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Cheap flights from San José del Cabo to Chicago from $207

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 9/25. 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

Delta Logo
6:01 am - 9:36 pmSJD-MDW
13h 35m2 stops
Delta Logo
6:00 am - 7:23 pmMDW-SJD
15h 23m2 stops
$360Delta
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
10:40 am - 8:50 pmSJD-MDW
8h 10m1 stop
Southwest Logo
5:45 am - 9:45 amMDW-SJD
6h 00m1 stop
$414Southwest
Find Deal
Thu, Sep 25 - Mon, Sep 29
Southwest Logo
1:45 pm - 11:40 pmSJD-MDW
7h 55m1 stop
Southwest Logo
5:45 am - 12:50 pmMDW-SJD
9h 05m2 stops
$457Southwest
Find Deal
Fri, Aug 15 - Fri, Aug 22
Southwest Logo
1:45 pm - 11:45 amSJD-MDW
20h 00m2 stops
Southwest Logo
5:20 am - 11:20 amMDW-SJD
8h 00m1 stop
$542Southwest
Find Deal
Tue, Aug 26 - Sat, Aug 30
Delta Logo
6:01 am - 9:44 pmSJD-MDW
13h 43m2 stops
Delta Logo
6:00 am - 7:00 pmMDW-SJD
15h 00m2 stops
$545Delta
Find Deal
Tue, Aug 19 - Tue, Aug 26
Southwest Logo
12:40 pm - 11:50 pmSJD-MDW
9h 10m2 stops
Southwest Logo
5:45 am - 12:50 pmMDW-SJD
9h 05m2 stops
$550Southwest
Find Deal
Fri, Aug 15 - Fri, Aug 22
Southwest Logo
1:45 pm - 11:00 pmSJD-MDW
7h 15m1 stop
Southwest Logo
6:25 am - 11:45 amMDW-SJD
7h 20m1 stop
$555Southwest
Find Deal
Wed, Aug 20 - Wed, Aug 27
Aeromexico Logo
12:30 pm - 3:26 pmSJD-MDW
24h 56m1 stop
Aeromexico Logo
6:00 am - 11:25 amMDW-SJD
7h 25m1 stop
$566Aeromexico
Find Deal
Fri, Sep 12 - Tue, Sep 16
Aeromexico Logo
1:35 pm - 10:05 pmSJD-MDW
7h 30m1 stop
Aeromexico Logo
12:10 pm - 1:52 pmMDW-SJD
26h 42m1 stop
$671Aeromexico
Find Deal
Tue, Dec 23 - Mon, Dec 29
Aeromexico Logo
1:35 pm - 10:05 pmSJD-MDW
7h 30m1 stop
Aeromexico Logo
12:10 pm - 1:52 pmMDW-SJD
26h 42m1 stop
$720Aeromexico
Find Deal
Tue, Dec 23 - Mon, Dec 29

Aeromexico flights from San José del Cabo to Chicago Midway Airport

Our best Aeromexico deals on San José del Cabo to Chicago Midway Airport flight tickets
Aeromexico
Sep 12
SJD12:30 pmSan José del Cabo Los Cabos
24h 56m
1 stop
MDW3:26 pmChicago Midway
Sep 16
MDW6:00 amChicago Midway
7h 25m
1 stop
SJD11:25 amSan José del Cabo Los Cabos
$566
Find similar
Aeromexico
Dec 23
SJD1:35 pmSan José del Cabo Los Cabos
7h 30m
1 stop
MDW10:05 pmChicago Midway
Dec 29
MDW12:10 pmChicago Midway
26h 42m
1 stop
SJD1:52 pmSan José del Cabo Los Cabos
$671
Find similar
Aeromexico
Dec 23
SJD1:35 pmSan José del Cabo Los Cabos
7h 30m
1 stop
MDW10:05 pmChicago Midway
Dec 29
MDW12:10 pmChicago Midway
26h 42m
1 stop
SJD1:52 pmSan José del Cabo Los Cabos
$720
Find similar

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
Sep 25
SJD10:40 amSan José del Cabo Los Cabos
8h 10m
1 stop
MDW8:50 pmChicago Midway
Sep 29
MDW5:45 amChicago Midway
6h 00m
1 stop
SJD9:45 amSan José del Cabo Los Cabos
$414
Find similar
Southwest
Aug 15
SJD1:45 pmSan José del Cabo Los Cabos
7h 55m
1 stop
MDW11:40 pmChicago Midway
Aug 22
MDW5:45 amChicago Midway
9h 05m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
$457
Find similar
Southwest
Aug 26
SJD1:45 pmSan José del Cabo Los Cabos
20h 00m
2 stops
MDW11:45 amChicago Midway
Aug 30
MDW5:20 amChicago Midway
8h 00m
1 stop
SJD11:20 amSan José del Cabo Los Cabos
$542
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 August 2, 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

Thu 9/25

6:01 am-9:36 pm

2 stops13h 35m

Chicago Midway

Mon 9/29

6:00 am-7:23 pm

2 stops15h 23m

$360

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 9/25

10:40 am-8:50 pm

1 stop8h 10m

Chicago Midway

Mon 9/29

5:45 am-9:45 am

1 stop6h 00m

$414

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 8/15

1:45 pm-11:40 pm

1 stop7h 55m

Chicago Midway

Fri 8/22

5:45 am-12:50 pm

2 stops9h 05m

$457

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 8/26

1:45 pm-11:45 am

2 stops20h 00m

Chicago Midway

Sat 8/30

5:20 am-11:20 am

1 stop8h 00m

$542

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 8/19

6:01 am-9:44 pm

2 stops13h 43m

Chicago Midway

Tue 8/26

6:00 am-7:00 pm

2 stops15h 00m

$545

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 8/15

12:40 pm-11:50 pm

2 stops9h 10m

Chicago Midway

Fri 8/22

5:45 am-12:50 pm

2 stops9h 05m

$550

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 8/20

1:45 pm-11:00 pm

1 stop7h 15m

Chicago Midway

Wed 8/27

6:25 am-11:45 am

1 stop7h 20m

$555

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 9/12

12:30 pm-3:26 pm

1 stop24h 56m

Chicago Midway

Tue 9/16

6:00 am-11:25 am

1 stop7h 25m

$566

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 12/23

1:35 pm-10:05 pm

1 stop7h 30m

Chicago Midway

Mon 12/29

12:10 pm-1:52 pm

1 stop26h 42m

$671

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 12/23

1:35 pm-10:05 pm

1 stop7h 30m

Chicago Midway

Mon 12/29

12:10 pm-1:52 pm

1 stop26h 42m

$720

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 are 1 cabin classes 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 18% 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

Best Price Found

$207

Fastest flight time

6h 55m

Direct flights

Sun
The best one-way flight to Chicago Midway Airport from San José del Cabo in the past 72 hours is $207. The best round-trip flight deal from San José del Cabo to Chicago Midway Airport found on momondo in the last 72 hours is $360.
The fastest flight from San José del Cabo to Chicago Midway Airport takes 6h 55m
Direct flights go from San José del Cabo to Chicago Midway Airport on Sunday. The only airline offering direct flights is Southwest.
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 7h 15m 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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