HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
San José del Cabo

$89+ Cheap flights from Chicago (CHI) to San José del Cabo (SJD)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Mar 2 — Mar 91
Mon 3/2
Mon 3/9
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to San José del Cabo with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.
Cheapflights Tip: The best prices from Chicago to San José del Cabo Los Cabos are usually found in September or August, booked 2 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Chicago to San José del Cabo

Cheapest flights from Chicago to San José del Cabo
Explore the most affordable flight options available from Chicago to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 31, 2026.

This Mytrip deal was found by Cheapflights users on 1/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/168:53 pm
ORD
-
SJD
2 stops20h 11m
Multiple Airlines
Sun 4/264:49 pm
SJD
-
ORD
2 stops17h 20m
Multiple Airlines
Deal found 1/28$476
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/95:59 pm
ORD
-
SJD
2 stops15h 41m
Delta
Wed 2/189:35 am
SJD
-
ORD
2 stops13h 21m
Delta
Deal found 1/30$477
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/192:54 pm
ORD
-
SJD
1 stop8h 33m
Delta
Tue 2/244:56 pm
SJD
-
ORD
2 stops14h 44m
Delta
Deal found 1/30$478
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
MDW
-
SJD
1 stop7h 40m
Delta
Sat 2/281:45 pm
SJD
-
MDW
1 stop7h 46m
Delta
Deal found 1/29$478
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1812:15 am
ORD
-
SJD
2 stops11h 21m
Multiple Airlines
Mon 2/239:00 am
SJD
-
ORD
2 stops13h 50m
Multiple Airlines
Deal found 1/29$479
This Aeromexico deal was found by Cheapflights users on 1/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:00 am
MDW
-
SJD
1 stop7h 31m
Aeromexico
Tue 5/512:36 pm
SJD
-
MDW
1 stop7h 52m
Aeromexico
Deal found 1/31$479
This Alaska Airlines deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/269:00 am
ORD
-
SJD
1 stop9h 36m
Alaska Airlines
Tue 6/24:39 pm
SJD
-
ORD
2 stops20h 08m
Alaska Airlines
Deal found 1/30$480
This Southwest deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:05 am
MDW
-
SJD
Nonstop4h 55m
Southwest
Fri 3/133:20 pm
SJD
-
MDW
1 stop12h 25m
Southwest
Deal found 1/30$480
This Kiwi.com deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/112:15 am
ORD
-
SJD
2 stops11h 21m
Multiple Airlines
Mon 2/95:10 pm
SJD
-
ORD
1 stop17h 09m
Multiple Airlines
Deal found 1/30$481
This Delta deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/146:30 pm
ORD
-
SJD
2 stops15h 10m
Delta
Wed 2/184:56 pm
SJD
-
ORD
2 stops14h 42m
Delta
Deal found 1/29$482
This Delta deal was found by Cheapflights users on 1/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/196:40 pm
MDW
-
SJD
2 stops15h 00m
Delta
Wed 2/254:56 pm
SJD
-
MDW
2 stops15h 10m
Delta
Deal found 1/30$482
This Kiwi.com deal was found by Cheapflights users on 1/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/103:22 pm
ORD
-
SJD
3 stops18h 08m
Multiple Airlines
Sat 2/1412:11 pm
SJD
-
ORD
1 stop9h 34m
Multiple Airlines
Deal found 1/29$483

Find flight deals from Chicago to San José del Cabo

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to San José del Cabo (SJD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 31, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$476
(Mytrip)

One-way from

$89
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$575

Good round-trip deal

$583 or less

Good one-way deal

$300 or less
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
Search Deals
From Chicago (CHI) to San José del Cabo Los Cabos
Search Deals
One-way flight from Chicago (CHI) to San José del Cabo Los Cabos
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($60 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to San José del Cabo Los Cabos.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to San José del Cabo Los Cabos.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to San José del Cabo that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 31, 2026.
Use the filters below to find and compare flights from Chicago to San José del Cabo that are best for you.

