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

3 flights are operational weekly from Chicago to San José del Cabo as of September 2025. The most popular departure day for this route is Sat, with 100% of flights per week taking off on this day.

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 $275.

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

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 6h 30m.

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

Guadalajara (GDL) was the most common stop: 60% of momondo users choosing 1-stop flights on this route connected there.

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

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

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.

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 September 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.

$121 Cheap Flights from Chicago to San José del Cabo in 2025/26

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

Prices are currently low for flights on this route. Typical prices usually range from $446 to $631. The lowest price recently found on this route was $424.

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Find the cheapest flights from Chicago to San José del Cabo

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

3:50 pm - 10:52 amORD-SJD

21h 02m2 stops

11:45 am - 11:59 pmSJD-ORD

10h 14m1 stop

$424Alaska Airlines

Find Deal

Tue, Oct 14 - Wed, Oct 22

12:59 pm - 11:34 amORD-SJD

23h 35m1 stop

7:45 pm - 3:10 pmSJD-ORD

42h 25m2 stops

$425Multiple Airlines

Find Deal

Tue, Nov 18 - Mon, Nov 24

9:00 am - 11:45 amORD-SJD

4h 45mnonstop

1:40 pm - 7:10 pmSJD-ORD

4h 30mnonstop

$431American Airlines

Find Deal

Thu, Oct 30 - Thu, Nov 6

5:00 am - 3:25 pmORD-SJD

12h 25m1 stop

1:40 pm - 7:10 pmSJD-ORD

4h 30mnonstop

$435American Airlines

Find Deal

Thu, Oct 30 - Thu, Nov 6

7:25 am - 7:54 pmORD-SJD

14h 29m1 stop

2:02 pm - 5:42 amSJD-ORD

13h 40m1 stop

$438Volaris

Find Deal

Thu, Oct 2 - Sun, Oct 5

6:31 am - 6:00 pmORD-SJD

13h 29m1 stop

2:57 pm - 12:15 amSJD-ORD

7h 18m1 stop

$439Volaris

Find Deal

Fri, Oct 3 - Tue, Oct 7

8:50 am - 11:28 amORD-SJD

4h 38mnonstop

11:08 am - 5:23 pmSJD-ORD

4h 15mnonstop

$449United Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 11

5:10 am - 1:45 pmMDW-SJD

9h 35m1 stop

2:40 pm - 10:55 pmSJD-MDW

7h 15m1 stop

$450Southwest

Find Deal

Fri, Nov 14 - Tue, Nov 18

9:40 pm - 11:20 amMDW-SJD

14h 40m2 stops

11:50 am - 10:10 pmSJD-MDW

9h 20m1 stop

$455Southwest

Find Deal

Fri, Nov 14 - Tue, Nov 18

8:50 am - 11:28 amORD-SJD

4h 38mnonstop

11:52 am - 6:06 pmSJD-ORD

4h 14mnonstop

$460United Airlines

Find Deal

Mon, Oct 13 - Mon, Oct 20

Hawaiian Airlines flights from Chicago to San José del Cabo

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

Hawaiian Airlines

Nov 14

ORD9:20 amChicago O'Hare Intl

8h 00m

1 stop

SJD4:20 pmSan José del Cabo Los Cabos

Nov 17

SJD11:40 amSan José del Cabo Los Cabos

25h 14m

1 stop

ORD1:54 pmChicago O'Hare Intl

$453

Find similar

Hawaiian Airlines

Dec 4

ORD7:59 pmChicago O'Hare Intl

17h 40m

1 stop

SJD12:39 pmSan José del Cabo Los Cabos

Dec 8

SJD11:40 amSan José del Cabo Los Cabos

25h 29m

1 stop

ORD2:09 pmChicago O'Hare Intl

$459

Find similar

Hawaiian Airlines

Nov 13

ORD8:59 pmChicago O'Hare Intl

20h 21m

1 stop

SJD4:20 pmSan José del Cabo Los Cabos

Nov 17

SJD11:40 amSan José del Cabo Los Cabos

25h 14m

1 stop

ORD1:54 pmChicago O'Hare Intl

$470

Find similar

Alaska Airlines flights from Chicago to San José del Cabo

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

Alaska Airlines

Oct 14

ORD3:50 pmChicago O'Hare Intl

21h 02m

2 stops

SJD10:52 amSan José del Cabo Los Cabos

Oct 22

SJD11:45 amSan José del Cabo Los Cabos

10h 14m

1 stop

ORD11:59 pmChicago O'Hare Intl

$424

Find similar

Alaska Airlines

Oct 6

ORD7:59 pmChicago O'Hare Intl

22h 39m

2 stops

SJD4:38 pmSan José del Cabo Los Cabos

Oct 9

SJD4:02 pmSan José del Cabo Los Cabos

29h 57m

1 stop

ORD11:59 pmChicago O'Hare Intl

$433

Find similar

Alaska Airlines

Oct 31

ORD9:20 amChicago O'Hare Intl

8h 00m

1 stop

SJD3:20 pmSan José del Cabo Los Cabos

Nov 7

SJD5:21 pmSan José del Cabo Los Cabos

12h 01m

1 stop

ORD6:22 amChicago O'Hare Intl

$437

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

Tue 10/14

3:50 pm-10:52 am

2 stops21h 02m

San José del Cabo Los Cabos

Wed 10/22

11:45 am-11:59 pm

1 stop10h 14m

$424

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 11/18

12:59 pm-11:34 am

1 stop23h 35m

San José del Cabo Los Cabos

Mon 11/24

7:45 pm-3:10 pm

2 stops42h 25m

$425

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 10/30

9:00 am-11:45 am

Nonstop4h 45m

San José del Cabo Los Cabos

Thu 11/6

1:40 pm-7:10 pm

Nonstop4h 30m

$431

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 10/30

5:00 am-3:25 pm

1 stop12h 25m

