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Cheap flights from Chicago Midway Airport to San José del Cabo from $163

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 San José del Cabo departing on 10/21. 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 San José del Cabo

Cheap round-trip flights

Southwest Logo
5:10 am - 1:45 pmMDW-SJD
9h 35m1 stop
Southwest Logo
2:40 pm - 10:55 pmSJD-MDW
7h 15m1 stop
$450Southwest
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Fri, Nov 14 - Tue, Nov 18
Aeromexico Logo
6:00 am - 11:42 amMDW-SJD
7h 42m1 stop
Aeromexico Logo
8:13 pm - 10:14 pmSJD-MDW
24h 01m2 stops
$453Aeromexico
Find Deal
Tue, Oct 7 - Tue, Oct 14
Southwest Logo
9:40 pm - 11:20 amMDW-SJD
14h 40m2 stops
Southwest Logo
11:50 am - 10:10 pmSJD-MDW
9h 20m1 stop
$455Southwest
Find Deal
Fri, Nov 14 - Tue, Nov 18
Southwest Logo
5:25 am - 2:55 pmMDW-SJD
10h 30m1 stop
Southwest Logo
12:15 pm - 8:05 pmSJD-MDW
6h 50m1 stop
$461Southwest
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Sat, Nov 22 - Thu, Nov 27
Delta Logo
6:00 am - 2:30 pmMDW-SJD
10h 30m2 stops
Delta Logo
12:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
$463Delta
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Sat, Oct 18 - Sat, Oct 25
Southwest Logo
5:25 am - 2:55 pmMDW-SJD
10h 30m1 stop
Southwest Logo
12:15 pm - 5:05 amSJD-MDW
15h 50m2 stops
$466Southwest
Find Deal
Sat, Nov 22 - Thu, Nov 27
Southwest Logo
5:25 am - 1:20 pmMDW-SJD
9h 55m2 stops
Southwest Logo
2:20 pm - 12:10 amSJD-MDW
7h 50m1 stop
$468Southwest
Find Deal
Mon, Oct 6 - Fri, Oct 10
Multiple Airlines Logo
8:39 pm - 2:45 pmMDW-SJD
20h 06m1 stop
Multiple Airlines Logo
9:55 pm - 12:37 pmSJD-MDW
13h 42m2 stops
$511Multiple Airlines
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Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
6:49 pm - 2:56 pmMDW-SJD
21h 07m1 stop
Multiple Airlines Logo
6:25 pm - 5:34 pmSJD-MDW
22h 09m1 stop
$523Multiple Airlines
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Wed, Nov 26 - Sun, Nov 30
Delta Logo
6:00 am - 5:22 pmMDW-SJD
12h 22m2 stops
Delta Logo
9:32 am - 11:32 pmSJD-MDW
13h 00m2 stops
$560Delta
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Tue, Nov 18 - Tue, Nov 25

Delta flights from Chicago Midway Airport to San José del Cabo

Our best Delta deals on Chicago Midway Airport to San José del Cabo flight tickets
Delta
Oct 18
MDW6:00 amChicago Midway
10h 30m
2 stops
SJD2:30 pmSan José del Cabo Los Cabos
Oct 25
SJD12:47 pmSan José del Cabo Los Cabos
7h 27m
1 stop
MDW10:14 pmChicago Midway
$463
Find similar
Delta
Nov 18
MDW6:00 amChicago Midway
12h 22m
2 stops
SJD5:22 pmSan José del Cabo Los Cabos
Nov 25
SJD9:32 amSan José del Cabo Los Cabos
13h 00m
2 stops
MDW11:32 pmChicago Midway
$560
Find similar
Delta
Oct 18
MDW6:00 amChicago Midway
10h 30m
2 stops
SJD2:30 pmSan José del Cabo Los Cabos
Oct 25
SJD6:00 amSan José del Cabo Los Cabos
14h 14m
2 stops
MDW10:14 pmChicago Midway
$583
Find similar

Southwest flights from Chicago Midway Airport to San José del Cabo

Our best Southwest deals on Chicago Midway Airport to San José del Cabo flight tickets
Southwest
Nov 14
MDW5:10 amChicago Midway
9h 35m
1 stop
SJD1:45 pmSan José del Cabo Los Cabos
Nov 18
SJD2:40 pmSan José del Cabo Los Cabos
7h 15m
1 stop
MDW10:55 pmChicago Midway
$450
Find similar
Southwest
Nov 14
MDW9:40 pmChicago Midway
14h 40m
2 stops
SJD11:20 amSan José del Cabo Los Cabos
Nov 18
SJD11:50 amSan José del Cabo Los Cabos
9h 20m
1 stop
MDW10:10 pmChicago Midway
$455
Find similar
Southwest
Nov 22
MDW5:25 amChicago Midway
10h 30m
1 stop
SJD2:55 pmSan José del Cabo Los Cabos
Nov 27
SJD12:15 pmSan José del Cabo Los Cabos
6h 50m
1 stop
MDW8:05 pmChicago Midway
$461
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to San José del Cabo 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to San José del Cabo that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/14

