How many flights depart from Los Cabos to Chicago Midway Airport on average per week?

The number of flights available between Los Cabos and Chicago Midway Airport is 2 per week as of March 2026. The most frequent departure day is Thu, with 50% of weekly flights leaving on this day.

What is the cheapest airline that flies from Los Cabos to Chicago Midway?

Delta and Southwest are the most popular carriers operating from Los Cabos to Chicago Midway

When did momondo last update prices for flights from Los Cabos to Chicago Midway Airport?

Prices for flights from Los Cabos to Chicago Midway Airport were last updated today.

How old do you have to be to fly from Los Cabos to Chicago Midway Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Los Cabos to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$216 Cheap Flights from Los Cabos to Chicago Midway Airport in 2026

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Find the cheapest flights from Los Cabos to Chicago

Round-trip

One-way

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:05 pm - 4:26 pm

SJD

MDW

19h 21m

2 stops

10:41 am - 10:30 pm

MDW

SJD

13h 49m

2 stops

$379Aeromexico

Thu, Apr 23 - Mon, Apr 27

6:00 am - 10:28 pm

SJD

MDW

14h 28m

2 stops

10:41 am - 10:30 pm

MDW

SJD

13h 49m

2 stops

$392Aeromexico

Thu, Apr 23 - Mon, Apr 27

12:36 pm - 10:28 pm

SJD

MDW

7h 52m

1 stop

6:00 am - 11:31 am

MDW

SJD

7h 31m

1 stop

$393Aeromexico

Thu, Apr 23 - Mon, Apr 27

7:05 pm - 4:26 pm

SJD

MDW

19h 21m

2 stops

6:00 am - 1:04 pm

MDW

SJD

9h 04m

1 stop

$398Aeromexico

Thu, Apr 23 - Mon, Apr 27

12:36 pm - 10:28 pm

SJD

MDW

7h 52m

1 stop

10:41 am - 10:25 pm

MDW

SJD

13h 44m

2 stops

$447Delta

Wed, Apr 22 - Sat, Apr 25

6:00 am - 10:28 pm

SJD

MDW

14h 28m

2 stops

6:00 am - 10:20 pm

MDW

SJD

18h 20m

2 stops

$491Aeromexico

Wed, Apr 15 - Wed, Apr 22

6:00 am - 10:28 pm

SJD

MDW

14h 28m

2 stops

10:41 am - 10:25 pm

MDW

SJD

13h 44m

2 stops

$499Delta

Wed, Apr 22 - Sat, Apr 25

12:36 pm - 10:28 pm

SJD

MDW

7h 52m

1 stop

6:00 am - 11:31 am

MDW

SJD

7h 31m

1 stop

$529Delta

Wed, Apr 15 - Wed, Apr 22

2:59 pm - 6:34 pm

SJD

MDW

25h 35m

2 stops

7:54 pm - 11:14 am

MDW

SJD

17h 20m

2 stops

$571Volaris

Mon, Mar 16 - Wed, Mar 18

12:35 pm - 10:31 pm

SJD

MDW

7h 56m

1 stop

6:00 am - 5:50 pm

MDW

SJD

13h 50m

2 stops

$602Delta

Thu, Apr 2 - Thu, Apr 9

Delta flights from Los Cabos to Chicago Midway Airport

Our best Delta deals on Los Cabos to Chicago Midway Airport flight tickets

Delta

Apr 22

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

Apr 25

MDW10:41 amChicago Midway

13h 44m

2 stops

SJD10:25 pmSan José del Cabo Los Cabos

$447

Delta

Apr 22

SJD6:00 amSan José del Cabo Los Cabos

14h 28m

2 stops

MDW10:28 pmChicago Midway

Apr 25

MDW10:41 amChicago Midway

13h 44m

2 stops

SJD10:25 pmSan José del Cabo Los Cabos

$499

Delta

Apr 15

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

Apr 22

MDW6:00 amChicago Midway

7h 31m

1 stop

SJD11:31 amSan José del Cabo Los Cabos

$529

Aeromexico flights from Los Cabos to Chicago Midway Airport

Our best Aeromexico deals on Los Cabos to Chicago Midway Airport flight tickets

Aeromexico

Apr 23

SJD7:05 pmSan José del Cabo Los Cabos

19h 21m

2 stops

