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Cheap flights from San José del Cabo to Chicago from $196

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San José del Cabo to Chicago departing on 1/10. 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 San José del Cabo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Aeromexico Logo
1:45 pm - 10:42 pm
SJD
-
MDW
7h 57m1 stop
Aeromexico Logo
6:00 am - 12:40 pm
MDW
-
SJD
7h 40m1 stop
$451Aeromexico
Fri, Feb 13 - Tue, Feb 17
Delta Logo
12:15 pm - 9:45 pm
SJD
-
MDW
7h 30m1 stop
Delta Logo
10:35 am - 10:28 pm
MDW
-
SJD
13h 53m2 stops
$487Delta
Wed, Apr 29 - Tue, May 5
Delta Logo
1:45 pm - 10:07 pm
SJD
-
MDW
7h 22m1 stop
Delta Logo
5:31 pm - 8:40 am
MDW
-
SJD
16h 09m2 stops
$497Delta
Mon, Jan 12 - Sat, Jan 17
Delta Logo
1:45 pm - 10:07 pm
SJD
-
MDW
7h 22m1 stop
Delta Logo
5:31 pm - 8:40 am
MDW
-
SJD
16h 09m2 stops
$498Delta
Mon, Jan 12 - Sat, Jan 17
Southwest Logo
2:20 pm - 5:00 am
SJD
-
MDW
12h 40m1 stop
Southwest Logo
7:30 am - 1:25 pm
MDW
-
SJD
7h 55m1 stop
$522Southwest
Wed, Apr 29 - Tue, May 5
Southwest Logo
2:20 pm - 5:25 am
SJD
-
MDW
13h 05m2 stops
Southwest Logo
5:40 am - 1:25 pm
MDW
-
SJD
9h 45m2 stops
$527Southwest
Wed, Apr 29 - Tue, May 5
Delta Logo
1:52 pm - 10:22 pm
SJD
-
MDW
7h 30m1 stop
Delta Logo
6:00 am - 2:10 pm
MDW
-
SJD
9h 10m1 stop
$554Delta
Mon, Dec 29 - Fri, Jan 2
Aeromexico Logo
6:05 am - 10:42 pm
SJD
-
MDW
15h 37m2 stops
Aeromexico Logo
10:53 am - 9:31 am
MDW
-
SJD
23h 38m2 stops
$576Aeromexico
Fri, Feb 13 - Tue, Feb 17
Aeromexico Logo
6:05 am - 10:42 pm
SJD
-
MDW
15h 37m2 stops
Aeromexico Logo
10:53 am - 9:31 am
MDW
-
SJD
23h 38m2 stops
$577Aeromexico
Fri, Feb 13 - Tue, Feb 17
Delta Logo
1:45 pm - 10:07 pm
SJD
-
MDW
7h 22m1 stop
Delta Logo
6:45 am - 2:09 pm
MDW
-
SJD
8h 24m1 stop
$628Delta
Mon, Jan 12 - Sat, Jan 17

Southwest flights from San José del Cabo to Chicago Midway Airport

Our best Southwest deals on San José del Cabo to Chicago Midway Airport flight tickets
Southwest
Apr 17
SJD1:25 pmSan José del Cabo Los Cabos
6h 30m
1 stop
MDW9:55 pmChicago Midway
Apr 21
MDW6:10 amChicago Midway
6h 40m
1 stop
SJD10:50 amSan José del Cabo Los Cabos
$511
Find similar
Southwest
Apr 17
SJD12:25 pmSan José del Cabo Los Cabos
9h 15m
2 stops
MDW11:40 pmChicago Midway
Apr 21
MDW6:10 amChicago Midway
6h 40m
1 stop
SJD10:50 amSan José del Cabo Los Cabos
$515
Find similar
Southwest
Apr 29
SJD2:20 pmSan José del Cabo Los Cabos
12h 40m
1 stop
MDW5:00 amChicago Midway
May 5
MDW7:30 amChicago Midway
7h 55m
1 stop
SJD1:25 pmSan José del Cabo Los Cabos
$522
Find similar

