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Cheap flights from Chicago Midway Airport to San José del Cabo from $164

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 1/16. 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
5:10 am - 1:45 pmMDW-SJD
9h 35m1 stop
Southwest Logo
2:05 pm - 9:55 pmSJD-MDW
6h 50m1 stop
$418Southwest
Find Deal
dom., dic. 7 - vie., dic. 12
Delta Logo
6:00 am - 5:36 pmMDW-SJD
12h 36m2 stops
Delta Logo
6:05 am - 10:22 pmSJD-MDW
15h 17m2 stops
$430Delta
Find Deal
lun., ene. 26 - vie., ene. 30
Delta Logo
6:00 am - 5:36 pmMDW-SJD
12h 36m2 stops
Delta Logo
4:32 pm - 8:52 amSJD-MDW
15h 20m2 stops
$435Delta
Find Deal
lun., ene. 19 - vie., ene. 23
Delta Logo
6:40 pm - 8:40 amMDW-SJD
15h 00m2 stops
Delta Logo
9:35 am - 10:42 pmSJD-MDW
12h 07m2 stops
$437Delta
Find Deal
dom., mar. 1 - vie., mar. 6
Southwest Logo
7:50 pm - 12:15 pmMDW-SJD
17h 25m2 stops
Southwest Logo
12:35 pm - 6:30 pmSJD-MDW
3h 55mnonstop
$455Southwest
Find Deal
mié., mar. 4 - jue., mar. 12
Southwest Logo
5:00 am - 2:50 pmMDW-SJD
10h 50m2 stops
Southwest Logo
11:50 am - 9:50 pmSJD-MDW
9h 00m1 stop
$459Southwest
Find Deal
dom., dic. 14 - jue., dic. 18
Southwest Logo
5:50 am - 1:55 pmMDW-SJD
9h 05m2 stops
Southwest Logo
12:00 pm - 8:45 pmSJD-MDW
7h 45m1 stop
$460Southwest
Find Deal
lun., feb. 23 - jue., feb. 26
Southwest Logo
5:10 am - 1:45 pmMDW-SJD
9h 35m1 stop
Southwest Logo
11:50 am - 10:00 pmSJD-MDW
9h 10m2 stops
$463Southwest
Find Deal
dom., dic. 7 - vie., dic. 12
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
Delta Logo
9:40 am - 10:22 pmSJD-MDW
11h 42m2 stops
$468Delta
Find Deal
dom., dic. 14 - dom., dic. 21
Delta Logo
6:00 am - 12:40 pmMDW-SJD
7h 40m1 stop
Delta Logo
6:05 am - 10:22 pmSJD-MDW
15h 17m2 stops
$475Delta
Find Deal
vie., ene. 23 - vie., ene. 30

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 10
MDW6:45 amChicago Midway
8h 24m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
Jan 31
SJD1:45 pmSan José del Cabo Los Cabos
7h 37m
1 stop
MDW10:22 pmChicago Midway
$514
Find similar
Aeromexico
Dec 4
MDW6:00 amChicago Midway
27h 42m
2 stops
SJD8:42 amSan José del Cabo Los Cabos
Dec 8
SJD6:00 amSan José del Cabo Los Cabos
16h 47m
2 stops
MDW11:47 pmChicago Midway
$1,081
Find similar
Aeromexico
Dec 4
MDW6:00 amChicago Midway
13h 07m
2 stops
SJD6:07 pmSan José del Cabo Los Cabos
Dec 10
SJD1:15 pmSan José del Cabo Los Cabos
9h 32m
1 stop
MDW11:47 pmChicago Midway
$1,102
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
Jan 26
MDW6:00 amChicago Midway
9h 09m
1 stop
SJD2:09 pmSan José del Cabo Los Cabos
Jan 30
SJD1:45 pmSan José del Cabo Los Cabos
7h 37m
1 stop
MDW10:22 pmChicago Midway
$430
Find similar
Delta
Jan 17
MDW5:31 pmChicago Midway
16h 09m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
Jan 21
SJD9:35 amSan José del Cabo Los Cabos
11h 47m
2 stops
MDW10:22 pmChicago Midway
$435
Find similar
Delta
Dec 14
MDW6:00 amChicago Midway
7h 10m
1 stop
SJD12:10 pmSan José del Cabo Los Cabos
Dec 21
SJD1:52 pmSan José del Cabo Los Cabos
7h 30m
1 stop
MDW10:22 pmChicago Midway
$463
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 noviembre 24, 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

dom. 12/7

5:10 am-1:45 pm

1 stop9h 35m

San José del Cabo Los Cabos

vie. 12/12

2:05 pm-9:55 pm

1 stop6h 50m

$418

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 1/26

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

vie. 1/30

6:05 am-10:22 pm

2 stops15h 17m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 1/19

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

vie. 1/23

4:32 pm-8:52 am

2 stops15h 20m

$435

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 3/1

6:40 pm-8:40 am

2 stops15h 00m

San José del Cabo Los Cabos

vie. 3/6

9:35 am-10:42 pm

2 stops12h 07m

$437

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 3/4

7:50 pm-12:15 pm

2 stops17h 25m

San José del Cabo Los Cabos

jue. 3/12

12:35 pm-6:30 pm

Nonstop3h 55m

$455

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 12/14

5:00 am-2:50 pm

2 stops10h 50m

San José del Cabo Los Cabos

jue. 12/18

11:50 am-9:50 pm

1 stop9h 00m

$459

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 2/23

5:50 am-1:55 pm

2 stops9h 05m

San José del Cabo Los Cabos

jue. 2/26

12:00 pm-8:45 pm

1 stop7h 45m

$460

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 12/7

5:10 am-1:45 pm

1 stop9h 35m

San José del Cabo Los Cabos

vie. 12/12

11:50 am-10:00 pm

2 stops9h 10m

$463

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 12/14

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

dom. 12/21

9:40 am-10:22 pm

2 stops11h 42m

$468

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 1/23

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

vie. 1/30

6:05 am-10:22 pm

2 stops15h 17m

$475

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 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 $588. 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 $705.

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 $644. 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?

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

Fastest flight time

4h 50m

Direct flights

Every day

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 every day.
There is 1 airport near San José del Cabo: 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 6h 45m 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
4,252 reviews
Search Southwest flights

  • Southwest Flights From Chicago Midway Airport to San José del Cabo

    Across 1 Southwest flight from Chicago Midway Airport to San José del Cabo this week, the average price was $720, with the best Southwest deals starting from $545 round-trip. 4,252 users have rated Southwest on momondo, with an average score of 8.0/10.

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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