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Cheap flights from Chicago Midway Airport to San José del Cabo from $141

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 2/21. 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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0 bags

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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
6:00 am - 12:17 pm
MDW
-
SJD
8h 17m1 stop
Frontier Logo
9:40 am - 11:42 pm
SJD
-
MDW
12h 02m1 stop
$462Frontier
Sat, Apr 4 - Sat, Apr 11
Multiple Airlines Logo
6:48 pm - 1:23 pm
MDW
-
SJD
19h 35m1 stop
Multiple Airlines Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m1 stop
$490Multiple Airlines
Fri, Feb 20 - Fri, Feb 27
Frontier Logo
6:00 am - 1:23 pm
MDW
-
SJD
8h 23m1 stop
Frontier Logo
3:59 pm - 2:26 pm
SJD
-
MDW
21h 27m2 stops
$495Frontier
Sat, Feb 21 - Sat, Feb 28
Delta Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m1 stop
Delta Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$503Delta
Sun, Feb 8 - Wed, Feb 11
Multiple Airlines Logo
6:54 pm - 4:25 pm
MDW
-
SJD
22h 31m1 stop
Multiple Airlines Logo
8:00 am - 6:34 pm
SJD
-
MDW
8h 34m1 stop
$506Multiple Airlines
Sat, Mar 7 - Sun, Mar 15
Delta Logo
11:45 am - 8:40 am
MDW
-
SJD
21h 55m2 stops
Delta Logo
11:46 am - 8:54 am
SJD
-
MDW
20h 08m2 stops
$507Delta
Sat, Feb 7 - Fri, Feb 13
Aeromexico Logo
6:00 am - 10:30 pm
MDW
-
SJD
17h 30m2 stops
Aeromexico Logo
6:05 am - 10:22 pm
SJD
-
MDW
15h 17m2 stops
$508Aeromexico
Sun, Jan 25 - Wed, Jan 28
Frontier Logo
6:00 am - 1:23 pm
MDW
-
SJD
8h 23m1 stop
Frontier Logo
3:59 pm - 2:26 pm
SJD
-
MDW
21h 27m2 stops
$510Frontier
Sat, Feb 21 - Sat, Feb 28
Aeromexico Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m1 stop
Aeromexico Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m1 stop
$511Aeromexico
Sun, Jan 25 - Wed, Jan 28
Delta Logo
6:00 am - 2:09 pm
MDW
-
SJD
9h 09m1 stop
Delta Logo
6:05 am - 10:33 pm
SJD
-
MDW
15h 28m2 stops
$514Delta
Tue, Feb 24 - Tue, Mar 3

Aeromexico flights from Chicago Midway Airport to San José del Cabo

Our best Aeromexico deals on Chicago Midway Airport to San José del Cabo flight tickets
Aeromexico
Jan 25
MDW6:00 amChicago Midway
17h 30m
2 stops
SJD10:30 pmSan José del Cabo Los Cabos
Jan 28
SJD6:05 amSan José del Cabo Los Cabos
15h 17m
2 stops
MDW10:22 pmChicago Midway
$508
Aeromexico
Jan 25
MDW6:00 amChicago Midway
9h 09m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
Jan 28
SJD1:45 pmSan José del Cabo Los Cabos
7h 37m
1 stop
MDW10:22 pmChicago Midway
$511
Aeromexico
Jan 11
MDW6:45 amChicago Midway
8h 24m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
Jan 13
SJD1:45 pmSan José del Cabo Los Cabos
7h 22m
1 stop
MDW10:07 pmChicago Midway
$663

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
Jan 21
MDW6:00 amChicago Midway
7h 40m
1 stop
SJD12:40 pmSan José del Cabo Los Cabos
Jan 27
SJD6:05 amSan José del Cabo Los Cabos
15h 17m
2 stops
MDW10:22 pmChicago Midway
$503
Delta
Feb 7
MDW11:45 amChicago Midway
21h 55m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
Feb 13
SJD11:46 amSan José del Cabo Los Cabos
20h 08m
2 stops
MDW8:54 amChicago Midway
$507
Delta
Feb 24
MDW6:00 amChicago Midway
9h 09m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
Mar 3
SJD6:05 amSan José del Cabo Los Cabos
15h 28m
2 stops
MDW10:33 pmChicago Midway
$514

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 January 8, 2026.
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

Sat 4/4

6:00 am-12:17 pm

1 stop8h 17m

San José del Cabo Los Cabos

Sat 4/11

9:40 am-11:42 pm

1 stop12h 02m

$462

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/20

6:48 pm-1:23 pm

1 stop19h 35m

San José del Cabo Los Cabos

Fri 2/27

1:45 pm-10:31 pm

1 stop7h 46m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/21

6:00 am-1:23 pm

1 stop8h 23m

San José del Cabo Los Cabos

Sat 2/28

3:59 pm-2:26 pm

2 stops21h 27m

$495

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 2/8

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Wed 2/11

6:05 am-10:22 pm

2 stops15h 17m

$503

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 3/7

6:54 pm-4:25 pm

1 stop22h 31m

San José del Cabo Los Cabos

Sun 3/15

8:00 am-6:34 pm

1 stop8h 34m

$506

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/7

11:45 am-8:40 am

2 stops21h 55m

San José del Cabo Los Cabos

Fri 2/13

11:46 am-8:54 am

2 stops20h 08m

$507

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

6:00 am-10:30 pm

2 stops17h 30m

San José del Cabo Los Cabos

Wed 1/28

6:05 am-10:22 pm

2 stops15h 17m

$508

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 2/21

6:00 am-1:23 pm

1 stop8h 23m

San José del Cabo Los Cabos

Sat 2/28

3:59 pm-2:26 pm

2 stops21h 27m

$510

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Wed 1/28

1:45 pm-10:22 pm

1 stop7h 37m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Tue 3/3

6:05 am-10:33 pm

2 stops15h 28m

$514

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 January is your next best option. Flight prices from Chicago Midway Airport to San José del Cabo during January average around $475.

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 $583. 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 $688.

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

$604

Fastest flight time

4h 55m

Direct flights

Every day

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 $604
The fastest flight from Chicago Midway Airport to San José del Cabo takes 4h 55m
Direct flights go from Chicago Midway Airport to San José del Cabo every day.
There is 1 airport in San José del Cabo. From Chicago Midway Airport there are direct flights to 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 4h 55m 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 $485Free CancellationRating
8.0
4,250 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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