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Los Cabos

$126+ Cheap flights from Chicago (CHI) to Los Cabos

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 9/13. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
1 adult, Economy
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Cheap flight deals from Chicago to Los Cabos

Keep the following information in mind while searching for Chicago to Los Cabos flight deals. Data was last updated June 16, 2025.

Round-trip from

$392
(American Airlines)

One-way from

$126
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$590
From Chicago (CHI) to Los Cabos
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One-way flight from Chicago (CHI) to Los Cabos
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Highest demand for flights based on searches. 7% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($21 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Chicago to Los Cabos

Cheapest flights from Chicago to Los Cabos
Explore the most affordable flight options available from Chicago to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 16, 2025.

This American Airlines deal was found by Cheapflights users on 6/16. 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.
Sun 10/128:05 amORD - SJD
Nonstop4h 40mAmerican Airlines
Tue 10/1412:25 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 6/16$390
This Kiwi.com deal was found by Cheapflights users on 6/16. 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 8/251:55 amORD - SJD
1 stop15h 00mMultiple Airlines
Thu 9/42:57 pmSJD - ORD
1 stop7h 18mMultiple Airlines
Deal found 6/16$391
This Aeromexico deal was found by Cheapflights users on 6/14. 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 7/296:00 amORD - SJD
2 stops15h 22mAeromexico
Tue 8/512:27 pmSJD - ORD
1 stop9h 42mAeromexico
Deal found 6/14$393
This Delta deal was found by Cheapflights users on 6/15. 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 8/315:45 amORD - SJD
1 stop7h 38mDelta
Tue 9/212:49 pmSJD - ORD
1 stop9h 06mDelta
Deal found 6/15$395
This CheapOair deal was found by Cheapflights users on 6/14. 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.
Mon 9/81:40 amORD - SJD
1 stop10h 29mVolaris
Mon 9/156:41 pmSJD - ORD
1 stop8h 10mVolaris
Deal found 6/14$397
This Trip.com deal was found by Cheapflights users on 6/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/308:42 pmORD - SJD
1 stop17h 35mHawaiian Airlines
Wed 8/63:37 pmSJD - ORD
1 stop12h 03mHawaiian Airlines
Deal found 6/14$398
This Delta deal was found by Cheapflights users on 6/14. 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 8/246:04 amMDW - SJD
2 stops14h 27mDelta
Fri 8/296:02 amSJD - MDW
2 stops13h 47mDelta
Deal found 6/14$400
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 8/226:55 amORD - SJD
1 stop10h 00mViva
Thu 8/283:25 pmSJD - ORD
1 stop6h 55mViva
Deal found 6/14$421
This Alaska Airlines deal was found by Cheapflights users on 6/15. 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.
Wed 7/307:00 amORD - SJD
2 stops13h 12mAlaska Airlines
Wed 8/63:37 pmSJD - ORD
1 stop12h 03mAlaska Airlines
Deal found 6/15$437
This Southwest deal was found by Cheapflights users on 6/13. 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.
Sun 9/75:30 amMDW - SJD
2 stops9h 40mSouthwest
Fri 9/121:45 pmSJD - MDW
1 stop7h 55mSouthwest
Deal found 6/13$439
This Aeromexico deal was found by Cheapflights users on 6/15. 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.
Sun 10/266:00 amMDW - SJD
1 stop7h 30mAeromexico
Fri 11/146:00 amSJD - MDW
2 stops14h 44mAeromexico
Deal found 6/15$449
This United Airlines deal was found by Cheapflights users on 6/15. 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 6/245:02 amORD - SJD
1 stop9h 08mUnited Airlines
Fri 6/272:50 pmSJD - ORD
1 stop7h 40mUnited Airlines
Deal found 6/15$460

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Los Cabos 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 16, 2025.
Use the filters below to find and compare flights from Chicago to Los Cabos that are best for you.

