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

Mexico City (MEX) was the most common stop: 33% of momondo users choosing 1-stop flights on this route connected there.

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 Southwest 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 January 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

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 61% 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 Guadalajara (GDL) offer the lowest average round-trip price of $294.

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.

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 January 2026. The most popular departure day for this route is Mon, with 17% 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 January 2026, 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 2026

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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

Enter your travel dates to find the best prices.

12:55 am - 11:30 am

ORD

SJD

11h 35m

1 stop

12:11 pm - 11:25 pm

SJD

ORD

10h 14m

1 stop

$432Multiple Airlines

Mon, Feb 16 - Wed, Feb 25

1:55 am - 4:25 pm

ORD

SJD

16h 30m

1 stop

5:05 pm - 11:19 am

SJD

ORD

16h 14m

1 stop

$433Multiple Airlines

Tue, Mar 17 - Sun, Mar 22

12:55 am - 11:30 am

ORD

SJD

11h 35m

1 stop

12:11 pm - 11:25 pm

SJD

ORD

10h 14m

1 stop

$434Multiple Airlines

Tue, Feb 17 - Wed, Feb 25

2:20 am - 8:00 am

ORD

SJD

7h 40m

1 stop

11:20 am - 12:25 am

SJD

ORD

11h 05m

1 stop

$435Viva

Fri, Mar 13 - Sat, Mar 21

5:29 pm - 1:25 pm

ORD

SJD

20h 56m

1 stop

12:21 pm - 11:59 pm

SJD

ORD

10h 38m

1 stop

$440Alaska Airlines

Thu, Feb 19 - Wed, Feb 25

1:20 am - 8:00 am

ORD

SJD

7h 40m

1 stop

8:30 am - 11:50 pm

SJD

ORD

14h 20m

1 stop

$441Viva

Sun, Feb 15 - Fri, Feb 20

6:25 am - 1:14 pm

MDW

SJD

8h 49m

1 stop

12:15 pm - 10:29 pm

SJD

MDW

8h 14m

1 stop

$478Delta

Sun, Apr 12 - Sat, Apr 18

6:40 pm - 8:45 am

MDW

SJD

15h 05m

2 stops

2:46 pm - 8:53 am

SJD

MDW

16h 07m

2 stops

$482Delta

Fri, Mar 6 - Fri, Mar 13

10:15 pm - 11:05 am

MDW

SJD

13h 50m

1 stop

1:35 pm - 6:30 pm

SJD

MDW

3h 55mnonstop

$502Southwest

Sun, Mar 1 - Fri, Mar 6

5:15 am - 1:55 pm

MDW

SJD

9h 40m

2 stops

1:35 pm - 6:30 pm

SJD

MDW

3h 55mnonstop

$506Southwest

Sun, Mar 1 - Fri, Mar 6

Delta flights from Chicago to San José del Cabo

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

Delta

Apr 12

MDW6:25 amChicago Midway

8h 49m

1 stop

SJD1:14 pmSan José del Cabo Los Cabos

Apr 18

SJD12:15 pmSan José del Cabo Los Cabos

8h 14m

1 stop

MDW10:29 pmChicago Midway

$478

Delta

Mar 6

MDW6:00 amChicago Midway

9h 09m

1 stop

SJD2:09 pmSan José del Cabo Los Cabos

Mar 13

SJD2:46 pmSan José del Cabo Los Cabos

16h 07m

2 stops

MDW8:53 amChicago Midway

$482

Delta

Feb 3

MDW6:00 amChicago Midway

12h 41m

2 stops

SJD5:41 pmSan José del Cabo Los Cabos

Feb 10

SJD6:05 amSan José del Cabo Los Cabos

15h 17m

2 stops

MDW10:22 pmChicago Midway

$493

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

Feb 19

ORD5:29 pmChicago O'Hare Intl

20h 56m

1 stop

SJD1:25 pmSan José del Cabo Los Cabos

Feb 25

SJD12:21 pmSan José del Cabo Los Cabos

10h 38m

1 stop

ORD11:59 pmChicago O'Hare Intl

$440

Alaska Airlines

Feb 8

ORD9:00 amChicago O'Hare Intl

30h 41m

2 stops

SJD2:41 pmSan José del Cabo Los Cabos

Feb 11

SJD11:42 amSan José del Cabo Los Cabos

10h 55m

1 stop

ORD11:37 pmChicago O'Hare Intl

$444

Alaska Airlines

Feb 27

ORD3:07 pmChicago O'Hare Intl

21h 04m

2 stops

SJD11:11 amSan José del Cabo Los Cabos

Feb 28

SJD1:51 pmSan José del Cabo Los Cabos

33h 08m

1 stop

ORD11:59 pmChicago O'Hare Intl

$445

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

Mon 2/16

12:55 am-11:30 am

1 stop11h 35m

San José del Cabo Los Cabos

Wed 2/25

12:11 pm-11:25 pm

1 stop10h 14m

$432

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 3/17

1:55 am-4:25 pm

1 stop16h 30m

San José del Cabo Los Cabos

Sun 3/22

5:05 pm-11:19 am

1 stop16h 14m

$433

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Tue 2/17

12:55 am-11:30 am

1 stop11h 35m

San José del Cabo Los Cabos

Wed 2/25

12:11 pm-11:25 pm

1 stop10h 14m

$434

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 3/13

2:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Sat 3/21

11:20 am-12:25 am

1 stop11h 05m

$435

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 2/19

5:29 pm-1:25 pm

1 stop20h 56m

