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Cheap flights from San José del Cabo to Chicago from $298

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 7/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from San José del Cabo to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$535Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$539Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$570Delta
Tue, Sep 1 - Sun, Sep 6
Delta Logo
12:12 pm - 9:17 am
SJD
-
MDW
19h 05m
2 stops
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$591Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
6:15 am - 10:36 pm
SJD
-
MDW
14h 21m
2 stops
Delta Logo
6:05 am - 6:33 pm
MDW
-
SJD
14h 28m
2 stops
$597Delta
Wed, Sep 2 - Sat, Sep 5
Southwest Logo
10:40 am - 10:15 pm
SJD
-
MDW
9h 35m
1 stop
Southwest Logo
5:55 am - 9:45 am
MDW
-
SJD
5h 50m
1 stop
$600Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
2:24 pm - 8:39 am
SJD
-
MDW
16h 15m
2 stops
Delta Logo
6:05 am - 5:25 pm
MDW
-
SJD
13h 20m
2 stops
$601Delta
Thu, Sep 3 - Sun, Sep 6
Southwest Logo
11:40 am - 11:20 pm
SJD
-
MDW
9h 40m
2 stops
Southwest Logo
5:30 am - 12:50 pm
MDW
-
SJD
9h 20m
2 stops
$604Southwest
Thu, Aug 6 - Mon, Aug 10
Delta Logo
12:12 pm - 10:36 pm
SJD
-
MDW
8h 24m
1 stop
Delta Logo
6:05 am - 11:07 am
MDW
-
SJD
7h 02m
1 stop
$627Delta
Thu, Sep 3 - Sun, Sep 6
Volaris Logo
8:50 am - 7:04 pm
SJD
-
MDW
8h 14m
1 stop
Volaris Logo
8:49 pm - 8:16 am
MDW
-
SJD
13h 27m
1 stop
$630Volaris
Fri, Jul 31 - Thu, Aug 6

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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
Aug 6
SJD10:40 amSan José del Cabo Los Cabos
9h 35m
1 stop
MDW10:15 pmChicago Midway
Aug 10
MDW5:55 amChicago Midway
5h 50m
1 stop
SJD9:45 amSan José del Cabo Los Cabos
$600
Southwest
Aug 6
SJD11:40 amSan José del Cabo Los Cabos
9h 40m
2 stops
MDW11:20 pmChicago Midway
Aug 10
MDW5:30 amChicago Midway
9h 20m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
$604
Southwest
Aug 4
SJD11:40 amSan José del Cabo Los Cabos
9h 30m
1 stop
MDW11:10 pmChicago Midway
Aug 7
MDW7:25 amChicago Midway
7h 25m
1 stop
SJD12:50 pmSan José del Cabo Los Cabos
$661

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
Aug 6
SJD12:12 pmSan José del Cabo Los Cabos
8h 24m
1 stop
MDW10:36 pmChicago Midway
Aug 10
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$535
Delta
Aug 6
SJD12:12 pmSan José del Cabo Los Cabos
8h 24m
1 stop
MDW10:36 pmChicago Midway
Aug 10
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$539
Delta
Sep 1
SJD12:12 pmSan José del Cabo Los Cabos
8h 24m
1 stop
MDW10:36 pmChicago Midway
Sep 6
MDW6:05 amChicago Midway
7h 02m
1 stop
SJD11:07 amSan José del Cabo Los Cabos
$570

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 June 19, 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

Cheapest round-trip

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/6

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Mon 8/10

6:05 am-11:07 am

1 stop7h 02m

$535

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/6

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Mon 8/10

6:05 am-11:07 am

1 stop7h 02m

$539

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 9/1

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Sun 9/6

6:05 am-11:07 am

1 stop7h 02m

$570

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/6

12:12 pm-9:17 am

2 stops19h 05m

Chicago Midway

Mon 8/10

6:05 am-11:07 am

1 stop7h 02m

$591

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 9/2

6:15 am-10:36 pm

2 stops14h 21m

Chicago Midway

Sat 9/5

6:05 am-6:33 pm

2 stops14h 28m

$597
Quickest round-trip

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/6

10:40 am-10:15 pm

1 stop9h 35m

Chicago Midway

Mon 8/10

5:55 am-9:45 am

1 stop5h 50m

$600

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/3

2:24 pm-8:39 am

2 stops16h 15m

Chicago Midway

Sun 9/6

6:05 am-5:25 pm

2 stops13h 20m

$601

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/6

11:40 am-11:20 pm

2 stops9h 40m

Chicago Midway

Mon 8/10

5:30 am-12:50 pm

2 stops9h 20m

$604

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/3

12:12 pm-10:36 pm

1 stop8h 24m

Chicago Midway

Sun 9/6

6:05 am-11:07 am

1 stop7h 02m

$627

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 7/31

8:50 am-7:04 pm

1 stop8h 14m

Chicago Midway

Thu 8/6

8:49 pm-8:16 am

1 stop13h 27m

$630

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 to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on San José del Cabo to Chicago Midway Airport 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 51% 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 47m

Direct flights

None
The fastest flight from San José del Cabo to Chicago Midway Airport takes 7h 47m
There are no direct flights from San José del Cabo to Chicago Midway Airport. There are no popular flight routes from San José del Cabo to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from San José del Cabo to Chicago Midway Airport

  • 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 7h 47m 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
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
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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