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San José del Cabo

$97+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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The best prices from Chicago to San José del Cabo Los Cabos are usually found in July or August, booked 17 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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(CheapOair)

One-way from

$97
(Viva)

Popular in

December

Cheapest in

July

Average price

$649

Good round-trip deal

$601 or less

Good one-way deal

$245 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
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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.
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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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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 4/181:40 amORD - SJD
1 stop10h 29mVolaris
Sat 4/2612:01 pmSJD - ORD
1 stop10h 14mVolaris
Deal found 2/19$407
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 6/1212:35 pmORD - SJD
1 stop10h 00mViva
Sun 6/159:00 amSJD - ORD
2 stops12h 40mViva
Deal found 2/18$408
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 2/223:50 pmORD - SJD
3 stops20h 00mMultiple Airlines
Sat 3/15:08 pmSJD - ORD
2 stops20h 17mMultiple Airlines
Deal found 2/19$410
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop20h 20mMultiple Airlines
Sun 3/25:49 pmSJD - MDW
1 stop14h 56mMultiple Airlines
Deal found 2/20$417
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop21h 28mVolaris
Wed 3/56:19 pmSJD - MDW
1 stop13h 26mVolaris
Deal found 2/20$420
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Tue 3/119:04 amORD - SJD
Nonstop4h 53mUnited Airlines
Fri 3/1411:49 amSJD - ORD
Nonstop4h 09mUnited Airlines
Deal found 2/18$497
This Delta deal was found by Cheapflights users on 2/19. 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.
Wed 3/125:45 amORD - SJD
1 stop9h 20mDelta
Tue 3/1810:32 amSJD - ORD
1 stop11h 44mDelta
Deal found 2/19$501
This Hawaiian Airlines deal was found by Cheapflights users on 2/20. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/137:45 amORD - SJD
1 stop10h 34mHawaiian Airlines
Mon 3/1711:19 amSJD - ORD
1 stop27h 39mHawaiian Airlines
Deal found 2/20$509
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/186:00 amMDW - SJD
1 stop9h 05mDelta
Tue 3/2512:37 pmSJD - MDW
1 stop7h 46mDelta
Deal found 2/20$511
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/107:00 amORD - SJD
1 stop11h 14mAlaska Airlines
Mon 4/147:16 pmSJD - ORD
2 stops21h 00mAlaska Airlines
Deal found 2/20$519
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/318:19 amORD - SJD
Nonstop4h 45mAmerican Airlines
Tue 4/83:26 pmSJD - ORD
1 stop7h 14mAmerican Airlines
Deal found 2/20$523
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/3110:40 pmMDW - SJD
1 stop14h 00mSouthwest
Tue 4/812:30 pmSJD - MDW
2 stops14h 50mSouthwest
Deal found 2/20$533

Find flights from Chicago to San José del Cabo within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

San José del Cabo

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 4/18

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

Sat 4/26

12:01 pm-12:15 am

1 stop10h 14m

$407

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 6/12

12:35 pm-8:35 pm

1 stop10h 00m

San José del Cabo Los Cabos

Sun 6/15

9:00 am-11:40 pm

2 stops12h 40m

$408

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 3/24

6:30 pm-2:51 pm

3 stops22h 21m

San José del Cabo Los Cabos

Sun 3/30

8:29 am-9:45 am

3 stops47h 16m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/1

8:50 pm-11:20 am

1 stop16h 30m

San José del Cabo Los Cabos

Mon 4/7

9:15 am-10:41 pm

3 stops11h 26m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/2

11:00 am-5:19 pm

1 stop7h 19m

San José del Cabo Los Cabos

Mon 3/10

8:29 am-7:10 pm

1 stop8h 41m

$420

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 4/9

7:40 am-4:44 pm

1 stop11h 04m

San José del Cabo Los Cabos

Wed 4/16

4:23 pm-5:40 am

1 stop11h 17m

$452

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 3/11

9:04 am-11:57 am

Nonstop4h 53m

San José del Cabo Los Cabos

Fri 3/14

11:49 am-5:58 pm

Nonstop4h 09m

$497

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

5:45 am-1:05 pm

1 stop9h 20m

San José del Cabo Los Cabos

Tue 3/18

10:32 am-12:16 am

1 stop11h 44m

$501

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

7:00 pm-4:19 pm

2 stops23h 19m

San José del Cabo Los Cabos

Wed 3/19

12:57 pm-5:40 am

1 stop14h 43m

$503

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

8:21 am-11:06 am

Nonstop4h 45m

San José del Cabo Los Cabos

Thu 3/13

1:30 pm-12:12 am

1 stop8h 42m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 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 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.

Travel insights for flights from Chicago to San José del Cabo

Get recent, data-driven insights about flights from Chicago to San José del Cabo including ideal travel times, pricing trends, and more.

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 February 14, 2025.

Booking 17 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 February 20, 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 51% on the cost of your flight, compared to a flight in the morning.

What is the cheapest day to fly from Chicago to San José del Cabo?

Use this chart to determine the cheapest time to fly round-trip from Chicago to San José del Cabo. Price data was last updated on February 16, 2025.

Travelers seeking maximum savings on their Chicago to San José del Cabo flight should consider departing on Saturday at noon when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 February 20, 2025.

The most flights from CHI to SJD are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, 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 February 20, 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Overall

8.1

Comfort

8.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $407 on this airline. Additional options worth looking into are Viva and United Airlines, starting at $411 and $497 round-trip. Volaris is 32% 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?

    $97 is the cheapest one-way deal found within the past few days, from Viva. You may also be able to find cheap deals on Volaris and Frontier, with prices starting from $121 and $153, 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 (88%), Emirates (77%), United Airlines( 77%).

  • 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 $1,035, our data shows the cheapest flight currently is $241. When looking at the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos), you can expect to pay $252 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$270Average$360FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$315Average$399FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$392Average$570FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$414Average$616FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$422Average$673FlexibilityNo cancel feeOn-time69%
DeltaCheapest$431Average$800FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%
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