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Cheap flights from Chicago Midway Airport to San José del Cabo from $208

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 8/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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.
Volaris Logo
8:49 pm - 8:16 am
MDW
-
SJD
13h 27m
1 stop
Volaris Logo
8:50 am - 7:34 pm
SJD
-
MDW
8h 44m
1 stop
$464Volaris
Sat, Aug 8 - Sat, Aug 15
Volaris Logo
8:49 pm - 8:16 am
MDW
-
SJD
13h 27m
1 stop
Volaris Logo
8:50 am - 7:04 pm
SJD
-
MDW
8h 14m
1 stop
$496Volaris
Thu, Aug 6 - Wed, Aug 12
Delta Logo
5:35 pm - 10:45 am
MDW
-
SJD
18h 10m
1 stop
Delta Logo
10:25 am - 9:52 am
SJD
-
MDW
22h 27m
2 stops
$498Delta
Sat, Jan 9 - Wed, Jan 20
Volaris Logo
8:23 pm - 10:53 am
MDW
-
SJD
16h 30m
2 stops
Volaris Logo
7:37 pm - 7:04 pm
SJD
-
MDW
21h 27m
2 stops
$499Volaris
Sun, Sep 6 - Sat, Sep 12
Delta Logo
5:35 pm - 12:40 pm
MDW
-
SJD
20h 05m
2 stops
Delta Logo
10:25 am - 9:52 am
SJD
-
MDW
22h 27m
2 stops
$502Delta
Sat, Jan 9 - Wed, Jan 20
Volaris Logo
8:23 pm - 11:29 am
MDW
-
SJD
17h 06m
1 stop
Volaris Logo
7:37 pm - 7:04 pm
SJD
-
MDW
21h 27m
2 stops
$505Volaris
Sun, Sep 6 - Sat, Sep 12
Volaris Logo
8:49 pm - 8:16 am
MDW
-
SJD
13h 27m
1 stop
Volaris Logo
8:50 am - 7:34 pm
SJD
-
MDW
8h 44m
1 stop
$530Volaris
Thu, Aug 6 - Thu, Aug 13
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
$536Delta
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
5:25 am - 9:45 am
MDW
-
SJD
6h 20m
1 stop
Southwest Logo
10:40 am - 8:10 pm
SJD
-
MDW
7h 30m
1 stop
$542Southwest
Mon, Aug 17 - Thu, Aug 20
Delta Logo
6:05 am - 5:25 pm
MDW
-
SJD
13h 20m
2 stops
Delta Logo
6:15 am - 10:44 pm
SJD
-
MDW
14h 29m
2 stops
$543Delta
Fri, Sep 25 - Fri, Oct 2

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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
Aug 18
MDW6:00 amChicago Midway
8h 50m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
Aug 25
SJD11:40 amSan José del Cabo Los Cabos
8h 10m
2 stops
MDW9:50 pmChicago Midway
$502
Southwest
Aug 16
MDW6:05 amChicago Midway
9h 05m
2 stops
SJD1:10 pmSan José del Cabo Los Cabos
Aug 19
SJD11:40 amSan José del Cabo Los Cabos
9h 30m
1 stop
MDW11:10 pmChicago Midway
$568
Southwest
Aug 16
MDW7:20 amChicago Midway
7h 50m
1 stop
SJD1:10 pmSan José del Cabo Los Cabos
Aug 19
SJD11:40 amSan José del Cabo Los Cabos
9h 30m
1 stop
MDW11:10 pmChicago Midway
$575

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
Sep 28
MDW6:05 amChicago Midway
13h 20m
2 stops
SJD5:25 pmSan José del Cabo Los Cabos
Oct 2
SJD9:14 amSan José del Cabo Los Cabos
11h 31m
2 stops
MDW10:45 pmChicago Midway
$498
Delta
Aug 18
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
Aug 25
SJD12:12 pmSan José del Cabo Los Cabos
8h 24m
1 stop
MDW10:36 pmChicago Midway
$536
Delta
Sep 25
MDW6:05 amChicago Midway
13h 20m
2 stops
SJD5:25 pmSan José del Cabo Los Cabos
Oct 2
SJD6:15 amSan José del Cabo Los Cabos
14h 29m
2 stops
MDW10:44 pmChicago Midway
$543

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 July 22, 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

Cheapest round-trip

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 8/8

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Sat 8/15

8:50 am-7:34 pm

1 stop8h 44m

$464

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 8/6

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 8/12

8:50 am-7:04 pm

1 stop8h 14m

$496

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/9

5:35 pm-10:45 am

1 stop18h 10m

San José del Cabo Los Cabos

Wed 1/20

10:25 am-9:52 am

2 stops22h 27m

$498

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/6

8:23 pm-10:53 am

2 stops16h 30m

San José del Cabo Los Cabos

Sat 9/12

7:37 pm-7:04 pm

2 stops21h 27m

$499

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/9

5:35 pm-12:40 pm

2 stops20h 05m

San José del Cabo Los Cabos

Wed 1/20

10:25 am-9:52 am

2 stops22h 27m

$502

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/6

8:23 pm-11:29 am

1 stop17h 06m

San José del Cabo Los Cabos

Sat 9/12

7:37 pm-7:04 pm

2 stops21h 27m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 8/6

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Thu 8/13

8:50 am-7:34 pm

1 stop8h 44m

$530

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 8/18

6:05 am-11:07 am

1 stop7h 02m

San José del Cabo Los Cabos

Tue 8/25

12:12 pm-10:36 pm

1 stop8h 24m

$536
Quickest round-trip

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/17

5:25 am-9:45 am

1 stop6h 20m

San José del Cabo Los Cabos

Thu 8/20

10:40 am-8:10 pm

1 stop7h 30m

$542

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 9/25

6:05 am-5:25 pm

2 stops13h 20m

San José del Cabo Los Cabos

Fri 10/2

6:15 am-10:44 pm

2 stops14h 29m

$543

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 $611. 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 $694.

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 Airport to San José del Cabo flights?

There is only 1 cabin class available to choose from on Chicago Midway Airport to San José del Cabo 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 26% 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

6h 20m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José del Cabo takes 6h 20m
There are no direct flights from Chicago Midway Airport to San José del Cabo. There are no popular flight routes from Chicago Midway Airport to San José del Cabo.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to San José del Cabo

  • 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 20m 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 $475Free CancellationRating
8.0
4,238 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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