Fly from

Chicago

Fly to

Los Cabos

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 8/25

1:55 am-2:55 pm

1 stop15h 00m

San José del Cabo Los Cabos

Thu 9/4

2:57 pm-12:15 am

1 stop7h 18m

$391

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 7/15

10:05 pm-7:53 am

1 stop11h 48m

San José del Cabo Los Cabos

Tue 7/22

12:45 pm-7:10 pm

Nonstop4h 25m

$392

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 7/29

6:00 am-7:22 pm

2 stops15h 22m

San José del Cabo Los Cabos

Tue 8/5

12:27 pm-12:09 am

1 stop9h 42m

$393

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 8/31

5:45 am-11:23 am

1 stop7h 38m

San José del Cabo Los Cabos

Tue 9/2

12:49 pm-11:55 pm

1 stop9h 06m

$395

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 9/8

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

Mon 9/15

6:41 pm-4:51 am

1 stop8h 10m

$397

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 7/30

8:42 pm-12:17 pm

1 stop17h 35m

San José del Cabo Los Cabos

Wed 8/6

3:37 pm-5:40 am

1 stop12h 03m

$398

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/24

6:04 am-6:31 pm

2 stops14h 27m

San José del Cabo Los Cabos

Fri 8/29

6:02 am-9:49 pm

2 stops13h 47m

$400

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 8/22

6:55 am-2:55 pm

1 stop10h 00m

San José del Cabo Los Cabos

Thu 8/28

3:25 pm-12:20 am

1 stop6h 55m

$421

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 7/30

7:00 am-6:12 pm

2 stops13h 12m

San José del Cabo Los Cabos

Wed 8/6

3:37 pm-5:40 am

1 stop12h 03m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/7

5:30 am-1:10 pm

2 stops9h 40m

San José del Cabo Los Cabos

Fri 9/12

1:45 pm-11:40 pm

1 stop7h 55m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/16

Showing 1-10 of 29 results
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Best time to book a flight from Chicago to Los Cabos

Have a flexible travel schedule? Discover the best time to fly to Los Cabos 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 Los Cabos

What is the cheapest month to book a flight from Chicago to Los Cabos?

Currently, January is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $437). Flying from Chicago to Los Cabos 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 KPG?

Find hourly flight availability from Chicago to Los Cabos. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Los Cabos as you normally would.

Weekly flight availability from Chicago to Los Cabos

Explore weekly flight availability from Chicago to Los Cabos. 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 June 16, 2025.

The most flights from CHI to zzKPG are scheduled on a Saturday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Rainfall in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Los Cabos 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 Los Cabos when rainfall is around 0.0 in.

Temperature in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Los Cabos, 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 Los Cabos

Get insights into the airlines that provide service to Los Cabos. 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 Los Cabos. Reviews last updated June 16, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Chicago to Los Cabos by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,278 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,963 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Hawaiian Airlines
7.9
Good
2,500 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Aeromexico
7.5
Good
1,711 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Overall

8.0

Boarding

8.1

Comfort

7.8

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Los Cabos. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Los Cabos one-way?

    To fly one-way, consider booking your trip with Viva, which is currently one of the cheapest options available, starting at $126. Volaris flights start at $145 while deals on American Airlines start at $173 one-way.

  • What are the most reliable airlines from Chicago to Los Cabos?

    Before booking your flight to Los Cabos from Chicago, check out the most reliable airlines to get you to your destination on time: American Airlines (90%), Emirates (79%), United Airlines( 79%).

  • What are the cheapest flights from Chicago to Los Cabos?

    Looking for the cheapest flight from Chicago to Los Cabos? While on average our users pay $1,231, our data indicates the cheapest price to be $148. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $334.

  • Can I find deals for flights from Chicago to Los Cabos that include hotel bookings?

    Yes. In addition to deals on Chicago to Los Cabos flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Los Cabos?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Los Cabos.

  • Can I find deals for business class flights from Chicago to Los Cabos?

    Yes. Cheapflights offers flight deals from Chicago to Los Cabos 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 Los Cabos?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $437). Flying from Chicago to Los Cabos 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 7 airlines flying from Chicago to Los Cabos

Discover the top 7 airlines that operate flights from Chicago to Los Cabos. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$350FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$311Average$398FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$597FlexibilityNo cancel feeOn-timeN/A
AeromexicoCheapest$426Average$498FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$451Average$643FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$463Average$684FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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