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

Delta is the most popular carrier operating from Chicago Midway to Los Cabos

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

Prices for flights from Chicago Midway Airport to Los Cabos were last updated today.

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

The number of operators available for flights from Chicago Midway Airport to Los Cabos is 1 as of April 2026.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport 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.

$200 Cheap Flights from Chicago Midway Airport to Los Cabos in 2026

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Find the cheapest flights from Chicago Midway Airport to Los Cabos

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:49 pm - 8:16 am

MDW

SJD

13h 27m

1 stop

8:50 am - 7:04 pm

SJD

MDW

8h 14m

1 stop

$465Volaris

Thu, Aug 6 - Mon, Aug 10

6:00 am - 11:31 am

MDW

SJD

7h 31m

1 stop

6:07 am - 9:09 pm

SJD

MDW

13h 02m

2 stops

$476Delta

Tue, May 5 - Tue, May 12

8:49 pm - 8:16 am

MDW

SJD

13h 27m

1 stop

8:50 am - 7:04 pm

SJD

MDW

8h 14m

1 stop

$480Volaris

Thu, Jun 4 - Mon, Jun 8

9:22 am - 12:30 pm

MDW

SJD

29h 08m

2 stops

1:09 pm - 8:42 am

SJD

MDW

17h 33m

2 stops

$481Delta

Sat, May 9 - Wed, May 13

8:49 pm - 8:16 am

MDW

SJD

13h 27m

1 stop

8:50 am - 7:04 pm

SJD

MDW

8h 14m

1 stop

$485Volaris

Sat, Jun 20 - Wed, Jun 24

6:00 am - 5:49 pm

MDW

SJD

13h 49m

2 stops

12:36 pm - 10:28 pm

SJD

MDW

7h 52m

1 stop

$504Delta

Sun, Apr 26 - Wed, Apr 29

8:49 pm - 8:16 am

MDW

SJD

13h 27m

1 stop

8:50 am - 7:04 pm

SJD

MDW

8h 14m

1 stop

$510Volaris

Thu, Jun 18 - Mon, Jun 22

6:05 am - 11:11 am

MDW

SJD

7h 06m

1 stop

12:16 pm - 10:15 pm

SJD

MDW

7h 59m

1 stop

$511Delta

Tue, Jul 28 - Tue, Aug 4

6:00 am - 1:04 pm

MDW

SJD

9h 04m

1 stop

2:19 pm - 10:00 am

SJD

MDW

17h 41m

1 stop

$512Delta

Fri, May 1 - Wed, May 6

8:49 pm - 8:16 am

MDW

SJD

13h 27m

1 stop

8:50 am - 7:04 pm

SJD

MDW

8h 14m

1 stop

$515Volaris

Thu, Jun 25 - Mon, Jun 29

Delta flights from Chicago Midway Airport to Los Cabos

Our best Delta deals on Chicago Midway Airport to Los Cabos flight tickets

Delta

May 5

MDW6:00 amChicago Midway

7h 31m

1 stop

SJD11:31 amSan José del Cabo Los Cabos

May 12

SJD6:07 amSan José del Cabo Los Cabos

13h 02m

2 stops

MDW9:09 pmChicago Midway

$476

Delta

May 9

MDW9:22 amChicago Midway

29h 08m

2 stops

SJD12:30 pmSan José del Cabo Los Cabos

May 13

SJD1:09 pmSan José del Cabo Los Cabos

17h 33m

2 stops

MDW8:42 amChicago Midway

$481

Delta

Apr 26

MDW6:00 amChicago Midway

13h 49m

2 stops

SJD5:49 pmSan José del Cabo Los Cabos

Apr 29

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

$504

Southwest flights from Chicago Midway Airport to Los Cabos

Our best Southwest deals on Chicago Midway Airport to Los Cabos flight tickets

Southwest

May 5

MDW7:30 amChicago Midway

7h 55m

1 stop

SJD1:25 pmSan José del Cabo Los Cabos

May 8

SJD1:25 pmSan José del Cabo Los Cabos

6h 30m

1 stop

MDW9:55 pmChicago Midway

$554

Southwest

May 11

MDW6:55 amChicago Midway

7h 15m

1 stop

SJD12:10 pmSan José del Cabo Los Cabos

May 14

SJD1:55 pmSan José del Cabo Los Cabos

12h 40m

1 stop

MDW4:35 amChicago Midway

$555

Southwest

May 5

MDW7:25 amChicago Midway

6h 45m

1 stop

SJD12:10 pmSan José del Cabo Los Cabos

May 12

SJD1:05 pmSan José del Cabo Los Cabos

8h 00m

1 stop

MDW11:05 pmChicago Midway

$570

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Los Cabos that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 8/6

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 8/10

8:50 am-7:04 pm

1 stop8h 14m

$465

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 5/5

6:00 am-11:31 am

1 stop7h 31m

San José del Cabo Los Cabos

Tue 5/12

6:07 am-9:09 pm

2 stops13h 02m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/4

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/8

8:50 am-7:04 pm

1 stop8h 14m

$480

