How many flights depart from Chicago to Los Cabos on average per day?

As of October 2025, 2 flights take off from Chicago and land in Los Cabos each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

What airlines fly to Los Cabos?

American Airlines, United Airlines and Volaris are the top three most popular airlines that fly to Los Cabos from Chicago according to our data. American Airlines is the first choice among our users, with 62% of people opting to fly with this airline when traveling to Los Cabos. Keep in mind that there are 6 different airlines that fly to Los Cabos on a routine basis, so you have a few additional options to choose from.

How many flights depart from Chicago to Los Cabos on average per week?

As of October 2025, there are 17 flights per week flying from Chicago to Los Cabos. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.

What is the cheapest airline that flies from Chicago to Los Cabos?

Viva, Volaris, and United Airlines are the most popular carriers operating from Chicago to Los Cabos

When did momondo last update prices for flights from Chicago to Los Cabos?

Prices for flights from Chicago to Los Cabos are updated daily.

How many operators does momondo search for flights from Chicago to Los Cabos?

The number of operators available for flights from Chicago to Los Cabos is 6 as of October 2025.

How old do you have to be to fly from Chicago to Los Cabos?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Los Cabos.

What documentation or ID do you need to fly to Los Cabos?

The necessary travel and health documents for your Los Cabos trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$107 Cheap Flights from Chicago to Los Cabos in 2025/26