Fly from

Chicago

Fly to

San José del Cabo

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/19

1:00 pm-4:10 pm

1 stop28h 10m

San José del Cabo Los Cabos

Wed 2/25

4:47 pm-11:59 pm

2 stops30h 12m

$477

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 3/23

7:15 am-10:08 am

Nonstop4h 53m

San José del Cabo Los Cabos

Fri 3/27

10:10 am-9:38 pm

1 stop9h 28m

$478

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/19

2:54 pm-10:27 pm

1 stop8h 33m

San José del Cabo Los Cabos

Tue 2/24

4:56 pm-8:41 am

2 stops14h 45m

$478

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/27

7:50 am-1:25 pm

1 stop6h 35m

San José del Cabo Los Cabos

Tue 3/3

12:00 pm-10:55 pm

1 stop9h 55m

$478

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 2/25

8:40 am-2:42 pm

1 stop7h 02m

San José del Cabo Los Cabos

Mon 3/2

12:50 pm-6:01 pm

Nonstop4h 11m

$480

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 5/1

7:59 pm-11:37 am

1 stop17h 38m

San José del Cabo Los Cabos

Sat 5/9

3:47 pm-1:13 pm

1 stop19h 26m

$480

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 2/23

7:10 am-2:42 pm

1 stop8h 32m

San José del Cabo Los Cabos

Mon 3/2

12:50 pm-6:01 pm

Nonstop4h 11m

$480

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 2/25

5:25 am-5:37 pm

2 stops13h 12m

San José del Cabo Los Cabos

Sat 2/28

4:44 pm-8:38 am

2 stops14h 54m

$482

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/21

6:15 am-5:37 pm

2 stops12h 22m

San José del Cabo Los Cabos

Tue 2/24

4:56 pm-8:41 am

2 stops14h 45m

$482

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 2/19

6:40 pm-8:40 am

2 stops15h 00m

San José del Cabo Los Cabos

Tue 2/24

9:35 am-10:33 pm

2 stops11h 58m

$482

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

Showing 1-10 of 44 results
1
2
3
...
5

Compare providers for flights from Chicago to San José del Cabo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to San José del Cabo in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago-San José del Cabo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-San José del Cabo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-San José del Cabo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago-San José del Cabo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-San José del Cabo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Chicago to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to San José del Cabo

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

Use this chart to determine the optimal time to book a round-trip flight from Chicago to San José del Cabo. Price data was last updated on January 30, 2026.

Booking 2 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to San José del Cabo. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Chicago to San José del Cabo?

Currently, March is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $268). Flying from Chicago to San José del Cabo in October is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to SJD?

Find hourly flight availability from Chicago to San José del Cabo. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 31, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to San José del Cabo as you normally would.

Weekly flight availability from Chicago to San José del Cabo

Explore weekly flight availability from Chicago to San José del Cabo. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 31, 2026.

The most flights from CHI to SJD are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Chicago to San José del Cabo?

What’s the top layover airport for flights from Chicago to San José del Cabo?

Share of 1-stop round-trip flights from Chicago to San José del Cabo chosen by Cheapflights users in the past 12 months, using the same layover each way.

Guadalajara (GDL) – chosen by Cheapflights users on 56% of 1-stop itineraries from Chicago to San José del Cabo on Cheapflights.

What’s the cheapest layover airport for flights from Chicago to San José del Cabo?

Average round-trip fare for 1-stop flights from Chicago to San José del Cabo, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Monterrey (MTY) is the most affordable 1-stop option, with an average round-trip price of $355.

What’s the fastest layover option from Chicago to San José del Cabo?

Shortest average travel time for 1-stop one-way flights from Chicago to San José del Cabo, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Houston (IAH) have the shortest average one-way travel time for 1-stop routes: 6h 30m.

Which airport typically offers the quickest layover for flights from Chicago to San José del Cabo?

Average layover duration for 1-stop one-way flights from Chicago to San José del Cabo, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Houston (IAH) offer the fastest connection on this route, with an average layover time of 1h 09m.

Reviews of airlines servicing San José del Cabo

Get insights into the airlines that provide service to San José del Cabo. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San José del Cabo. Reviews last updated January 31, 2026.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,219 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,211 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Viva
7.0
Good
816 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Volaris
6.6
Okay
1,175 reviews
Southwest
8.0
Very good
4,267 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Chicago to San José del Cabo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 3 flights from Chicago to Los Cabos per day from 6 different airlines.

  • How long is the flight from Chicago to San José del Cabo?

    Alaska Airlines, United Airlines, and Delta can get you from Chicago to San José del Cabo in just under 4h 53m. Your travel time can differ by up to 23h 17m. Airlines will cover a distance of 1806 mi. 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 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 $252 on this airline. Additional options worth looking into are Viva and Delta, starting at $268 and $278 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?

    $126 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Viva and American Airlines, with prices starting from $136 and $178, respectively.

  • 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 (81%), Emirates (79%), American Airlines( 58%).

  • 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 $824, our data shows the cheapest flight currently is $264. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $310 for that flight.

  • Can I find deals for flights from Chicago to San José del Cabo that include hotel bookings?

    Yes. In addition to deals on Chicago to San José del Cabo flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to San José del Cabo?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to San José del Cabo.

  • Can I find deals for business class flights from Chicago to San José del Cabo?

    Yes. Cheapflights offers flight deals from Chicago to San José del Cabo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to San José del Cabo?

    Currently, March is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $268). Flying from Chicago to San José del Cabo in October is currently the most expensive (average of $390). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 6 airlines flying from Chicago to San José del Cabo

Discover the top 6 airlines that operate flights from Chicago to San José del Cabo. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 31, 2026.
AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$252Average$388FlexibilityNo cancel feeOn-time79%
VivaCheapest$268Average$355FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$278Average$543FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$417Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$418Average$640FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$485Average$696FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.