska, JetBlue, Spirit, United $103
Chicago to Tampa American, Alaska, Spirit, United $137

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Liberia American, Alaska, JetBlue, Avianca LACSA, United $346
Chicago to Cancun Silver, Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris, Great Lakes $282
Chicago to Quepos American, Alaska, United $647

Cheap International Flights to San Jose - SJO

FlightsAirlineLowest Price
Milwaukee to San Jose American, Alaska, JetBlue, Spirit, United $358
Indianapolis to San Jose American, Alaska, JetBlue, Avianca LACSA, Spirit, United $380
Grand Rapids to San Jose American, Alaska, United $380
Madison to San Jose American, Alaska, United $394
Ft Wayne to San Jose American, Alaska, United $398
Appleton to San Jose Alaska, United $410
Peoria to San Jose American, Alaska, United Check Dates
Green Bay to San Jose American, Alaska, United $512
Moline to San Jose American, Alaska, United $494
South Bend to San Jose Alaska, United $532
Kalamazoo to San Jose American, Alaska, United $532
Bloomington - Normal to San Jose American, Alaska, United Check Dates
Champaign to San Jose American, United Check Dates
Cheap Flights from Chicago to San Jose, CR, Costa Rica, from $319 Round trip from CHI to SJO