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Los Cabos

$116+ 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 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$379
(CheapOair)

One-way from

$116
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$565
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 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. 5% potential increase in price ($36 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This CheapOair deal was found by Cheapflights users on 4/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/131:40 amORD - SJD
1 stop10h 29mVolaris
Sun 8/173:02 pmSJD - ORD
1 stop12h 40mVolaris
Deal found 4/29$379
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/266:34 pmORD - SJD
2 stops16h 06mMultiple Airlines
Wed 5/289:15 amSJD - ORD
2 stops12h 20mMultiple Airlines
Deal found 4/29$381
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/612:35 pmORD - SJD
1 stop27h 50mViva
Fri 5/98:30 amSJD - ORD
1 stop13h 05mViva
Deal found 4/29$400
This SmartFares deal was found by Cheapflights users on 4/28. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/105:35 amORD - SJD
1 stop7h 55mAeromexico
Sat 6/1412:23 pmSJD - ORD
1 stop9h 30mAeromexico
Deal found 4/28$405
This American Airlines deal was found by Cheapflights users on 4/29. 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 7/189:05 amORD - SJD
Nonstop4h 40mAmerican Airlines
Tue 7/2212:45 pmSJD - ORD
Nonstop4h 25mAmerican Airlines
Deal found 4/29$415
This Delta deal was found by Cheapflights users on 4/29. 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.
Sat 6/77:05 amORD - SJD
1 stop7h 38mDelta
Sat 6/1412:23 pmSJD - ORD
1 stop9h 30mDelta
Deal found 4/29$420
This Delta deal was found by Cheapflights users on 4/29. 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.
Fri 6/136:00 amMDW - SJD
1 stop7h 30mDelta
Fri 6/206:03 amSJD - MDW
2 stops13h 42mDelta
Deal found 4/29$430
This Alaska Airlines deal was found by Cheapflights users on 4/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:59 pmORD - SJD
1 stop16h 07mAlaska Airlines
Tue 5/277:28 pmSJD - ORD
1 stop21h 31mAlaska Airlines
Deal found 4/29$440
This Frontier deal was found by Cheapflights users on 4/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:00 amORD - SJD
1 stop7h 09mFrontier
Sat 5/3112:23 pmSJD - ORD
1 stop9h 29mFrontier
Deal found 4/28$442
This Hawaiian Airlines deal was found by Cheapflights users on 4/29. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:59 pmORD - SJD
1 stop16h 07mHawaiian Airlines
Sat 5/314:21 pmSJD - ORD
1 stop11h 19mHawaiian Airlines
Deal found 4/29$444
This Southwest deal was found by Cheapflights users on 4/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/206:00 amMDW - SJD
1 stop6h 40mSouthwest
Fri 7/2510:05 amSJD - MDW
1 stop9h 50mSouthwest
Deal found 4/27$458
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/58:39 pmMDW - SJD
1 stop13h 08mVolaris
Sat 5/108:22 amSJD - MDW
1 stop8h 44mVolaris
Deal found 4/29$495

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 April 29, 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

Wed 5/21

1:45 am-7:47 am

1 stop8h 02m

San José del Cabo Los Cabos

Sun 5/25

12:01 pm-12:15 am

1 stop10h 14m

$379

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 5/26

6:34 pm-8:40 am

2 stops16h 06m

San José del Cabo Los Cabos

Wed 5/28

9:15 am-11:35 pm

2 stops12h 20m

$381

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 5/6

12:35 pm-2:25 pm

1 stop27h 50m

San José del Cabo Los Cabos

Fri 5/9

8:30 am-11:35 pm

1 stop13h 05m

$400

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 6/7

7:05 am-12:43 pm

1 stop7h 38m

San José del Cabo Los Cabos

Sat 6/14

12:23 pm-11:53 pm

1 stop9h 30m

$420

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/31

6:00 am-10:37 am

1 stop6h 37m

San José del Cabo Los Cabos

Sat 6/7

1:24 pm-10:31 pm

1 stop7h 07m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 6/13

6:00 am-11:30 am

1 stop7h 30m

San José del Cabo Los Cabos

Fri 6/20

6:03 am-9:45 pm

2 stops13h 42m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/24

7:59 pm-10:06 am

1 stop16h 07m

San José del Cabo Los Cabos

Tue 5/27

7:28 pm-6:59 pm

1 stop21h 31m

$440

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 5/24

7:59 pm-10:06 am

1 stop16h 07m

San José del Cabo Los Cabos

Sat 5/31

4:21 pm-5:40 am

1 stop11h 19m

$444

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 7/20

6:00 am-10:40 am

1 stop6h 40m

San José del Cabo Los Cabos

Fri 7/25

10:05 am-9:55 pm

1 stop9h 50m

$458

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 5/5

8:39 pm-7:47 am

1 stop13h 08m

San José del Cabo Los Cabos

Sat 5/10

8:22 am-7:06 pm

1 stop8h 44m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Showing 1-10 of 27 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 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 April 29, 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 April 29, 2025.

The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Thursday, 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 April 29, 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
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
9,961 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,295 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,936 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,406 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Aeromexico
7.5
Good
1,698 reviews
Alaska Airlines
8.0
Very good
9,961 reviews

Crew

8.5

Entertainment

7.1

Boarding

8.2

Comfort

7.9

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Volaris, which is currently one of the cheapest options available, starting at $126. American Airlines flights start at $146 while deals on Viva start at $148 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 (89%), Emirates (82%), United Airlines( 66%).

  • 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 $720, our data indicates the cheapest price to be $246. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $316.

  • 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

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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$352FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$397FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$426Average$552FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$442Average$638FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$461Average$684FlexibilityNo cancel feeOn-time69%
DeltaCheapest$483Average$649FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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