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Cheap flights from Chicago (CHI) to San Jose Cabo (SJD)

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The best prices from Chicago to San Jose Cabo are usually found in May or September, booked 60 days in advance, depart on a Monday or Tuesday and return on a Wednesday

How to find the cheapest flight from
Chicago (CHI) to San Jose Cabo (SJD)

CHI - SJD
Price
$389 - $577
SJD
Temperature
77 - 100.4 °F
SJD
Rainfall
0 - 1.5 inches
Popular in December High demand for flights, 25% potential price rise
Cheapest in May Best time to find cheap flights, 10% potential price drop
Round-trip from $389 From Chicago to San Jose Cabo
One-way from $131 One-way flight from Chicago to San Jose Cabo
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to San Jose Cabo?

Travelers have found that booking a Sunday departure is the best way to save up to 7% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

When is the cheapest time to fly from Chicago to San Jose Cabo (CHI - SJD)?

It’s optimal to fly from Chicago to San Jose Cabo in the afternoon. By choosing this option you can save up to 47% on the cost of your flight, compared to a flight in the morning.

Cheap flights from Chicago to San Jose Cabo in August, September 2020

The best prices found for CHI to SJD flights for August, September
5 Aug - 12 Aug
$279pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
9 Aug - 10 Aug
$284pp
ORD
Chicago O'Hare Intl
Aeromexico
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Aeromexico
 
1 STOP
ORD
Chicago O'Hare Intl
9 Aug - 15 Aug
$285pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to San Jose Cabo 2020 flight deals

Cheap flights to San Jose Cabo from Chicago found for this year
21 Sep - 6 Oct
$268pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Volaris
 
1 STOP
ORD
Chicago O'Hare Intl
8 Sep - 12 Sep
$277pp
ORD
Chicago O'Hare Intl
Interjet
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Interjet
 
1 STOP
ORD
Chicago O'Hare Intl
5 Aug - 12 Aug
$279pp
ORD
Chicago O'Hare Intl
Multiple Airlines
     
3 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Non-stop flights to San Jose Cabo from Chicago

Save time with Chicago to San Jose Cabo direct flight deals
13 Nov - 16 Nov
$367pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
21 Oct - 25 Oct
$370pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Jul - 1 Aug
$386pp
ORD
Chicago O'Hare Intl
British Airways
Non-Stop
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
British Airways
Non-Stop
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to San Jose Cabo

Late deals on round-trip flights to San Jose Cabo from Chicago, departing today and this week
26 Jul - 4 Aug
$316pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
27 Jul - 3 Aug
$341pp
ORD
Chicago O'Hare Intl
Aeromexico
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Aeromexico
 
1 STOP
ORD
Chicago O'Hare Intl
27 Jul - 3 Aug
$351pp
ORD
Chicago O'Hare Intl
Delta
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Delta
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to San Jose Cabo from Chicago

The cheapest one-way flights from Chicago to San Jose Cabo
3:45 pm - 7:52 am
Lufthansa
1 Stop
17h 07m
ORD - SJD
Lufthansa
$131
Ovago
2:10 pm - 9:04 am
SAS
1 Stop
19h 54m
ORD - SJD
SAS
$137
Ovago
2:40 am - 10:05 am
Asiana Airlines
1 Stop
8h 25m
ORD - SJD
Asiana Airlines
$143
Ovago

Related info for your journey

Useful info, stats and facts about Chicago to San Jose Cabo flights.

Flight FAQs

From Chicago to San Jose Cabo

Are flight prices decreasing from Chicago to San Jose Cabo due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and San Jose Cabo for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to San Jose Cabo for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to San Jose Cabo for under $300. The cheapest flight booked recently is on Multiple Airlines for just $268, but on average you can expect to pay $288.

Are there nonstop flights from Chicago to San Jose Cabo for under $400 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San Jose Cabo under $400. A good price for a nonstop flight from Chicago to San Jose Cabo is less than $457.

Are there last-minute flights available from Chicago to San Jose Cabo for under $400?

There are currently 20+ open flights from Chicago to San Jose Cabo within the next 7 days for less than $400.

Is Chicago weather warmer or cooler than San Jose Cabo?

Temperatures around the 100 °F's can be experienced in July. The weather in San Jose Cabo is hotter than in Chicago. Plan for potential changes in flight availability as peak weather approaches in this location.

How long is the flight from Chicago to San Jose Cabo?

Airlines like Cape Air, Aeromexico, and Delta fly from Chicago to San Jose Cabo in about 4h 39m. The time it takes to get you to your destination can typically vary by up to 7h 01m. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

What are the cheapest airlines flying from Chicago to San Jose Cabo round-trip?

According to our current data, Interjet ($277), Aeromexico ($284), and Aer Lingus ($291) offers the cheapest pricing from Chicago to San Jose Cabo. You may be able to fly from Chicago to San Jose Cabo for 36% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Chicago to San Jose Cabo one-way?

To fly one-way, consider booking your trip with Interjet, which is currently one of the cheapest options available, starting at $111. Lufthansa flights start at $131 while deals on SAS start at $137 one-way.

Destination information for San Jose Cabo

Things to know before you go. Useful info for your trip from Chicago to San Jose Cabo
Today's exchange rate
$1 = $22.37
Average temperature for August in San Jose Cabo
100.4 °F
Avg rainfall for August in San Jose Cabo
1.2 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing San José del Cabo

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