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Cheap flights from Chicago Midway Airport to San José del Cabo from $163

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 10/7. 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

Southwest Logo
7:50 am - 12:50 pmMDW-SJD
7h 00m1 stop
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$437Southwest
Find Deal
Mon, Sep 15 - Fri, Sep 19
Southwest Logo
7:00 am - 1:10 pmMDW-SJD
7h 10m1 stop
Southwest Logo
11:50 am - 10:10 pmSJD-MDW
9h 20m1 stop
$442Southwest
Find Deal
Wed, Dec 3 - Tue, Dec 9
Southwest Logo
5:00 am - 1:10 pmMDW-SJD
9h 10m2 stops
Southwest Logo
2:40 pm - 10:55 pmSJD-MDW
7h 15m1 stop
$447Southwest
Find Deal
Wed, Dec 3 - Tue, Dec 9
Delta Logo
6:00 am - 3:00 pmMDW-SJD
11h 00m2 stops
Delta Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
$452Delta
Find Deal
Tue, Oct 7 - Sat, Oct 11
Delta Logo
10:47 am - 2:00 pmMDW-SJD
28h 13m2 stops
Delta Logo
3:05 pm - 9:01 amSJD-MDW
16h 56m2 stops
$457Delta
Find Deal
Thu, Nov 13 - Wed, Nov 19
Southwest Logo
6:00 am - 10:50 amMDW-SJD
6h 50m1 stop
Southwest Logo
1:10 pm - 12:05 amSJD-MDW
8h 55m2 stops
$476Southwest
Find Deal
Sun, Sep 28 - Tue, Oct 7
Southwest Logo
5:45 am - 12:50 pmMDW-SJD
9h 05m2 stops
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
$477Southwest
Find Deal
Mon, Sep 15 - Fri, Sep 19
Southwest Logo
5:25 am - 2:50 pmMDW-SJD
10h 25m1 stop
Southwest Logo
12:00 pm - 8:35 pmSJD-MDW
7h 35m1 stop
$487Southwest
Find Deal
Wed, Nov 5 - Sat, Nov 8
Delta Logo
6:00 am - 6:07 pmMDW-SJD
13h 07m2 stops
Delta Logo
6:00 am - 9:44 pmSJD-MDW
14h 44m2 stops
$497Delta
Find Deal
Fri, Nov 28 - Sat, Dec 6
Logo
8:39 pm - 7:53 amMDW-SJD
13h 14m1 stop
Logo
7:59 pm - 11:25 pmSJD-MDW
26h 26m2 stops
$515
Find Deal
Fri, Oct 31 - Mon, Nov 3

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
Sep 15
MDW7:50 amChicago Midway
7h 00m
1 stop
SJD12:50 pmSan José del Cabo Los Cabos
Sep 19
SJD1:45 pmSan José del Cabo Los Cabos
7h 55m
1 stop
MDW11:40 pmChicago Midway
$437
Find similar
Southwest
Dec 3
MDW7:00 amChicago Midway
7h 10m
1 stop
SJD1:10 pmSan José del Cabo Los Cabos
Dec 9
SJD11:50 amSan José del Cabo Los Cabos
9h 20m
1 stop
MDW10:10 pmChicago Midway
$442
Find similar
Southwest
Dec 3
MDW5:00 amChicago Midway
9h 10m
2 stops
SJD1:10 pmSan José del Cabo Los Cabos
Dec 9
SJD2:40 pmSan José del Cabo Los Cabos
7h 15m
1 stop
MDW10:55 pmChicago Midway
$447
Find similar

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
Oct 7
MDW6:00 amChicago Midway
11h 00m
2 stops
SJD3:00 pmSan José del Cabo Los Cabos
Oct 11
SJD6:00 amSan José del Cabo Los Cabos
14h 14m
2 stops
MDW10:14 pmChicago Midway
$452
Find similar
Delta
Nov 13
MDW10:47 amChicago Midway
28h 13m
2 stops
SJD2:00 pmSan José del Cabo Los Cabos
Nov 19
SJD3:05 pmSan José del Cabo Los Cabos
16h 56m
2 stops
MDW9:01 amChicago Midway
$457
Find similar
Delta
Nov 28
MDW6:00 amChicago Midway
13h 07m
2 stops
SJD6:07 pmSan José del Cabo Los Cabos
Dec 6
SJD6:00 amSan José del Cabo Los Cabos
14h 44m
2 stops
MDW9:44 pmChicago Midway
$497
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 August 27, 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

Mon 9/15

7:50 am-12:50 pm

1 stop7h 00m

San José del Cabo Los Cabos

Fri 9/19

1:45 pm-11:40 pm

1 stop7h 55m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 12/3

7:00 am-1:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Tue 12/9

11:50 am-10:10 pm

1 stop9h 20m

$442

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 12/3

5:00 am-1:10 pm

2 stops9h 10m

San José del Cabo Los Cabos

Tue 12/9

2:40 pm-10:55 pm

1 stop7h 15m

$447

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 10/7

6:00 am-3:00 pm

2 stops11h 00m

San José del Cabo Los Cabos

Sat 10/11

6:00 am-10:14 pm

2 stops14h 14m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 11/13

10:47 am-2:00 pm

2 stops28h 13m

San José del Cabo Los Cabos

Wed 11/19

3:05 pm-9:01 am

2 stops16h 56m

$457

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 9/28

6:00 am-10:50 am

1 stop6h 50m

San José del Cabo Los Cabos

Tue 10/7

1:10 pm-12:05 am

2 stops8h 55m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/15

5:45 am-12:50 pm

2 stops9h 05m

San José del Cabo Los Cabos

Fri 9/19

1:45 pm-11:40 pm

1 stop7h 55m

$477

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/5

5:25 am-2:50 pm

1 stop10h 25m

San José del Cabo Los Cabos

Sat 11/8

12:00 pm-8:35 pm

1 stop7h 35m

$487

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

6:00 am-6:07 pm

2 stops13h 07m

San José del Cabo Los Cabos

Sat 12/6

6:00 am-9:44 pm

2 stops14h 44m

$497

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 10/31

8:39 pm-7:53 am

1 stop13h 14m

San José del Cabo Los Cabos

Mon 11/3

7:59 pm-11:25 pm

2 stops26h 26m

$515

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 $505, 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 $599. 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 $701.

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 $649. 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?

You could potentially save up to 73% 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

4h 50m

Direct flights

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 Sunday. There are no airlines offering direct flights.
There is 1 airport near San José del Cabo: San José del Cabo Los Cabos (SJD)
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  • 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 00m 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
Cabo San Lucas
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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