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

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

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 61% 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 day?

As of July 2025, 1 flights take off from Chicago and land in Los Cabos each day. The most common flight departure time for this route is 9:00AM, with 100% of daily flights taking off at noon.

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

As of July 2025, there are 7 flights per week flying from Chicago to Los Cabos. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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 July 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.

$108 Cheap Flights from Chicago to Los Cabos in 2025

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Find the cheapest flights from Chicago to Los Cabos

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:25 am - 7:54 pmORD-SJD

14h 29m1 stop

2:57 pm - 12:15 amSJD-ORD

7h 18m1 stop

$303Volaris

Find Deal

Mon, Sep 29 - Sat, Oct 4

7:25 am - 7:54 pmORD-SJD

14h 29m1 stop

2:02 pm - 5:42 amSJD-ORD

13h 40m1 stop

$309Volaris

Find Deal

Thu, Sep 25 - Sun, Sep 28

12:25 pm - 8:35 pmORD-SJD

10h 10m1 stop

8:30 am - 11:50 pmSJD-ORD

13h 20m1 stop

$312Viva

Find Deal

Wed, Aug 27 - Wed, Sep 3

7:25 am - 7:54 pmORD-SJD

14h 29m1 stop

8:30 am - 11:50 pmSJD-ORD

13h 20m1 stop

$317

Find Deal

Fri, Sep 5 - Wed, Sep 10

7:25 am - 7:54 pmORD-SJD

14h 29m1 stop

8:30 am - 11:50 pmSJD-ORD

13h 20m1 stop

$322

Find Deal

Thu, Sep 11 - Mon, Sep 15

12:25 pm - 9:05 pmORD-SJD

10h 40m1 stop

8:30 am - 11:50 pmSJD-ORD

13h 20m1 stop

$343Viva

Find Deal

Sat, Aug 23 - Wed, Aug 27

6:40 am - 12:50 pmMDW-SJD

8h 10m1 stop

10:40 am - 12:05 amSJD-MDW

11h 25m1 stop

$401Southwest

Find Deal

Tue, Aug 12 - Fri, Aug 15

6:00 am - 11:23 amMDW-SJD

7h 23m1 stop

6:01 am - 9:26 pmSJD-MDW

13h 25m2 stops

$406Delta

Find Deal

Sun, Aug 31 - Thu, Sep 4

6:00 am - 11:35 amMDW-SJD

7h 35m1 stop

2:18 pm - 12:28 pmSJD-MDW

20h 10m2 stops

$410Delta

Find Deal

Mon, Sep 29 - Fri, Oct 3

5:30 am - 1:10 pmMDW-SJD

9h 40m2 stops

1:45 pm - 11:00 pmSJD-MDW

7h 15m1 stop

$434Southwest

Find Deal

Sun, Sep 21 - Wed, Sep 24

Volaris flights from Chicago to Los Cabos

Our best Volaris deals on Chicago to Los Cabos flight tickets

Volaris

Sep 29

ORD7:25 amChicago O'Hare Intl

14h 29m

1 stop

SJD7:54 pmSan José del Cabo Los Cabos

Oct 4

SJD2:57 pmSan José del Cabo Los Cabos

7h 18m

1 stop

ORD12:15 amChicago O'Hare Intl

$303

Find similar

Volaris

Sep 25

ORD7:25 amChicago O'Hare Intl

14h 29m

1 stop

SJD7:54 pmSan José del Cabo Los Cabos

Sep 28

SJD2:02 pmSan José del Cabo Los Cabos

13h 40m

1 stop

ORD5:42 amChicago O'Hare Intl

$309

Find similar

Volaris

Sep 18

ORD7:25 amChicago O'Hare Intl

14h 29m

1 stop

SJD7:54 pmSan José del Cabo Los Cabos

Sep 28

SJD2:02 pmSan José del Cabo Los Cabos

13h 40m

1 stop

ORD5:42 amChicago O'Hare Intl

$319

Find similar

Southwest flights from Chicago to Los Cabos

Our best Southwest deals on Chicago to Los Cabos flight tickets

Southwest

Aug 12

MDW6:40 amChicago Midway

8h 10m

1 stop

SJD12:50 pmSan José del Cabo Los Cabos

Aug 15

SJD10:40 amSan José del Cabo Los Cabos

11h 25m

1 stop

MDW12:05 amChicago Midway

$401

Find similar

Southwest

Sep 21

MDW5:30 amChicago Midway

9h 40m

2 stops

SJD1:10 pmSan José del Cabo Los Cabos

Sep 24

SJD1:45 pmSan José del Cabo Los Cabos

7h 15m

1 stop

MDW11:00 pmChicago Midway

$434

Find similar

Southwest

Nov 2

MDW5:10 amChicago Midway

9h 35m

1 stop

SJD1:45 pmSan José del Cabo Los Cabos

Nov 7

SJD1:05 pmSan José del Cabo Los Cabos

10h 00m

1 stop

MDW12:05 amChicago Midway

$454

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Mon 9/29

7:25 am-7:54 pm

1 stop14h 29m

San José del Cabo Los Cabos

Sat 10/4

2:57 pm-12:15 am

1 stop7h 18m

$303

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 9/25

7:25 am-7:54 pm

1 stop14h 29m

San José del Cabo Los Cabos

Sun 9/28

2:02 pm-5:42 am

1 stop13h 40m

$309

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Wed 8/27

12:25 pm-8:35 pm

1 stop10h 10m

San José del Cabo Los Cabos

Wed 9/3

8:30 am-11:50 pm

1 stop13h 20m

$312

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Fri 9/5

7:25 am-7:54 pm

1 stop14h 29m

San José del Cabo Los Cabos

Wed 9/10

8:30 am-11:50 pm

