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San José del Cabo

$103+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Chicago to San José del Cabo with Cheapflights

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Cheapflights Tip: The best prices from Chicago to San José del Cabo Los Cabos are usually found in September or July, booked 33 days in advance, depart on a Tuesday or Monday and return on a Wednesday

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 October 30, 2025.

This Aeromexico deal was found by Cheapflights users on 10/29. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/285:23 amORD - SJD
1 stop7h 47mAeromexico
Tue 12/26:50 pmSJD - ORD
2 stops20h 52mAeromexico
Deal found 10/29$416
This Delta deal was found by Cheapflights users on 10/29. 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 12/16:00 amMDW - SJD
1 stop7h 10mDelta
Sat 12/62:40 pmSJD - MDW
1 stop8h 07mDelta
Deal found 10/29$416
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:10 amORD - SJD
1 stop8h 32mUnited Airlines
Wed 11/192:11 pmSJD - ORD
1 stop9h 04mUnited Airlines
Deal found 10/28$417
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/35:00 amORD - SJD
1 stop9h 23mAmerican Airlines
Sat 12/62:02 pmSJD - ORD
1 stop8h 49mAmerican Airlines
Deal found 10/29$418
This Southwest deal was found by Cheapflights users on 10/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/195:25 amMDW - SJD
1 stop7h 45mSouthwest
Wed 12/32:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 10/28$418
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Fri 11/284:58 pmORD - SJD
1 stop19h 42mMultiple Airlines
Wed 12/33:36 pmSJD - ORD
2 stops29h 39mMultiple Airlines
Deal found 10/27$419
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Tue 12/28:20 amORD - SJD
3 stops31h 59mMultiple Airlines
Fri 12/54:34 pmSJD - ORD
2 stops17h 45mMultiple Airlines
Deal found 10/28$420
This United Airlines deal was found by Cheapflights users on 10/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/119:03 amORD - SJD
Nonstop5h 00mUnited Airlines
Tue 12/1612:50 pmSJD - ORD
Nonstop4h 11mUnited Airlines
Deal found 10/28$421
This Aeromexico deal was found by Cheapflights users on 10/28. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:23 amORD - SJD
1 stop9h 12mAeromexico
Tue 12/26:50 pmSJD - ORD
2 stops20h 52mAeromexico
Deal found 10/28$423
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amMDW - SJD
1 stop7h 10mDelta
Mon 11/249:32 amSJD - MDW
2 stops13h 08mDelta
Deal found 10/28$423
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/125:00 amORD - SJD
1 stop7h 43mAmerican Airlines
Mon 11/172:37 pmSJD - ORD
1 stop6h 43mAmerican Airlines
Deal found 10/28$424
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/710:10 amORD - SJD
Nonstop4h 49mAmerican Airlines
Tue 11/1112:29 pmSJD - ORD
Nonstop4h 21mAmerican Airlines
Deal found 10/29$425

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$415
(Delta)

One-way from

$103
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$576

Good round-trip deal

$488 or less

Good one-way deal

$255 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. 7% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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

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 October 30, 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

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/19

5:25 am-12:10 pm

1 stop7h 45m

San José del Cabo Los Cabos

Wed 12/3

2:05 pm-10:10 pm

1 stop7h 05m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/1

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/6

4:50 pm-8:54 am

2 stops15h 04m

$421

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/10

12:49 am-1:51 pm

1 stop14h 02m

San José del Cabo Los Cabos

Sun 2/15

9:40 am-9:56 pm

2 stops11h 16m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 12/14

8:00 am-1:45 pm

1 stop6h 45m

San José del Cabo Los Cabos

Wed 12/24

2:40 pm-5:05 am

2 stops13h 25m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Sun 1/25

1:45 pm-10:26 pm

1 stop7h 41m

$423

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/15

8:59 pm-1:15 pm

1 stop17h 16m

San José del Cabo Los Cabos

Tue 11/18

1:09 pm-11:59 pm

1 stop9h 50m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 1/22

6:17 pm-8:40 am

2 stops15h 23m

San José del Cabo Los Cabos

Thu 1/29

1:45 pm-10:26 pm

1 stop7h 41m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/21

9:00 am-12:28 pm

1 stop28h 28m

San José del Cabo Los Cabos

Sat 2/28

2:30 pm-1:59 pm

2 stops22h 29m

$444

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 12/10

3:05 pm-11:10 am

2 stops21h 05m

San José del Cabo Los Cabos

Sun 12/14

11:40 am-11:50 pm

1 stop11h 10m

$454

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

9:00 am-1:07 pm

1 stop29h 07m

San José del Cabo Los Cabos

Tue 2/3

1:28 pm-11:37 pm

2 stops33h 09m

$459

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 39 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 October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago-San José del Cabo flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 October 24, 2025.

Booking 33 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 $124). Flying from Chicago to San José del Cabo in December is currently the most expensive (average of $404). 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 October 30, 2025.

It’s optimal to fly from Chicago to San José del Cabo at noon. By choosing this option you can save up to 59% on the cost of your flight, compared to a flight in the morning.

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 45% 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 $318.

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 October 30, 2025.
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
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Viva
7.0
Good
790 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,243 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the 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 6 different airlines.

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

    Southwest, Delta, and Alaska Airlines can get you from Chicago to San José del Cabo in just under 7h 10m. Your travel time can differ by up to 10h 06m. 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 Viva. Our recent data shows that you can find tickets from as low as $267 on this airline. Additional options worth looking into are Volaris and Delta, starting at $310 and $356 round-trip. Viva is 55% 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?

    $161 is the cheapest one-way deal found within the past few days, from United Airlines. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $165 and $165, 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 (91%), American Airlines (90%), Emirates( 82%).

  • 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 $781, our data shows the cheapest flight currently is $210. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $321 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 $124). Flying from Chicago to San José del Cabo in December is currently the most expensive (average of $404). 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 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$267Average$359FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$402FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$500FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$421Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$448Average$664FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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