Los Cabos

$104+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Jan 27 — Feb 31
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Cheap 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 December 28, 2025.

This Booking.com deal was found by Cheapflights users on 12/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/314:30 pmORD - SJD
1 stop16h 30mViva
Mon 1/510:05 pmSJD - ORD
1 stop24h 50mViva
Deal found 12/26$544
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:55 pmORD - SJD
1 stop22h 15mAir Canada
Mon 1/122:10 pmSJD - ORD
1 stop28h 35mAir Canada
Deal found 12/25$605
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/303:55 pmORD - SJD
1 stop22h 15mAir Canada
Fri 1/92:30 pmSJD - ORD
1 stop28h 40mAir Canada
Deal found 12/25$606
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:30 pmORD - SJD
1 stop17h 40mAir Canada
Thu 1/82:10 pmSJD - ORD
1 stop24h 00mAir Canada
Deal found 12/25$609
This Air Canada deal was found by Cheapflights users on 12/25. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/319:20 pmORD - SJD
1 stop16h 50mAir Canada
Mon 1/122:10 pmSJD - ORD
1 stop26h 38mAir Canada
Deal found 12/25$612
This CheapOair deal was found by Cheapflights users on 12/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:30 pmORD - SJD
1 stop15h 35mMultiple Airlines
Wed 12/312:10 pmSJD - ORD
1 stop30h 55mMultiple Airlines
Deal found 12/27$621
This Mytrip deal was found by Cheapflights users on 12/26. 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.
Sat 12/274:30 pmORD - SJD
1 stop16h 20mMultiple Airlines
Wed 12/312:10 pmSJD - ORD
1 stop21h 51mMultiple Airlines
Deal found 12/26$625
This Booking.com deal was found by Cheapflights users on 12/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/294:30 pmORD - SJD
1 stop16h 20mViva
Wed 1/78:30 amSJD - ORD
1 stop14h 20mViva
Deal found 12/26$637
This CheapOair deal was found by Cheapflights users on 12/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/284:30 pmORD - SJD
1 stop15h 35mViva
Tue 12/303:00 pmSJD - ORD
1 stop23h 00mViva
Deal found 12/27$642
This Southwest deal was found by Cheapflights users on 12/26. 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.
Wed 12/318:15 amMDW - SJD
1 stop7h 35mSouthwest
Mon 1/52:05 pmSJD - MDW
1 stop8h 15mSouthwest
Deal found 12/26$903
This Southwest deal was found by Cheapflights users on 12/25. 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.
Tue 12/306:05 amMDW - SJD
1 stop7h 25mSouthwest
Wed 12/312:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 12/25$906
This Southwest deal was found by Cheapflights users on 12/26. 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 12/288:00 amMDW - SJD
1 stop7h 15mSouthwest
Mon 1/52:05 pmSJD - MDW
1 stop8h 15mSouthwest
Deal found 12/26$915

Find 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 December 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$382
(Cheapflightsfares)

One-way from

$104
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$706
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
From Chicago (CHI) to Los Cabos
One-way flight from Chicago (CHI) to Los Cabos
Highest demand for flights based on searches. 8% potential increase in price ($54 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in December 2025

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 December 28, 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

Sun 2/8

3:44 pm-2:41 pm

2 stops23h 57m

San José del Cabo Los Cabos

Wed 2/11

2:42 pm-12:01 pm

1 stop20h 19m

$403

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 2/9

3:44 pm-2:30 pm

2 stops23h 46m

San José del Cabo Los Cabos

Fri 2/13

5:20 pm-11:56 pm

1 stop29h 36m

$411

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 1/26

3:44 pm-1:06 pm

1 stop22h 22m

San José del Cabo Los Cabos

Thu 1/29

3:42 pm-2:29 pm

2 stops21h 47m

$412

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 1/25

9:05 am-1:03 pm

Nonstop4h 58m

San José del Cabo Los Cabos

Wed 1/28

12:50 pm-6:01 pm

Nonstop4h 11m

$415

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/17

1:11 am-9:31 am

1 stop9h 20m

San José del Cabo Los Cabos

Tue 2/24

10:27 am-11:00 pm

1 stop11h 33m

$415

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 2/4

1:20 am-4:30 pm

2 stops16h 10m

San José del Cabo Los Cabos

Mon 2/9

9:00 am-11:50 pm

2 stops13h 50m

$418

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 2/9

5:59 pm-8:40 am

2 stops15h 41m

San José del Cabo Los Cabos

Fri 2/13

10:27 am-11:00 pm

1 stop11h 33m

$424

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

Wed 1/28

10:25 am-11:00 pm

1 stop11h 35m

$424

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

3:44 pm-11:32 am

2 stops20h 48m

San José del Cabo Los Cabos

Fri 1/30

11:42 am-11:37 pm

1 stop10h 55m

$428

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/23

3:44 pm-11:32 am

2 stops20h 48m

San José del Cabo Los Cabos

Wed 1/28

11:42 am-11:37 pm

1 stop10h 55m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/27

Showing 1-10 of 37 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, April is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $315). Flying from Chicago to Los Cabos in February is currently the most expensive (average of $415). 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 December 28, 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 December 28, 2025.

The most flights from CHI to zzKPG are scheduled on a Tuesday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 December 28, 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.

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Crew

8.6

Overall

8.0

Boarding

8.1

Food

7.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 12h 36m. Chicago and Los Cabos are separated by a distance of 1804 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 $88. Volaris flights start at $158 while deals on American Airlines start at $180 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 (91%), Emirates (82%), American Airlines( 54%).

  • 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 $825, our data indicates the cheapest price to be $162. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $299.

  • 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, April is the cheapest month in which you can book a flight from Chicago to Los Cabos (average of $315). Flying from Chicago to Los Cabos in February is currently the most expensive (average of $415). 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 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 December 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$356FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$289Average$397FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$543FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$417Average$608FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$421Average$644FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$485Average$707FlexibilityNo cancel feeOn-time63%

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