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San José del Cabo

$121+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
may. 6 — may. 131
mar. 5/6
mar. 5/13
1 adult, Economy
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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 mayo 1, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$377
(CheapOair)

One-way from

$121
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$600

Good round-trip deal

$545 or less

Good one-way deal

$296 or less
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
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From Chicago (CHI) to San José del Cabo Los Cabos
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One-way flight from Chicago (CHI) to San José del Cabo Los Cabos
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Highest demand for flights based on searches. 5% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Price to beat on a round-trip flight from Chicago (CHI) to San José del Cabo Los Cabos.
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Price to beat on a one-way flight from Chicago (CHI) to San José del Cabo Los Cabos.
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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 mayo 1, 2025.

This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/76:00 amORD - SJD
1 stop6h 46mMultiple Airlines
mié. 6/1111:53 amSJD - ORD
1 stop10h 22mMultiple Airlines
Deal found 4/30$377
This CheapOair deal was found by Cheapflights users on 4/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/211:45 amORD - SJD
1 stop8h 02mVolaris
lun. 5/266:41 pmSJD - ORD
1 stop8h 10mVolaris
Deal found 4/30$379
This American Airlines deal was found by Cheapflights users on 4/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/168:25 amORD - SJD
1 stop8h 55mAmerican Airlines
mié. 7/3012:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 4/30$380
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
sáb. 5/1712:35 pmORD - SJD
1 stop21h 25mViva
mar. 5/208:30 amSJD - ORD
1 stop13h 05mViva
Deal found 4/30$402
This Delta deal was found by Cheapflights users on 4/30. 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.
sáb. 6/75:30 amORD - SJD
1 stop8h 13mDelta
sáb. 6/1412:23 pmSJD - ORD
1 stop9h 30mDelta
Deal found 4/30$420
This Delta deal was found by Cheapflights users on 4/30. 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.
sáb. 6/146:00 amMDW - SJD
1 stop8h 37mDelta
sáb. 6/216:03 amSJD - MDW
2 stops13h 42mDelta
Deal found 4/30$430
This Hawaiian Airlines deal was found by Cheapflights users on 4/30. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/247:59 pmORD - SJD
1 stop16h 07mHawaiian Airlines
sáb. 5/314:21 pmSJD - ORD
1 stop11h 19mHawaiian Airlines
Deal found 4/30$444
This Southwest deal was found by Cheapflights users on 4/30. 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.
lun. 7/215:15 amMDW - SJD
1 stop5h 50mSouthwest
vie. 7/252:20 pmSJD - MDW
2 stops8h 35mSouthwest
Deal found 4/30$462
This Atrapalo deal was found by Cheapflights users on 4/30. 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 Atrapalo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/65:30 amORD - SJD
1 stop8h 13mAeromexico
mar. 6/1012:35 pmSJD - ORD
1 stop9h 22mAeromexico
Deal found 4/30$466
This Alaska Airlines deal was found by Cheapflights users on 4/30. 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.
sáb. 5/247:59 pmORD - SJD
1 stop16h 07mAlaska Airlines
sáb. 5/314:21 pmSJD - ORD
2 stops18h 47mAlaska Airlines
Deal found 4/30$469
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/29:40 pmORD - SJD
1 stop16h 30mUnited Airlines
sáb. 6/711:52 amSJD - ORD
Nonstop4h 18mUnited Airlines
Deal found 4/30$510
This Kiwi.com deal was found by Cheapflights users on 4/30. 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.
lun. 11/248:39 pmMDW - SJD
1 stop11h 54mVolaris
jue. 11/278:13 amSJD - MDW
1 stop9h 01mVolaris
Deal found 4/30$578

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 mayo 1, 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

sáb. 6/7

6:00 am-10:46 am

1 stop6h 46m

San José del Cabo Los Cabos

mié. 6/11

11:53 am-12:15 am

1 stop10h 22m

$377

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mié. 5/21

1:45 am-7:47 am

1 stop8h 02m

San José del Cabo Los Cabos

lun. 5/26

6:41 pm-4:51 am

1 stop8h 10m

$379

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mié. 7/16

8:25 am-3:20 pm

1 stop8h 55m

San José del Cabo Los Cabos

mié. 7/30

12:45 pm-7:10 pm

Nonstop4h 25m

$380

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 5/17

12:35 pm-8:00 am

1 stop21h 25m

San José del Cabo Los Cabos

mar. 5/20

8:30 am-11:35 pm

1 stop13h 05m

$402

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 6/7

5:30 am-11:43 am

1 stop8h 13m

San José del Cabo Los Cabos

sáb. 6/14

12:23 pm-11:53 pm

1 stop9h 30m

$420

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 6/14

6:00 am-12:37 pm

1 stop8h 37m

San José del Cabo Los Cabos

sáb. 6/21

6:03 am-9:45 pm

2 stops13h 42m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 5/24

7:59 pm-10:06 am

1 stop16h 07m

San José del Cabo Los Cabos

sáb. 5/31

4:21 pm-5:40 am

1 stop11h 19m

$444

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 7/21

5:15 am-9:05 am

1 stop5h 50m

San José del Cabo Los Cabos

vie. 7/25

2:20 pm-12:55 am

2 stops8h 35m

$462

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 6/6

5:30 am-11:43 am

1 stop8h 13m

San José del Cabo Los Cabos

mar. 6/10

12:35 pm-11:57 pm

1 stop9h 22m

$466

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 5/24

7:59 pm-10:06 am

1 stop16h 07m

San José del Cabo Los Cabos

sáb. 5/31

4:21 pm-1:08 pm

2 stops18h 47m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 30 results
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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 May.
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 Accuracy2 starsTrust 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 25, 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 mayo 1, 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.

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 mayo 1, 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
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,968 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,294 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,934 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,698 reviews
Alaska Airlines
8.0
Very good
9,968 reviews

Overall

8.0

Comfort

7.9

Boarding

8.2

Food

7.1

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 is 1 flight 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 $379 on this airline. Additional options worth looking into are American Airlines and Viva, starting at $380 and $402 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?

    $133 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on American Airlines and Viva, with prices starting from $146 and $148, 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 $720, 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 $338 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

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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 mayo 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$352FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$397FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$426Average$552FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$442Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$461Average$684FlexibilityNo cancel feeOn-time69%
DeltaCheapest$483Average$649FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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