Which layover airport has the shortest connection time from Chicago to San José del Cabo?

Phoenix (PHX) has the shortest average layover time for this route: 0h 57m.

What is the cheapest airline that flies from Chicago to San José del Cabo Los Cabos?

Volaris, Viva, and Frontier are the most popular carriers operating from Chicago to San José del Cabo Los Cabos

How many flights depart from Chicago to San José del Cabo on average per day?

The number of flights available between Chicago and San José del Cabo is 3 per day as of December 2025. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

Which airport is the most popular layover for flights between Chicago and San José del Cabo?

Guadalajara (GDL) was the most common stop: 47% of momondo users choosing 1-stop flights on this route connected there.

How many flights depart from Chicago to San José del Cabo on average per week?

24 flights are operational weekly from Chicago to San José del Cabo as of December 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

Which layover airport has the shortest travel time from Chicago to San José del Cabo?

Flights connecting via Dallas (DFW) have the shortest average one-way travel time: 6h 20m.

What airlines fly to San José del Cabo?

American Airlines, United Airlines and Volaris are the top three most popular airlines that fly to San José del Cabo from Chicago according to our data. American Airlines is the first choice among our users, with 59% of people opting to fly with this airline when traveling to San José del Cabo. Keep in mind that there are 6 different airlines that fly to San José del Cabo on a routine basis, so you have a few additional options to choose from.

Which layover airport offers the lowest fares from Chicago to San José del Cabo?

Flights via Monterrey (MTY) offer the lowest average round-trip price of $262.

When did momondo last update prices for flights from Chicago to San José del Cabo Los Cabos Airport?

Prices for flights from Chicago to San José del Cabo Los Cabos Airport refresh daily.

How many operators does momondo search for flights from Chicago to San José del Cabo Los Cabos Airport?

As of December 2025, there are 6 operators available to choose from for flights from Chicago to San José del Cabo Los Cabos Airport.

How old do you have to be to fly from Chicago to San José del Cabo Los Cabos Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San José del Cabo Los Cabos Airport.

What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?

The travel and health documents required for your trip to San José del Cabo Los Cabos Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José del Cabo Los Cabos Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$99 Cheap Flights from Chicago to San José del Cabo in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

