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Cheap flights from Chicago Midway Airport to San José del Cabo from $191

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
6:17 pm - 10:35 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 18m1 stop Guadalajara Miguel Hidal
Volaris Logo
11:15 am - 4:51 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
28h 36m2 stops Guadalajara Miguel Hidal San Luis Potosi
$502Volaris
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
6:17 pm - 6:47 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
13h 30m1 stop 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
$506Multiple Airlines
Sun, Nov 29 - Sat, Dec 5
Multiple Airlines Logo
6:17 pm - 4:31 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
23h 14m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
7:27 am - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 20m1 stop Guadalajara Miguel Hidal
$517Multiple Airlines
Fri, Nov 6 - Mon, Nov 9
Volaris Logo
6:17 pm - 2:46 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
21h 29m1 stop Guadalajara Miguel Hidal
Volaris Logo
5:18 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
22h 29m1 stop Guadalajara Miguel Hidal
$524Volaris
Wed, Jan 20 - Sun, Jan 24
Volaris Logo
6:17 pm - 10:35 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 18m1 stop Guadalajara Miguel Hidal
Volaris Logo
5:18 pm - 11:41 amSJD  San José del Cabo Los Cabos-MDW Chicago Midway
17h 23m3 stops Guadalajara Miguel Hidal Tijuana Rodriguez Zacatecas La Calera
$525Volaris
Mon, Nov 9 - Sat, Nov 14
Volaris Logo
6:17 pm - 10:35 amMDW  Chicago Midway-SJD San José del Cabo Los Cabos
17h 18m1 stop Guadalajara Miguel Hidal
Volaris Logo
4:49 pm - 4:51 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
23h 02m3 stops Culiacán Fedl De Bachigualato Guadalajara Miguel Hidal San Luis Potosi
$535Volaris
Fri, Nov 6 - Mon, Nov 9
Multiple Airlines Logo
6:20 pm - 4:10 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
22h 50m2 stops San Luis Potosi Guadalajara Miguel Hidal
Multiple Airlines Logo
5:18 pm - 4:47 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
22h 29m1 stop Guadalajara Miguel Hidal
$545Multiple Airlines
Sun, Nov 29 - Sat, Dec 5
Multiple Airlines Logo
6:17 pm - 1:05 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
19h 48m1 stop Guadalajara Miguel Hidal
Multiple Airlines Logo
8:40 pm - 2:48 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
17h 08m2 stops Guadalajara Miguel Hidal Durango Guadalupe Victoria
$545Multiple Airlines
Fri, Jan 15 - Mon, Jan 18
Southwest Logo
6:40 am - 2:15 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
8h 35m1 stop Houston Hobby
Southwest Logo
2:05 pm - 12:10 amSJD  San José del Cabo Los Cabos-MDW Chicago Midway
9h 05m1 stop Las Vegas Harry Reid Intl
$565Southwest
Tue, Nov 3 - Tue, Nov 10
Southwest Logo
7:55 am - 1:55 pmMDW  Chicago Midway-SJD San José del Cabo Los Cabos
7h 00m1 stop Phoenix Sky Harbor Intl
Southwest Logo
12:00 pm - 9:00 pmSJD  San José del Cabo Los Cabos-MDW Chicago Midway
8h 00m1 stop Houston Hobby
$565Southwest
Wed, Jan 6 - Wed, Jan 13

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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 29
MDW6:00 amChicago Midway
12h 41m
2 stops
SJD5:41 pmSan José del Cabo Los Cabos
Feb 1
SJD1:30 pmSan José del Cabo Los Cabos
7h 40m
1 stop
MDW10:10 pmChicago Midway
$623
Delta
Feb 23
MDW6:00 amChicago Midway
17h 30m
2 stops
SJD10:30 pmSan José del Cabo Los Cabos
Mar 2
SJD6:05 amSan José del Cabo Los Cabos
15h 05m
2 stops
MDW10:10 pmChicago Midway
$645
Delta
Sep 10
MDW6:05 amChicago Midway
13h 30m
2 stops
SJD5:35 pmSan José del Cabo Los Cabos
Sep 15
SJD6:11 amSan José del Cabo Los Cabos
14h 33m
2 stops
MDW10:44 pmChicago Midway
$902

