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Cheap flights from Chicago Midway Airport to Los Cabos from $133

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 Midway Airport to Los Cabos departing on 2/14. 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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Find the cheapest flights from Chicago Midway Airport to Los Cabos

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
10:15 pm - 11:05 am
MDW
-
SJD
13h 50m1 stop
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$455Southwest
Sun, Mar 1 - Fri, Mar 6
Southwest Logo
5:20 am - 2:30 pm
MDW
-
SJD
10h 10m2 stops
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$459Southwest
Sun, Mar 1 - Fri, Mar 6
Southwest Logo
5:55 am - 11:40 am
MDW
-
SJD
6h 45m1 stop
Southwest Logo
12:00 pm - 10:55 pm
SJD
-
MDW
9h 55m1 stop
$465Southwest
Sun, Jan 25 - Fri, Jan 30
Volaris Logo
6:54 pm - 11:30 am
MDW
-
SJD
17h 36m1 stop
Volaris Logo
5:37 pm - 5:34 pm
SJD
-
MDW
21h 57m2 stops
$468Volaris
Fri, Mar 6 - Thu, Mar 12
Southwest Logo
5:20 am - 1:40 pm
MDW
-
SJD
9h 20m2 stops
Southwest Logo
12:00 pm - 10:55 pm
SJD
-
MDW
9h 55m1 stop
$470Southwest
Sun, Jan 25 - Fri, Jan 30
Aeromexico Logo
6:30 am - 1:00 pm
MDW
-
SJD
8h 30m1 stop
Aeromexico Logo
12:15 pm - 9:45 pm
SJD
-
MDW
7h 30m1 stop
$475Aeromexico
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
8:40 am - 11:40 am
MDW
-
SJD
5h 00mnonstop
Southwest Logo
12:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$485Southwest
Mon, Mar 9 - Thu, Mar 12
Southwest Logo
6:15 am - 1:10 pm
MDW
-
SJD
7h 55m1 stop
Southwest Logo
1:35 pm - 6:30 pm
SJD
-
MDW
3h 55mnonstop
$490Southwest
Tue, Mar 3 - Fri, Mar 6
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m1 stop
Aeromexico Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m1 stop
$494Aeromexico
Fri, Jan 23 - Fri, Jan 30
Southwest Logo
10:40 am - 1:35 pm
MDW
-
SJD
4h 55mnonstop
Southwest Logo
1:20 pm - 7:15 pm
SJD
-
MDW
3h 55mnonstop
$495Southwest
Wed, Mar 18 - Sun, Mar 22

Volaris flights from Chicago Midway Airport to Los Cabos

Our best Volaris deals on Chicago Midway Airport to Los Cabos flight tickets
Volaris
Mar 6
MDW6:54 pmChicago Midway
17h 36m
1 stop
SJD11:30 amSan José del Cabo Los Cabos
Mar 12
SJD5:37 pmSan José del Cabo Los Cabos
21h 57m
2 stops
MDW5:34 pmChicago Midway
$468
Find similar
Volaris
Feb 4
MDW6:54 pmChicago Midway
21h 25m
2 stops
SJD3:19 pmSan José del Cabo Los Cabos
Feb 8
SJD3:59 pmSan José del Cabo Los Cabos
24h 35m
3 stops
MDW5:34 pmChicago Midway
$591
Find similar

Southwest flights from Chicago Midway Airport to Los Cabos

Our best Southwest deals on Chicago Midway Airport to Los Cabos flight tickets
Southwest
Mar 11
MDW10:40 amChicago Midway
4h 55m
SJD1:35 pmSan José del Cabo Los Cabos
Mar 18
SJD10:35 amSan José del Cabo Los Cabos
3h 55m
MDW4:30 pmChicago Midway
$485
Find similar
Southwest
Dec 15
MDW5:25 amChicago Midway
7h 45m
1 stop
SJD12:10 pmSan José del Cabo Los Cabos
Dec 17
SJD1:05 pmSan José del Cabo Los Cabos
8h 50m
1 stop
MDW10:55 pmChicago Midway
$488
Find similar
Southwest
Mar 3
MDW5:05 amChicago Midway
9h 35m
1 stop
SJD1:40 pmSan José del Cabo Los Cabos
Mar 6
SJD1:35 pmSan José del Cabo Los Cabos
3h 55m
MDW6:30 pmChicago Midway
$490
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Los Cabos that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 11, 2025.
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

Sun 3/1

10:15 pm-11:05 am

1 stop13h 50m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/1

5:20 am-2:30 pm

2 stops10h 10m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$459

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

5:55 am-11:40 am

1 stop6h 45m

San José del Cabo Los Cabos

Fri 1/30

12:00 pm-10:55 pm

1 stop9h 55m

$465

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/6

6:54 pm-11:30 am

1 stop17h 36m

San José del Cabo Los Cabos

Thu 3/12

5:37 pm-5:34 pm

2 stops21h 57m

$468

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

5:20 am-1:40 pm

2 stops9h 20m

San José del Cabo Los Cabos

Fri 1/30

12:00 pm-10:55 pm

1 stop9h 55m

$470

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/7

6:30 am-1:00 pm

1 stop8h 30m

San José del Cabo Los Cabos

Tue 4/14

12:15 pm-9:45 pm

1 stop7h 30m

$475

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/9

8:40 am-11:40 am

Nonstop5h 00m

San José del Cabo Los Cabos

Thu 3/12

12:35 pm-6:30 pm

Nonstop3h 55m

$485

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/3

6:15 am-1:10 pm

1 stop7h 55m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 1/23

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Fri 1/30

1:45 pm-10:22 pm

1 stop7h 37m

$494

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 3/18

10:40 am-1:35 pm

Nonstop4h 55m

San José del Cabo Los Cabos

Sun 3/22

1:20 pm-7:15 pm

Nonstop3h 55m

$495

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Los Cabos from

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

What is the cheapest month to fly to Los Cabos?

The month of October is, on average, the cheapest month to fly to Los Cabos from Chicago Midway Airport, with most prices found around $471. The month of August is another great option to travel to Los Cabos, with average flight prices from Chicago Midway Airport averaging around $548.

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 Tuesday. Travelers who choose to depart for Los Cabos on a Tuesday will often find tickets for as low as $627. On the other hand, Sunday 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 $1,121.

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?

  • 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?

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
SouthwestPriceFrom $545Free CancellationRating
7.9
4,253 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.

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