11:59 pm - 11:30 am

ORD

SJD

12h 31m1 stop

4:08 pm - 4:36 am

SJD

ORD

11h 28m1 stop

$372Volaris

Sat, Jan 24 - Fri, Jan 30

12:55 am - 4:30 pm

ORD

SJD

16h 35m1 stop

8:00 am - 11:25 pm

SJD

ORD

14h 25m1 stop

$373Viva

Sat, Jan 31 - Sun, Feb 8

11:59 pm - 7:15 am

ORD

SJD

8h 16m1 stop

9:00 am - 12:45 am

SJD

ORD

13h 45m2 stops

$374Multiple Airlines

Sat, Mar 7 - Wed, Mar 11

3:44 pm - 1:06 pm

ORD

SJD

22h 22m1 stop

11:42 am - 11:37 pm

SJD

ORD

10h 55m1 stop

$375Alaska Airlines

Tue, Feb 3 - Wed, Feb 11

1:20 am - 8:00 am

ORD

SJD

7h 40m1 stop

6:30 pm - 11:50 pm

SJD

ORD

52h 20m2 stops

$377Viva

Sun, Jan 11 - Fri, Jan 23

8:58 pm - 1:06 pm

ORD

SJD

17h 08m1 stop

11:42 am - 11:37 pm

SJD

ORD

10h 55m1 stop

$379Alaska Airlines

Tue, Jan 6 - Thu, Jan 8

8:40 am - 11:40 am

MDW

SJD

5h 00mnonstop

12:35 pm - 6:30 pm

SJD

MDW

3h 55mnonstop

$415Southwest

Mon, Mar 9 - Fri, Mar 13

6:00 am - 2:09 pm

MDW

SJD

9h 09m1 stop

6:30 pm - 5:29 pm

SJD

MDW

21h 59m2 stops

$421Aeromexico

Mon, Jan 19 - Wed, Jan 21

6:00 am - 5:36 pm

MDW

SJD

12h 36m2 stops

6:30 pm - 5:29 pm

SJD

MDW

21h 59m2 stops

$422Aeromexico

Mon, Jan 19 - Wed, Jan 21

10:40 am - 1:35 pm

MDW

SJD

4h 55mnonstop

1:05 pm - 11:05 pm

SJD

MDW

8h 00m1 stop

$426Southwest

Tue, Mar 31 - Wed, Apr 8

United Airlines flights from Chicago to San José del Cabo

Our best United Airlines deals on Chicago to San José del Cabo flight tickets

United Airlines

Mar 4

ORD9:03 amChicago O'Hare Intl

5h 00m

SJD1:03 pmSan José del Cabo Los Cabos

Mar 10

SJD11:10 amSan José del Cabo Los Cabos

4h 09m

ORD5:19 pmChicago O'Hare Intl

$415

Find similar

United Airlines

Dec 9

ORD9:03 amChicago O'Hare Intl

5h 00m

SJD1:03 pmSan José del Cabo Los Cabos

Dec 11

SJD12:50 pmSan José del Cabo Los Cabos

4h 11m

ORD6:01 pmChicago O'Hare Intl

$444

Find similar

United Airlines

Dec 9

ORD7:10 amChicago O'Hare Intl

7h 00m

1 stop

SJD1:10 pmSan José del Cabo Los Cabos

Dec 11

SJD12:50 pmSan José del Cabo Los Cabos

4h 11m

ORD6:01 pmChicago O'Hare Intl

$448

Find similar

Southwest flights from Chicago to San José del Cabo

Our best Southwest deals on Chicago to San José del Cabo flight tickets

Southwest

Mar 9

MDW8:40 amChicago Midway

5h 00m

SJD11:40 amSan José del Cabo Los Cabos

Mar 13

SJD12:35 pmSan José del Cabo Los Cabos

3h 55m

MDW6:30 pmChicago Midway

$415

Find similar

Southwest

Mar 31

MDW10:40 amChicago Midway

4h 55m

SJD1:35 pmSan José del Cabo Los Cabos

Apr 8

SJD1:05 pmSan José del Cabo Los Cabos

8h 00m

1 stop

MDW11:05 pmChicago Midway

$426

Find similar

Southwest

Mar 1

MDW10:15 pmChicago Midway

13h 50m

1 stop

SJD11:05 amSan José del Cabo Los Cabos

Mar 6

SJD1:35 pmSan José del Cabo Los Cabos

3h 55m

MDW6:30 pmChicago Midway

$445

Find similar

momondo Fare Finder

Use the filters below to find and compare flights from Chicago to San José del Cabo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/24

11:59 pm-11:30 am

1 stop12h 31m

San José del Cabo Los Cabos

Fri 1/30

4:08 pm-4:36 am

1 stop11h 28m

$372

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 1/31

12:55 am-4:30 pm

1 stop16h 35m

San José del Cabo Los Cabos

Sun 2/8

8:00 am-11:25 pm

1 stop14h 25m

$373

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 3/7

11:59 pm-7:15 am

1 stop8h 16m

San José del Cabo Los Cabos

Wed 3/11

9:00 am-12:45 am

2 stops13h 45m

$374

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/3

3:44 pm-1:06 pm

1 stop22h 22m

San José del Cabo Los Cabos

Wed 2/11

11:42 am-11:37 pm

1 stop10h 55m

$375

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 1/11

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Fri 1/23

6:30 pm-11:50 pm

2 stops52h 20m

$377

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 1/6

8:58 pm-1:06 pm

1 stop17h 08m

San José del Cabo Los Cabos

Thu 1/8

11:42 am-11:37 pm

1 stop10h 55m

$379

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/9

8:40 am-11:40 am

Nonstop5h 00m

San José del Cabo Los Cabos

Fri 3/13

12:35 pm-6:30 pm

Nonstop3h 55m

$415

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/19

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Wed 1/21

6:30 pm-5:29 pm

2 stops21h 59m

$421

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/19

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

Wed 1/21

6:30 pm-5:29 pm

2 stops21h 59m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/31

10:40 am-1:35 pm

Nonstop4h 55m

San José del Cabo Los Cabos

Wed 4/8

1:05 pm-11:05 pm

1 stop8h 00m

$426

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How to get the cheapest flight ticket from Chicago to San José del Cabo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Layovers

Other information

What is the typical price of a round-trip flight between Chicago and San José del Cabo?