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11:59 pm - 11:34 amORD-SJD

13h 35m1 stop

4:43 pm - 5:37 amSJD-ORD

10h 54m1 stop

$415Volaris

Find Deal

Sat, Mar 21 - Sat, Mar 28

12:59 pm - 4:30 pmORD-SJD

28h 31m1 stop

4:34 pm - 11:19 amSJD-ORD

17h 45m2 stops

$416Multiple Airlines

Find Deal

Wed, Jan 14 - Mon, Jan 19

5:00 am - 11:50 amORD-SJD

7h 50m1 stop

12:50 pm - 12:23 amSJD-ORD

10h 33m1 stop

$417American Airlines

Find Deal

Wed, Jan 14 - Sun, Jan 18

5:00 am - 11:43 amORD-SJD

7h 43m1 stop

4:23 pm - 12:31 amSJD-ORD

7h 08m1 stop

$418American Airlines

Find Deal

Fri, Nov 28 - Sat, Dec 6

5:30 am - 11:40 amMDW-SJD

7h 10m1 stop

1:05 pm - 8:55 pmSJD-MDW

6h 50m1 stop

$418Southwest

Find Deal

Fri, Nov 28 - Wed, Dec 3

8:25 am - 2:20 pmMDW-SJD

6h 55m1 stop

2:40 pm - 10:55 pmSJD-MDW

7h 15m1 stop

$419Southwest

Find Deal

Sat, Nov 15 - Wed, Nov 19

3:05 pm - 11:10 amORD-SJD

21h 05m2 stops

2:23 pm - 2:37 pmSJD-ORD

23h 14m1 stop

$419Alaska Airlines

Find Deal

Mon, Dec 15 - Sun, Dec 21

12:55 am - 10:45 amORD-SJD

10h 50m1 stop

8:30 am - 11:50 pmSJD-ORD

14h 20m1 stop

$425Viva

Find Deal

Fri, Jan 30 - Fri, Feb 6

1:20 am - 8:00 amORD-SJD

7h 40m1 stop

10:05 pm - 11:50 pmSJD-ORD

24h 45m1 stop

$428Viva

Find Deal

Wed, Jan 21 - Sun, Jan 25

9:05 am - 1:03 pmORD-SJD

4h 58mnonstop

12:50 pm - 6:03 pmSJD-ORD

4h 13mnonstop

$445United Airlines

Find Deal

Thu, Nov 20 - Sun, Nov 23

Volaris flights from Chicago to Los Cabos

Our best Volaris deals on Chicago to Los Cabos flight tickets

Volaris

Mar 21

ORD11:59 pmChicago O'Hare Intl

13h 35m

1 stop

SJD11:34 amSan José del Cabo Los Cabos

Mar 28

SJD4:43 pmSan José del Cabo Los Cabos

10h 54m

1 stop

ORD5:37 amChicago O'Hare Intl

$415

Find similar

Volaris

Nov 11

ORD6:23 amChicago O'Hare Intl

9h 57m

1 stop

SJD3:20 pmSan José del Cabo Los Cabos

Nov 25

SJD4:43 pmSan José del Cabo Los Cabos

10h 53m

1 stop

ORD4:36 amChicago O'Hare Intl

$422

Find similar

Volaris

Nov 11

ORD6:23 amChicago O'Hare Intl

30h 51m

3 stops

SJD12:14 pmSan José del Cabo Los Cabos

Nov 25

SJD4:34 pmSan José del Cabo Los Cabos

17h 45m

2 stops

ORD11:19 amChicago O'Hare Intl

$429

Find similar

Aeromexico flights from Chicago to Los Cabos

Our best Aeromexico deals on Chicago to Los Cabos flight tickets

Aeromexico

Jan 10

MDW10:35 amChicago Midway

23h 10m

2 stops

SJD8:45 amSan José del Cabo Los Cabos

Jan 31

SJD6:04 amSan José del Cabo Los Cabos

14h 42m

2 stops

MDW9:46 pmChicago Midway

$592

Find similar

Aeromexico

Nov 2

MDW5:00 amChicago Midway

7h 42m

1 stop

SJD11:42 amSan José del Cabo Los Cabos

Dec 2

SJD6:00 amSan José del Cabo Los Cabos

16h 47m

2 stops

MDW11:47 pmChicago Midway

$613

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 3/21

11:59 pm-11:34 am

1 stop13h 35m

San José del Cabo Los Cabos

Sat 3/28

4:43 pm-5:37 am

1 stop10h 54m

$415

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 1/14

12:59 pm-4:30 pm

1 stop28h 31m

San José del Cabo Los Cabos

Mon 1/19

4:34 pm-11:19 am

2 stops17h 45m

$416

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 1/14

5:00 am-11:50 am

1 stop7h 50m

San José del Cabo Los Cabos

Sun 1/18

12:50 pm-12:23 am

1 stop10h 33m

$417

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 11/28

5:00 am-11:43 am

1 stop7h 43m

San José del Cabo Los Cabos

Sat 12/6

4:23 pm-12:31 am

1 stop7h 08m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

5:30 am-11:40 am

1 stop7h 10m

San José del Cabo Los Cabos

Wed 12/3

1:05 pm-8:55 pm

1 stop6h 50m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/15

8:25 am-2:20 pm

1 stop6h 55m

San José del Cabo Los Cabos

Wed 11/19

2:40 pm-10:55 pm

1 stop7h 15m

$419

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 12/15

3:05 pm-11:10 am

2 stops21h 05m

San José del Cabo Los Cabos

Sun 12/21

2:23 pm-2:37 pm

1 stop23h 14m

$419

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 1/30

12:55 am-10:45 am

1 stop10h 50m

San José del Cabo Los Cabos

Fri 2/6

8:30 am-11:50 pm

1 stop14h 20m

$425

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 1/21

1:20 am-8:00 am

1 stop7h 40m

San José del Cabo Los Cabos

Sun 1/25

10:05 pm-11:50 pm

1 stop24h 45m

$428

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 11/20

9:05 am-1:03 pm

Nonstop4h 58m

San José del Cabo Los Cabos

Sun 11/23

12:50 pm-6:03 pm

Nonstop4h 13m

$445

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How to get the cheapest flight ticket from Chicago to Los Cabos

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

Other information

What is the cheapest month to fly to Los Cabos?

The month of September is, on average, the cheapest month to fly to Los Cabos from Chicago, with most prices found around $482. The month of July is another great option to travel to Los Cabos, with average flight prices from Chicago averaging around $540.

What is the cheapest day to depart on your flight to Los Cabos?

The cheapest day to depart from Chicago to Los Cabos is on a Tuesday. Travelers who choose to depart for Los Cabos on a Tuesday will often find tickets for as low as $588. 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 $703.

What is the cheapest time of day to depart on your flight to Los Cabos?

At noon is the cheapest time of day to fly from Chicago to Los Cabos when you can find flight prices for as low as $318. Flying to Los Cabos at noon is an ideal time because this is during off-peak travel hours. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $642 on average. Flights to Los Cabos from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Chicago to Los Cabos flight route?

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

How far in advance should I book a flight to Los Cabos?

You are more likely to see cheaper flights to Los Cabos from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Los Cabos for around $607 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Los Cabos from Chicago for as low as $522 on momondo.

What cabin class options are available on Chicago to Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to 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 Los Cabos flights?

No. A direct flight is the cheapest option for a flight between Chicago to Los Cabos.

Cheap Chicago to Los Cabos flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Los Cabos

Fastest flight time	4h 37m
Direct flights	Every day
Airports in Los Cabos	1 airport

The fastest flight from Chicago to Los Cabos takes 4h 37m

Direct flights go from Chicago to Los Cabos every day.

