Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

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 6/4. 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
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 - 7:04 pm
SJD
-
MDW
8h 14m
1 stop
$412Volaris
Thu, Jun 11 - Wed, Jun 17
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
$422Volaris
Sat, Jun 20 - Wed, Jun 24
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
$423Volaris
Thu, Jun 11 - Wed, Jun 17
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
$425Volaris
Thu, Jun 4 - Mon, Jun 8
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
$426Volaris
Sat, Jun 20 - Wed, Jun 24
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
$437Volaris
Thu, Jun 18 - Mon, Jun 22
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
$449Volaris
Thu, Jun 4 - Sun, Jun 7
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
$453Volaris
Thu, Jun 25 - Mon, Jun 29
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
$460Volaris
Thu, Jun 18 - Sun, Jun 21
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
$461Volaris
Thu, Jun 25 - Mon, Jun 29

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 11
MDW8:50 pmChicago Midway
18h 00m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
Aug 18
SJD1:45 pmSan José del Cabo Los Cabos
13h 55m
2 stops
MDW5:40 amChicago Midway
$545
Southwest
Aug 24
MDW5:55 amChicago Midway
8h 55m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
Aug 28
SJD10:40 amSan José del Cabo Los Cabos
10h 40m
2 stops
MDW11:20 pmChicago Midway
$552
Southwest
Jun 23
MDW7:10 amChicago Midway
9h 10m
1 stop
SJD2:20 pmSan José del Cabo Los Cabos
Jun 30
SJD3:15 pmSan José del Cabo Los Cabos
6h 50m
1 stop
MDW12:05 amChicago Midway
$602

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
Jun 11
MDW8:49 pmChicago Midway
13h 27m
1 stop
SJD8:16 amSan José del Cabo Los Cabos
Jun 17
SJD8:50 amSan José del Cabo Los Cabos
8h 14m
1 stop
MDW7:04 pmChicago Midway
$412
Volaris
Jun 20
MDW8:49 pmChicago Midway
13h 27m
1 stop
SJD8:16 amSan José del Cabo Los Cabos
Jun 24
SJD8:50 amSan José del Cabo Los Cabos
8h 14m
1 stop
MDW7:04 pmChicago Midway
$422
Volaris
Jun 11
MDW8:49 pmChicago Midway
13h 27m
1 stop
SJD8:16 amSan José del Cabo Los Cabos
Jun 17
SJD8:50 amSan José del Cabo Los Cabos
8h 14m
1 stop
MDW7:04 pmChicago Midway
$423

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 April 23, 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
Quickest round-trip

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/11

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 6/17

8:50 am-7:04 pm

1 stop8h 14m

$412

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/20

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 6/24

8:50 am-7:04 pm

1 stop8h 14m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/11

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 6/17

8:50 am-7:04 pm

1 stop8h 14m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/4

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/8

8:50 am-7:04 pm

1 stop8h 14m

$425

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/20

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Wed 6/24

8:50 am-7:04 pm

1 stop8h 14m

$426

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/18

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/22

8:50 am-7:04 pm

1 stop8h 14m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/4

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Sun 6/7

8:50 am-7:04 pm

1 stop8h 14m

$449

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/25

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/29

8:50 am-7:04 pm

1 stop8h 14m

$453

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/18

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Sun 6/21

8:50 am-7:04 pm

1 stop8h 14m

$460

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 6/25

8:49 pm-8:16 am

1 stop13h 27m

San José del Cabo Los Cabos

Mon 6/29

8:50 am-7:04 pm

1 stop8h 14m

$461

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 typical price of a round-trip flight between Chicago Midway Airport and San José del Cabo?

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 $596. 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 $686.

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 16% 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

5h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to San José del Cabo takes 5h 50m
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 5h 50m 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
4,327 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.

An easier way to manage your San José del Cabo trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 5/23
Sat 5/30
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Mexico

Airports servicing Baja California Sur

La Paz Leon Airport
Loreto Airport
Los Cabos Airport