Delta flights from San José del Cabo to Chicago Midway Airport

Our best Delta deals on San José del Cabo to Chicago Midway Airport flight tickets
Delta
Apr 29
SJD12:15 pmSan José del Cabo Los Cabos
7h 30m
1 stop
MDW9:45 pmChicago Midway
May 5
MDW6:00 amChicago Midway
8h 46m
1 stop
SJD12:46 pmSan José del Cabo Los Cabos
$487
Find similar
Delta
Jan 12
SJD1:45 pmSan José del Cabo Los Cabos
7h 22m
1 stop
MDW10:07 pmChicago Midway
Jan 17
MDW5:31 pmChicago Midway
16h 09m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
$497
Find similar
Delta
Jan 12
SJD9:35 amSan José del Cabo Los Cabos
11h 32m
2 stops
MDW10:07 pmChicago Midway
Jan 17
MDW5:31 pmChicago Midway
16h 09m
2 stops
SJD8:40 amSan José del Cabo Los Cabos
$498
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San José del Cabo to Chicago Midway Airport 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 December 8, 2025.
Use the filters below to find and compare flights from San José del Cabo to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

1:45 pm-10:42 pm

1 stop7h 57m

Chicago Midway

Tue 2/17

6:00 am-12:40 pm

1 stop7h 40m

$451

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/29

12:15 pm-9:45 pm

1 stop7h 30m

Chicago Midway

Tue 5/5

10:35 am-10:28 pm

2 stops13h 53m

$487

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 1/12

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

Sat 1/17

5:31 pm-8:40 am

2 stops16h 09m

$497

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 1/12

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

Sat 1/17

5:31 pm-8:40 am

2 stops16h 09m

$498

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/29

2:20 pm-5:00 am

1 stop12h 40m

Chicago Midway

Tue 5/5

7:30 am-1:25 pm

1 stop7h 55m

$522

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/29

2:20 pm-5:25 am

2 stops13h 05m

Chicago Midway

Tue 5/5

5:40 am-1:25 pm

2 stops9h 45m

$527

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 12/29

1:52 pm-10:22 pm

1 stop7h 30m

Chicago Midway

Fri 1/2

6:00 am-2:10 pm

1 stop9h 10m

$554

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

6:05 am-10:42 pm

2 stops15h 37m

Chicago Midway

Tue 2/17

10:53 am-9:31 am

2 stops23h 38m

$576

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

6:05 am-10:42 pm

2 stops15h 37m

Chicago Midway

Tue 2/17

10:53 am-9:31 am

2 stops23h 38m

$577

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 1/12

1:45 pm-10:07 pm

1 stop7h 22m

Chicago Midway

Sat 1/17

6:45 am-2:09 pm

1 stop8h 24m

$628

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 Chicago from

How to get the cheapest flight ticket from San José del Cabo to Chicago Midway Airport

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 San José del Cabo Los Cabos to Chicago Midway flight route?

Fly from San José del Cabo Los Cabos to Chicago Midway for the best San José del Cabo Los Cabos - Chicago Midway flight prices

What cabin class options are available on San José del Cabo Los Cabos to Chicago Midway flights?

There is only 1 cabin class available to choose from on San José del Cabo Los Cabos to Chicago Midway 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 San José del Cabo to Chicago Midway Airport flights?

You could potentially save up to 53% on your flight if you consider stops on a San José del Cabo to Chicago Midway Airport flight.

When to book flights from San José del Cabo to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from San José del Cabo to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap San José del Cabo to Chicago Midway Airport (SJD to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San José del Cabo to Chicago Midway Airport

Fastest flight time

7h 22m

Direct flights

Mon, Wed, Thu, Fri, Sat and Sun
The fastest flight from San José del Cabo to Chicago Midway Airport takes 7h 22m
Direct flights go from San José del Cabo to Chicago Midway Airport on Monday, Wednesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
Search flight deals

  • How far is San José del Cabo Los Cabos to Chicago Midway by plane?

    The straight-line distance from San José del Cabo Los Cabos to Chicago Midway is 1808.5 mi. Typically, this will take 6h 30m by plane in normal conditions.

  • When did momondo last update prices for flights from San José del Cabo Los Cabos Airport to Chicago Midway Airport?

    Prices for flights from San José del Cabo Los Cabos Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from San José del Cabo Los Cabos Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San José del Cabo Los Cabos Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from San José del Cabo to Chicago?

It is quick and easy to find San José del Cabo to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from San José del Cabo to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from San José del Cabo with this policy.

How can momondo help me find flights from San José del Cabo to Chicago?

Once all potential San José del Cabo to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from San José del Cabo to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of San José del Cabo to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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