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Cheap flights from San José del Cabo to Chicago from $213

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 11/19. 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

Southwest Logo
2:05 pm - 12:55 amSJD-MDW
9h 50m1 stop
Southwest Logo
5:50 am - 2:50 pmMDW-SJD
10h 00m1 stop
$388Southwest
Find Deal
Wed, Nov 26 - Sun, Nov 30
Southwest Logo
2:05 pm - 10:05 pmSJD-MDW
7h 00m1 stop
Southwest Logo
5:25 am - 2:50 pmMDW-SJD
10h 25m1 stop
$412Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
12:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
$426Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15
Southwest Logo
2:05 pm - 11:20 pmSJD-MDW
8h 15m1 stop
Southwest Logo
5:15 am - 2:50 pmMDW-SJD
10h 35m2 stops
$447Southwest
Find Deal
Thu, Nov 13 - Mon, Nov 17
Delta Logo
12:47 pm - 10:14 pmSJD-MDW
7h 27m1 stop
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
$450Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15
Delta Logo
1:40 pm - 9:46 pmSJD-MDW
7h 06m1 stop
Delta Logo
6:00 am - 12:35 pmMDW-SJD
7h 35m1 stop
$456Delta
Find Deal
Sat, Feb 14 - Tue, Feb 17
Southwest Logo
11:50 am - 9:20 pmSJD-MDW
8h 30m2 stops
Southwest Logo
10:40 pm - 11:40 amMDW-SJD
14h 00m2 stops
$519Southwest
Find Deal
Wed, Nov 26 - Sun, Nov 30
Delta Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
Delta Logo
6:00 am - 12:10 pmMDW-SJD
7h 10m1 stop
$551Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15
Delta Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
Delta Logo
6:00 am - 5:52 pmMDW-SJD
12h 52m2 stops
$553Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15
Delta Logo
6:00 am - 10:14 pmSJD-MDW
14h 14m2 stops
Delta Logo
6:00 am - 5:52 pmMDW-SJD
12h 52m2 stops
$678Delta
Find Deal
Sat, Nov 1 - Sat, Nov 15

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
Nov 26
SJD2:05 pmSan José del Cabo Los Cabos
9h 50m
1 stop
MDW12:55 amChicago Midway
Nov 30
MDW5:50 amChicago Midway
10h 00m
1 stop
SJD2:50 pmSan José del Cabo Los Cabos
$388
Find similar
Southwest
Nov 13
SJD2:05 pmSan José del Cabo Los Cabos
7h 00m
1 stop
MDW10:05 pmChicago Midway
Nov 17
MDW5:25 amChicago Midway
10h 25m
1 stop
SJD2:50 pmSan José del Cabo Los Cabos
$412
Find similar
Southwest
Nov 13
SJD2:05 pmSan José del Cabo Los Cabos
8h 15m
1 stop
MDW11:20 pmChicago Midway
Nov 17
MDW5:15 amChicago Midway
10h 35m
2 stops
SJD2:50 pmSan José del Cabo Los Cabos
$447
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
Nov 1
SJD12:47 pmSan José del Cabo Los Cabos
7h 27m
1 stop
MDW10:14 pmChicago Midway
Nov 15
MDW6:00 amChicago Midway
7h 10m
1 stop
SJD12:10 pmSan José del Cabo Los Cabos
$426
Find similar
Delta
Nov 1
SJD12:47 pmSan José del Cabo Los Cabos
7h 27m
1 stop
MDW10:14 pmChicago Midway
Nov 15
MDW6:00 amChicago Midway
7h 10m
1 stop
SJD12:10 pmSan José del Cabo Los Cabos
$450
Find similar
Delta
Feb 14
SJD1:40 pmSan José del Cabo Los Cabos
7h 06m
1 stop
MDW9:46 pmChicago Midway
Feb 17
MDW6:00 amChicago Midway
7h 35m
1 stop
SJD12:35 pmSan José del Cabo Los Cabos
$456
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 September 25, 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

Wed 11/26

2:05 pm-12:55 am

1 stop9h 50m

Chicago Midway

Sun 11/30

5:50 am-2:50 pm

1 stop10h 00m

$388

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 11/13

2:05 pm-10:05 pm

1 stop7h 00m

Chicago Midway

Mon 11/17

5:25 am-2:50 pm

1 stop10h 25m

$412

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

12:47 pm-10:14 pm

1 stop7h 27m

Chicago Midway

Sat 11/15

6:00 am-12:10 pm

1 stop7h 10m

$426

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 11/13

2:05 pm-11:20 pm

1 stop8h 15m

Chicago Midway

Mon 11/17

5:15 am-2:50 pm

2 stops10h 35m

$447

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

12:47 pm-10:14 pm

1 stop7h 27m

Chicago Midway

Sat 11/15

6:00 am-12:10 pm

1 stop7h 10m

$450

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 2/14

1:40 pm-9:46 pm

1 stop7h 06m

Chicago Midway

Tue 2/17

6:00 am-12:35 pm

1 stop7h 35m

$456

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 11/26

11:50 am-9:20 pm

2 stops8h 30m

Chicago Midway

Sun 11/30

10:40 pm-11:40 am

2 stops14h 00m

$519

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

6:00 am-10:14 pm

2 stops14h 14m

Chicago Midway

Sat 11/15

6:00 am-12:10 pm

1 stop7h 10m

$551

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

6:00 am-10:14 pm

2 stops14h 14m

Chicago Midway

Sat 11/15

6:00 am-5:52 pm

2 stops12h 52m

$553

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Sat 11/1

6:00 am-10:14 pm

2 stops14h 14m

Chicago Midway

Sat 11/15

6:00 am-5:52 pm

2 stops12h 52m

$678

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 30% 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

3h 55m

Direct flights

Mon, Tue, Wed 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 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 7h 00m 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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