Cheap flights from Chicago (CHI) to San José del Cabo (SJD)

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The best prices from Chicago to San José del Cabo Los Cabos are usually found in January or August, booked 60 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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

All the information you need to plan the best CHI to SJD flight in 2022: compare Chicago to San José del Cabo flight prices with the expected peak season, weather and rainfall in San José del Cabo.
CHI - SJD
Price
$452 - $558
SJD
Temperature
66.2 - 84.2 °F
SJD
Rainfall
0 - 4.5 inches

Popular in

June

High demand for flights, 9% potential price rise

Cheapest in

January

Best time to find cheap flights, 11% potential price drop

Round-trip from

$452

From Chicago (CHI) to San José del Cabo Los Cabos

One-way from

$166

One-way flight from Chicago (CHI) to San José del Cabo Los Cabos

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Chicago to San José del Cabo?

January can be a great time to fly to San José del Cabo from Chicago with a flight ticket averaging about $506. Cheapflights users have found deals in the month of January for as cheap as $294. The most expensive prices can be found in the month of June.

How far in advance should I book a flight from Chicago to San José del Cabo?

Find a great deal and save up to 9% by booking at least 61 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to San José del Cabo within the next two weeks, with the cheapest ticket starting at $539.

What is the cheapest day to fly round-trip from Chicago to San José del Cabo?

Leaving on a Monday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 13% on the overall cost on flights from Chicago to San José del Cabo.

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

It’s optimal to fly from Chicago to San José del 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 José del Cabo in August, September 2022

The best prices found for CHI to SJD flights for August, September
30 Sep - 8 Oct
$251pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Frontier
 
1 STOP
MDW
Chicago Midway
20 Sep - 19 Oct
$277pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
3 Sep - 10 Sep
$282pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to San José del Cabo 2022 flight deals

Cheap flights to San José del Cabo from Chicago found for this year
30 Sep - 8 Oct
$251pp
MDW
Chicago Midway
Frontier
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Frontier
 
1 STOP
MDW
Chicago Midway
20 Sep - 19 Oct
$277pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
3 Sep - 10 Sep
$282pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Frontier
 
1 STOP
ORD
Chicago O'Hare Intl

Cheap VivaAerobus flights from Chicago to San José del Cabo

17 Jan - 24 Jan
$271pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
20 Jan - 27 Jan
$274pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
30 Jan - 4 Feb
$275pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl

If you’re traveling from Chicago to San José del Cabo, one of the more common airlines traveling that route is VivaAerobus. Chicago to San José del Cabo flights are typically 47% cheaper than other airlines traveling the same route. Flights from VivaAerobus typically cost $571.34 RT. The cheapest VivaAerobus flight found for this route was $246. The most popular departure airport in Chicago when flying to San José del Cabo is Chicago O'Hare Intl Airport. The most popular airport to fly into when visiting San José del Cabo is San José del Cabo Los Cabos Airport. When flying from Chicago to San José del Cabo, VivaAerobus flights are 4% more popular than any other airline flying that same route.

Cheap Spirit Airlines flights from Chicago to San José del Cabo

20 Aug - 3 Sep
$379pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Spirit Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
20 Aug - 27 Aug
$424pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
21 Aug - 24 Aug
$433pp
ORD
Chicago O'Hare Intl
Spirit Airlines
   
2 STOPS
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
Spirit Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

If you’re traveling from Chicago to San José del Cabo, one of the more common airlines traveling that route is Spirit Airlines. Chicago to San José del Cabo flights are typically 72% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $524.15 RT. The cheapest Spirit Airlines flight found for this route was $241. When traveling from Chicago to San José del Cabo on Spirit Airlines, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is San José del Cabo Los Cabos Airport. When flying from Chicago to San José del Cabo, Spirit Airlines flights are 3% more popular than any other airline flying that same route.

Non-stop flights to San José del Cabo from Chicago

Save time with Chicago to San José del Cabo direct flight deals
11 Dec - 16 Dec
$467pp
ORD
Chicago O'Hare Intl
United 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
31 Oct - 4 Nov
$473pp
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
7 Nov - 15 Nov
$478pp
ORD
Chicago O'Hare Intl
American 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

Last minute flights from Chicago to San José del Cabo

Late deals on round-trip flights to San José del Cabo from Chicago, departing today and this week
20 Aug - 3 Sep
$341pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
20 Aug - 31 Aug
$353pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl
19 Aug - 3 Sep
$363pp
ORD
Chicago O'Hare Intl
VivaAerobus
 
1 STOP
SJD
San José del Cabo Los Cabos
SJD
San José del Cabo Los Cabos
VivaAerobus
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Los Cabos from Chicago

The cheapest one-way flights from Chicago to San José del Cabo
3:07 pm - 9:36 am
Frontier
1 Stop
19h 29m
MDW - SJD
Frontier
$166
Kiwi.com
12:52 am - 2:29 pm
Volaris
2 Stops
14h 37m
ORD - SJD
Volaris
$171
SmartFares
8:25 pm - 6:33 am
Multiple Airlines
2 Stops
35h 08m
ORD - SJD
Multiple Airlines
$178
SmartFares

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">San José del Cabo</span> flights.

