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Cheap flights from San José del Cabo to Chicago from $275

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 6/3. 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.
Delta Logo
1:39 pm - 8:38 am
SJD
-
MDW
16h 59m
2 stops
Delta Logo
6:00 am - 11:22 am
MDW
-
SJD
7h 22m
1 stop
$594Delta
Wed, Aug 12 - Sun, Aug 16
Multiple Airlines Logo
6:50 am - 7:34 pm
SJD
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
8:49 pm - 12:30 pm
MDW
-
SJD
17h 41m
1 stop
$605Multiple Airlines
Thu, Jun 18 - Thu, Jun 25
Multiple Airlines Logo
6:50 am - 7:34 pm
SJD
-
MDW
10h 44m
1 stop
Multiple Airlines Logo
4:10 pm - 7:20 am
MDW
-
SJD
17h 10m
2 stops
$607Multiple Airlines
Thu, Jun 18 - Thu, Jun 25
Delta Logo
6:07 am - 10:17 pm
SJD
-
MDW
14h 10m
2 stops
Delta Logo
6:00 am - 11:25 am
MDW
-
SJD
7h 25m
1 stop
$622Delta
Tue, Jun 16 - Fri, Jun 19
Southwest Logo
11:15 am - 12:35 am
SJD
-
MDW
11h 20m
1 stop
Southwest Logo
5:45 am - 11:00 am
MDW
-
SJD
7h 15m
1 stop
$633Southwest
Thu, Jun 18 - Mon, Jun 22
Southwest Logo
11:35 am - 11:55 pm
SJD
-
MDW
10h 20m
1 stop
Southwest Logo
8:50 pm - 12:50 pm
MDW
-
SJD
18h 00m
2 stops
$642Southwest
Thu, Jul 30 - Tue, Aug 4
Delta Logo
6:07 am - 9:09 pm
SJD
-
MDW
13h 02m
2 stops
Delta Logo
6:23 am - 5:48 pm
MDW
-
SJD
13h 25m
2 stops
$652Delta
Fri, May 22 - Mon, May 25
Delta Logo
12:30 pm - 10:17 pm
SJD
-
MDW
7h 47m
1 stop
Delta Logo
6:00 am - 11:25 am
MDW
-
SJD
7h 25m
1 stop
$653Delta
Tue, Jun 16 - Fri, Jun 19
Delta Logo
12:30 pm - 10:17 pm
SJD
-
MDW
7h 47m
1 stop
Delta Logo
6:00 am - 11:25 am
MDW
-
SJD
7h 25m
1 stop
$657Delta
Tue, Jun 16 - Fri, Jun 19
Southwest Logo
1:05 pm - 1:00 am
SJD
-
MDW
9h 55m
2 stops
Southwest Logo
8:50 pm - 12:50 pm
MDW
-
SJD
18h 00m
2 stops
$658Southwest
Thu, Jul 30 - Tue, Aug 4

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 12
SJD1:39 pmSan José del Cabo Los Cabos
16h 59m
2 stops
MDW8:38 amChicago Midway
Aug 16
MDW6:00 amChicago Midway
7h 22m
1 stop
SJD11:22 amSan José del Cabo Los Cabos
$594
Delta
Jun 16
SJD6:07 amSan José del Cabo Los Cabos
14h 10m
2 stops
MDW10:17 pmChicago Midway
Jun 19
MDW6:00 amChicago Midway
7h 25m
1 stop
SJD11:25 amSan José del Cabo Los Cabos
$622
Delta
May 22
SJD6:07 amSan José del Cabo Los Cabos
13h 02m
2 stops
MDW9:09 pmChicago Midway
May 25
MDW6:23 amChicago Midway
13h 25m
2 stops
SJD5:48 pmSan José del Cabo Los Cabos
$652

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
Jun 18
SJD11:15 amSan José del Cabo Los Cabos
11h 20m
1 stop
MDW12:35 amChicago Midway
Jun 22
MDW5:45 amChicago Midway
7h 15m
1 stop
SJD11:00 amSan José del Cabo Los Cabos
$633
Southwest
Jul 30
SJD11:35 amSan José del Cabo Los Cabos
10h 20m
1 stop
MDW11:55 pmChicago Midway
Aug 4
MDW8:50 pmChicago Midway
18h 00m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
$642
Southwest
Jul 30
SJD1:05 pmSan José del Cabo Los Cabos
9h 55m
2 stops
MDW1:00 amChicago Midway
Aug 4
MDW8:50 pmChicago Midway
18h 00m
2 stops
SJD12:50 pmSan José del Cabo Los Cabos
$658

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 May 3, 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

Wed 8/12

1:39 pm-8:38 am

2 stops16h 59m

Chicago Midway

Sun 8/16

6:00 am-11:22 am

1 stop7h 22m

$594

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 6/18

6:50 am-7:34 pm

1 stop10h 44m

Chicago Midway

Thu 6/25

8:49 pm-12:30 pm

1 stop17h 41m

$605

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 6/18

6:50 am-7:34 pm

1 stop10h 44m

Chicago Midway

Thu 6/25

4:10 pm-7:20 am

2 stops17h 10m

$607

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 6/16

6:07 am-10:17 pm

2 stops14h 10m

Chicago Midway

Fri 6/19

6:00 am-11:25 am

1 stop7h 25m

$622

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 6/18

11:15 am-12:35 am

1 stop11h 20m

Chicago Midway

Mon 6/22

5:45 am-11:00 am

1 stop7h 15m

$633

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/30

11:35 am-11:55 pm

1 stop10h 20m

Chicago Midway

Tue 8/4

8:50 pm-12:50 pm

2 stops18h 00m

$642

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Fri 5/22

6:07 am-9:09 pm

2 stops13h 02m

Chicago Midway

Mon 5/25

6:23 am-5:48 pm

2 stops13h 25m

$652
Quickest round-trip

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 6/16

12:30 pm-10:17 pm

1 stop7h 47m

Chicago Midway

Fri 6/19

6:00 am-11:25 am

1 stop7h 25m

$653

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Tue 6/16

12:30 pm-10:17 pm

1 stop7h 47m

Chicago Midway

Fri 6/19

6:00 am-11:25 am

1 stop7h 25m

$657

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 7/30

1:05 pm-1:00 am

2 stops9h 55m

Chicago Midway

Tue 8/4

8:50 pm-12:50 pm

2 stops18h 00m

$658

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

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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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