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Cheap flights from Chicago Midway Airport to San José del Cabo from $140

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 1/9. 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.
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
1:15 pm - 11:47 pmSJD-MDW
9h 32m1 stop
$416Delta
Find Deal
mar., dic. 9 - jue., dic. 11
Southwest Logo
8:25 am - 3:00 pmMDW-SJD
7h 35m1 stop
Southwest Logo
2:05 pm - 10:15 pmSJD-MDW
7h 10m1 stop
$418Southwest
Find Deal
sáb., dic. 6 - sáb., dic. 13
Southwest Logo
6:15 am - 1:10 pmMDW-SJD
7h 55m1 stop
Southwest Logo
12:00 pm - 9:20 pmSJD-MDW
8h 20m1 stop
$427Southwest
Find Deal
mié., feb. 11 - sáb., feb. 14
Delta Logo
6:40 pm - 8:45 amMDW-SJD
15h 05m2 stops
Delta Logo
9:40 am - 10:44 pmSJD-MDW
12h 04m2 stops
$428Delta
Find Deal
mar., feb. 17 - lun., feb. 23
Southwest Logo
5:55 am - 1:55 pmMDW-SJD
9h 00m1 stop
Southwest Logo
2:20 pm - 5:05 amSJD-MDW
13h 45m2 stops
$432Southwest
Find Deal
lun., ene. 19 - vie., ene. 30
Volaris Logo
6:54 pm - 6:07 pmMDW-SJD
24h 13m2 stops
Volaris Logo
3:36 pm - 9:40 amSJD-MDW
17h 04m1 stop
$444Volaris
Find Deal
mié., dic. 3 - mié., dic. 10
Volaris Logo
6:54 pm - 3:57 pmMDW-SJD
22h 03m2 stops
Volaris Logo
4:34 pm - 9:40 amSJD-MDW
16h 06m2 stops
$445Volaris
Find Deal
mié., dic. 3 - mié., dic. 10
Volaris Logo
6:54 pm - 11:30 amMDW-SJD
17h 36m1 stop
Volaris Logo
3:36 pm - 9:40 amSJD-MDW
17h 04m1 stop
$448Volaris
Find Deal
mié., dic. 3 - mié., dic. 10
Aeromexico Logo
6:45 am - 2:09 pmMDW-SJD
8h 24m1 stop
Aeromexico Logo
6:05 am - 10:26 pmSJD-MDW
15h 21m2 stops
$507Aeromexico
Find Deal
sáb., ene. 10 - sáb., ene. 31
Aeromexico Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Aeromexico Logo
2:40 pm - 11:47 pmSJD-MDW
8h 07m1 stop
$562Aeromexico
Find Deal
sáb., dic. 6 - sáb., dic. 13

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 6
MDW8:25 amChicago Midway
7h 35m
1 stop
SJD3:00 pmSan José del Cabo Los Cabos
Dec 13
SJD2:05 pmSan José del Cabo Los Cabos
7h 10m
1 stop
MDW10:15 pmChicago Midway
$418
Find similar
Southwest
Feb 11
MDW6:15 amChicago Midway
7h 55m
1 stop
SJD1:10 pmSan José del Cabo Los Cabos
Feb 14
SJD12:00 pmSan José del Cabo Los Cabos
8h 20m
1 stop
MDW9:20 pmChicago Midway
$427
Find similar
Southwest
Jan 19
MDW5:55 amChicago Midway
9h 00m
1 stop
SJD1:55 pmSan José del Cabo Los Cabos
Jan 30
SJD2:20 pmSan José del Cabo Los Cabos
13h 45m
2 stops
MDW5:05 amChicago Midway
$432
Find similar

Volaris flights from Chicago Midway Airport to San José del Cabo

Our best Volaris deals on Chicago Midway Airport to San José del Cabo flight tickets
Volaris
Dec 3
MDW6:54 pmChicago Midway
24h 13m
2 stops
SJD6:07 pmSan José del Cabo Los Cabos
Dec 10
SJD3:36 pmSan José del Cabo Los Cabos
17h 04m
1 stop
MDW9:40 amChicago Midway
$444
Find similar
Volaris
Dec 3
MDW6:54 pmChicago Midway
22h 03m
2 stops
SJD3:57 pmSan José del Cabo Los Cabos
Dec 10
SJD4:34 pmSan José del Cabo Los Cabos
16h 06m
2 stops
MDW9:40 amChicago Midway
$445
Find similar
Volaris
Dec 3
MDW6:54 pmChicago Midway
17h 36m
1 stop
SJD11:30 amSan José del Cabo Los Cabos
Dec 10
SJD3:36 pmSan José del Cabo Los Cabos
17h 04m
1 stop
MDW9:40 amChicago Midway
$448
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 noviembre 6, 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

mar. 12/9

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

jue. 12/11

1:15 pm-11:47 pm

1 stop9h 32m

$416

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 12/6

8:25 am-3:00 pm

1 stop7h 35m

San José del Cabo Los Cabos

sáb. 12/13

2:05 pm-10:15 pm

1 stop7h 10m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 2/11

6:15 am-1:10 pm

1 stop7h 55m

San José del Cabo Los Cabos

sáb. 2/14

12:00 pm-9:20 pm

1 stop8h 20m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 2/17

6:40 pm-8:45 am

2 stops15h 05m

San José del Cabo Los Cabos

lun. 2/23

9:40 am-10:44 pm

2 stops12h 04m

$428

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 1/19

5:55 am-1:55 pm

1 stop9h 00m

San José del Cabo Los Cabos

vie. 1/30

2:20 pm-5:05 am

2 stops13h 45m

$432

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 12/3

6:54 pm-6:07 pm

2 stops24h 13m

San José del Cabo Los Cabos

mié. 12/10

3:36 pm-9:40 am

1 stop17h 04m

$444

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 12/3

6:54 pm-3:57 pm

2 stops22h 03m

San José del Cabo Los Cabos

mié. 12/10

4:34 pm-9:40 am

2 stops16h 06m

$445

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 12/3

6:54 pm-11:30 am

1 stop17h 36m

San José del Cabo Los Cabos

mié. 12/10

3:36 pm-9:40 am

1 stop17h 04m

$448

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 1/10

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

sáb. 1/31

6:05 am-10:26 pm

2 stops15h 21m

$507

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 12/6

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

sáb. 12/13

2:40 pm-11:47 pm

1 stop8h 07m

$562

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, 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 $588. 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 $705.

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 $644. 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

Fastest flight time

4h 50m

Direct flights

Mon, Thu, Fri, 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, 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 6h 25m 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
4,241 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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