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

Frontier 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 March 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.

$169 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

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:23 am - 5:50 pm

MDW

SJD

13h 27m

2 stops

6:55 pm - 4:12 pm

SJD

MDW

19h 17m

2 stops

$469Aeromexico

Sat, May 9 - Wed, May 13

6:00 am - 1:14 pm

MDW

SJD

9h 14m

1 stop

12:36 pm - 10:28 pm

SJD

MDW

7h 52m

1 stop

$470Aeromexico

Fri, Apr 10 - Tue, Apr 14

5:10 am - 10:40 am

MDW

SJD

7h 30m

1 stop

1:55 pm - 4:35 am

SJD

MDW

12h 40m

1 stop

$474Southwest

Sun, Apr 12 - Thu, Apr 16

6:00 am - 1:14 pm

MDW

SJD

9h 14m

1 stop

6:00 am - 10:28 pm

SJD

MDW

14h 28m

2 stops

$481Delta

Fri, Apr 10 - Wed, Apr 15

5:10 am - 1:00 pm

MDW

SJD

9h 50m

1 stop

2:20 pm - 11:20 pm

SJD

MDW

7h 00m

1 stop

$484Southwest

Sat, Apr 11 - Wed, Apr 15

6:05 am - 10:16 am

MDW

SJD

30h 11m

1 stop

11:31 am - 10:09 pm

SJD

MDW

8h 38m

1 stop

$486Frontier

Fri, Mar 13 - Sat, Mar 21

2:41 pm - 10:16 am

MDW

SJD

21h 35m

1 stop

11:31 am - 10:09 pm

SJD

MDW

8h 38m

1 stop

$498Frontier

Fri, Mar 13 - Sat, Mar 21

6:55 am - 1:40 pm

MDW

SJD

8h 45m

1 stop

12:25 pm - 10:20 pm

SJD

MDW

7h 55m

1 stop

$499Southwest

Sun, Apr 12 - Fri, Apr 17

5:00 am - 11:45 am

MDW

SJD

8h 45m

1 stop

2:20 pm - 5:00 am

SJD

MDW

12h 40m

1 stop

$507Southwest

Sat, May 9 - Wed, May 13

6:00 am - 12:30 pm

MDW

SJD

8h 30m

1 stop

1:55 pm - 4:35 am

SJD

MDW

12h 40m

1 stop

$509Southwest

Mon, Apr 13 - Mon, Apr 20

Delta flights from Chicago Midway Airport to Los Cabos

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

Delta

Apr 10

MDW6:00 amChicago Midway

9h 14m

1 stop

SJD1:14 pmSan José del Cabo Los Cabos

Apr 14

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

$481

Delta

May 2

MDW11:18 amChicago Midway

13h 07m

2 stops

SJD10:25 pmSan José del Cabo Los Cabos

May 9

SJD6:00 amSan José del Cabo Los Cabos

13h 09m

2 stops

MDW9:09 pmChicago Midway

$512

Delta

May 2

MDW5:40 amChicago Midway

9h 24m

1 stop

SJD1:04 pmSan José del Cabo Los Cabos

May 9

SJD6:00 amSan José del Cabo Los Cabos

13h 09m

2 stops

MDW9:09 pmChicago Midway

$514

Aeromexico flights from Chicago Midway Airport to Los Cabos

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

Aeromexico

May 9

MDW6:23 amChicago Midway

13h 27m

2 stops

SJD5:50 pmSan José del Cabo Los Cabos

May 13

SJD6:55 pmSan José del Cabo Los Cabos

19h 17m

2 stops

MDW4:12 pmChicago Midway

$469

Aeromexico

Apr 10

MDW6:00 amChicago Midway

18h 30m

2 stops

SJD10:30 pmSan José del Cabo Los Cabos

Apr 14

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

$470

Aeromexico

May 8

MDW6:23 amChicago Midway

13h 27m

2 stops

SJD5:50 pmSan José del Cabo Los Cabos

May 12

SJD6:00 amSan José del Cabo Los Cabos

13h 09m

2 stops

MDW9:09 pmChicago Midway

$475

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

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/9

6:23 am-5:50 pm

2 stops13h 27m

San José del Cabo Los Cabos

Wed 5/13

6:55 pm-4:12 pm

2 stops19h 17m

$469

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 4/10

6:00 am-1:14 pm

1 stop9h 14m

San José del Cabo Los Cabos

Tue 4/14

12:36 pm-10:28 pm

1 stop7h 52m

$470

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/12

5:10 am-10:40 am

1 stop7h 30m

San José del Cabo Los Cabos

Thu 4/16

1:55 pm-4:35 am

1 stop12h 40m

$474

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 4/10

6:00 am-1:14 pm

1 stop9h 14m

San José del Cabo Los Cabos

Wed 4/15

6:00 am-10:28 pm

2 stops14h 28m

$481

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 4/11

5:10 am-1:00 pm

1 stop9h 50m

San José del Cabo Los Cabos

Wed 4/15

2:20 pm-11:20 pm

1 stop7h 00m

$484

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/13

6:05 am-10:16 am

1 stop30h 11m

San José del Cabo Los Cabos

Sat 3/21

11:31 am-10:09 pm

1 stop8h 38m

$486

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/13

2:41 pm-10:16 am

1 stop21h 35m

San José del Cabo Los Cabos

Sat 3/21

11:31 am-10:09 pm

1 stop8h 38m

$498

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/12

6:55 am-1:40 pm

1 stop8h 45m

San José del Cabo Los Cabos

Fri 4/17

12:25 pm-10:20 pm

1 stop7h 55m

$499

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/9

5:00 am-11:45 am

1 stop8h 45m

San José del Cabo Los Cabos

Wed 5/13

2:20 pm-5:00 am

1 stop12h 40m

$507

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 4/13

6:00 am-12:30 pm

1 stop8h 30m

San José del Cabo Los Cabos

Mon 4/20

1:55 pm-4:35 am

1 stop12h 40m

$509

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 Monday. Travelers who choose to depart for Los Cabos on a Monday will often find tickets for as low as $626. 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	4h 55m
Direct flights	Every day
Airports in Los Cabos	2 airports

The fastest flight from Chicago Midway Airport to Los Cabos takes 4h 55m

Direct flights go from Chicago Midway Airport to Los Cabos every day.

There are 2 airports in Los Cabos. From Chicago Midway Airport there are direct flights to San José del Cabo Los Cabos (SJD).

Search flight deals

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 March 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 14.55% of all bookings. The subsequent popular models are Boeing 737-800 Passenger/BBJ2 (winglets) at 12.09%, Airbus A320neo at 11.98%, and Airbus A321neo at 10.48%.

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 4,306 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.