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Cheap Flights from Chicago to San Jose Cabo, MX, Mexico - CHI to SJD

Popular flights from Chicago to San Jose Cabo

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.

Aeromexico
Departure Date Return Date Lowest Price
Aug 27, 2016 Aug 29, 2016 $286
Alaska Airlines
Departure Date Return Date Lowest Price
Aug 16, 2016 Aug 30, 2016 $667
American Airlines
Departure Date Return Date Lowest Price
Jun 25, 2016 Jun 29, 2016 $290
Jul 9, 2016 Jul 15, 2016 $290
Aug 27, 2016 Aug 29, 2016 $290
United Airlines
Departure Date Return Date Lowest Price
May 21, 2016 May 28, 2016 $284
Virgin America
Departure Date Return Date Lowest Price
May 21, 2016 May 28, 2016 $637
Jun 4, 2016 Jun 7, 2016 $637

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

We have collected flight cost data from across the web for travel from Chicago to San Jose Cabo, and have found the average flight price for this trip to be $292.

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

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

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

Non Stop versus 1-Stop
Advanced PurchaseNon StopOne Stop
< 7 days $287 $291
7-14 days $332 $289
14-21 days $284 $289
21-30 days $436 $380
30-60 days $362 $290
60-90 days $537 $290
90+ days $287 $286

Cheapest Day To Fly from Chicago to San Jose Cabo

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

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$289 $291 $301 $291 $301 $284 $289

Lowest Fares Chart By Month from Chicago to San Jose Cabo

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

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago San Jose Cabo United 5/21/16 5/28/16 0 $284
June Chicago San Jose Cabo American 6/25/16 6/29/16 1 $290
July Chicago San Jose Cabo American 7/9/16 7/15/16 1 $290
August Chicago San Jose Cabo AeroMexico 8/27/16 8/29/16 1 $286
September Chicago San Jose Cabo AeroMexico 9/12/16 9/19/16 2 $288
October Chicago San Jose Cabo AeroMexico 10/16/16 10/20/16 2 $288
November Chicago San Jose Cabo AeroMexico 11/10/16 11/14/16 1 $286
December Chicago San Jose Cabo American 12/9/16 12/16/16 0 $287

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

Your Chicago to San Jose Cabo 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 Cabo is $510.

The average price for non-stop flights from Chicago to San Jose Cabo is $450.

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

Nonstop Flight Details from Chicago to San Jose Cabo
CarrierMonTueWedThuFriSatSunEarliest FlightLatest Flight
American 0 0 0 0 0 1 0 08:45 08:45
United 0 0 0 0 0 1 1 09:15 09:15

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

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 Cabo. 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 Cabo is $248.

The average price for round trip flights from Chicago to San Jose Cabo is $509.

Chicago to San Jose Cabo 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 Cabo?
Answer: The average Chicago to San Jose Cabo flight time is 4 hours and 29 minutes.
Question: How many miles are there between Chicago and San Jose Cabo?
Answer: The distance from Chicago to San Jose Cabo is 1806 miles.
Question: How common are direct flights from Chicago to San Jose Cabo?
Answer: There are 3 direct flights from Chicago to San Jose Cabo.
Question: What is the most popular airline for non-stop flights from Chicago to San Jose Cabo?
Answer: United Airlines provides 66% of the non-stop flights between Chicago and San Jose Cabo.
Question: What are the most popular connecting cities when flying from Chicago to San Jose Cabo?
Answer: Atlanta, GA

Airlines Flying from Chicago to San Jose Cabo (CHI to SJD)

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

Chicago to San Jose Cabo
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American - X
American DFW X X X X X X X
AeroMexico MEX X X X X X X X
AeroMexico GDL / MEX X X X X X X X
Delta ATL X X X X X X X
Delta CVG / ATL X X X X X
United - X X
United IAH X X X X X X X
Virgin America SFO X X X X X X X
Southwest DEN X X X X X X X
Volaris GDL X X X X X X
Volaris GDL / TIJ X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and San Jose Cabo, 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 Los Angeles American, Alaska, Frontier, Spirit, United, Virgin America $81
Chicago to Las Vegas American, Alaska, Frontier, Spirit, United, Virgin America $97
Chicago to New York American, Alaska, JetBlue, Spirit, United $94
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $177
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $186
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $79
Chicago to Orlando American, JetBlue, Frontier, Spirit, United $132
Chicago to Denver American, Alaska, Frontier, Spirit, United $81
Chicago to Houston American, Spirit, United $117
Chicago to San Diego American, Alaska, Frontier, Spirit, United, Virgin America $177
Chicago to Atlanta American, Spirit, United $71
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to Seattle American, Alaska, Frontier, Spirit, United, Virgin America $197
Chicago to Washington American, Alaska, Frontier, United $118
Chicago to Minneapolis - St Paul American, Frontier, Spirit, United $48

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Puerto Vallarta Interjet, American, AeroMexico, Alaska, Frontier, Spirit, United, Virgin America, Volaris $284
Chicago to Guadalajara Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, United, Aeromar, Virgin America, Volaris $336
Chicago to Mexico City Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, United, Virgin America, Volaris $332

Cheap International Flights to San Jose Cabo - SJD

FlightsAirlineLowest Price
Indianapolis to San Jose Cabo American, AeroMexico, Alaska, United, Virgin America $323
Milwaukee to San Jose Cabo American, AeroMexico, Alaska, United $410
Grand Rapids to San Jose Cabo American, AeroMexico, Alaska, United $429
Green Bay to San Jose Cabo American, AeroMexico, Alaska, United Check Dates
Peoria to San Jose Cabo American, AeroMexico, Alaska, United $807
Madison to San Jose Cabo American, AeroMexico, Alaska, United $642
Moline to San Jose Cabo American, AeroMexico, Alaska, United $721
Appleton to San Jose Cabo American, AeroMexico, Alaska, United $749
Bloomington - Normal to San Jose Cabo American, AeroMexico, Alaska, United Check Dates
Ft Wayne to San Jose Cabo American, AeroMexico, Alaska, United $759
Lansing to San Jose Cabo American, AeroMexico, Alaska, United $689
South Bend to San Jose Cabo American, AeroMexico, Alaska, United $631
Cheap Flights from Chicago to San Jose Cabo, MX, Mexico, from $284 Round trip from CHI to SJD