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Los Cabos

$112+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$387
(Delta)

One-way from

$112
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$532
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 ($49 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 July 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 julio 3, 2025.

This Mytrip deal was found by Cheapflights users on 7/2. 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.
sáb. 11/1512:55 amORD - SJD
1 stop7h 30mMultiple Airlines
sáb. 11/2212:11 pmSJD - ORD
1 stop9h 18mMultiple Airlines
Deal found 7/2$386
This Delta deal was found by Cheapflights users on 7/3. 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.
dom. 8/177:02 amORD - SJD
1 stop12h 43mDelta
mié. 8/206:10 amSJD - ORD
1 stop15h 48mDelta
Deal found 7/3$387
This Aeromexico deal was found by Cheapflights users on 7/1. 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.
sáb. 8/236:00 pmORD - SJD
2 stops29h 50mAeromexico
jue. 8/287:25 pmSJD - ORD
1 stop17h 05mAeromexico
Deal found 7/1$388
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/1511:59 pmORD - SJD
1 stop12h 35mVolaris
mar. 11/183:39 pmSJD - ORD
1 stop11h 58mVolaris
Deal found 7/3$389
This Delta deal was found by Cheapflights users on 7/1. 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.
lun. 8/186:04 amMDW - SJD
1 stop7h 19mDelta
vie. 8/226:10 amSJD - MDW
2 stops13h 34mDelta
Deal found 7/1$400
This American Airlines deal was found by Cheapflights users on 7/3. 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.
mar. 9/96:00 amORD - SJD
1 stop7h 25mAmerican Airlines
mar. 9/1611:40 amSJD - ORD
1 stop8h 44mAmerican Airlines
Deal found 7/3$406
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
mar. 8/128:39 pmMDW - SJD
1 stop16h 32mMultiple Airlines
vie. 8/157:25 amSJD - MDW
1 stop9h 51mMultiple Airlines
Deal found 7/3$423
This Southwest deal was found by Cheapflights users on 7/1. 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.
lun. 7/145:15 amMDW - SJD
1 stop5h 35mSouthwest
mié. 7/1611:55 amSJD - MDW
1 stop10h 55mSouthwest
Deal found 7/1$431
This Alaska Airlines deal was found by Cheapflights users on 7/3. 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.
mar. 9/161:01 pmORD - SJD
2 stops23h 35mAlaska Airlines
vie. 9/2611:46 amSJD - ORD
2 stops17h 17mAlaska Airlines
Deal found 7/3$432
This Aeromexico deal was found by Cheapflights users on 7/2. 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.
vie. 9/196:00 amMDW - SJD
2 stops18h 30mAeromexico
lun. 9/227:55 pmSJD - MDW
2 stops23h 41mAeromexico
Deal found 7/2$546

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 julio 3, 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

dom. 8/17

7:02 am-5:45 pm

1 stop12h 43m

San José del Cabo Los Cabos

mié. 8/20

6:10 am-11:58 pm

1 stop15h 48m

$387

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 8/23

6:00 pm-9:50 pm

2 stops29h 50m

San José del Cabo Los Cabos

jue. 8/28

7:25 pm-2:30 pm

1 stop17h 05m

$388

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

sáb. 8/9

12:25 pm-3:35 pm

3 stops29h 10m

San José del Cabo Los Cabos

sáb. 8/16

12:54 pm-7:42 pm

3 stops28h 48m

$389

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

vie. 8/15

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

sáb. 8/23

11:53 am-12:15 am

1 stop10h 22m

$392

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 8/18

6:04 am-11:23 am

1 stop7h 19m

San José del Cabo Los Cabos

vie. 8/22

6:10 am-9:44 pm

2 stops13h 34m

$400

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 7/15

9:05 am-11:45 am

Nonstop4h 40m

San José del Cabo Los Cabos

mar. 7/22

12:45 pm-7:10 pm

Nonstop4h 25m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 8/12

8:39 pm-11:11 am

1 stop16h 32m

San José del Cabo Los Cabos

vie. 8/15

7:25 am-7:16 pm

1 stop9h 51m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 7/14

5:15 am-8:50 am

1 stop5h 35m

San José del Cabo Los Cabos

mié. 7/16

11:55 am-12:50 am

1 stop10h 55m

$431

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

mar. 9/16

1:01 pm-10:36 am

2 stops23h 35m

San José del Cabo Los Cabos

vie. 9/26

11:46 am-7:03 am

2 stops17h 17m

$432

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 9/19

6:00 am-10:30 pm

2 stops18h 30m

San José del Cabo Los Cabos

lun. 9/22

7:55 pm-9:36 pm

2 stops23h 41m

$546

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 19 results
1
2

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 julio 3, 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.

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 julio 3, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico 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
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,718 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,270 reviews

Crew

8.6

Food

7.0

Entertainment

7.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 $112. Frontier flights start at $168 while deals on Delta start at $179 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: Emirates (100%), United Airlines (100%), American Airlines( 89%).

  • 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 $421, our data indicates the cheapest price to be $173. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $313.

  • 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

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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$343FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$311Average$397FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$597FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$447Average$643FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$461Average$690FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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