What is the cheapest month to fly to San José del Cabo?

The cheapest month to fly to San José del Cabo from Chicago is in September. Flight prices, which tend to average around $482, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in September, then July is your next best option. Flight prices from Chicago to San José del Cabo during July average around $540.

What is the cheapest day to depart on your flight to San José del Cabo?

According to our data, Monday is the cheapest day to fly to San José del Cabo from Chicago. The lowest ticket price found for a Monday departure recently was $587. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $696.

What is the cheapest time of day to depart on your flight to San José del Cabo?

Flying to San José del Cabo from Chicago in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $313 when looking at flights departing in the afternoon. Flights to San José del Cabo are more costly in the morning, with an average ticket price of $638. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to San José del Cabo Los Cabos flight route?

Fly from Chicago O'Hare Intl to San José del Cabo Los Cabos for the best Chicago - San José del Cabo Los Cabos flight prices

How far in advance should I book a flight to San José del Cabo?

You are more likely to see cheaper flights to San José del Cabo from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $606 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José del Cabo from Chicago for as low as $542 on momondo.

What cabin class options are available on Chicago to San José del Cabo Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to San José del Cabo Los Cabos flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San José del Cabo flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago to San José del Cabo flight.

How have Chicago to San José del Cabo flight prices changed over time?

As of December 2025, prices for Chicago to San José del Cabo flights are approximately 2% more expensive when compared to flights at the same time last year.

When to book flights from Chicago to San José del Cabo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to San José del Cabo according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Chicago to San José del Cabo (CHI to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San José del Cabo

Best Price Found	$183
Fastest flight time	4h 40m
Direct flights	Every day
Airports in San José del Cabo	1 airport

The best one-way flight to San José del Cabo from Chicago in the past 72 hours is $183. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $494.

The fastest flight from Chicago to San José del Cabo takes 4h 40m

Direct flights go from Chicago to San José del Cabo every day.

There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)

Search flight deals

How far is Chicago to San José del Cabo Los Cabos by plane?
There are 1817.1 mi between Chicago and San José del Cabo Los Cabos. By plane, this route typically takes 4h 50m.
When did momondo last update prices for flights from Chicago to San José del Cabo Los Cabos Airport?
Prices for flights from Chicago to San José del Cabo Los Cabos Airport refresh daily.
How many operators does momondo search for flights from Chicago to San José del Cabo Los Cabos Airport?
As of December 2025, there are 6 operators available to choose from for flights from Chicago to San José del Cabo Los Cabos Airport.
How old do you have to be to fly from Chicago to San José del Cabo Los Cabos Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to San José del Cabo Los Cabos Airport.
What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?
The travel and health documents required for your trip to San José del Cabo Los Cabos Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at San José del Cabo Los Cabos Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to San José del Cabo?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San José del Cabo is Boeing 737-800 (53.79% of total bookings). The next most popular plane models are Airbus A321-100/200 (23.07%), Airbus A320-100/200 (14.71%), and Boeing 737 MAX 9 (3.79%).
What is the most popular airline from Chicago to San José del Cabo?
momondo data reveals that the most frequently booked airline on the route from Chicago to San José del Cabo is American Airlines, representing 52% of all bookings. The subsequent popular airlines are United Airlines at 30%, Southwest at 6%, and Volaris at 6%.

Best airlines flying from Chicago to San José del Cabo

Compare and see reviews for airlines that fly from Chicago to San José del Cabo with momondo

Airline	Rating	Free Cancellation	Price
Viva	PriceFrom $266	Free Cancellation	Rating 7.0 791 reviews	Search Viva flights
Volaris	PriceFrom $289	Free Cancellation	Rating 6.7 1,155 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 7.9 8,009 reviews	Search Delta flights
American Airlines	PriceFrom $417	Free Cancellation	Rating 7.2 11,047 reviews	Search American Airlines flights
United Airlines	PriceFrom $419	Free Cancellation	Rating 7.4 9,065 reviews	Search United Airlines flights
Southwest	PriceFrom $545	Free Cancellation	Rating 8.0 4,251 reviews	Search Southwest flights

United Airlines Flights From Chicago to San José del Cabo
United Airlines flight deals from Chicago to San José del Cabo start from $419 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $656 round-trip - but some users have found much cheaper deals with momondo.
American Airlines Flights From Chicago to San José del Cabo
American Airlines (7.2/10 from 11,047 reviews) operates around 12 flights from Chicago to San José del Cabo in any given week. The average American Airlines airfare for this route is around $613, with deals from around $417 rare but found on momondo. Referenced prices are for round-trip Chicago to San José del Cabo flight searches in the last 72 hours.

