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

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

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 60% 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.

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 August 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.

$86 Cheap Flights from Chicago to San José del Cabo (CHI-SJD) in 2025

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Find the cheapest flights from Chicago to San José del Cabo (CHI-SJD)

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

1:55 am - 11:11 amORD-SJD

11h 16m1 stop

11:53 am - 12:15 amSJD-ORD

10h 22m1 stop

$275Volaris

Find Deal

Fri, Oct 10 - Tue, Oct 14

6:23 am - 3:25 pmORD-SJD

10h 02m1 stop

12:11 pm - 10:29 pmSJD-ORD

9h 18m1 stop

$300Volaris

Find Deal

Sat, Nov 29 - Sat, Dec 6

11:59 pm - 4:35 pmORD-SJD

17h 36m1 stop

9:00 am - 3:00 pmSJD-ORD

29h 00m2 stops

$323

Find Deal

Sat, Nov 8 - Sat, Nov 15

11:59 pm - 4:35 pmORD-SJD

17h 36m1 stop

8:10 pm - 10:15 pmSJD-ORD

25h 05m1 stop

$329

Find Deal

Sat, Nov 8 - Sat, Nov 15

6:00 am - 11:42 amMDW-SJD

7h 42m1 stop

12:47 pm - 10:14 pmSJD-MDW

7h 27m1 stop

$407Delta

Find Deal

Mon, Oct 20 - Fri, Oct 31

6:30 am - 11:45 amMDW-SJD

7h 15m1 stop

11:15 am - 12:05 amSJD-MDW

10h 50m2 stops

$412Southwest

Find Deal

Sun, Oct 26 - Wed, Oct 29

7:30 am - 1:40 pmMDW-SJD

8h 10m1 stop

12:45 pm - 12:05 amSJD-MDW

9h 20m1 stop

$431Southwest

Find Deal

Tue, Oct 14 - Tue, Oct 21

6:00 am - 12:42 pmMDW-SJD

7h 42m1 stop

6:00 am - 10:14 pmSJD-MDW

15h 14m2 stops

$455Delta

Find Deal

Mon, Nov 3 - Thu, Nov 6

6:00 am - 9:40 pmMDW-SJD

16h 40m2 stops

6:00 am - 9:46 pmSJD-MDW

14h 46m2 stops

$460Aeromexico

Find Deal

Wed, Jan 21 - Tue, Jan 27

6:00 am - 11:42 amMDW-SJD

7h 42m1 stop

12:47 pm - 10:14 pmSJD-MDW

7h 27m1 stop

$551Aeromexico

Find Deal

Fri, Oct 10 - Mon, Oct 13

Volaris flights from Chicago to San José del Cabo

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

Volaris

Oct 10

ORD1:55 amChicago O'Hare Intl

11h 16m

1 stop

SJD11:11 amSan José del Cabo Los Cabos

Oct 14

SJD11:53 amSan José del Cabo Los Cabos

10h 22m

1 stop

ORD12:15 amChicago O'Hare Intl

$275

Find similar

Volaris

Nov 29

ORD6:23 amChicago O'Hare Intl

10h 02m

1 stop

SJD3:25 pmSan José del Cabo Los Cabos

Dec 6

SJD12:11 pmSan José del Cabo Los Cabos

9h 18m

1 stop

ORD10:29 pmChicago O'Hare Intl

$300

Find similar

Volaris

Sep 5

ORD1:40 amChicago O'Hare Intl

10h 29m

1 stop

SJD10:09 amSan José del Cabo Los Cabos

Sep 13

SJD11:53 amSan José del Cabo Los Cabos

10h 22m

1 stop

ORD12:15 amChicago O'Hare Intl

$306

Find similar

American Airlines flights from Chicago to San José del Cabo

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

American Airlines

Aug 23

ORD8:25 pmChicago O'Hare Intl

17h 51m

1 stop

SJD12:16 pmSan José del Cabo Los Cabos

Aug 27

SJD12:10 pmSan José del Cabo Los Cabos

10h 02m

1 stop

ORD12:12 amChicago O'Hare Intl

$432

Find similar

American Airlines

Aug 26

ORD6:00 amChicago O'Hare Intl

9h 30m

1 stop

SJD1:30 pmSan José del Cabo Los Cabos

Aug 30

SJD10:55 amSan José del Cabo Los Cabos

4h 25m

ORD5:20 pmChicago O'Hare Intl

$437

Find similar

American Airlines

Aug 23

ORD7:30 amChicago O'Hare Intl

4h 25m

SJD9:55 amSan José del Cabo Los Cabos

Aug 27

SJD12:10 pmSan José del Cabo Los Cabos

10h 02m

1 stop

ORD12:12 amChicago O'Hare Intl

$468

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

Fri 10/10

1:55 am-11:11 am

1 stop11h 16m

San José del Cabo Los Cabos

Tue 10/14

11:53 am-12:15 am

1 stop10h 22m

$275

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/29

6:23 am-3:25 pm

1 stop10h 02m

San José del Cabo Los Cabos

Sat 12/6

12:11 pm-10:29 pm

1 stop9h 18m

$300

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/8

11:59 pm-4:35 pm

1 stop17h 36m

San José del Cabo Los Cabos

Sat 11/15

9:00 am-3:00 pm

2 stops29h 00m

$323

