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Los Cabos

$89+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Chicago to Los Cabos

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Los Cabos (zzKPG). 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 January 21, 2025.

Round-trip from

$417
(Mytrip)

One-way from

$89
(Viva)
From Chicago (CHI) to Los Cabos
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One-way flight from Chicago (CHI) to Los Cabos
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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 January 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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 2/227:55 pmMDW - SJD
1 stop12h 35mMultiple Airlines
Tue 3/47:57 pmSJD - MDW
1 stop11h 48mMultiple Airlines
Deal found 1/21$419
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Tue 4/16:35 amORD - SJD
1 stop10h 15mViva
Sat 4/53:20 pmSJD - ORD
1 stop6h 55mViva
Deal found 1/20$432
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Sun 2/237:55 pmMDW - SJD
1 stop12h 36mVolaris
Sun 3/24:10 pmSJD - MDW
2 stops15h 35mVolaris
Deal found 1/21$433
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/291:45 amORD - SJD
1 stop16h 45mMultiple Airlines
Fri 4/48:05 amSJD - ORD
2 stops19h 39mMultiple Airlines
Deal found 1/20$437
This Mytrip deal was found by Cheapflights users on 1/19. 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.
Sun 2/25:40 pmORD - SJD
3 stops22h 44mVolaris
Tue 5/134:15 pmSJD - ORD
3 stops22h 45mVolaris
Deal found 1/19$439
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:40 amMDW - SJD
1 stop27h 44mFrontier
Sat 3/810:44 amSJD - MDW
1 stop12h 33mFrontier
Deal found 1/21$476
This Alaska Airlines deal was found by Cheapflights users on 1/19. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/285:54 pmORD - SJD
2 stops17h 38mAlaska Airlines
Mon 3/37:59 pmSJD - ORD
2 stops19h 59mAlaska Airlines
Deal found 1/19$482
This Aeromexico deal was found by Cheapflights users on 1/20. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/251:08 amORD - SJD
1 stop10h 00mAeromexico
Tue 3/1110:42 amSJD - ORD
1 stop11h 34mAeromexico
Deal found 1/20$523
This American Airlines deal was found by Cheapflights users on 1/20. 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.
Sat 5/108:20 pmORD - SJD
1 stop13h 38mAmerican Airlines
Sat 5/1712:35 pmSJD - ORD
Nonstop4h 15mAmerican Airlines
Deal found 1/20$529
This Southwest deal was found by Cheapflights users on 1/21. 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 3/210:35 pmMDW - SJD
1 stop14h 05mSouthwest
Mon 3/101:00 pmSJD - MDW
Nonstop4h 00mSouthwest
Deal found 1/21$529
This Delta deal was found by Cheapflights users on 1/21. 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 3/46:00 amMDW - SJD
1 stop7h 36mDelta
Tue 3/1112:42 pmSJD - MDW
1 stop7h 41mDelta
Deal found 1/21$538
This Delta deal was found by Cheapflights users on 1/21. 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 2/116:15 amORD - SJD
2 stops13h 17mDelta
Tue 2/185:35 pmSJD - ORD
2 stops14h 24mDelta
Deal found 1/21$542

Find flights from Chicago to Los Cabos within your budget

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 January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/1

7:55 pm-7:30 am

1 stop12h 35m

San José del Cabo Los Cabos

Tue 2/11

5:08 pm-8:45 am

1 stop14h 37m

$416

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/18

6:23 am-3:20 pm

1 stop9h 57m

San José del Cabo Los Cabos

Tue 2/25

3:20 pm-1:02 am

1 stop8h 42m

$416

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/7

7:55 pm-10:42 am

1 stop15h 47m

San José del Cabo Los Cabos

Wed 2/12

4:10 pm-8:45 am

2 stops15h 35m

$417

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/21

12:48 am-4:55 pm

1 stop17h 07m

San José del Cabo Los Cabos

Sun 3/2

4:10 pm-4:00 pm

3 stops22h 50m

$418

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/14

3:50 pm-9:25 am

1 stop18h 35m

San José del Cabo Los Cabos

Tue 2/18

4:00 pm-2:20 pm

1 stop21h 20m

$423

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 4/23

8:35 am-11:15 am

Nonstop4h 40m

San José del Cabo Los Cabos

Wed 4/30

12:15 pm-6:30 pm

Nonstop4h 15m

$475

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/28

5:54 pm-10:32 am

2 stops17h 38m

San José del Cabo Los Cabos

Mon 3/3

7:59 pm-4:58 pm

2 stops19h 59m

$482

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 2/21

5:45 am-9:47 pm

2 stops17h 02m

San José del Cabo Los Cabos

Tue 2/25

3:16 pm-11:48 pm

1 stop7h 32m

$489

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 3/8

9:38 pm-9:59 am

1 stop13h 21m

San José del Cabo Los Cabos

Tue 3/11

11:49 am-5:58 pm

Nonstop4h 09m

$504

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/25

1:08 am-10:08 am

1 stop10h 00m

San José del Cabo Los Cabos

Thu 3/6

10:42 am-11:21 pm

1 stop11h 39m

$523

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 26 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.

Travel insights for flights from Chicago to Los Cabos

Get recent, data-driven insights about flights from Chicago to Los Cabos including ideal travel times, pricing trends, and more.

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 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 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 January 21, 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 January 21, 2025.

The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 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 January 21, 2025.
Get a feel of what it's like to fly with Volaris, Viva and Alaska Airlines 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.
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,706 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,985 reviews
Southwest
8.1
Very good
4,662 reviews

Crew

8.7

Comfort

8.1

Entertainment

7.7

Boarding

8.2

Food

7.2

Overall

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $89. Volaris flights start at $133 while deals on Frontier start at $177 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 (96%), Emirates (74%), United Airlines( 74%).

  • 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 $935, our data indicates the cheapest price to be $241. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $259.

  • 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 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$271Average$365FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$323Average$404FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$392Average$580FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$404Average$655FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$405Average$601FlexibilityNo cancel feeOn-time71%
DeltaCheapest$405Average$699FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$734FlexibilityNo cancel feeOn-time63%
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