HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Los Cabos

$97+ 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 6/26. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Los Cabos with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(CheapOair)

One-way from

$97
(Viva)

Popular in

December

Cheapest in

July

Average price

$649
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
Search Deals
From Chicago (CHI) to Los Cabos
Search Deals
One-way flight from Chicago (CHI) to Los Cabos
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals

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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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.
Fri 4/181:40 amORD - SJD
1 stop10h 29mVolaris
Sat 4/2612:01 pmSJD - ORD
1 stop10h 14mVolaris
Deal found 2/19$407
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 6/1212:35 pmORD - SJD
1 stop10h 00mViva
Sun 6/159:00 amSJD - ORD
2 stops12h 40mViva
Deal found 2/18$408
This Mytrip deal was found by Cheapflights users on 2/19. 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 2/223:50 pmORD - SJD
3 stops20h 00mMultiple Airlines
Sat 3/15:08 pmSJD - ORD
2 stops20h 17mMultiple Airlines
Deal found 2/19$410
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop20h 20mMultiple Airlines
Sun 3/25:49 pmSJD - MDW
1 stop14h 56mMultiple Airlines
Deal found 2/20$417
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop21h 28mVolaris
Wed 3/56:19 pmSJD - MDW
1 stop13h 26mVolaris
Deal found 2/20$420
This United Airlines deal was found by Cheapflights users on 2/18. 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.
Tue 3/119:04 amORD - SJD
Nonstop4h 53mUnited Airlines
Fri 3/1411:49 amSJD - ORD
Nonstop4h 09mUnited Airlines
Deal found 2/18$497
This Delta deal was found by Cheapflights users on 2/19. 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 3/125:45 amORD - SJD
1 stop9h 20mDelta
Tue 3/1810:32 amSJD - ORD
1 stop11h 44mDelta
Deal found 2/19$501
This Hawaiian Airlines deal was found by Cheapflights users on 2/20. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/137:45 amORD - SJD
1 stop10h 34mHawaiian Airlines
Mon 3/1711:19 amSJD - ORD
1 stop27h 39mHawaiian Airlines
Deal found 2/20$509
This Delta deal was found by Cheapflights users on 2/20. 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.
Tue 3/186:00 amMDW - SJD
1 stop9h 05mDelta
Tue 3/2512:37 pmSJD - MDW
1 stop7h 46mDelta
Deal found 2/20$511
This Alaska Airlines deal was found by Cheapflights users on 2/20. 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.
Thu 4/107:00 amORD - SJD
1 stop11h 14mAlaska Airlines
Mon 4/147:16 pmSJD - ORD
2 stops21h 00mAlaska Airlines
Deal found 2/20$519
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 3/318:19 amORD - SJD
Nonstop4h 45mAmerican Airlines
Tue 4/83:26 pmSJD - ORD
1 stop7h 14mAmerican Airlines
Deal found 2/20$523
This Southwest deal was found by Cheapflights users on 2/20. 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.
Mon 3/3110:40 pmMDW - SJD
1 stop14h 00mSouthwest
Tue 4/812:30 pmSJD - MDW
2 stops14h 50mSouthwest
Deal found 2/20$533

Find flights from Chicago to Los Cabos within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Los Cabos

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 4/18

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

Sat 4/26

12:01 pm-12:15 am

1 stop10h 14m

$407

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 6/12

12:35 pm-8:35 pm

1 stop10h 00m

San José del Cabo Los Cabos

Sun 6/15

9:00 am-11:40 pm

2 stops12h 40m

$408

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 3/24

6:30 pm-2:51 pm

3 stops22h 21m

San José del Cabo Los Cabos

Sun 3/30

8:29 am-9:45 am

3 stops47h 16m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/1

8:50 pm-11:20 am

1 stop16h 30m

San José del Cabo Los Cabos

Mon 4/7

9:15 am-10:41 pm

3 stops11h 26m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/2

11:00 am-5:19 pm

1 stop7h 19m

San José del Cabo Los Cabos

Mon 3/10

8:29 am-7:10 pm

1 stop8h 41m

$420

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 4/9

7:40 am-4:44 pm

1 stop11h 04m

San José del Cabo Los Cabos

Wed 4/16

4:23 pm-5:40 am

1 stop11h 17m

$452

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 3/11

9:04 am-11:57 am

Nonstop4h 53m

San José del Cabo Los Cabos

Fri 3/14

11:49 am-5:58 pm

Nonstop4h 09m

$497

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

5:45 am-1:05 pm

1 stop9h 20m

San José del Cabo Los Cabos

Tue 3/18

10:32 am-12:16 am

1 stop11h 44m

$501

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

7:00 pm-4:19 pm

2 stops23h 19m

San José del Cabo Los Cabos

Wed 3/19

12:57 pm-5:40 am

1 stop14h 43m

$503

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 3/12

8:21 am-11:06 am

Nonstop4h 45m

San José del Cabo Los Cabos

Thu 3/13

1:30 pm-12:12 am

1 stop8h 42m

$507

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 30 results
1
2
3

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.

Travel insights for flights from Chicago to Los Cabos

Get recent, data-driven insights about flights from Chicago to Los Cabos including ideal travel times, pricing trends, and more.

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 June is currently the most expensive (average of $560). 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 February 20, 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 February 20, 2025.

The most flights from CHI to zzKPG are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Los Cabos ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit Los Cabos when rainfall is around 0.0 in.

Temperature in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Los Cabos, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Chicago to Los Cabos by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,697 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Hawaiian Airlines
7.9
Good
2,317 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Boarding

8.2

Overall

8.1

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Viva, which is currently one of the cheapest options available, starting at $97. Volaris flights start at $121 while deals on Frontier start at $153 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: American Airlines (88%), Emirates (77%), United Airlines( 77%).

  • 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 $1,035, our data indicates the cheapest price to be $241. The most popular route (Chicago O'Hare Intl - San José del Cabo Los Cabos), is priced around $252.

  • 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 June is currently the most expensive (average of $560). 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 7 airlines flying from Chicago to Los Cabos

Discover the top 7 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$270Average$360FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$315Average$399FlexibilityNo cancel feeOn-time79%
AeromexicoCheapest$392Average$570FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$414Average$616FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$422Average$673FlexibilityNo cancel feeOn-time69%
DeltaCheapest$431Average$800FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.