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Cheap flights from Chicago Midway Airport to San José del Cabo from $152

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 1/12. 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

Enter your travel dates to find the best prices.
Frontier Logo
5:01 pm - 1:36 pm
MDW
-
SJD
21h 35m1 stop
Frontier Logo
12:52 pm - 11:25 pm
SJD
-
MDW
9h 33m1 stop
$394Frontier
Fri, Feb 6 - Sat, Feb 14
Frontier Logo
1:00 pm - 1:36 pm
MDW
-
SJD
25h 36m2 stops
Frontier Logo
12:52 pm - 11:25 pm
SJD
-
MDW
9h 33m1 stop
$434Frontier
Fri, Feb 6 - Sat, Feb 14
Multiple Airlines Logo
6:00 am - 10:30 pm
MDW
-
SJD
17h 30m2 stops
Multiple Airlines Logo
3:01 pm - 11:45 am
SJD
-
MDW
19h 44m1 stop
$443Multiple Airlines
Wed, Jan 28 - Sat, Jan 31
Frontier Logo
6:00 am - 1:17 pm
MDW
-
SJD
8h 17m1 stop
Frontier Logo
9:40 am - 11:42 pm
SJD
-
MDW
12h 02m1 stop
$446Frontier
Sat, Mar 7 - Sat, Mar 14
Frontier Logo
1:00 pm - 1:36 pm
MDW
-
SJD
25h 36m2 stops
Frontier Logo
12:52 pm - 9:43 pm
SJD
-
MDW
31h 51m2 stops
$476Frontier
Fri, Feb 6 - Sat, Feb 14
Aeromexico Logo
6:00 am - 10:30 pm
MDW
-
SJD
17h 30m2 stops
Aeromexico Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m1 stop
$494Aeromexico
Wed, Jan 28 - Wed, Feb 4
Delta Logo
6:45 am - 2:09 pm
MDW
-
SJD
8h 24m1 stop
Delta Logo
1:45 pm - 10:07 pm
SJD
-
MDW
7h 22m1 stop
$500Delta
Sun, Jan 11 - Wed, Jan 14
Delta Logo
5:31 pm - 8:40 am
MDW
-
SJD
16h 09m2 stops
Delta Logo
2:50 pm - 9:08 am
SJD
-
MDW
17h 18m1 stop
$505Delta
Tue, Jan 6 - Thu, Jan 15
Aeromexico Logo
6:45 am - 2:09 pm
MDW
-
SJD
8h 24m1 stop
Aeromexico Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$511Aeromexico
Mon, Jan 12 - Tue, Jan 20
Delta Logo
5:31 pm - 8:40 am
MDW
-
SJD
16h 09m2 stops
Delta Logo
9:35 am - 10:22 pm
SJD
-
MDW
11h 47m2 stops
$516Delta
Tue, Jan 13 - Wed, Jan 21

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
Dec 15
MDW5:25 amChicago Midway
10h 25m
1 stop
SJD2:50 pmSan José del Cabo Los Cabos
Dec 18
SJD11:50 amSan José del Cabo Los Cabos
8h 25m
2 stops
MDW9:15 pmChicago Midway
$493
Find similar
Southwest
Jan 28
MDW8:55 pmChicago Midway
17h 45m
2 stops
SJD1:40 pmSan José del Cabo Los Cabos
Feb 3
SJD2:20 pmSan José del Cabo Los Cabos
13h 45m
2 stops
MDW5:05 amChicago Midway
$523
Find similar
Southwest
Mar 12
MDW8:40 amChicago Midway
5h 00m
SJD11:40 amSan José del Cabo Los Cabos
Mar 17
SJD10:35 amSan José del Cabo Los Cabos
3h 55m
MDW4:30 pmChicago Midway
$530
Find similar

Frontier flights from Chicago Midway Airport to San José del Cabo

Our best Frontier deals on Chicago Midway Airport to San José del Cabo flight tickets
Frontier
Feb 6
MDW5:01 pmChicago Midway
21h 35m
1 stop
SJD1:36 pmSan José del Cabo Los Cabos
Feb 14
SJD12:52 pmSan José del Cabo Los Cabos
9h 33m
1 stop
MDW11:25 pmChicago Midway
$394
Find similar
Frontier
Feb 6
MDW1:00 pmChicago Midway
25h 36m
2 stops
SJD1:36 pmSan José del Cabo Los Cabos
Feb 14
SJD12:52 pmSan José del Cabo Los Cabos
9h 33m
1 stop
MDW11:25 pmChicago Midway
$434
Find similar
Frontier
Mar 7
MDW6:00 amChicago Midway
8h 17m
1 stop
SJD1:17 pmSan José del Cabo Los Cabos
Mar 14
SJD9:40 amSan José del Cabo Los Cabos
12h 02m
1 stop
MDW11:42 pmChicago Midway
$446
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 December 8, 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 2/6

5:01 pm-1:36 pm

1 stop21h 35m

San José del Cabo Los Cabos

Sat 2/14

12:52 pm-11:25 pm

1 stop9h 33m

$394

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/6

1:00 pm-1:36 pm

2 stops25h 36m

San José del Cabo Los Cabos

Sat 2/14

12:52 pm-11:25 pm

1 stop9h 33m

$434

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 1/28

6:00 am-10:30 pm

2 stops17h 30m

San José del Cabo Los Cabos

Sat 1/31

3:01 pm-11:45 am

1 stop19h 44m

$443

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 3/7

6:00 am-1:17 pm

1 stop8h 17m

San José del Cabo Los Cabos

Sat 3/14

9:40 am-11:42 pm

1 stop12h 02m

$446

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/6

1:00 pm-1:36 pm

2 stops25h 36m

San José del Cabo Los Cabos

Sat 2/14

12:52 pm-9:43 pm

2 stops31h 51m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 1/28

6:00 am-10:30 pm

2 stops17h 30m

San José del Cabo Los Cabos

Wed 2/4

1:45 pm-10:22 pm

1 stop7h 37m

$494

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/11

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Wed 1/14

1:45 pm-10:07 pm

1 stop7h 22m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 1/6

5:31 pm-8:40 am

2 stops16h 09m

San José del Cabo Los Cabos

Thu 1/15

2:50 pm-9:08 am

1 stop17h 18m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/12

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Tue 1/20

6:05 am-10:22 pm

2 stops15h 17m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 1/13

5:31 pm-8:40 am

2 stops16h 09m

San José del Cabo Los Cabos

Wed 1/21

9:35 am-10:22 pm

2 stops11h 47m

$516

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 month to fly to San José del Cabo?

The cheapest month to fly to San José del Cabo from Chicago Midway Airport is in October. Flight prices, which tend to average around $471, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in October, then August is your next best option. Flight prices from Chicago Midway Airport to San José del Cabo during August average around $548.

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

According to our data, Monday is the cheapest day to fly to San José del Cabo from Chicago Midway Airport. The lowest ticket price found for a Monday departure recently was $590. 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 $693.

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 $636. 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?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to San José del Cabo.

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

Best Price Found

$580

Fastest flight time

4h 50m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in San José del Cabo

1 airport
The best flight deal from Chicago Midway Airport to San José del Cabo found on momondo in the last 72 hours is $580
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, Tuesday, Thursday, Friday, 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)
Search flight deals

  • 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 5h 00m 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
4,254 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.

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