5:10 am-1:45 pm

1 stop9h 35m

San José del Cabo Los Cabos

Tue 11/18

2:40 pm-10:55 pm

1 stop7h 15m

$450

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/7

6:00 am-11:42 am

1 stop7h 42m

San José del Cabo Los Cabos

Tue 10/14

8:13 pm-10:14 pm

2 stops24h 01m

$453

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/14

9:40 pm-11:20 am

2 stops14h 40m

San José del Cabo Los Cabos

Tue 11/18

11:50 am-10:10 pm

1 stop9h 20m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/22

5:25 am-2:55 pm

1 stop10h 30m

San José del Cabo Los Cabos

Thu 11/27

12:15 pm-8:05 pm

1 stop6h 50m

$461

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 10/18

6:00 am-2:30 pm

2 stops10h 30m

San José del Cabo Los Cabos

Sat 10/25

12:47 pm-10:14 pm

1 stop7h 27m

$463

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/22

5:25 am-2:55 pm

1 stop10h 30m

San José del Cabo Los Cabos

Thu 11/27

12:15 pm-5:05 am

2 stops15h 50m

$466

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 10/6

5:25 am-1:20 pm

2 stops9h 55m

San José del Cabo Los Cabos

Fri 10/10

2:20 pm-12:10 am

1 stop7h 50m

$468

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 10/29

8:39 pm-2:45 pm

1 stop20h 06m

San José del Cabo Los Cabos

Wed 11/5

9:55 pm-12:37 pm

2 stops13h 42m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/26

6:49 pm-2:56 pm

1 stop21h 07m

San José del Cabo Los Cabos

Sun 11/30

6:25 pm-5:34 pm

1 stop22h 09m

$523

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 11/18

6:00 am-5:22 pm

2 stops12h 22m

San José del Cabo Los Cabos

Tue 11/25

9:32 am-11:32 pm

2 stops13h 00m

$560

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 San José del Cabo from

How to get the cheapest flight ticket from Chicago Midway Airport to San José del Cabo

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 day to depart on your flight to San José del Cabo?

According to our data, Tuesday is the cheapest day to fly to San José del Cabo from Chicago Midway Airport. The lowest ticket price found for a Tuesday departure recently was $598. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Thursday 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 $699.

What is the cheapest time of day to depart on your flight to San José del Cabo?

Flying to San José del Cabo from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $313 when looking at flights departing in the afternoon. Flights to San José del Cabo are more costly in the morning, with an average ticket price of $648. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to San José del Cabo Los Cabos flight route?

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

What cabin class options are available on Chicago Midway to San José del Cabo Los Cabos flights?

There is only 1 cabin class available to choose from on Chicago Midway to San José del Cabo 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 San José del Cabo flights?

You could potentially save up to 23% on your flight if you consider stops on a Chicago Midway Airport to San José del Cabo flight.

When to book flights from Chicago Midway Airport to San José del Cabo

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to San José del Cabo according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to San José del Cabo (MDW to SJD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San José del Cabo

Fastest flight time

4h 50m

Direct flights

Mon, Sat and Sun

Airports in San José del Cabo

1 airport
The fastest flight from Chicago Midway Airport to San José del Cabo takes 4h 50m
Direct flights go from Chicago Midway Airport to San José del Cabo on Monday, Saturday and Sunday. There are no airlines offering direct flights.
There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)
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  • How far is Chicago Midway to San José del Cabo Los Cabos by plane?

    Chicago Midway and San José del Cabo Los Cabos are 1808.5 mi apart from one another. Typically, this will take 6h 40m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport?

    Prices for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport are updated daily.

  • How many operators does momondo search for flights from Chicago Midway Airport to San José del Cabo Los Cabos Airport?

  • How old do you have to be to fly from Chicago Midway Airport to San José del Cabo Los Cabos Airport?

    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 San José del Cabo Los Cabos Airport.

  • What documentation or ID do you need to fly to San José del Cabo Los Cabos Airport?

    The travel and health documents you'll need for your trip to San José del Cabo Los Cabos Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San José del Cabo Los Cabos Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to San José del Cabo?

  • What is the most popular airline from Chicago Midway Airport to San José del Cabo?

Best airlines flying from Chicago Midway Airport to San José del Cabo

Compare and see reviews for airlines that fly from Chicago Midway Airport to San José del Cabo with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $545Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

Traveling to a place near San José del Cabo?

Book flights to San José del Cabo if you plan to visit one of these locations
Todos Santos
Los Barriles

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to San José del Cabo?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San José del Cabo from Chicago.

Can I find flights from Chicago to San José del Cabo with flexible booking policies on momondo?

All flight searches from Chicago to San José del Cabo on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to San José del Cabo?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to San José del Cabo.

I’m not ready to book a flight from Chicago to San José del Cabo right now. Can momondo alert me if prices change?

If you are simply researching potential flights to San José del Cabo, momondo offers a useful price alert feature which will track prices for flights to San José del Cabo from Chicago and alert you when they change.

An easier way to manage your San José del Cabo trip

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