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

$113+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Apr 27 — May 41
Sun 4/27
Sun 5/4
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 July or January, booked 49 days in advance, depart on a Tuesday or Monday and return on a Saturday

Cheap 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 April 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$384
(Trip.com)

One-way from

$113
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$565

Good round-trip deal

$554 or less

Good one-way deal

$280 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. 5% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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

Find 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 April 22, 2025.

This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/291:55 amORD - SJD
1 stop11h 16mVolaris
Sat 9/63:32 pmSJD - ORD
1 stop6h 43mVolaris
Deal found 4/21$384
This Trip.com deal was found by Cheapflights users on 4/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:25 pmORD - SJD
1 stop10h 10mMultiple Airlines
Mon 9/16:41 pmSJD - ORD
1 stop8h 10mMultiple Airlines
Deal found 4/21$385
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Thu 5/112:35 pmORD - SJD
1 stop21h 25mViva
Mon 5/57:55 pmSJD - ORD
2 stops25h 40mViva
Deal found 4/20$400
This Aeromexico deal was found by Cheapflights users on 4/21. 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.
Mon 9/81:55 amORD - SJD
1 stop10h 08mAeromexico
Tue 9/166:01 amSJD - ORD
2 stops13h 11mAeromexico
Deal found 4/21$402
This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 9/96:00 amORD - SJD
1 stop7h 30mDelta
Tue 9/1612:35 pmSJD - ORD
1 stop9h 18mDelta
Deal found 4/21$407
This Trip.com deal was found by Cheapflights users on 4/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/36:00 amMDW - SJD
1 stop7h 43mMultiple Airlines
Thu 6/128:29 amSJD - MDW
1 stop8h 47mMultiple Airlines
Deal found 4/20$462
This Hawaiian Airlines deal was found by Cheapflights users on 4/22. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/297:59 pmORD - SJD
1 stop16h 07mHawaiian Airlines
Mon 6/27:28 pmSJD - ORD
1 stop21h 31mHawaiian Airlines
Deal found 4/22$469
This Alaska Airlines deal was found by Cheapflights users on 4/22. 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.
Sat 5/247:59 pmORD - SJD
2 stops24h 19mAlaska Airlines
Sat 5/3111:16 amSJD - ORD
2 stops16h 24mAlaska Airlines
Deal found 4/22$470
This American Airlines deal was found by Cheapflights users on 4/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/138:05 amORD - SJD
Nonstop4h 40mAmerican Airlines
Sat 9/2012:25 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 4/21$472
This Delta deal was found by Cheapflights users on 4/22. 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 5/36:04 amMDW - SJD
1 stop7h 06mDelta
Sat 5/106:06 amSJD - MDW
2 stops13h 08mDelta
Deal found 4/22$486
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/55:05 amORD - SJD
1 stop10h 38mUnited Airlines
Fri 11/2112:49 pmSJD - ORD
Nonstop4h 09mUnited Airlines
Deal found 4/21$511
This Southwest deal was found by Cheapflights users on 4/22. 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.
Tue 7/16:55 amMDW - SJD
2 stops8h 30mSouthwest
Tue 7/81:15 pmSJD - MDW
1 stop7h 15mSouthwest
Deal found 4/22$520

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 April 22, 2025.
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

Tue 6/3

6:31 am-2:10 pm

1 stop9h 39m

San José del Cabo Los Cabos

Thu 6/12

11:53 am-12:15 am

1 stop10h 22m

$384

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 5/19

1:45 am-7:47 am

1 stop8h 02m

San José del Cabo Los Cabos

Tue 5/27

2:10 pm-11:35 pm

2 stops31h 25m

$386

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 5/1

12:35 pm-8:00 am

1 stop21h 25m

San José del Cabo Los Cabos

Mon 5/5

7:55 pm-11:35 pm

2 stops25h 40m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 6/3

6:00 am-11:43 am

1 stop7h 43m

San José del Cabo Los Cabos

Thu 6/12

8:29 am-7:16 pm

1 stop8h 47m

$462

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 5/29

7:59 pm-10:06 am

1 stop16h 07m

San José del Cabo Los Cabos

Mon 6/2

7:28 pm-6:59 pm

1 stop21h 31m

$469

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/24

7:59 pm-6:18 pm

2 stops24h 19m

San José del Cabo Los Cabos

Sat 5/31

11:16 am-5:40 am

2 stops16h 24m

$470

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 6/27

6:59 am-4:16 pm

1 stop11h 17m

San José del Cabo Los Cabos

Wed 7/2

1:42 pm-12:15 am

1 stop8h 33m

$471

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 6/28

5:35 am-12:37 pm

1 stop9h 02m

San José del Cabo Los Cabos

Mon 6/30

1:42 pm-12:15 am

1 stop8h 33m

$476

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 5/8

6:50 pm-10:37 am

1 stop17h 47m

San José del Cabo Los Cabos

Wed 5/14

12:50 pm-7:10 pm

Nonstop4h 20m

$478

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/3

6:04 am-5:17 pm

2 stops13h 13m

San José del Cabo Los Cabos

Sat 5/10

6:06 am-9:14 pm

2 stops13h 08m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 31 results
1
2
3
4

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust 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 AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Chicago-San José del Cabo flight deals on Cheapflights vs. AranGrant >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 AranGrant the most. AranGrant 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 April 18, 2025.

Booking 49 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, January is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $437). Flying from Chicago to San José del Cabo in June is currently the most expensive (average of $560). 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 April 22, 2025.

It’s optimal to fly from Chicago to San José del Cabo in the afternoon. By choosing this option you can save up to 52% on the cost of your flight, compared to a flight in the morning.

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 April 22, 2025.

The most flights from CHI to SJD are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in San José del Cabo by month

Plan your trip to San José del Cabo by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in San José del Cabo ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit San José del Cabo when rainfall is around 0.0 in.

Temperature in San José del Cabo by month

Plan your trip to San José del Cabo by taking into account the average temperature totals by month.

If weather is an important factor for your trip to San José del Cabo, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

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 April 22, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Chicago to San José del Cabo. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,906 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,286 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Hawaiian Airlines
7.9
Good
2,392 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Aeromexico
7.5
Good
1,700 reviews
Alaska Airlines
8.0
Very good
9,906 reviews

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 2 flights from Chicago to Los Cabos per day from 7 different airlines.

  • 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 $384 on this airline. Additional options worth looking into are Viva and Hawaiian Airlines, starting at $400 and $469 round-trip. Volaris is 37% 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?

    $125 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 Frontier, with prices starting from $167 and $189, 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: American Airlines (89%), Emirates (82%), United Airlines( 66%).

  • 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 $803, our data shows the cheapest flight currently is $246. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $306 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, January is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $437). Flying from Chicago to San José del Cabo in June is currently the most expensive (average of $560). 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 7 airlines flying from Chicago to San José del Cabo

Discover the top 7 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 April 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$352FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$398FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$426Average$552FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$440Average$640FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$460Average$686FlexibilityNo cancel feeOn-time69%
DeltaCheapest$483Average$649FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$545Average$720FlexibilityNo 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.