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/9

9:22 am-12:30 pm

2 stops29h 08m

San José del Cabo Los Cabos

Wed 5/13

1:09 pm-8:42 am

2 stops17h 33m

$481

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/20

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 6/24

8:50 am-7:04 pm

1 stop8h 14m

$485

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/26

6:00 am-5:49 pm

2 stops13h 49m

San José del Cabo Los Cabos

Wed 4/29

12:36 pm-10:28 pm

1 stop7h 52m

$504

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/18

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/22

8:50 am-7:04 pm

1 stop8h 14m

$510

Quickest round-trip

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 7/28

6:05 am-11:11 am

1 stop7h 06m

San José del Cabo Los Cabos

Tue 8/4

12:16 pm-10:15 pm

1 stop7h 59m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 5/1

6:00 am-1:04 pm

1 stop9h 04m

San José del Cabo Los Cabos

Wed 5/6

2:19 pm-10:00 am

1 stop17h 41m

$512

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/25

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/29

8:50 am-7:04 pm

1 stop8h 14m

$515

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 Midway Airport 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

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

The cheapest day to depart from Chicago Midway Airport to Los Cabos is on a Thursday. Travelers who choose to depart for Los Cabos on a Thursday will often find tickets for as low as $615. On the other hand, Saturday is the most expensive day to depart from Chicago Midway Airport because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $954.

What is the cheapest Chicago Midway to Los Cabos flight route?

Fly from Chicago Midway to San José del Cabo Los Cabos for the best Chicago Midway - Los Cabos flight prices

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

There is only 1 cabin class available to choose from on Chicago Midway 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 Midway Airport to Los Cabos flights?

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

Cheap Chicago Midway Airport to Los Cabos flight deals and tips

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

Fastest flight time	6h 55m
Direct flights	None

The fastest flight from Chicago Midway Airport to Los Cabos takes 6h 55m

There are no direct flights from Chicago Midway Airport to Los Cabos. There are no popular flight routes from Chicago Midway Airport to Los Cabos.

Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Los Cabos

When did momondo last update prices for flights from Chicago Midway Airport to Los Cabos?
Prices for flights from Chicago Midway Airport to Los Cabos were last updated today.
How many operators does momondo search for flights from Chicago Midway Airport to Los Cabos?
The number of operators available for flights from Chicago Midway Airport to Los Cabos is 1 as of April 2026.
How old do you have to be to fly from Chicago Midway Airport to Los Cabos?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport 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 Midway Airport to Los Cabos?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to Los Cabos is Boeing 737 MAX 8, representing 16.31% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 12.25%, Airbus A320neo at 11.04%, and Airbus A321neo at 10.37%.

Best airlines flying from Chicago Midway Airport to Los Cabos

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

Airline	Rating	Free Cancellation	Price
Southwest	PriceFrom $475	Free Cancellation	Rating 8.0 4,331 reviews		Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Los Cabos. Millions of users trust and use momondo every year so you are in good hands.

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

All flight searches from Chicago to Los Cabos on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search for Chicago to Los Cabos flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Price alerts on flights to Los Cabos from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.