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
Nov 6
MDW6:17 pmChicago Midway
17h 18m
1 stop
SJD10:35 amSan José del Cabo Los Cabos
Nov 9
SJD11:15 amSan José del Cabo Los Cabos
28h 36m
2 stops
MDW4:51 pmChicago Midway
$502
Volaris
Jan 20
MDW6:17 pmChicago Midway
21h 29m
1 stop
SJD2:46 pmSan José del Cabo Los Cabos
Jan 24
SJD5:18 pmSan José del Cabo Los Cabos
22h 29m
1 stop
MDW4:47 pmChicago Midway
$524
Volaris
Nov 9
MDW6:17 pmChicago Midway
17h 18m
1 stop
SJD10:35 amSan José del Cabo Los Cabos
Nov 14
SJD5:18 pmSan José del Cabo Los Cabos
17h 23m
3 stops
MDW11:41 amChicago Midway
$525

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

Fri 11/6

6:17 pm-10:35 am

1 stop17h 18m

San José del Cabo Los Cabos

Mon 11/9

11:15 am-4:51 pm

2 stops28h 36m

$502

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Sun 11/29

6:17 pm-6:47 am

1 stop13h 30m

San José del Cabo Los Cabos

Sat 12/5

3:21 pm-4:47 pm

1 stop24h 26m

$506

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Fri 11/6

6:17 pm-4:31 pm

1 stop23h 14m

San José del Cabo Los Cabos

Mon 11/9

7:27 am-4:47 pm

1 stop8h 20m

$517

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Wed 1/20

6:17 pm-2:46 pm

1 stop21h 29m

San José del Cabo Los Cabos

Sun 1/24

5:18 pm-4:47 pm

1 stop22h 29m

$524

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Mon 11/9

6:17 pm-10:35 am

1 stop17h 18m

San José del Cabo Los Cabos

Sat 11/14

5:18 pm-11:41 am

3 stops17h 23m

$525

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Fri 11/6

6:17 pm-10:35 am

1 stop17h 18m

San José del Cabo Los Cabos

Mon 11/9

4:49 pm-4:51 pm

3 stops23h 02m

$535

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Sun 11/29

6:20 pm-4:10 pm

2 stops22h 50m

San José del Cabo Los Cabos

Sat 12/5

5:18 pm-4:47 pm

1 stop22h 29m

$545

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Fri 1/15

6:17 pm-1:05 pm

1 stop19h 48m

San José del Cabo Los Cabos

Mon 1/18

8:40 pm-2:48 pm

2 stops17h 08m

$545

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Tue 11/3

6:40 am-2:15 pm

1 stop8h 35m

San José del Cabo Los Cabos

Tue 11/10

2:05 pm-12:10 am

1 stop9h 05m

$565
Quickest round-trip

ChicagoSan José del Cabo

MDW Chicago Midway - SJD San José del Cabo Los Cabos

MDWSJD

Chicago Midway

Wed 1/6

7:55 am-1:55 pm

1 stop7h 00m

San José del Cabo Los Cabos

Wed 1/13

12:00 pm-9:00 pm

1 stop8h 00m

$565

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 February is your next best option. Flight prices from Chicago Midway Airport to San José del Cabo during February 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 $625. 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 $724.

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?

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

Best Price Found

$191

Fastest flight time

4h 40m

Direct flights

None
The best one-way flight to San José del Cabo from Chicago Midway Airport in the past 72 hours is $191. The best round-trip flight deal from Chicago Midway Airport to San José del Cabo found on momondo in the last 72 hours is $502.
The fastest flight from Chicago Midway Airport to San José del Cabo takes 4h 40m
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 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 $475Free CancellationRating
8.0
4,195 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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