San José del Cabo Los Cabos

Wed 2/25

12:21 pm-11:59 pm

1 stop10h 38m

$440

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sun 2/15

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Fri 2/20

8:30 am-11:50 pm

1 stop14h 20m

$441

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/12

6:25 am-1:14 pm

1 stop8h 49m

San José del Cabo Los Cabos

Sat 4/18

12:15 pm-10:29 pm

1 stop8h 14m

$478

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/6

6:40 pm-8:45 am

2 stops15h 05m

San José del Cabo Los Cabos

Fri 3/13

2:46 pm-8:53 am

2 stops16h 07m

$482

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

10:15 pm-11:05 am

1 stop13h 50m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$502

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

5:15 am-1:55 pm

2 stops9h 40m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$506

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 $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 August is your next best option. Flight prices from Chicago to San José del Cabo during August average around $543.

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 $588. 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 $686.

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 $599 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 $535 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 13% 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 January 2026, prices for Chicago to San José del Cabo flights are approximately 29% 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	$261
Fastest flight time	4h 36m
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 $261. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $557.

The fastest flight from Chicago to San José del Cabo takes 4h 36m

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

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 36m.
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 January 2026, 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 (44.06% of total bookings). The next most popular plane models are Airbus A321-100/200 (28.76%), Airbus A320-100/200 (15.05%), and Boeing 737 MAX 9 (8.35%).
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 31%, Volaris at 6%, 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
Viva	PriceFrom $266	Free Cancellation	Rating 7.0 815 reviews	Search Viva flights
Volaris	PriceFrom $289	Free Cancellation	Rating 6.6 1,170 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 7.9 8,040 reviews	Search Delta flights
American Airlines	PriceFrom $417	Free Cancellation	Rating 7.2 11,120 reviews	Search American Airlines flights
United Airlines	PriceFrom $421	Free Cancellation	Rating 7.4 9,156 reviews	Search United Airlines flights
Southwest	PriceFrom $485	Free Cancellation	Rating 8.0 4,258 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 $421 round-trip. Over the 6 United Airlines flights for this route in a normal week, average airfare is usually $646 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 11,120 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 $607, 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

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.

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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 2/24. 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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Big names and deals

Filter for what you want

Filter for what you want

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Delta flights from Chicago to San José del Cabo

Our best Delta 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

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?

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 13% 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 January 2026, prices for Chicago to San José del Cabo flights are approximately 29% cheaper 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 Southwest 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?

Mexico City (MEX) was the most common stop: 33% 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 Guadalajara (GDL) offer the lowest average round-trip price of $294.

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 January 2026. 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 January 2026. 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.

Find better results for your trip to Mexico

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