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Cheap flights from Chicago Midway Airport to San José del Cabo from $154

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 2/28. 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.
Southwest Logo
8:40 pm - 11:40 am
MDW
-
SJD
16h 00m
2 stops
Southwest Logo
2:20 pm - 12:35 am
SJD
-
MDW
9h 15m
1 stop
$462Southwest
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
7:25 pm - 12:41 pm
MDW
-
SJD
18h 16m
2 stops
Multiple Airlines Logo
8:00 am - 5:34 pm
SJD
-
MDW
8h 34m
1 stop
$477Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m
2 stops
Delta Logo
1:45 pm - 10:33 pm
SJD
-
MDW
7h 48m
1 stop
$483Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m
2 stops
Delta Logo
4:56 pm - 9:06 am
SJD
-
MDW
15h 10m
2 stops
$487Delta
Tue, Feb 17 - Tue, Feb 24
Aeromexico Logo
12:45 pm - 9:31 am
MDW
-
SJD
21h 46m
2 stops
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m
2 stops
$488Aeromexico
Mon, Feb 23 - Thu, Feb 26
Frontier Logo
9:51 pm - 1:59 pm
MDW
-
SJD
17h 08m
2 stops
Frontier Logo
11:31 am - 11:20 pm
SJD
-
MDW
9h 49m
1 stop
$496Frontier
Fri, Mar 6 - Sat, Mar 14
Southwest Logo
5:05 am - 11:40 am
MDW
-
SJD
7h 35m
1 stop
Southwest Logo
2:35 pm - 10:55 pm
SJD
-
MDW
7h 20m
1 stop
$503Southwest
Tue, Feb 3 - Tue, Feb 10
Aeromexico Logo
12:45 pm - 9:31 am
MDW
-
SJD
21h 46m
2 stops
Aeromexico Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
$504Aeromexico
Mon, Feb 16 - Fri, Feb 20
Delta Logo
6:00 am - 5:41 pm
MDW
-
SJD
12h 41m
2 stops
Delta Logo
9:35 am - 10:22 pm
SJD
-
MDW
11h 47m
2 stops
$507Delta
Tue, Feb 3 - Tue, Feb 10
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m
1 stop
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m
2 stops
$520Aeromexico
Tue, Mar 3 - Fri, Mar 6

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
Feb 23
MDW8:40 pmChicago Midway
16h 00m
2 stops
SJD11:40 amSan José del Cabo Los Cabos
Feb 27
SJD2:20 pmSan José del Cabo Los Cabos
9h 15m
1 stop
MDW12:35 amChicago Midway
$462
Southwest
Feb 3
MDW5:05 amChicago Midway
7h 35m
1 stop
SJD11:40 amSan José del Cabo Los Cabos
Feb 10
SJD2:35 pmSan José del Cabo Los Cabos
7h 20m
1 stop
MDW10:55 pmChicago Midway
$503
Southwest
May 6
MDW8:55 pmChicago Midway
18h 30m
2 stops
SJD1:25 pmSan José del Cabo Los Cabos
May 13
SJD12:25 pmSan José del Cabo Los Cabos
8h 55m
1 stop
MDW11:20 pmChicago Midway
$521

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
Feb 23
MDW12:45 pmChicago Midway
21h 46m
2 stops
SJD9:31 amSan José del Cabo Los Cabos
Feb 26
SJD6:05 amSan José del Cabo Los Cabos
15h 26m
2 stops
MDW10:31 pmChicago Midway
$488
Aeromexico
Feb 16
MDW12:45 pmChicago Midway
21h 46m
2 stops
SJD9:31 amSan José del Cabo Los Cabos
Feb 20
SJD1:45 pmSan José del Cabo Los Cabos
7h 46m
1 stop
MDW10:31 pmChicago Midway
$504
Aeromexico
Mar 3
MDW6:00 amChicago Midway
7h 40m
1 stop
SJD12:40 pmSan José del Cabo Los Cabos
Mar 6
SJD6:05 amSan José del Cabo Los Cabos
15h 26m
2 stops
MDW10:31 pmChicago Midway
$520

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 21, 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

Mon 2/23

8:40 pm-11:40 am

2 stops16h 00m

San José del Cabo Los Cabos

Fri 2/27

2:20 pm-12:35 am

1 stop9h 15m

$462

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/23

7:25 pm-12:41 pm

2 stops18h 16m

San José del Cabo Los Cabos

Fri 2/27

8:00 am-5:34 pm

1 stop8h 34m

$477

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 3/3

1:45 pm-10:33 pm

1 stop7h 48m

$483

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/17

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Tue 2/24

4:56 pm-9:06 am

2 stops15h 10m

$487

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/23

12:45 pm-9:31 am

2 stops21h 46m

San José del Cabo Los Cabos

Thu 2/26

6:05 am-10:31 pm

2 stops15h 26m

$488

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/6

9:51 pm-1:59 pm

2 stops17h 08m

San José del Cabo Los Cabos

Sat 3/14

11:31 am-11:20 pm

1 stop9h 49m

$496

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/3

5:05 am-11:40 am

1 stop7h 35m

San José del Cabo Los Cabos

Tue 2/10

2:35 pm-10:55 pm

1 stop7h 20m

$503

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/16

12:45 pm-9:31 am

2 stops21h 46m

San José del Cabo Los Cabos

Fri 2/20

1:45 pm-10:31 pm

1 stop7h 46m

$504

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/3

6:00 am-5:41 pm

2 stops12h 41m

San José del Cabo Los Cabos

Tue 2/10

9:35 am-10:22 pm

2 stops11h 47m

$507

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/3

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Fri 3/6

6:05 am-10:31 pm

2 stops15h 26m

$520

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 $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 $685.

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 42% 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

Best Price Found

$626

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 $626
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
4,266 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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