Todos Santos

$95+ Cheap flights from Chicago (CHI) to Todos Santos, Mexico

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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Feb 1 — Feb 81
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Cheapflights Tip: The best prices from Chicago to Todos Santos are usually found in September or August, booked 2 days in advance, depart on a Tuesday or Monday and return on a Thursday

Cheap flight deals from Chicago to Todos Santos

Cheapest flights from Chicago to Todos Santos
Explore the most affordable flight options available from Chicago to Todos Santos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 2, 2026.

This Expedia deal was found by Cheapflights users on 12/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:59 pmORD - SJD
1 stop12h 31mMultiple Airlines
Sat 1/32:05 pmSJD - ORD
1 stop27h 28mMultiple Airlines
Deal found 12/31$719
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/314:30 pmORD - SJD
1 stop16h 30mViva
Fri 1/27:55 amSJD - ORD
1 stop8h 45mViva
Deal found 12/30$736
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/314:30 pmORD - SJD
1 stop16h 30mViva
Sun 1/410:15 pmSJD - ORD
1 stop15h 45mViva
Deal found 12/30$783
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/314:30 pmORD - SJD
2 stops20h 00mMultiple Airlines
Fri 1/27:55 amSJD - ORD
1 stop8h 45mMultiple Airlines
Deal found 12/30$792
This Gotogate deal was found by Cheapflights users on 12/30. 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 Gotogate 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
Sat 1/39:20 pmSJD - ORD
1 stop25h 05mViva
Deal found 12/30$848
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Wed 12/3111:59 pmORD - SJD
2 stops16h 21mMultiple Airlines
Sun 1/410:15 pmSJD - ORD
1 stop15h 45mMultiple Airlines
Deal found 12/30$865
This United Airlines deal was found by Cheapflights users on 12/30. 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.
Wed 12/319:09 amORD - SJD
Nonstop5h 00mUnited Airlines
Fri 1/22:22 pmSJD - ORD
1 stop7h 52mUnited Airlines
Deal found 12/30$1,029
This Alaska Airlines deal was found by Cheapflights users on 12/30. 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.
Wed 12/316:08 pmORD - SJD
2 stops22h 22mAlaska Airlines
Sun 1/47:15 pmSJD - ORD
2 stops23h 47mAlaska Airlines
Deal found 12/30$1,121
This Southwest deal was found by Cheapflights users on 12/30. 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 12/317:00 amMDW - SJD
1 stop7h 10mSouthwest
Sat 1/33:55 pmSJD - MDW
1 stop7h 45mSouthwest
Deal found 12/30$1,203
This American Airlines deal was found by Cheapflights users on 12/31. 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.
Wed 12/317:30 pmORD - SJD
1 stop14h 31mAmerican Airlines
Sat 1/312:30 pmSJD - ORD
Nonstop4h 27mAmerican Airlines
Deal found 12/31$1,272
This Delta deal was found by Cheapflights users on 12/31. 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 12/315:59 pmMDW - SJD
2 stops18h 34mDelta
Sat 1/39:40 amSJD - MDW
2 stops11h 42mDelta
Deal found 12/31$1,635
This Delta deal was found by Cheapflights users on 12/30. 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 12/316:00 amMDW - SJD
1 stop9h 10mDelta
Fri 1/21:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 12/30$1,691

Find flight deals from Chicago to Todos Santos

Keep the following information in mind while searching for Chicago to Todos Santos flight deals. Data was last updated January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$390
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$567
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 Todos Santos
One-way flight from Chicago (CHI) to Todos Santos
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 January 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Todos Santos 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 January 2, 2026.
Use the filters below to find and compare flights from Chicago to Todos Santos that are best for you.

Fly from

Chicago

Fly to

Todos Santos

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 2/8

9:05 am-1:03 pm

Nonstop4h 58m

San José del Cabo Los Cabos

Fri 2/13

12:50 pm-6:01 pm

Nonstop4h 11m

$415

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/26

5:29 pm-4:10 pm

1 stop23h 41m

San José del Cabo Los Cabos

Sat 2/28

1:51 pm-11:59 pm

1 stop33h 08m

$427

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

$427

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 2/14

6:30 pm-8:45 am

2 stops15h 15m

San José del Cabo Los Cabos

Wed 2/18

10:27 am-11:00 pm

1 stop11h 33m

$427

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/20

3:44 pm-2:30 pm

2 stops23h 46m

San José del Cabo Los Cabos

Sun 1/25

11:42 am-11:37 pm

1 stop10h 55m

$428

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 2/8

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Fri 2/13

1:45 pm-10:31 pm

1 stop7h 46m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/2

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Thu 2/5

1:45 pm-10:22 pm

1 stop7h 37m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 1/27

6:00 am-5:41 pm

2 stops12h 41m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$433

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 2/15

6:15 am-5:37 pm

2 stops12h 22m

San José del Cabo Los Cabos

Thu 2/19

6:05 am-9:01 pm

2 stops13h 56m

$433

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/31

Showing 1-10 of 42 results
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Best time to book a flight from Chicago to Todos Santos

Have a flexible travel schedule? Discover the best time to fly to Todos Santos 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 Todos Santos

How far ahead should I book a flight from Chicago to Todos Santos?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Todos Santos. Price data was last updated on December 26, 2025.

The price you pay for your flight from Chicago to Todos Santos may vary depending on when you book. For the best chance of a lower fare, look to book 2 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago to Todos Santos?

Currently, January is the cheapest month in which you can book a flight from Chicago to Todos Santos (average of $124). Flying from Chicago to Todos Santos 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 TD9?

Find hourly flight availability from Chicago to Todos Santos. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 2, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Todos Santos as you normally would.

Reviews of airlines servicing Todos Santos

Get insights into the airlines that provide service to Todos Santos. 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 Todos Santos. Reviews last updated January 2, 2026.
Get a feel of what it's like to fly with Southwest, United Airlines, and American Airlines from Chicago to Todos Santos by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Crew

8.6

Boarding

8.1

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 Todos Santos. 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 Todos Santos?

    For as low as $415, United Airlines can have you in Todos Santos from Chicago in 4h 58m. There are 1806 mi between Chicago and Todos Santos. 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 Todos Santos one-way?

    The cheapest airline one-way is Viva, with whom users have recently found tickets for as low as $88. However, be on the lookout for offers from Volaris and American Airlines, as they are both options that can get you from Chicago to Todos Santos for a low price.

  • What are the most reliable airlines from Chicago to Todos Santos?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Chicago to Todos Santos on time: United Airlines (79%), Emirates (79%), American Airlines (58%).

  • What are the cheapest flights from Chicago to Todos Santos?

    On average you can expect to pay $796 for a flight from Chicago to Todos Santos. The cheapest flight overall is $187 while the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos) is currently priced at $289.

  • Can I find deals for flights from Chicago to Todos Santos that include hotel bookings?

    Yes. In addition to deals on Chicago to Todos Santos flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Todos Santos?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Todos Santos.

  • Can I find deals for business class flights from Chicago to Todos Santos?

    Yes. Cheapflights offers flight deals from Chicago to Todos Santos 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 Todos Santos?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Todos Santos (average of $124). Flying from Chicago to Todos Santos 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

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Top 6 airlines flying from Chicago to Todos Santos

Discover the top 6 airlines that operate flights from Chicago to Todos Santos. 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 January 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$263Average$347FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$279Average$390FlexibilityNo 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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