Flight FAQs

From Chicago to San José del Cabo

What airport do you fly into for flights to San José del Cabo from Chicago?

If you book a flight to San José del Cabo from Chicago, you will be flying to Los Cabos, which is the city’s only airport. San José del Cabo Los Cabos (SJD) is located 6.6 mi from the center of San José del Cabo. There are 2 flights from Chicago to Los Cabos per day from 14 different airlines.

Which airlines flying from Chicago to San José del Cabo Los Cabos have flexible cancellations due to COVID-19?

American Airlines, United Airlines, and Interjet are some of the carriers that may have flexible cancellation policies. You can use our site to filter for other airlines that may also have this kind of flexibility.

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

Yes, there are multiple flights from Chicago to San José del Cabo for under $300. The cheapest flight booked recently is on Volaris for just $217, but on average you can expect to pay $261.

Are there nonstop flights from Chicago to San José del Cabo for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to San José del Cabo under $500. A good price for a nonstop flight from Chicago to San José del Cabo is less than $504.

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

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

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

Our cheapest airline available from Chicago to San José del Cabo is Volaris. Our recent data shows that you can find tickets from as low as $217 on this airline. Additional options worth looking into are Frontier and VivaAerobus, starting at $251 and $271 round-trip. Volaris is 57% cheaper than the average price of flights available within the next 90 days to this destination.

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

$116 is the cheapest one-way deal found within the past few days, from VivaAerobus. You may also be able to find cheap deals on Spirit Airlines and Volaris, with prices starting from $128 and $145, respectively.

What are the most popular airlines that fly from Chicago to San José del Cabo?

Interjet, Undisclosed Carrier and American Airlines are the most popular airlines when flying from Chicago to San José del Cabo.

What are the most reliable airlines from Chicago to San José del Cabo?

Before booking your flight to San José del Cabo from Chicago, check out the most reliable airlines to get you to your destination on time: United Airlines (84%), Qatar Airways (80%), American Airlines( 70%).

What are the cheapest flights from Chicago to San José del Cabo?

While on average a flight from Chicago to San José del Cabo is generally $694, our data shows the cheapest flight currently is $119. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $215 for that flight.

COVID Restrictions

View COVID Travel Restrictions for San José del Cabo, Mexico

Do I need a COVID test to fly to San José del Cabo from Chicago?

Information is based on travel restrictions from Chicago to San José del Cabo Los Cabos

Most visitors from Chicago can enter San José del Cabo Los Cabos without restrictions.

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering San José del Cabo Los Cabos.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering San José del Cabo Los Cabos.

Documents
Tourist Card - The printed tourist card must be presented upon arrival in Mexico.


Do I need a test to fly back to Chicago from San José del Cabo?

Returning to Chicago from San José del Cabo Los Cabos

COVID-19 testing requirements
Visitors from San José del Cabo Los Cabos are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from San José del Cabo Los Cabos are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for San José del Cabo, Mexico

Alternative routes for Chicago to San José del Cabo

See prices for flight routes from nearby airports that may be better suited for you.

Top 10 airlines flying from Chicago to San José del Cabo Los Cabos

The chart below displays the airlines Cheapflights users traveling from Chicago to San José del Cabo choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
$14 $22 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Frontier
$122 $183 No cancel fee 62%
Spirit Airlines
$135 $275 No cancel fee 65%
Volaris
$195 $355 No cancel fee 79%
Alaska Airlines
$195 $655 No cancel fee 75%
VivaAerobus
$228 $332 No cancel fee N/A
American Airlines
$241 $524 No cancel fee 71%
United Airlines
$246 $571 No cancel fee 69%
Interjet
$260 $440 No cancel fee 68%

We couldn't confirm the COVID-19 safety measures taken by Interjet. Please check directly on their website for additional information.

Aeromexico
$280 $581 No cancel fee N/A

Hourly flight availability from Chicago to San José del Cabo

See what time of day planes typically take off from Chicago towards San José del Cabo.
Morning 6 AM to noon 100% of CHI to SJD departures
Early morning Midnight to 6 AM 0% of CHI to SJD departures
Afternoon Noon to 6 PM 0% of CHI to SJD departures
Evening 6 PM to midnight 0% of CHI to SJD departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Chicago to San José del Cabo
See how many times per day planes take to the skies headed from Chicago to San José del Cabo.
Sunday
3 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
3 daily flights
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