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

Denver (DEN) has the shortest average layover time for this route: 1h 33m.

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 57% of people opting to fly with this airline when traveling to San José del Cabo. Keep in mind that there are 5 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 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 offers the lowest fares from Chicago to San José del Cabo?

Flights via Mexico City (MEX) offer the lowest average round-trip price of $318.

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 1 per day as of June 2026. The most frequent departure time is 8:00AM, with 100% of daily flights leaving at noon.

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

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

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

Mexico City (MEX) was the most common stop: 42% 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?

7 flights are operational weekly from Chicago to San José del Cabo as of June 2026. The most popular departure day for this route is Sat, with 43% of flights per week taking off on this day.

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 June 2026, there are 5 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.

$112 Cheap Flights from Chicago to San José del Cabo in 2026

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 $486 to $766. The lowest price recently found on this route was $373.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to San José del Cabo

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:40 am - 10:09 am

ORD

SJD

10h 29m

1 stop

7:47 pm - 5:52 am

SJD

ORD

8h 05m

1 stop

$373Volaris

Wed, Sep 9 - Sat, Sep 12

2:53 am - 8:16 am

ORD

SJD

7h 23m

1 stop

3:36 pm - 12:55 am

SJD

ORD

7h 19m

1 stop

$374Volaris

Sat, Aug 15 - Tue, Sep 1

7:35 am - 7:04 pm

ORD

SJD

13h 29m

1 stop

12:02 pm - 11:47 pm

SJD

ORD

9h 45m

1 stop

$375Volaris

Tue, Sep 1 - Sun, Sep 6

6:21 am - 11:29 am

ORD

SJD

7h 08m

1 stop

7:47 pm - 5:52 am

SJD

ORD

8h 05m

1 stop

$376Volaris

Fri, Jul 3 - Wed, Jul 8

2:53 am - 8:16 am

ORD

SJD

7h 23m

1 stop

3:36 pm - 12:55 am

SJD

ORD

7h 19m

1 stop

$377Volaris

Thu, Aug 13 - Sat, Aug 29

5:25 am - 12:50 pm

MDW

SJD

9h 25m

1 stop

1:45 pm - 10:15 pm

SJD

MDW

6h 30m

1 stop

$498Southwest

Mon, Aug 17 - Thu, Aug 20

5:30 am - 12:50 pm

MDW

SJD

9h 20m

2 stops

10:40 am - 8:10 pm

SJD

MDW

7h 30m

1 stop

$502Southwest

Mon, Aug 17 - Thu, Aug 20

6:05 am - 11:07 am

MDW

SJD

7h 02m

1 stop

12:12 pm - 10:36 pm

SJD

MDW

8h 24m

1 stop

$542Delta

Mon, Aug 31 - Tue, Sep 1

12:46 pm - 10:30 pm

MDW

SJD

11h 44m

2 stops

12:12 pm - 10:36 pm

SJD

MDW

8h 24m

1 stop

$561Delta

Wed, Aug 26 - Sat, Aug 29

8:23 pm - 12:26 pm

MDW

SJD

18h 03m

1 stop

12:06 pm - 6:05 pm

SJD

MDW

27h 59m

2 stops

$580Multiple Airlines

Fri, Sep 18 - Fri, Sep 25

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Southwest flights from Chicago to San José del Cabo

