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.

$277 Cheap Flights from San José del Cabo to Chicago Midway Airport in 2026/27

Find the cheapest flights from San José del Cabo to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

10:35 am - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

12h 20m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

6:00 am - 2:19 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

9h 19m1 stop Atlanta Hartsfield-Jackson

$537Delta

Fri, Jan 29 - Mon, Feb 1

3:24 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 31m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:29 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 29m1 stop Atlanta Hartsfield-Jackson

$537Delta

Fri, Jan 29 - Sun, Jan 31

3:24 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 31m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:19 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

9h 19m1 stop Atlanta Hartsfield-Jackson

$537Delta

Fri, Jan 29 - Mon, Feb 1

3:24 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 31m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:29 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 29m1 stop Atlanta Hartsfield-Jackson

$537Delta

Fri, Jan 29 - Tue, Feb 2

3:24 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 31m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:19 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

9h 19m1 stop Atlanta Hartsfield-Jackson

$537Delta

Thu, Jan 28 - Mon, Feb 1

10:35 am - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

12h 20m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

6:00 am - 12:29 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 29m1 stop Atlanta Hartsfield-Jackson

$537Delta

Thu, Jan 28 - Sun, Jan 31

10:35 am - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

12h 20m2 stops Mexico City Benito Juarez Atlanta Hartsfield-Jackson

6:00 am - 5:39 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

12h 39m2 stops Atlanta Hartsfield-Jackson Mexico City Benito Juarez

$537Delta

Thu, Jan 28 - Sun, Jan 31

3:24 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 31m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:29 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 29m1 stop Atlanta Hartsfield-Jackson

$537Delta

Thu, Jan 28 - Tue, Feb 2

1:34 pm - 11:55 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

9h 21m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:29 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 29m1 stop Atlanta Hartsfield-Jackson

$537Delta

Thu, Jan 28 - Sun, Jan 31

2:04 pm - 10:54 pmSJD San José del Cabo Los Cabos-MDW Chicago Midway

7h 50m1 stop Atlanta Hartsfield-Jackson

6:00 am - 12:59 pmMDW Chicago Midway-SJD San José del Cabo Los Cabos

7h 59m1 stop Atlanta Hartsfield-Jackson

$541Delta

Fri, Dec 4 - Sun, Dec 13

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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

Dec 4

SJD2:45 pmSan José del Cabo Los Cabos

7h 25m

1 stop

MDW11:10 pmChicago Midway

Dec 13

MDW5:20 amChicago Midway

9h 55m

2 stops

SJD2:15 pmSan José del Cabo Los Cabos

$609

Southwest

Dec 15

SJD11:50 amSan José del Cabo Los Cabos

9h 50m

2 stops

MDW10:40 pmChicago Midway

Dec 22

MDW5:50 amChicago Midway

7h 45m

1 stop

SJD12:35 pmSan José del Cabo Los Cabos

$671

Southwest

Dec 15

SJD11:50 amSan José del Cabo Los Cabos

8h 45m

2 stops

MDW9:35 pmChicago Midway

Dec 17

MDW5:15 amChicago Midway

10h 00m

1 stop

SJD2:15 pmSan José del Cabo Los Cabos

$680

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

Jan 28

SJD10:35 amSan José del Cabo Los Cabos

12h 20m

2 stops

MDW11:55 pmChicago Midway

Jan 31

MDW6:00 amChicago Midway

7h 29m

1 stop

SJD12:29 pmSan José del Cabo Los Cabos

$537

Delta

Dec 4

SJD2:04 pmSan José del Cabo Los Cabos

7h 50m

1 stop

MDW10:54 pmChicago Midway

Dec 13

MDW6:00 amChicago Midway

7h 59m

1 stop

SJD12:59 pmSan José del Cabo Los Cabos

$541

Delta

Dec 15

SJD2:04 pmSan José del Cabo Los Cabos

7h 50m

1 stop

MDW10:54 pmChicago Midway

Dec 22

MDW6:00 amChicago Midway

9h 12m

1 stop

SJD2:12 pmSan José del Cabo Los Cabos

$605

momondo Fare Finder

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 San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 1/29

10:35 am-11:55 pm

2 stops12h 20m

Chicago Midway

Mon 2/1

6:00 am-2:19 pm

1 stop9h 19m

$537

Quickest round-trip

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 1/29

3:24 pm-11:55 pm

1 stop7h 31m

Chicago Midway

Sun 1/31

6:00 am-12:29 pm

1 stop7h 29m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 1/29

3:24 pm-11:55 pm

1 stop7h 31m

Chicago Midway

Mon 2/1

6:00 am-2:19 pm

1 stop9h 19m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 1/29

3:24 pm-11:55 pm

1 stop7h 31m

Chicago Midway

Tue 2/2

6:00 am-12:29 pm

1 stop7h 29m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 1/28

3:24 pm-11:55 pm

1 stop7h 31m

Chicago Midway

Mon 2/1

6:00 am-2:19 pm

1 stop9h 19m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 1/28

10:35 am-11:55 pm

2 stops12h 20m

Chicago Midway

Sun 1/31

6:00 am-12:29 pm

1 stop7h 29m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 1/28

10:35 am-11:55 pm

2 stops12h 20m

Chicago Midway

Sun 1/31

6:00 am-5:39 pm

2 stops12h 39m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 1/28

3:24 pm-11:55 pm

1 stop7h 31m

Chicago Midway

Tue 2/2

6:00 am-12:29 pm

1 stop7h 29m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Thu 1/28

1:34 pm-11:55 pm

1 stop9h 21m

Chicago Midway

Sun 1/31

6:00 am-12:29 pm

1 stop7h 29m

$537

San José del CaboChicago

SJD San José del Cabo Los Cabos - MDW Chicago Midway

SJDMDW

San José del Cabo Los Cabos

Fri 12/4

2:04 pm-10:54 pm

1 stop7h 50m

Chicago Midway

Sun 12/13

6:00 am-12:59 pm

1 stop7h 59m

$541

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Can stopping save me money on San José del Cabo to Chicago Midway Airport flights?

You could potentially save up to 1% 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	$277
Fastest flight time	15h 21m
Direct flights	Fri and Sat

The best one-way flight to Chicago Midway Airport from San José del Cabo in the past 72 hours is $277. The best round-trip flight deal from San José del Cabo to Chicago Midway Airport found on momondo in the last 72 hours is $537.

The fastest flight from San José del Cabo to Chicago Midway Airport takes 15h 21m

Direct flights go from San José del Cabo to Chicago Midway Airport on Friday and Saturday. The only airline offering direct flights is Southwest.

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 15h 21m 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?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from San José del Cabo to Chicago Midway Airport is Boeing 737-800 (66.67% of total bookings). The next most popular plane model is Airbus A321-100/200 (33.33%).

Merrillville

New Buffalo

Hammond

Portage

Lansing

Saint Joseph

Benton Harbor

Valparaiso

Schererville

Munster

Chesterton

Monticello

Crown Point

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.