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Los Cabos

$84+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$406
(American Airlines)

One-way from

$84
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$613
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 ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($13 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 13, 2025.

This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2810:10 amORD - SJD
Nonstop4h 49mAmerican Airlines
Tue 12/212:34 pmSJD - ORD
Nonstop4h 21mAmerican Airlines
Deal found 11/13$406
This Aeromexico deal was found by Cheapflights users on 11/13. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/95:30 amORD - SJD
1 stop7h 40mAeromexico
Mon 12/154:55 pmSJD - ORD
2 stops16h 54mAeromexico
Deal found 11/13$407
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/148:10 amORD - SJD
1 stop7h 45mAmerican Airlines
Mon 11/172:59 pmSJD - ORD
1 stop14h 44mAmerican Airlines
Deal found 11/12$413
This United Airlines deal was found by Cheapflights users on 11/11. 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.
Thu 12/187:15 amORD - SJD
Nonstop4h 53mUnited Airlines
Mon 12/222:11 pmSJD - ORD
1 stop9h 03mUnited Airlines
Deal found 11/11$416
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:30 amORD - SJD
1 stop7h 40mDelta
Mon 12/221:52 pmSJD - ORD
1 stop9h 10mDelta
Deal found 11/13$417
This Delta deal was found by Cheapflights users on 11/12. 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.
Mon 12/16:00 amMDW - SJD
1 stop7h 10mDelta
Sat 12/61:15 pmSJD - MDW
1 stop9h 32mDelta
Deal found 11/12$417
This Delta deal was found by Cheapflights users on 11/11. 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.
Wed 11/122:57 pmORD - SJD
1 stop8h 33mDelta
Tue 11/183:05 pmSJD - ORD
2 stops16h 01mDelta
Deal found 11/11$418
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/295:00 amORD - SJD
1 stop11h 23mAmerican Airlines
Sat 12/611:35 amSJD - ORD
1 stop7h 09mAmerican Airlines
Deal found 11/13$420
This Southwest deal was found by Cheapflights users on 11/11. 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 12/148:00 amMDW - SJD
1 stop6h 45mSouthwest
Thu 12/181:25 pmSJD - MDW
1 stop11h 05mSouthwest
Deal found 11/11$420
This American Airlines deal was found by Cheapflights users on 11/12. 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 11/12$421
This Delta deal was found by Cheapflights users on 11/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/175:30 amORD - SJD
1 stop7h 40mDelta
Sun 12/284:35 pmSJD - ORD
2 stops15h 26mDelta
Deal found 11/13$422
This Delta deal was found by Cheapflights users on 11/10. 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.
Wed 12/2411:48 amMDW - SJD
2 stops21h 57mDelta
Mon 12/293:15 pmSJD - MDW
1 stop16h 50mDelta
Deal found 11/10$422

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 13, 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 1/14

7:00 am-1:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 1/17

12:50 pm-6:01 pm

Nonstop4h 11m

$412

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/27

12:59 am-9:32 am

1 stop9h 33m

San José del Cabo Los Cabos

Sun 2/1

10:35 am-11:57 pm

2 stops12h 22m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/1

6:05 am-12:30 pm

1 stop7h 25m

San José del Cabo Los Cabos

Thu 12/4

1:05 pm-8:55 pm

1 stop6h 50m

$420

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/1

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/6

4:50 pm-9:19 am

2 stops15h 29m

$422

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

5:59 pm-8:40 am

2 stops15h 41m

San José del Cabo Los Cabos

Sat 1/31

9:35 am-11:57 pm

2 stops13h 22m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Sun 2/1

9:35 am-10:26 pm

2 stops11h 51m

$427

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 12/30

8:07 pm-12:47 pm

1 stop17h 40m

San José del Cabo Los Cabos

Tue 1/6

12:37 pm-10:59 am

2 stops21h 22m

$445

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/31

7:00 am-3:25 pm

1 stop9h 25m

San José del Cabo Los Cabos

Sat 2/7

12:55 pm-8:25 pm

1 stop6h 30m

$452

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 1/8

7:05 am-2:09 pm

1 stop8h 04m

San José del Cabo Los Cabos

Sun 1/11

3:14 pm-11:57 pm

1 stop7h 43m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 1/23

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Mon 2/2

1:45 pm-10:26 pm

1 stop7h 41m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 40 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, February is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $323). Flying from Chicago to Los Cabos in October is currently the most expensive (average of $392). 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 13, 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 13, 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 13, 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
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
788 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
1,148 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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 7h 10m. 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 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 $133. Volaris flights start at $137 while deals on United Airlines start at $162 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: 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 $268.

  • 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, February is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $323). Flying from Chicago to Los Cabos in October is currently the most expensive (average of $392). 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 13, 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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