1 stop13h 20m

$317

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Thu 9/11

7:25 am-7:54 pm

1 stop14h 29m

San José del Cabo Los Cabos

Mon 9/15

8:30 am-11:50 pm

1 stop13h 20m

$322

ChicagoSan José del Cabo

ORD - SJD

ORDSJD

Chicago O'Hare Intl

Sat 8/23

12:25 pm-9:05 pm

1 stop10h 40m

San José del Cabo Los Cabos

Wed 8/27

8:30 am-11:50 pm

1 stop13h 20m

$343

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 8/12

6:40 am-12:50 pm

1 stop8h 10m

San José del Cabo Los Cabos

Fri 8/15

10:40 am-12:05 am

1 stop11h 25m

$401

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/31

6:00 am-11:23 am

1 stop7h 23m

San José del Cabo Los Cabos

Thu 9/4

6:01 am-9:26 pm

2 stops13h 25m

$406

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/29

6:00 am-11:35 am

1 stop7h 35m

San José del Cabo Los Cabos

Fri 10/3

2:18 pm-12:28 pm

2 stops20h 10m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/21

5:30 am-1:10 pm

2 stops9h 40m

San José del Cabo Los Cabos

Wed 9/24

1:45 pm-11:00 pm

1 stop7h 15m

$434

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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 $550. The month of July is another great option to travel to Los Cabos, with average flight prices from Chicago averaging around $553.

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 Monday. Travelers who choose to depart for Los Cabos on a Monday 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 $710.

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 $652 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 $610 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 $557 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

Best Price Found	$108
Fastest flight time	6h 00m
Direct flights	Every day
Airports in Los Cabos	1 airport

The best one-way flight to Los Cabos from Chicago in the past 72 hours is $108. The best round-trip flight deal from Chicago to Los Cabos found on momondo in the last 72 hours is $303.

The fastest flight from Chicago to Los Cabos takes 6h 00m

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 July 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 17.22% of all bookings. The subsequent popular models are Airbus A321neo at 8.77%, Boeing 737-900 at 7.92%, and Airbus A321-100/200 at 6.72%.

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 7.0 788 reviews	Search Viva flights
Volaris	PriceFrom $310	Free Cancellation	Rating 6.6 1,164 reviews	Search Volaris flights
Delta	PriceFrom $356	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $439	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $454	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
Southwest	PriceFrom $543	Free Cancellation	Rating 8.0 4,246 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

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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Find better results for your trip to Los Cabos

Popular cities in Los Cabos

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Cheap flights from Chicago to Los Cabos from $108

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 9/20. 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

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Find the cheapest flights from Chicago to Los Cabos

Cheap round-trip flights

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Volaris flights from Chicago to Los Cabos

Our best Volaris deals on Chicago to Los Cabos flight tickets

Southwest flights from Chicago to Los Cabos

Our best Southwest 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 $550. The month of July is another great option to travel to Los Cabos, with average flight prices from Chicago averaging around $553.

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?

Volaris, Viva, and Aeromexico 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 July 2025, 1 flights take off from Chicago and land in Los Cabos each day. The most common flight departure time for this route is 9:00AM, with 100% of daily flights taking off at noon.

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

As of July 2025, there are 7 flights per week flying from Chicago to Los Cabos. The most common day of the week flights depart is Mon, with 14% 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

Best Price Found

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