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Todos Santos

$86+ 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJD
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from Chicago to Todos Santos are usually found in July or August, booked 49 days in advance, depart on a Monday or Tuesday and return on a Friday

Cheap 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 August 14, 2025.

Round-trip from

$426
(Kiwi.com)

One-way from

$86
(Mytrip)

Popular in

December

Cheapest in

July

Average price

$551
From Chicago (CHI) to Todos Santos
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One-way flight from Chicago (CHI) to Todos Santos
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Highest demand for flights based on searches. 8% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find 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 August 14, 2025.

This Mytrip deal was found by Cheapflights users on 8/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/178:56 pmORD - SJD
2 stops20h 08mMultiple Airlines
Mon 10/208:17 pmSJD - ORD
3 stops25h 28mMultiple Airlines
Deal found 8/12$425
This CheapOair deal was found by Cheapflights users on 8/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/171:55 amORD - SJD
1 stop11h 16mVolaris
Sun 9/212:02 pmSJD - ORD
1 stop13h 40mVolaris
Deal found 8/12$426
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:25 pmORD - SJD
2 stops8h 50mMultiple Airlines
Sat 11/111:11 amSJD - ORD
2 stops10h 19mMultiple Airlines
Deal found 8/12$427
This Booking.com deal was found by Cheapflights users on 8/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2812:25 pmORD - SJD
1 stop10h 10mViva
Tue 9/27:55 pmSJD - ORD
1 stop13h 00mViva
Deal found 8/12$428
This Booking.com deal was found by Cheapflights users on 8/13. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1912:25 pmORD - SJD
1 stop10h 10mViva
Tue 8/268:30 amSJD - ORD
1 stop13h 20mViva
Deal found 8/13$429
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/22:00 amORD - SJD
1 stop11h 11mMultiple Airlines
Sun 9/77:55 pmSJD - ORD
1 stop7h 47mMultiple Airlines
Deal found 8/13$430
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:00 amORD - SJD
1 stop8h 40mAmerican Airlines
Fri 12/193:35 pmSJD - ORD
1 stop6h 34mAmerican Airlines
Deal found 8/14$431
This Southwest deal was found by Cheapflights users on 8/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/147:30 amMDW - SJD
1 stop8h 10mSouthwest
Tue 10/2112:45 pmSJD - MDW
1 stop9h 20mSouthwest
Deal found 8/13$431
This American Airlines deal was found by Cheapflights users on 8/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/237:03 pmORD - SJD
1 stop17h 32mAmerican Airlines
Wed 8/2712:10 pmSJD - ORD
1 stop10h 02mAmerican Airlines
Deal found 8/14$432
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1012:25 pmORD - SJD
2 stops8h 50mViva
Mon 10/137:50 amSJD - ORD
2 stops13h 45mViva
Deal found 8/12$433
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/197:25 amORD - SJD
1 stop14h 29mMultiple Airlines
Thu 10/239:00 amSJD - ORD
2 stops12h 35mMultiple Airlines
Deal found 8/12$434
This Mytrip deal was found by Cheapflights users on 8/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/167:09 pmORD - SJD
2 stops18h 02mMultiple Airlines
Tue 9/3012:54 pmSJD - ORD
2 stops14h 48mMultiple Airlines
Deal found 8/13$435

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 August 14, 2025.
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

Fri 10/24

12:25 pm-7:15 pm

2 stops8h 50m

San José del Cabo Los Cabos

Sat 11/1

11:11 am-11:30 pm

2 stops10h 19m

$425

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 10/6

8:20 am-3:25 pm

1 stop9h 05m

San José del Cabo Los Cabos

Thu 10/9

11:45 am-11:59 pm

1 stop10h 14m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 10/27

1:55 am-3:35 pm

2 stops15h 40m

San José del Cabo Los Cabos

Sun 11/2

4:02 pm-11:19 am

2 stops18h 17m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 10/8

1:40 am-7:54 pm

1 stop20h 14m

San José del Cabo Los Cabos

Sun 10/12

8:37 pm-10:55 am

1 stop12h 18m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 9/17

1:55 am-11:11 am

1 stop11h 16m

San José del Cabo Los Cabos

Sun 9/21

2:02 pm-5:42 am

1 stop13h 40m

$426

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 8/30

8:15 pm-6:55 am

1 stop12h 40m

San José del Cabo Los Cabos

Tue 9/2

2:05 pm-11:50 pm

2 stops31h 45m

$429

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 9/2

2:00 am-11:11 am

1 stop11h 11m

San José del Cabo Los Cabos

Sun 9/7

7:55 pm-5:42 am

1 stop7h 47m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 10/10

6:31 am-6:00 pm

1 stop13h 29m

San José del Cabo Los Cabos

Mon 10/13

4:50 pm-5:00 pm

3 stops22h 10m

$430

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 9/11

7:09 pm-10:36 am

1 stop17h 27m

San José del Cabo Los Cabos

Thu 9/18

3:25 pm-11:05 am

1 stop17h 40m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/14

7:30 am-1:40 pm

1 stop8h 10m

San José del Cabo Los Cabos

Tue 10/21

12:45 pm-12:05 am

1 stop9h 20m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 38 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 August 8, 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 49 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 $437). Flying from Chicago to Todos Santos in March is currently the most expensive (average of $549). 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 August 14, 2025.

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.

How much does it cost to fly round-trip from Chicago to Todos Santos?

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 August 14, 2025.
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.
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,916 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Viva
7.0
Good
790 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Volaris
6.6
Okay
1,163 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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.

  • 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: American Airlines (90%), Emirates (88%), United Airlines (88%).

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

    On average you can expect to pay $868 for a flight from Chicago to Todos Santos. The cheapest flight overall is $204 while the most popular route, (Chicago O'Hare Intl - San José del Cabo Los Cabos) is currently priced at $275.

  • 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 $437). Flying from Chicago to Todos Santos in March is currently the most expensive (average of $549). 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 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 August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
VivaCheapest$268Average$377FlexibilityNo cancel feeOn-timeN/A
VolarisCheapest$287Average$413FlexibilityNo cancel feeOn-time79%
DeltaCheapest$356Average$545FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$438Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$455Average$672FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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