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Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José del Cabo?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to San José del Cabo. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?

Flights from Chicago to San José del Cabo with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to San José del Cabo?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to San José del Cabo from Chicago.

I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to San José del Cabo from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your San José del Cabo trip

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Cheap flights from Chicago to San José del Cabo from $99

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San José del Cabo departing on 3/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Chicago to San José del Cabo

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Use the filters below to find and compare flights from Chicago to San José del Cabo that are best for you.

See travel insights to San José del Cabo from

How to get the cheapest flight ticket from Chicago to San José del Cabo

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Chicago and San José del Cabo?

What is the cheapest month to fly to San José del Cabo?

What is the cheapest day to depart on your flight to San José del Cabo?

What is the cheapest time of day to depart on your flight to San José del Cabo?

What is the cheapest Chicago to San José del Cabo Los Cabos flight route?

Fly from Chicago O'Hare Intl to San José del Cabo Los Cabos for the best Chicago - San José del Cabo Los Cabos flight prices

How far in advance should I book a flight to San José del Cabo?

What cabin class options are available on Chicago to San José del Cabo Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to San José del Cabo Los Cabos flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to San José del Cabo flights?

You could potentially save up to 2% on your flight if you consider stops on a Chicago to San José del Cabo flight.

How have Chicago to San José del Cabo flight prices changed over time?

As of December 2025, prices for Chicago to San José del Cabo flights are approximately 2% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Chicago to San José del Cabo Los Cabos?

Volaris, Viva, and Frontier are the most popular carriers operating from Chicago to San José del Cabo Los Cabos

What airlines fly to San José del Cabo?

Which airport is the most popular layover for flights between Chicago and San José del Cabo?

Guadalajara (GDL) was the most common stop: 47% of momondo users choosing 1-stop flights on this route connected there.

Which layover airport offers the lowest fares from Chicago to San José del Cabo?

Flights via Monterrey (MTY) offer the lowest average round-trip price of $262.

Which layover airport has the shortest travel time from Chicago to San José del Cabo?

Flights connecting via Dallas (DFW) have the shortest average one-way travel time: 6h 20m.

Which layover airport has the shortest connection time from Chicago to San José del Cabo?

Phoenix (PHX) has the shortest average layover time for this route: 0h 57m.

How many flights depart from Chicago to San José del Cabo on average per day?

The number of flights available between Chicago and San José del Cabo is 3 per day as of December 2025. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

How many flights depart from Chicago to San José del Cabo on average per week?

24 flights are operational weekly from Chicago to San José del Cabo as of December 2025. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.

When to book flights from Chicago to San José del Cabo

Cheap Chicago to San José del Cabo (CHI to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to San José del Cabo

Best Price Found

Fastest flight time

Direct flights

Airports in San José del Cabo

How far is Chicago to San José del Cabo Los Cabos by plane?

When did momondo last update prices for flights from Chicago to San José del Cabo Los Cabos Airport?

How many operators does momondo search for flights from Chicago to San José del Cabo Los Cabos Airport?

How old do you have to be to fly from Chicago to San José del Cabo Los Cabos Airport?

What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?

What is the most popular plane model from Chicago to San José del Cabo?

What is the most popular airline from Chicago to San José del Cabo?

Best airlines flying from Chicago to San José del Cabo

Compare and see reviews for airlines that fly from Chicago to San José del Cabo with momondo

United Airlines Flights From Chicago to San José del Cabo

American Airlines Flights From Chicago to San José del Cabo

Traveling to a place near San José del Cabo?

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José del Cabo?

Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to San José del Cabo?

I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?

An easier way to manage your San José del Cabo trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.