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Cheap flights from Chicago Midway Airport to San José del Cabo from $192

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.
Multiple Airlines Logo
10:21 am - 4:31 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
31h 10m2 stops Dallas/Fort Worth Guadalajara Miguel Hidal
Multiple Airlines Logo
9:31 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 16m1 stop Guadalajara Miguel Hidal
$504Multiple Airlines
Wed, Dec 2 - Thu, Dec 10
Multiple Airlines Logo
10:21 am - 4:31 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
31h 10m2 stops Dallas/Fort Worth Guadalajara Miguel Hidal
Multiple Airlines Logo
9:31 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 16m1 stop Guadalajara Miguel Hidal
$511Multiple Airlines
Wed, Dec 2 - Thu, Dec 10
Multiple Airlines Logo
6:17 pm - 1:07 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
19h 50m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
9:29 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 18m1 stop Guadalajara Miguel Hidal
$531Multiple Airlines
Fri, Feb 5 - Sun, Feb 7
Multiple Airlines Logo
6:20 pm - 4:08 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
22h 48m2 stops San Luis Potosi Guadalajara Miguel Hidal
Multiple Airlines Logo
3:21 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
24h 26m1 stop Guadalajara Miguel Hidal
$546Multiple Airlines
Tue, Dec 1 - Tue, Dec 8
Multiple Airlines Logo
7:17 pm - 3:52 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
22h 35m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
8:41 am - 5:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
7h 06m1 stop Guadalajara Miguel Hidal
$548Multiple Airlines
Wed, Apr 14 - Sun, Apr 18
Multiple Airlines Logo
7:07 pm - 4:07 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
23h 00m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
9:36 pm - 5:39 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 03m1 stop Guadalajara Miguel Hidal
$552Multiple Airlines
Sun, Mar 14 - Thu, Mar 18
Multiple Airlines Logo
6:20 pm - 2:46 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
21h 26m2 stops San Luis Potosi Guadalajara Miguel Hidal
Multiple Airlines Logo
9:21 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 26m1 stop Guadalajara Miguel Hidal
$561Multiple Airlines
Thu, Jan 21 - Sun, Jan 24
Multiple Airlines Logo
6:20 pm - 4:08 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
22h 48m2 stops San Luis Potosi Guadalajara Miguel Hidal
Multiple Airlines Logo
9:31 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
18h 16m1 stop Guadalajara Miguel Hidal
$566Multiple Airlines
Tue, Dec 1 - Tue, Dec 8
Southwest Logo
5:15 am - 2:15 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
10h 00m1 stop Phoenix Sky Harbor Intl
Southwest Logo
2:45 pm - 11:10 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
7h 25m1 stop Houston Hobby
$590Southwest
Sun, Dec 6 - Wed, Dec 9
Southwest Logo
6:05 am - 1:10 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
8h 05m1 stop Denver Intl
Southwest Logo
2:45 pm - 11:10 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
7h 25m1 stop Houston Hobby
$590Southwest
Tue, Dec 15 - Wed, Dec 16

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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
Jan 20
MDW5:20 amChicago Midway
9h 20m
1 stop
SJD1:40 pmSan José del Cabo Los Cabos
Jan 27
SJD12:00 pmSan José del Cabo Los Cabos
8h 05m
1 stop
MDW9:05 pmChicago Midway
$590
Southwest
Dec 6
MDW9:30 pmChicago Midway
15h 10m
2 stops
SJD11:40 amSan José del Cabo Los Cabos
Dec 10
SJD2:05 pmSan José del Cabo Los Cabos
9h 10m
1 stop
MDW12:15 amChicago Midway
$595
Southwest
Jan 11
MDW6:15 amChicago Midway
8h 40m
2 stops
SJD1:55 pmSan José del Cabo Los Cabos
Jan 15
SJD10:55 amSan José del Cabo Los Cabos
10h 25m
2 stops
MDW10:20 pmChicago Midway
$599

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 3
MDW6:00 amChicago Midway
9h 12m
1 stop
SJD2:12 pmSan José del Cabo Los Cabos
Jan 8
SJD1:34 pmSan José del Cabo Los Cabos
7h 43m
1 stop
MDW10:17 pmChicago Midway
$613
Delta
Dec 29
MDW6:00 amChicago Midway
9h 12m
1 stop
SJD2:12 pmSan José del Cabo Los Cabos
Jan 8
SJD1:34 pmSan José del Cabo Los Cabos
7h 43m
1 stop
MDW10:17 pmChicago Midway
$633
Delta
Feb 1
MDW6:00 amChicago Midway
9h 19m
1 stop
SJD2:19 pmSan José del Cabo Los Cabos
Feb 8
SJD3:24 pmSan José del Cabo Los Cabos
7h 31m
1 stop
MDW11:55 pmChicago Midway
$658

momondo Fare Finder

 
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 Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Wed 12/2

10:21 am-4:31 pm

2 stops31h 10m

San José del Cabo Los Cabos

Thu 12/10

9:31 pm-4:47 pm

1 stop18h 16m

$504

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Wed 12/2

10:21 am-4:31 pm

2 stops31h 10m

San José del Cabo Los Cabos

Thu 12/10

9:31 pm-4:47 pm

1 stop18h 16m

$511

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Fri 2/5

6:17 pm-1:07 pm

1 stop19h 50m

San José del Cabo Los Cabos

Sun 2/7

9:29 pm-4:47 pm

1 stop18h 18m

$531

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Tue 12/1

6:20 pm-4:08 pm

2 stops22h 48m

San José del Cabo Los Cabos

Tue 12/8

3:21 pm-4:47 pm

1 stop24h 26m

$546

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Wed 4/14

7:17 pm-3:52 pm

1 stop22h 35m

San José del Cabo Los Cabos

Sun 4/18

8:41 am-5:47 pm

1 stop7h 06m

$548

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Sun 3/14

7:07 pm-4:07 pm

1 stop23h 00m

San José del Cabo Los Cabos

Thu 3/18

9:36 pm-5:39 pm

1 stop18h 03m

$552

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Thu 1/21

6:20 pm-2:46 pm

2 stops21h 26m

San José del Cabo Los Cabos

Sun 1/24

9:21 pm-4:47 pm

1 stop18h 26m

$561

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Tue 12/1

6:20 pm-4:08 pm

2 stops22h 48m

San José del Cabo Los Cabos

Tue 12/8

9:31 pm-4:47 pm

1 stop18h 16m

$566

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Sun 12/6

5:15 am-2:15 pm

1 stop10h 00m

San José del Cabo Los Cabos

Wed 12/9

2:45 pm-11:10 pm

1 stop7h 25m

$590
Quickest round-trip

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Tue 12/15

6:05 am-1:10 pm

1 stop8h 05m

San José del Cabo Los Cabos

Wed 12/16

2:45 pm-11:10 pm

1 stop7h 25m

$590

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 $0, 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 September is your next best option. Flight prices from Chicago Midway Airport to San José del Cabo during September average around $0.

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 $633. 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 $747.

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 64% 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

$192

Fastest flight time

4h 40m

Direct flights

Mon, Tue, Fri, Sat and Sun

Airports in San José del Cabo

1 airport
The best one-way flight to San José del Cabo from Chicago Midway Airport in the past 72 hours is $192. The best round-trip flight deal from Chicago Midway Airport to San José del Cabo found on momondo in the last 72 hours is $504.
The fastest flight from Chicago Midway Airport to San José del Cabo takes 4h 40m
Direct flights go from Chicago Midway Airport to San José del Cabo on Monday, Tuesday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
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

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 4h 40m 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 $612Free CancellationRating
8.0
4,214 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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