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San José del Cabo

$106+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jul 30 — Aug 61
Thu 7/30
Thu 8/6
1 adult, Economy
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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 June or September, booked 6 days in advance, depart on a Tuesday or Friday 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 June 30, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Mon 6/292:53 am
ORD
-
SJD
1 stop10h 36m
Volaris
Tue 7/77:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Deal found 6/29$368
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Fri 10/161:40 am
ORD
-
SJD
1 stop10h 29m
Volaris
Sun 10/257:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Deal found 6/29$369
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Mon 10/57:35 am
ORD
-
SJD
1 stop13h 29m
Multiple Airlines
Fri 10/99:02 am
SJD
-
ORD
2 stops27h 48m
Multiple Airlines
Deal found 6/27$370
This Cheapflightsfares deal was found by Cheapflights users on 6/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/277:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Sat 10/312:06 pm
SJD
-
ORD
1 stop10h 49m
Volaris
Deal found 6/26$371
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:23 am
ORD
-
SJD
1 stop10h 12m
Volaris
Sun 11/2211:16 am
SJD
-
ORD
1 stop11h 23m
Volaris
Deal found 6/28$372
This Kiwi.com deal was found by Cheapflights users on 6/25. 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.
Sat 6/277:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Fri 7/33:36 pm
SJD
-
ORD
1 stop7h 19m
Volaris
Deal found 6/25$373
This Kiwi.com deal was found by Cheapflights users on 6/25. 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.
Sat 9/127:35 am
ORD
-
SJD
1 stop13h 29m
Multiple Airlines
Sat 9/198:05 am
SJD
-
ORD
2 stops37h 54m
Multiple Airlines
Deal found 6/25$374
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
Sat 9/57:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Sat 9/127:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Deal found 6/26$375
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:35 am
ORD
-
SJD
1 stop13h 29m
Volaris
Mon 7/67:47 pm
SJD
-
ORD
1 stop8h 05m
Volaris
Deal found 6/28$376
This Kiwi.com deal was found by Cheapflights users on 6/26. 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.
Sat 9/57:35 am
ORD
-
SJD
1 stop13h 29m
Multiple Airlines
Sat 9/128:05 am
SJD
-
ORD
2 stops37h 54m
Multiple Airlines
Deal found 6/26$377
This Kiwi.com deal was found by Cheapflights users on 6/24. 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.
Fri 12/46:23 am
ORD
-
SJD
1 stop10h 12m
Volaris
Sun 12/611:16 am
SJD
-
ORD
1 stop11h 23m
Volaris
Deal found 6/24$378
This Kiwi.com deal was found by Cheapflights users on 6/25. 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 9/32:53 am
ORD
-
SJD
1 stop10h 36m
Multiple Airlines
Mon 9/78:05 am
SJD
-
ORD
2 stops37h 54m
Multiple Airlines
Deal found 6/25$379

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 June 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$371
(Cheapflightsfares)

One-way from

$106
(Super.com)

Popular in

March

Cheapest in

June

Average price

$499

Good round-trip deal

$654 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 ($35 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip 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 June 30, 2026.
Use the filters below to find and compare flights from Chicago to San José del Cabo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 9/25

7:35 am-7:04 pm

1 stop13h 29m

San José del Cabo Los Cabos

Thu 10/1

7:47 pm-5:52 am

1 stop8h 05m

$403

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 9/1

7:35 am-7:04 pm

1 stop13h 29m

San José del Cabo Los Cabos

Thu 9/10

12:02 pm-11:47 pm

1 stop9h 45m

$409

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 8/5

2:53 am-8:16 am

1 stop7h 23m

San José del Cabo Los Cabos

Mon 8/10

7:47 pm-5:52 am

1 stop8h 05m

$444

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 7/17

2:53 am-8:16 am

1 stop7h 23m

San José del Cabo Los Cabos

Tue 7/21

3:36 pm-12:55 am

1 stop7h 19m

$460

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 8/8

2:53 am-8:16 am

1 stop7h 23m

San José del Cabo Los Cabos

Sun 8/16

3:36 pm-12:55 am

1 stop7h 19m

$462

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 7/3

6:21 am-11:29 am

1 stop7h 08m

San José del Cabo Los Cabos

Sun 7/12

7:47 pm-5:52 am

1 stop8h 05m

$512

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/16

7:20 am-1:10 pm

1 stop7h 50m

San José del Cabo Los Cabos

Wed 8/19

11:40 am-11:10 pm

1 stop9h 30m

$564

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 9/9

8:05 am-5:25 pm

2 stops11h 20m

San José del Cabo Los Cabos

Sun 9/13

2:27 pm-8:35 am

2 stops16h 08m

$565
Quickest round-trip

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 9/23

6:30 am-12:48 pm

1 stop8h 18m

San José del Cabo Los Cabos

Sun 9/27

11:52 am-6:07 pm

Nonstop4h 15m

$597

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 9/1

6:05 am-11:07 am

1 stop7h 02m

San José del Cabo Los Cabos

Fri 9/4

12:12 pm-10:36 pm

1 stop8h 24m

$598

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/29

Showing 1-10 of 45 resultsSorted by cheapest first
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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 June.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
AranGrantPrice 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

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

Currently, July is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $127). Flying from Chicago to San José del Cabo in March is currently the most expensive (average of $1,086). 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 June 30, 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.

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.

Mexico City (MEX) – chosen by Cheapflights users on 71% 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.

Mexico City (MEX) is the most affordable 1-stop option, with an average round-trip price of $383.

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.

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

Booking 16 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.

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 June 30, 2026.
Peruse reviews from past customers who have flown with Southwest,United Airlines, andAmerican 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
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
7.9
Good
4,248 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
United Airlines
7.4
Good
9,898 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
American Airlines
7.1
Good
11,765 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Viva
7.0
Good
802 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Volaris
6.6
Okay
1,152 reviews
Southwest
7.9
Good
4,248 reviews

Overall

7.9

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 5 different airlines.

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

    Volaris, Southwest, and Delta can get you from Chicago to San José del Cabo in just under 7h 02m. Your travel time can differ by up to 6h 27m. Airlines will cover a distance of 1804 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 $185 on this airline. Additional options worth looking into are Viva and United Airlines, starting at $223 and $417 round-trip. Volaris is 69% 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?

    $121 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 $173 and $182, 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: Emirates (76%), United Airlines (76%), American Airlines( 71%).

  • 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 $1,664, our data shows the cheapest flight currently is $539. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $322 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, July is the cheapest month in which you can book a flight from Chicago to San José del Cabo (average of $127). Flying from Chicago to San José del Cabo in March is currently the most expensive (average of $1,086). 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

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Alternative routes for Chicago to San José del Cabo

See prices for flight routes from nearby airports that may be better suited for you.
St. Louis to San José del Cabo flights
O'Hare Intl to La Paz flights

Top 5 airlines flying from Chicago to San José del Cabo

Discover the top 5 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 June 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
VolarisCheapest$185Average$394FlexibilityNo cancel feeOn-time79%
VivaCheapest$223Average$470FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$417Average$641FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$431Average$640FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$475Average$695FlexibilityNo cancel feeOn-time63%

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