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San José del Cabo

$104+ 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 9/20. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 September or July, booked 49 days in advance, depart on a Monday or Tuesday 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 July 30, 2025.

Round-trip from

$399
(Mytrip)

One-way from

$108
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$553

Good round-trip deal

$546 or less

Good one-way deal

$209 or less
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. 7% potential increase in price ($49 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 30, 2025.

This Mytrip deal was found by Cheapflights users on 7/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/207:05 amORD - SJD
3 stops34h 30mMultiple Airlines
Tue 8/268:30 amSJD - ORD
1 stop13h 20mMultiple Airlines
Deal found 7/27$399
This Southwest deal was found by Cheapflights users on 7/28. 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.
Mon 8/117:50 amMDW - SJD
1 stop7h 00mSouthwest
Thu 8/1412:40 pmSJD - MDW
1 stop9h 25mSouthwest
Deal found 7/28$401
This Delta deal was found by Cheapflights users on 7/28. 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 8/125:45 amORD - SJD
1 stop7h 38mDelta
Wed 8/1312:28 pmSJD - ORD
1 stop18h 09mDelta
Deal found 7/28$401
This Hawaiian Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 10/2510:00 amORD - SJD
1 stop28h 15mHawaiian Airlines
Tue 10/2812:09 pmSJD - ORD
1 stop9h 50mHawaiian Airlines
Deal found 7/30$403
This Booking.com deal was found by Cheapflights users on 7/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/252:00 amORD - SJD
1 stop14h 55mViva
Tue 9/28:30 amSJD - ORD
1 stop13h 20mViva
Deal found 7/27$405
This Delta deal was found by Cheapflights users on 7/29. 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.
Sun 8/316:00 amMDW - SJD
2 stops12h 40mDelta
Thu 9/46:01 amSJD - MDW
2 stops13h 25mDelta
Deal found 7/29$406
This Alaska Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 11/159:20 amORD - SJD
1 stop28h 55mAlaska Airlines
Tue 11/1812:18 pmSJD - ORD
2 stops24h 36mAlaska Airlines
Deal found 7/30$407
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/151:55 amORD - SJD
1 stop11h 16mVolaris
Sat 8/2311:53 amSJD - ORD
1 stop10h 22mVolaris
Deal found 7/28$408
This Aeromexico deal was found by Cheapflights users on 7/30. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/95:45 amORD - SJD
2 stops11h 10mAeromexico
Tue 9/162:18 pmSJD - ORD
2 stops20h 17mAeromexico
Deal found 7/30$410
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Mon 8/115:00 amORD - SJD
1 stop9h 10mUnited Airlines
Thu 8/141:46 pmSJD - ORD
1 stop8h 29mUnited Airlines
Deal found 7/28$421
This Aeromexico deal was found by Cheapflights users on 7/29. 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.
Tue 10/146:00 amMDW - SJD
1 stop7h 41mAeromexico
Fri 10/1712:46 pmSJD - MDW
1 stop7h 28mAeromexico
Deal found 7/29$436
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 10/189:45 pmORD - SJD
1 stop14h 10mAmerican Airlines
Sat 10/2512:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 7/30$441

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 July 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

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 8/20

7:05 am-3:35 pm

3 stops34h 30m

San José del Cabo Los Cabos

Tue 8/26

8:30 am-11:50 pm

1 stop13h 20m

$399

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 8/12

5:45 am-11:23 am

1 stop7h 38m

San José del Cabo Los Cabos

Fri 8/15

12:40 pm-10:04 pm

1 stop7h 24m

$401

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/11

5:45 am-12:50 pm

2 stops9h 05m

San José del Cabo Los Cabos

Thu 8/14

12:40 pm-12:05 am

1 stop9h 25m

$401

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 10/25

10:00 am-12:15 pm

1 stop28h 15m

San José del Cabo Los Cabos

Tue 10/28

12:09 pm-11:59 pm

1 stop9h 50m

$403

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 8/25

2:00 am-2:55 pm

1 stop14h 55m

San José del Cabo Los Cabos

Tue 9/2

8:30 am-11:50 pm

1 stop13h 20m

$405

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/31

6:00 am-4:40 pm

2 stops12h 40m

San José del Cabo Los Cabos

Thu 9/4

6:01 am-9:26 pm

2 stops13h 25m

$406

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 9/25

1:55 am-7:53 am

1 stop7h 58m

San José del Cabo Los Cabos

Mon 9/29

11:53 am-12:15 am

1 stop10h 22m

$407

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 9/9

5:45 am-2:55 pm

2 stops11h 10m

San José del Cabo Los Cabos

Tue 9/16

2:18 pm-12:35 pm

2 stops20h 17m

$410

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 8/11

5:00 am-12:10 pm

1 stop9h 10m

San José del Cabo Los Cabos

Thu 8/14

1:46 pm-12:15 am

1 stop8h 29m

$421

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 10/18

3:50 pm-3:25 pm

1 stop25h 35m

San José del Cabo Los Cabos

Sat 10/25

1:31 pm-11:59 pm

1 stop8h 28m

$423

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 20 results
1
2

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 July 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 March is currently the most expensive (average of $549). 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 July 30, 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 53% 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 July 30, 2025.

The most flights from CHI to SJD are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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

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

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

Guadalajara (GDL) – chosen by Cheapflights users on 58% 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 Denver (DEN) have the shortest average one-way travel time for 1-stop routes: 6h 58m.

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 Mexico City (MEX) offer the fastest connection on this route, with an average layover time of 2h 15m.

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 July 30, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,241 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,980 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Aeromexico
7.5
Good
1,721 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Boarding

8.1

Overall

8.0

Food

7.1

Comfort

7.8

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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.

  • 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 Delta. Our recent data shows that you can find tickets from as low as $401 on this airline. Additional options worth looking into are Southwest and Hawaiian Airlines, starting at $401 and $403 round-trip. Delta is 34% 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?

    $108 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 Hawaiian Airlines, with prices starting from $136 and $173, 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 (100%), United Airlines (100%), American Airlines( 91%).

  • 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 $465, our data shows the cheapest flight currently is $197. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $301 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 March is currently the most expensive (average of $549). 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$344FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$397FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$576FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$439Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$454Average$678FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%

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