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

Southwest

Aug 17

MDW5:25 amChicago Midway

9h 25m

1 stop

SJD12:50 pmSan José del Cabo Los Cabos

Aug 20

SJD1:45 pmSan José del Cabo Los Cabos

6h 30m

1 stop

MDW10:15 pmChicago Midway

$498

Southwest

Aug 17

MDW5:30 amChicago Midway

9h 20m

2 stops

SJD12:50 pmSan José del Cabo Los Cabos

Aug 20

SJD10:40 amSan José del Cabo Los Cabos

7h 30m

1 stop

MDW8:10 pmChicago Midway

$502

Southwest

Sep 14

MDW5:30 amChicago Midway

9h 20m

2 stops

SJD12:50 pmSan José del Cabo Los Cabos

Sep 18

SJD10:40 amSan José del Cabo Los Cabos

7h 30m

1 stop

MDW8:10 pmChicago Midway

$546

Delta flights from Chicago to San José del Cabo

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

Delta

Aug 31

MDW6:05 amChicago Midway

18h 25m

2 stops

SJD10:30 pmSan José del Cabo Los Cabos

Sep 2

SJD12:12 pmSan José del Cabo Los Cabos

8h 24m

1 stop

MDW10:36 pmChicago Midway

$542

Delta

Aug 26

MDW12:46 pmChicago Midway

11h 44m

2 stops

SJD10:30 pmSan José del Cabo Los Cabos

Aug 29

SJD12:12 pmSan José del Cabo Los Cabos

8h 24m

1 stop

MDW10:36 pmChicago Midway

$561

Delta

Sep 1

MDW6:05 amChicago Midway

7h 02m

1 stop

SJD11:07 amSan José del Cabo Los Cabos

Sep 3

SJD12:12 pmSan José del Cabo Los Cabos

8h 24m

1 stop

MDW10:36 pmChicago Midway

$598

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

Cheapest round-trip

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 9/9

1:40 am-10:09 am

1 stop10h 29m

San José del Cabo Los Cabos

Sat 9/12

7:47 pm-5:52 am

1 stop8h 05m

$373

Quickest round-trip

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 8/15

2:53 am-8:16 am

1 stop7h 23m

San José del Cabo Los Cabos

Tue 9/1

3:36 pm-12:55 am

1 stop7h 19m

$374

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 9/1

7:35 am-7:04 pm

1 stop13h 29m

San José del Cabo Los Cabos

Sun 9/6

12:02 pm-11:47 pm

1 stop9h 45m

$375

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 7/3

6:21 am-11:29 am

1 stop7h 08m

San José del Cabo Los Cabos

Wed 7/8

7:47 pm-5:52 am

1 stop8h 05m

$376

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 8/13

2:53 am-8:16 am

1 stop7h 23m

San José del Cabo Los Cabos

Sat 8/29

3:36 pm-12:55 am

1 stop7h 19m

$377

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/17

5:25 am-12:50 pm

1 stop9h 25m

San José del Cabo Los Cabos

Thu 8/20

1:45 pm-10:15 pm

1 stop6h 30m

$498

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/17

5:30 am-12:50 pm

2 stops9h 20m

San José del Cabo Los Cabos

Thu 8/20

10:40 am-8:10 pm

1 stop7h 30m

$502

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/31

6:05 am-11:07 am

1 stop7h 02m

San José del Cabo Los Cabos

Tue 9/1

12:12 pm-10:36 pm

1 stop8h 24m

$542

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 8/26

12:46 pm-10:30 pm

2 stops11h 44m

San José del Cabo Los Cabos

Sat 8/29

12:12 pm-10:36 pm

1 stop8h 24m

$561

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 9/18

8:23 pm-12:26 pm

1 stop18h 03m

San José del Cabo Los Cabos

Fri 9/25

12:06 pm-6:05 pm

2 stops27h 59m

$580

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 July. Flight prices, which tend to average around $127, 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 July, then February is your next best option. Flight prices from Chicago to San José del Cabo during February average around $131.

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 $604. 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 $690.

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 from Chicago 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 $602 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 $507 on momondo.

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

There are 3 cabin classes available to choose from on Chicago to San José del Cabo 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 33% 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 June 2026, prices for Chicago to San José del Cabo flights are approximately 27% cheaper 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	$654
Fastest flight time	4h 29m
Direct flights	Every day
Airports in San José del Cabo	1 airport

The best flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $654

The fastest flight from Chicago to San José del Cabo takes 4h 29m

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

There is 1 airport in San José del Cabo. From Chicago there are direct flights to San José del Cabo Los Cabos (SJD).

Search flight deals

Frequently asked questions about flying from Chicago to San José del Cabo

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 29m.
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 June 2026, there are 5 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 Airbus A321-100/200 (52.20% of total bookings). The next most popular plane models are Boeing 737-800 (28.40%), Airbus A320-100/200 (11.80%), and Boeing 737 MAX 8 (2.20%).
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 55% of all bookings. The subsequent popular airlines are United Airlines at 28%, Volaris at 10%, and Southwest at 5%.

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
Volaris	PriceFrom $185	Free Cancellation	Rating 6.6 1,156 reviews	Search Volaris flights
Viva	PriceFrom $223	Free Cancellation	Rating 7.0 802 reviews	Search Viva flights
United Airlines	PriceFrom $417	Free Cancellation	Rating 7.4 9,901 reviews	Search United Airlines flights
American Airlines	PriceFrom $426	Free Cancellation	Rating 7.1 11,778 reviews	Search American Airlines flights
Southwest	PriceFrom $475	Free Cancellation	Rating 7.9 4,246 reviews	Search Southwest flights

American Airlines Flights From Chicago to San José del Cabo
American Airlines flight deals from Chicago to San José del Cabo start from $426 round-trip. Over the 6 American Airlines flights for this route in a normal week, average airfare is usually $640 round-trip - but some users have found much cheaper deals with momondo.

Todos Santos

Los Barriles

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 $112

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 7/12. 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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Southwest flights from Chicago to San José del Cabo

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

Delta flights from Chicago to San José del Cabo

Our best Delta 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

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 Chicago to San José del Cabo Los Cabos flight route?

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

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

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

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

What is the cheapest airline that flies 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?

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

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

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

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

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

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

Frequently asked questions about flying 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

American Airlines Flights From Chicago to San José del Cabo

Traveling to a place near San José del Cabo?

Why use momondo?

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

Fly your favorite airline to San José del Cabo

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to San José del Cabo

List of cabin classes available on flights landing in San José del Cabo. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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