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Los Cabos

$100+ 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
Nov 16 — Nov 231
Sun 11/16
Sun 11/23
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 October 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$416
(Delta)

One-way from

$100
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$576
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. 7% potential increase in price ($47 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 17, 2025.

This United Airlines deal was found by Cheapflights users on 10/16. 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.
Sun 11/29:05 amORD - SJD
Nonstop4h 58mUnited Airlines
Tue 11/113:46 pmSJD - ORD
1 stop7h 13mUnited Airlines
Deal found 10/16$416
This CheapOair deal was found by Cheapflights users on 10/15. 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.
Thu 11/136:23 amORD - SJD
1 stop9h 57mVolaris
Sun 11/164:43 pmSJD - ORD
1 stop10h 53mVolaris
Deal found 10/15$418
This Southwest deal was found by Cheapflights users on 10/15. 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 11/115:15 amMDW - SJD
2 stops10h 35mSouthwest
Tue 11/1811:50 amSJD - MDW
1 stop9h 20mSouthwest
Deal found 10/15$418
This American Airlines deal was found by Cheapflights users on 10/17. 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 11/1410:10 amORD - SJD
Nonstop4h 49mAmerican Airlines
Mon 11/174:23 pmSJD - ORD
1 stop16h 13mAmerican Airlines
Deal found 10/17$419
This United Airlines deal was found by Cheapflights users on 10/15. 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.
Mon 11/37:10 amORD - SJD
1 stop8h 32mUnited Airlines
Thu 11/612:49 pmSJD - ORD
1 stop10h 26mUnited Airlines
Deal found 10/15$420
This Southwest deal was found by Cheapflights users on 10/15. 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 11/25:30 amMDW - SJD
1 stop7h 10mSouthwest
Thu 11/62:40 pmSJD - MDW
1 stop8h 30mSouthwest
Deal found 10/15$420
This SmartFares deal was found by Cheapflights users on 10/16. 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 12/308:58 pmORD - SJD
1 stop16h 37mAlaska Airlines
Tue 1/611:44 amSJD - ORD
1 stop11h 15mAlaska Airlines
Deal found 10/16$424
This Kiwi.com deal was found by Cheapflights users on 10/16. 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 11/84:40 pmORD - SJD
2 stops16h 45mViva
Sat 11/158:10 pmSJD - ORD
1 stop25h 05mViva
Deal found 10/16$426
This Alaska Airlines deal was found by Cheapflights users on 10/17. 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 11/158:59 pmORD - SJD
1 stop17h 16mAlaska Airlines
Tue 11/181:09 pmSJD - ORD
1 stop9h 50mAlaska Airlines
Deal found 10/17$427
This Mytrip deal was found by Cheapflights users on 10/15. 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 11/118:28 amORD - SJD
3 stops34h 39mMultiple Airlines
Tue 11/184:43 pmSJD - ORD
1 stop10h 53mMultiple Airlines
Deal found 10/15$429
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Fri 11/76:30 amORD - SJD
1 stop12h 00mMultiple Airlines
Fri 11/77:59 pmSJD - ORD
1 stop10h 29mMultiple Airlines
Deal found 10/14$430
This Alaska Airlines deal was found by Cheapflights users on 10/15. 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 11/158:59 pmORD - SJD
1 stop17h 16mAlaska Airlines
Mon 11/176:40 pmSJD - ORD
2 stops24h 15mAlaska Airlines
Deal found 10/15$433

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 October 17, 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

Mon 1/12

7:15 am-2:45 pm

1 stop8h 30m

San José del Cabo Los Cabos

Sun 1/18

10:25 am-11:18 pm

1 stop11h 53m

$416

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/9

7:10 am-6:25 pm

2 stops12h 15m

San José del Cabo Los Cabos

Wed 1/14

9:40 am-11:54 pm

2 stops13h 14m

$431

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 12/14

8:55 am-4:31 pm

1 stop8h 36m

San José del Cabo Los Cabos

Wed 12/17

1:49 pm-11:50 pm

1 stop9h 01m

$433

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 12/15

8:55 am-4:31 pm

1 stop8h 36m

San José del Cabo Los Cabos

Thu 12/18

2:23 pm-11:59 pm

1 stop8h 36m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 12/4

8:59 pm-12:39 pm

1 stop16h 40m

San José del Cabo Los Cabos

Tue 12/9

1:49 pm-11:50 pm

1 stop9h 01m

$440

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/15

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Mon 12/22

1:52 pm-10:22 pm

1 stop7h 30m

$448

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/15

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sun 12/21

1:52 pm-10:22 pm

1 stop7h 30m

$448

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 12/14

7:53 pm-12:10 pm

1 stop17h 17m

San José del Cabo Los Cabos

Sun 12/21

12:21 pm-9:36 pm

1 stop8h 15m

$448

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 12/15

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/20

9:40 am-10:22 pm

2 stops11h 42m

$453

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 12/14

7:40 pm-12:40 pm

1 stop18h 00m

San José del Cabo Los Cabos

Sat 12/20

9:40 am-12:02 am

2 stops13h 22m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 42 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 December is currently the most expensive (average of $411). 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 October 17, 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 58% 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 October 17, 2025.

The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 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 October 17, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,984 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,243 reviews

Comfort

8.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Food

7.0

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 8h 30m. 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 Volaris, which is currently one of the cheapest options available, starting at $159. United Airlines flights start at $160 while deals on Southwest start at $164 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%), American Airlines (90%), Emirates( 82%).

  • 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 $707, our data indicates the cheapest price to be $158. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $321.

  • 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 December is currently the most expensive (average of $411). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 October 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$353FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$310Average$408FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$543FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$426Average$625FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$448Average$665FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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