San José del Cabo Los Cabos

Thu 11/6

1:40 pm-7:10 pm

Nonstop4h 30m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 10/2

7:25 am-7:54 pm

1 stop14h 29m

San José del Cabo Los Cabos

Sun 10/5

2:02 pm-5:42 am

1 stop13h 40m

$438

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 10/3

6:31 am-6:00 pm

1 stop13h 29m

San José del Cabo Los Cabos

Tue 10/7

2:57 pm-12:15 am

1 stop7h 18m

$439

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 10/4

8:50 am-11:28 am

Nonstop4h 38m

San José del Cabo Los Cabos

Sat 10/11

11:08 am-5:23 pm

Nonstop4h 15m

$449

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/14

5:10 am-1:45 pm

1 stop9h 35m

San José del Cabo Los Cabos

Tue 11/18

2:40 pm-10:55 pm

1 stop7h 15m

$450

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/14

9:40 pm-11:20 am

2 stops14h 40m

San José del Cabo Los Cabos

Tue 11/18

11:50 am-10:10 pm

1 stop9h 20m

$455

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 10/13

8:50 am-11:28 am

Nonstop4h 38m

San José del Cabo Los Cabos

Mon 10/20

11:52 am-6:06 pm

Nonstop4h 14m

$460

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 $502, 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, Tuesday is the cheapest day to fly to San José del Cabo from Chicago. The lowest ticket price found for a Tuesday departure recently was $598. 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 $699.

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 $648. 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 $524 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?

No. A direct flight is the cheapest option for a flight between Chicago to San José del Cabo.

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

As of September 2025, prices for Chicago to San José del Cabo flights are approximately 19% 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	$230
Fastest flight time	4h 15m
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 $230. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $483.

The fastest flight from Chicago to San José del Cabo takes 4h 15m

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 38m.
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 September 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 (69.83% of total bookings). The next most popular plane models are Airbus A321-100/200 (18.67%), Airbus A320-100/200 (7.73%), and Boeing 737 MAX 8 (0.99%).
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 50% of all bookings. The subsequent popular airlines are United Airlines at 30%, Viva at 7%, 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 $267	Free Cancellation	Rating 7.0 787 reviews	Search Viva flights
Volaris	PriceFrom $310	Free Cancellation	Rating 6.6 1,154 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 7.9 7,957 reviews	Search Delta flights
American Airlines	PriceFrom $436	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $447	Free Cancellation	Rating 7.4 8,924 reviews	Search United Airlines flights
Southwest	PriceFrom $545	Free Cancellation	Rating 8.0 4,242 reviews	Search Southwest flights

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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 $121

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 11/1. 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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Filter for what you want

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Cheap round-trip flights

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Cheap last minute flights

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Hawaiian Airlines flights from Chicago to San José del Cabo

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

Alaska Airlines flights from Chicago to San José del Cabo

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

momondo Fare Finder

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?

No. A direct flight is the cheapest option for a flight between Chicago to San José del Cabo.

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

As of September 2025, prices for Chicago to San José del Cabo flights are approximately 19% 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?

Viva, Volaris, and Alaska Airlines 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: 60% 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 $275.

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

Flights connecting via Houston (IAH) have the shortest average one-way travel time: 6h 30m.

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 week?

3 flights are operational weekly from Chicago to San José del Cabo as of September 2025. The most popular departure day for this route is Sat, with 100% 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

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.

Find better results for your trip to Mexico

Airports servicing Baja California Sur