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 11/8

11:59 pm-4:35 pm

1 stop17h 36m

San José del Cabo Los Cabos

Sat 11/15

8:10 pm-10:15 pm

1 stop25h 05m

$329

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 10/20

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Fri 10/31

12:47 pm-10:14 pm

1 stop7h 27m

$407

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 10/26

6:30 am-11:45 am

1 stop7h 15m

San José del Cabo Los Cabos

Wed 10/29

11:15 am-12:05 am

2 stops10h 50m

$412

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

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 11/3

6:00 am-12:42 pm

1 stop7h 42m

San José del Cabo Los Cabos

Thu 11/6

6:00 am-10:14 pm

2 stops15h 14m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 1/21

6:00 am-9:40 pm

2 stops16h 40m

San José del Cabo Los Cabos

Tue 1/27

6:00 am-9:46 pm

2 stops14h 46m

$460

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 10/10

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Mon 10/13

12:47 pm-10:14 pm

1 stop7h 27m

$551

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 $540, 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 August is your next best option. Flight prices from Chicago to San José del Cabo during August average around $551.

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 $592. 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 $706.

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 $651. 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 $610 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 $544 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 24% 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 August 2025, prices for Chicago to San José del Cabo flights are approximately 11% 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	$86
Fastest flight time	6h 00m
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 $86. The best round-trip flight deal from Chicago to San José del Cabo found on momondo in the last 72 hours is $275.

The fastest flight from Chicago to San José del Cabo takes 6h 00m

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 6h 20m.
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 August 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 (61.59% of total bookings). The next most popular plane models are Airbus A321-100/200 (27.09%), Airbus A319 (3.23%), and Boeing 737 MAX 8 (2.83%).
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 49% of all bookings. The subsequent popular airlines are United Airlines at 30%, Viva at 8%, 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 $268	Free Cancellation	Rating 7.0 790 reviews	Search Viva flights
Volaris	PriceFrom $310	Free Cancellation	Rating 6.6 1,163 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 8.0 7,980 reviews	Search Delta flights
American Airlines	PriceFrom $438	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $455	Free Cancellation	Rating 7.4 8,916 reviews	Search United Airlines flights
Southwest	PriceFrom $543	Free Cancellation	Rating 8.0 4,244 reviews	Search Southwest flights

Cabo San Lucas

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

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 $86

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 10/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Chicago to San José del Cabo (CHI-SJD)

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Volaris flights from Chicago to San José del Cabo

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

American Airlines flights from Chicago to San José del Cabo

Our best American 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?

You could potentially save up to 24% 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 August 2025, prices for Chicago to San José del Cabo flights are approximately 11% 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 and Viva 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.

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