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

Search flight deals

When did momondo last update prices for flights from Chicago to Los Cabos?
Prices for flights from Chicago to Los Cabos are updated daily.
How many operators does momondo search for flights from Chicago to Los Cabos?
The number of operators available for flights from Chicago to Los Cabos is 6 as of October 2025.
How old do you have to be to fly from Chicago to Los Cabos?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Los Cabos.
What documentation or ID do you need to fly to Los Cabos?
The necessary travel and health documents for your Los Cabos trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to Los Cabos?
momondo data reveals that the most frequently booked plane model on the route from Chicago to Los Cabos is Boeing 737-800, representing 20.17% of all bookings. The subsequent popular models are Airbus A321neo at 12.41%, Boeing 737-900 at 9.05%, and Airbus A320neo at 7.62%.

Best airlines flying from Chicago to Los Cabos

Compare and see reviews for airlines that fly from Chicago to Los Cabos 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 6.7 1,152 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 7.9 7,977 reviews	Search Delta flights
American Airlines	PriceFrom $424	Free Cancellation	Rating 7.2 11,028 reviews	Search American Airlines flights
United Airlines	PriceFrom $448	Free Cancellation	Rating 7.4 8,988 reviews	Search United Airlines flights
Southwest	PriceFrom $545	Free Cancellation	Rating 8.0 4,237 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Los Cabos?

Finding the right flight to Los Cabos from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Los Cabos quick and easy, saving you time and money.

Can I find flights from Chicago to Los Cabos with flexible booking policies on momondo?

Yes. All flights to Los Cabos from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Los Cabos?

momondo provides multiple filters to help you find the best flight to Los Cabos from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Los Cabos right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Chicago to Los Cabos flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

An easier way to manage your Los Cabos trip

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Popular cities in Los Cabos

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Cheap flights from Chicago to Los Cabos from $107

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 Los Cabos departing on 2/15. 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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Volaris flights from Chicago to Los Cabos

Our best Volaris deals on Chicago to Los Cabos flight tickets

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Our best Aeromexico deals on Chicago to Los Cabos flight tickets

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How to get the cheapest flight ticket from Chicago to Los Cabos

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 cheapest month to fly to Los Cabos?

The month of September is, on average, the cheapest month to fly to Los Cabos from Chicago, with most prices found around $482. The month of July is another great option to travel to Los Cabos, with average flight prices from Chicago averaging around $540.

What is the cheapest day to depart on your flight to Los Cabos?

What is the cheapest time of day to depart on your flight to Los Cabos?

What is the cheapest Chicago to Los Cabos flight route?

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

How far in advance should I book a flight to Los Cabos?

What cabin class options are available on Chicago to Los Cabos flights?

There are 3 cabin classes available to choose from on Chicago to 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 Los Cabos flights?

No. A direct flight is the cheapest option for a flight between Chicago to Los Cabos.

What is the cheapest airline that flies from Chicago to Los Cabos?

Viva, Volaris, and United Airlines are the most popular carriers operating from Chicago to Los Cabos

What airlines fly to Los Cabos?

How many flights depart from Chicago to Los Cabos on average per day?

As of October 2025, 2 flights take off from Chicago and land in Los Cabos each day. The most common flight departure time for this route is 8:00AM, with 100% of daily flights taking off at noon.

How many flights depart from Chicago to Los Cabos on average per week?

As of October 2025, there are 17 flights per week flying from Chicago to Los Cabos. The most common day of the week flights depart is Mon, with 18% of flights taking off on this day.

Cheap Chicago to Los Cabos flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Los Cabos

Fastest flight time

Direct flights

Airports in Los Cabos

When did momondo last update prices for flights from Chicago to Los Cabos?

How many operators does momondo search for flights from Chicago to Los Cabos?

How old do you have to be to fly from Chicago to Los Cabos?

What documentation or ID do you need to fly to Los Cabos?

What is the most popular plane model from Chicago to Los Cabos?

Best airlines flying from Chicago to Los Cabos

Compare and see reviews for airlines that fly from Chicago to Los Cabos with momondo

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Los Cabos?

Can I find flights from Chicago to Los Cabos with flexible booking policies on momondo?

How can momondo help me find flights from Chicago to Los Cabos?

I’m not ready to book a flight from Chicago to Los Cabos right now. Can momondo alert me if prices change?

An easier way to manage your Los Cabos 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 Los Cabos

Popular cities in Los Cabos

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