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Cheap flights from San José del Cabo to Chicago from $245

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 5/19. 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.
Southwest Logo
1:55 pm - 4:35 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
6:10 am - 10:50 am
MDW
-
SJD
6h 40m
1 stop
$463Southwest
Fri, May 1 - Tue, May 19
Southwest Logo
3:05 pm - 5:00 am
SJD
-
MDW
11h 55m
1 stop
Southwest Logo
5:40 am - 1:25 pm
MDW
-
SJD
9h 45m
2 stops
$509Southwest
Fri, May 1 - Tue, May 19
Southwest Logo
10:45 am - 11:30 pm
SJD
-
MDW
10h 45m
2 stops
Southwest Logo
6:30 am - 1:25 pm
MDW
-
SJD
8h 55m
2 stops
$565Southwest
Fri, May 1 - Tue, May 19
Delta Logo
6:04 am - 9:46 pm
SJD
-
MDW
13h 42m
2 stops
Delta Logo
6:00 am - 11:22 am
MDW
-
SJD
7h 22m
1 stop
$589Delta
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
3:05 pm - 5:45 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
6:50 am - 1:00 pm
MDW
-
SJD
8h 10m
1 stop
$613Southwest
Sun, May 3 - Sun, May 10
Southwest Logo
10:40 am - 8:10 pm
SJD
-
MDW
7h 30m
1 stop
Southwest Logo
5:55 am - 9:45 am
MDW
-
SJD
5h 50m
1 stop
$615Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
1:10 pm - 5:40 am
SJD
-
MDW
14h 30m
2 stops
Southwest Logo
5:55 am - 12:50 pm
MDW
-
SJD
8h 55m
2 stops
$619Southwest
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
11:40 am - 11:40 pm
SJD
-
MDW
10h 00m
1 stop
Southwest Logo
6:55 am - 12:10 pm
MDW
-
SJD
7h 15m
1 stop
$627Southwest
Thu, Apr 30 - Thu, May 7
Delta Logo
12:36 pm - 10:28 pm
SJD
-
MDW
7h 52m
1 stop
Delta Logo
6:00 am - 5:49 pm
MDW
-
SJD
13h 49m
2 stops
$632Delta
Tue, Apr 14 - Thu, Apr 16
Southwest Logo
3:05 pm - 5:45 am
SJD
-
MDW
12h 40m
1 stop
Southwest Logo
6:00 am - 1:40 pm
MDW
-
SJD
9h 40m
2 stops
$659Southwest
Sun, May 3 - Sun, May 10

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
May 1
SJD1:55 pmSan José del Cabo Los Cabos
12h 40m
1 stop
MDW4:35 amChicago Midway
May 19
MDW6:10 amChicago Midway
6h 40m
1 stop
SJD10:50 amSan José del Cabo Los Cabos
$463
Southwest
May 1
SJD3:05 pmSan José del Cabo Los Cabos
11h 55m
1 stop
MDW5:00 amChicago Midway
May 19
MDW5:40 amChicago Midway
9h 45m
2 stops
SJD1:25 pmSan José del Cabo Los Cabos
$509
Southwest
May 1
SJD10:45 amSan José del Cabo Los Cabos
10h 45m
2 stops
MDW11:30 pmChicago Midway
May 19
MDW6:30 amChicago Midway
8h 55m
2 stops
SJD1:25 pmSan José del Cabo Los Cabos
$565

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 14
SJD12:36 pmSan José del Cabo Los Cabos
7h 52m
1 stop
MDW10:28 pmChicago Midway
Apr 16
MDW6:00 amChicago Midway
13h 49m
2 stops
SJD5:49 pmSan José del Cabo Los Cabos
$632
Delta
May 3
SJD6:03 amSan José del Cabo Los Cabos
14h 25m
2 stops
MDW10:28 pmChicago Midway
May 10
MDW7:13 pmChicago Midway
19h 17m
2 stops
SJD12:30 pmSan José del Cabo Los Cabos
$662
Delta
Mar 31
SJD8:35 amSan José del Cabo Los Cabos
11h 56m
2 stops
MDW10:31 pmChicago Midway
Apr 5
MDW6:00 amChicago Midway
9h 14m
1 stop
SJD1:14 pmSan José del Cabo Los Cabos
$694

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 March 20, 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

Fri 5/1

1:55 pm-4:35 am

1 stop12h 40m

Chicago Midway

Tue 5/19

6:10 am-10:50 am

1 stop6h 40m

$463

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 5/1

3:05 pm-5:00 am

1 stop11h 55m

Chicago Midway

Tue 5/19

5:40 am-1:25 pm

2 stops9h 45m

$509

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 5/1

10:45 am-11:30 pm

2 stops10h 45m

Chicago Midway

Tue 5/19

6:30 am-1:25 pm

2 stops8h 55m

$565

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/27

6:04 am-9:46 pm

2 stops13h 42m

Chicago Midway

Mon 8/31

6:00 am-11:22 am

1 stop7h 22m

$589

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sun 5/3

3:05 pm-5:45 am

1 stop12h 40m

Chicago Midway

Sun 5/10

6:50 am-1:00 pm

1 stop8h 10m

$613
Quickest round-trip

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/27

10:40 am-8:10 pm

1 stop7h 30m

Chicago Midway

Mon 8/31

5:55 am-9:45 am

1 stop5h 50m

$615

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 8/27

1:10 pm-5:40 am

2 stops14h 30m

Chicago Midway

Mon 8/31

5:55 am-12:50 pm

2 stops8h 55m

$619

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/30

11:40 am-11:40 pm

1 stop10h 00m

Chicago Midway

Thu 5/7

6:55 am-12:10 pm

1 stop7h 15m

$627

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 4/14

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Thu 4/16

6:00 am-5:49 pm

2 stops13h 49m

$632

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sun 5/3

3:05 pm-5:45 am

1 stop12h 40m

Chicago Midway

Sun 5/10

6:00 am-1:40 pm

2 stops9h 40m

$659

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.

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

3h 55m

Direct flights

Mon, Tue, Wed, Thu and Sun
The fastest flight from San José del Cabo to Chicago Midway Airport takes 3h 55m
Direct flights go from San José del Cabo to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday 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 3h 55m 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
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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