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Cheap flights from San José del Cabo to Chicago from $203

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 2/22. 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 - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
Aeromexico Logo
6:00 am - 9:31 am
MDW
-
SJD
28h 31m
2 stops
$433Aeromexico
Fri, Feb 13 - Mon, Feb 16
Aeromexico Logo
1:45 pm - 10:31 pm
SJD
-
MDW
7h 46m
1 stop
Aeromexico Logo
6:00 am - 9:31 am
MDW
-
SJD
28h 31m
2 stops
$434Aeromexico
Fri, Feb 13 - Mon, Feb 16
Southwest Logo
2:20 pm - 12:35 am
SJD
-
MDW
9h 15m
1 stop
Southwest Logo
7:50 am - 1:25 pm
MDW
-
SJD
6h 35m
1 stop
$441Southwest
Fri, Feb 13 - Mon, Feb 16
Southwest Logo
2:35 pm - 12:55 am
SJD
-
MDW
9h 20m
2 stops
Southwest Logo
7:50 am - 1:25 pm
MDW
-
SJD
6h 35m
1 stop
$471Southwest
Fri, Feb 13 - Mon, Feb 16
Southwest Logo
2:35 pm - 11:10 pm
SJD
-
MDW
7h 35m
1 stop
Southwest Logo
5:00 am - 2:30 pm
MDW
-
SJD
10h 30m
1 stop
$549Southwest
Fri, Feb 20 - Sun, Feb 22
Southwest Logo
2:35 pm - 12:55 am
SJD
-
MDW
9h 20m
2 stops
Southwest Logo
5:15 am - 1:55 pm
MDW
-
SJD
9h 40m
2 stops
$559Southwest
Fri, Feb 13 - Mon, Feb 16
Southwest Logo
2:35 pm - 12:20 am
SJD
-
MDW
8h 45m
2 stops
Southwest Logo
5:15 am - 2:30 pm
MDW
-
SJD
10h 15m
2 stops
$590Southwest
Fri, Feb 20 - Sun, Feb 22
Delta Logo
1:45 pm - 10:22 pm
SJD
-
MDW
7h 37m
1 stop
Delta Logo
6:00 am - 5:37 pm
MDW
-
SJD
12h 37m
2 stops
$594Delta
Thu, Feb 5 - Wed, Feb 11
Southwest Logo
12:35 pm - 9:05 pm
SJD
-
MDW
7h 30m
1 stop
Southwest Logo
5:05 am - 1:40 pm
MDW
-
SJD
9h 35m
1 stop
$606Southwest
Thu, Feb 5 - Wed, Feb 11
Aeromexico Logo
6:05 am - 10:31 pm
SJD
-
MDW
15h 26m
2 stops
Aeromexico Logo
6:00 am - 9:31 am
MDW
-
SJD
28h 31m
2 stops
$616Aeromexico
Fri, Feb 13 - Mon, Feb 16

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
Feb 13
SJD2:20 pmSan José del Cabo Los Cabos
9h 15m
1 stop
MDW12:35 amChicago Midway
Feb 16
MDW7:50 amChicago Midway
6h 35m
1 stop
SJD1:25 pmSan José del Cabo Los Cabos
$441
Southwest
Feb 13
SJD2:35 pmSan José del Cabo Los Cabos
9h 20m
2 stops
MDW12:55 amChicago Midway
Feb 16
MDW7:50 amChicago Midway
6h 35m
1 stop
SJD1:25 pmSan José del Cabo Los Cabos
$471
Southwest
Feb 20
SJD2:35 pmSan José del Cabo Los Cabos
7h 35m
1 stop
MDW11:10 pmChicago Midway
Feb 22
MDW5:00 amChicago Midway
10h 30m
1 stop
SJD2:30 pmSan José del Cabo Los Cabos
$549

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
Feb 5
SJD1:45 pmSan José del Cabo Los Cabos
7h 37m
1 stop
MDW10:22 pmChicago Midway
Feb 11
MDW6:00 amChicago Midway
12h 37m
2 stops
SJD5:37 pmSan José del Cabo Los Cabos
$594
Delta
Jun 11
SJD11:36 amSan José del Cabo Los Cabos
8h 09m
1 stop
MDW9:45 pmChicago Midway
Jun 15
MDW6:00 amChicago Midway
7h 10m
1 stop
SJD11:10 amSan José del Cabo Los Cabos
$840
Delta
Jun 11
SJD6:00 amSan José del Cabo Los Cabos
13h 45m
2 stops
MDW9:45 pmChicago Midway
Jun 15
MDW1:05 pmChicago Midway
11h 25m
2 stops
SJD10:30 pmSan José del Cabo Los Cabos
$1,287

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 January 21, 2026.
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-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 2/16

6:00 am-9:31 am

2 stops28h 31m

$433

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

1:45 pm-10:31 pm

1 stop7h 46m

Chicago Midway

Mon 2/16

6:00 am-9:31 am

2 stops28h 31m

$434

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

2:20 pm-12:35 am

1 stop9h 15m

Chicago Midway

Mon 2/16

7:50 am-1:25 pm

1 stop6h 35m

$441

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

2:35 pm-12:55 am

2 stops9h 20m

Chicago Midway

Mon 2/16

7:50 am-1:25 pm

1 stop6h 35m

$471

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/20

2:35 pm-11:10 pm

1 stop7h 35m

Chicago Midway

Sun 2/22

5:00 am-2:30 pm

1 stop10h 30m

$549

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

2:35 pm-12:55 am

2 stops9h 20m

Chicago Midway

Mon 2/16

5:15 am-1:55 pm

2 stops9h 40m

$559

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/20

2:35 pm-12:20 am

2 stops8h 45m

Chicago Midway

Sun 2/22

5:15 am-2:30 pm

2 stops10h 15m

$590

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/5

1:45 pm-10:22 pm

1 stop7h 37m

Chicago Midway

Wed 2/11

6:00 am-5:37 pm

2 stops12h 37m

$594

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 2/5

12:35 pm-9:05 pm

1 stop7h 30m

Chicago Midway

Wed 2/11

5:05 am-1:40 pm

1 stop9h 35m

$606

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 2/13

6:05 am-10:31 pm

2 stops15h 26m

Chicago Midway

Mon 2/16

6:00 am-9:31 am

2 stops28h 31m

$616

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 1% 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

8h 10m

Direct flights

Every day
The fastest flight from San José del Cabo to Chicago Midway Airport takes 8h 10m
Direct flights go from San José del Cabo to Chicago Midway Airport every day.
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 8h 10m 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.

  • What is the most popular plane model from San José del Cabo to Chicago Midway Airport?

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
Munster
Crown Point
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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