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Los Cabos

$109+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$412
(Mytrip)

One-way from

$109
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$602
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. 6% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This American Airlines deal was found by Cheapflights users on 11/6. 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 12/510:04 amORD - SJD
Nonstop4h 56mAmerican Airlines
Mon 12/83:00 pmSJD - ORD
1 stop14h 46mAmerican Airlines
Deal found 11/6$414
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Tue 12/28:20 amORD - SJD
3 stops34h 37mMultiple Airlines
Tue 12/94:34 pmSJD - ORD
2 stops17h 45mMultiple Airlines
Deal found 11/4$415
This Delta deal was found by Cheapflights users on 11/5. 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 12/217:05 pmORD - SJD
1 stop17h 11mDelta
Mon 12/291:52 pmSJD - ORD
1 stop9h 10mDelta
Deal found 11/5$416
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Thu 12/48:50 pmORD - SJD
1 stop15h 56mAmerican Airlines
Mon 12/83:00 pmSJD - ORD
1 stop14h 46mAmerican Airlines
Deal found 11/6$418
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sat 12/68:25 amMDW - SJD
1 stop7h 35mSouthwest
Sat 12/132:05 pmSJD - MDW
1 stop7h 10mSouthwest
Deal found 11/6$418
This American Airlines deal was found by Cheapflights users on 11/6. 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.
Tue 12/910:04 amORD - SJD
Nonstop4h 56mAmerican Airlines
Sun 12/145:27 pmSJD - ORD
1 stop15h 18mAmerican Airlines
Deal found 11/6$419
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/69:06 pmORD - SJD
1 stop14h 24mMultiple Airlines
Sat 12/136:47 pmSJD - ORD
2 stops15h 32mMultiple Airlines
Deal found 11/6$422
This Alaska Airlines deal was found by Cheapflights users on 11/6. 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 12/33:05 pmORD - SJD
2 stops24h 18mAlaska Airlines
Fri 12/51:49 pmSJD - ORD
1 stop33h 01mAlaska Airlines
Deal found 11/6$424
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 12/49:06 pmORD - SJD
1 stop14h 24mMultiple Airlines
Tue 12/94:34 pmSJD - ORD
2 stops17h 45mMultiple Airlines
Deal found 11/5$428
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 12/811:01 amORD - SJD
2 stops30h 11mMultiple Airlines
Fri 12/128:00 amSJD - ORD
1 stop13h 29mMultiple Airlines
Deal found 11/6$432
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Wed 12/34:58 pmORD - SJD
2 stops39h 22mMultiple Airlines
Wed 12/103:36 pmSJD - ORD
1 stop18h 43mMultiple Airlines
Deal found 11/5$433
This Mytrip deal was found by Cheapflights users on 11/5. 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 12/36:54 pmMDW - SJD
2 stops24h 13mVolaris
Wed 12/103:36 pmSJD - MDW
1 stop17h 04mVolaris
Deal found 11/5$444

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 November 6, 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

Fri 1/23

10:19 am-2:16 pm

Nonstop4h 57m

San José del Cabo Los Cabos

Mon 2/2

1:52 pm-7:15 pm

Nonstop4h 23m

$413

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/20

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Fri 1/30

4:25 pm-11:19 am

1 stop17h 54m

$418

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 12/16

5:30 am-12:10 pm

1 stop7h 40m

San José del Cabo Los Cabos

Sun 12/21

9:40 am-12:02 am

2 stops13h 22m

$421

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/20

6:12 am-5:41 pm

2 stops12h 29m

San José del Cabo Los Cabos

Sun 1/25

3:14 pm-11:57 pm

1 stop7h 43m

$423

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/17

5:55 pm-8:40 am

2 stops15h 45m

San José del Cabo Los Cabos

Tue 1/20

10:25 am-11:57 pm

2 stops12h 32m

$428

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/3

8:39 am-4:00 pm

1 stop8h 21m

San José del Cabo Los Cabos

Thu 1/8

2:42 pm-2:29 pm

2 stops22h 47m

$442

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 1/19

3:49 pm-1:06 pm

1 stop22h 17m

San José del Cabo Los Cabos

Thu 1/29

11:42 am-11:37 pm

1 stop10h 55m

$446

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 12/11

3:05 pm-12:16 pm

2 stops22h 11m

San José del Cabo Los Cabos

Tue 12/16

1:26 pm-2:09 pm

2 stops23h 43m

$446

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 12/10

8:55 am-12:39 pm

1 stop28h 44m

San José del Cabo Los Cabos

Sun 12/14

6:14 pm-2:09 pm

2 stops18h 55m

$456

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/19

8:40 pm-11:40 am

2 stops16h 00m

San José del Cabo Los Cabos

Fri 1/30

2:20 pm-5:05 am

2 stops13h 45m

$472

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 39 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 $275). Flying from Chicago to Los Cabos in October is currently the most expensive (average of $401). 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 November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Los Cabos at noon. If you’re flexible enough to do this you can expect to save up to 59% on your trip compared to booking a flight in the morning.

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 November 6, 2025.

The most flights from CHI to zzKPG are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

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 November 6, 2025.
Peruse reviews from past customers who have flown with Southwest, United Airlines, and American Airlines from Chicago to Los Cabos to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Viva
7.0
Good
789 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Volaris
6.7
Okay
1,151 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Chicago to Los Cabos?

    Departing from Chicago to Los Cabos will take you 4h 57m. Chicago and Los Cabos are separated by a distance of 1806 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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: United Airlines (89%), American Airlines (88%), Emirates( 78%).

  • 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 $777, our data indicates the cheapest price to be $180. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $264.

  • 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 $275). Flying from Chicago to Los Cabos in October is currently the most expensive (average of $401). 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 6 airlines flying from Chicago to Los Cabos

Discover the top 6 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$267Average$358FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$405FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$500FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$422Average$617FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$449Average$668FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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