MDW4:26 pmChicago Midway

Apr 27

MDW10:41 amChicago Midway

13h 49m

2 stops

SJD10:30 pmSan José del Cabo Los Cabos

$379

Aeromexico

Apr 23

SJD7:05 pmSan José del Cabo Los Cabos

25h 23m

2 stops

MDW10:28 pmChicago Midway

Apr 27

MDW6:00 amChicago Midway

9h 04m

1 stop

SJD1:04 pmSan José del Cabo Los Cabos

$392

Aeromexico

Apr 23

SJD12:36 pmSan José del Cabo Los Cabos

7h 52m

1 stop

MDW10:28 pmChicago Midway

Apr 27

MDW6:00 amChicago Midway

7h 31m

1 stop

SJD11:31 amSan José del Cabo Los Cabos

$393

momondo Fare Finder

Use the filters below to find and compare flights from Los Cabos 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

Thu 4/23

7:05 pm-4:26 pm

2 stops19h 21m

Chicago Midway

Mon 4/27

10:41 am-10:30 pm

2 stops13h 49m

$379

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/23

6:00 am-10:28 pm

2 stops14h 28m

Chicago Midway

Mon 4/27

10:41 am-10:30 pm

2 stops13h 49m

$392

Quickest round-trip

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/23

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Mon 4/27

6:00 am-11:31 am

1 stop7h 31m

$393

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/23

7:05 pm-4:26 pm

2 stops19h 21m

Chicago Midway

Mon 4/27

6:00 am-1:04 pm

1 stop9h 04m

$398

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/22

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Sat 4/25

10:41 am-10:25 pm

2 stops13h 44m

$447

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/15

6:00 am-10:28 pm

2 stops14h 28m

Chicago Midway

Wed 4/22

6:00 am-10:20 pm

2 stops18h 20m

$491

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/22

6:00 am-10:28 pm

2 stops14h 28m

Chicago Midway

Sat 4/25

10:41 am-10:25 pm

2 stops13h 44m

$499

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Wed 4/15

12:36 pm-10:28 pm

1 stop7h 52m

Chicago Midway

Wed 4/22

6:00 am-11:31 am

1 stop7h 31m

$529

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Mon 3/16

2:59 pm-6:34 pm

2 stops25h 35m

Chicago Midway

Wed 3/18

7:54 pm-11:14 am

2 stops17h 20m

$571

San José del CaboChicago

SJD - MDW

SJDMDW

San José del Cabo Los Cabos

Thu 4/2

12:35 pm-10:31 pm

1 stop7h 56m

Chicago Midway

Thu 4/9

6:00 am-5:50 pm

2 stops13h 50m

$602

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 Los Cabos 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

Prices

Airlines

Other information

What is the cheapest Los Cabos to Chicago Midway flight route?

Fly from San José del Cabo Los Cabos to Chicago Midway for the best Los Cabos - Chicago Midway flight prices

What cabin class options are available on Los Cabos to Chicago Midway flights?

There is only 1 cabin class available to choose from on 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 Los Cabos to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Los Cabos to Chicago Midway Airport.

Cheap Los Cabos to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Los Cabos to Chicago Midway Airport

Fastest flight time	4h 00m
Direct flights	Every day

The fastest flight from Los Cabos to Chicago Midway Airport takes 4h 00m

Direct flights go from Los Cabos to Chicago Midway Airport every day.

Search flight deals

When did momondo last update prices for flights from Los Cabos to Chicago Midway Airport?
Prices for flights from Los Cabos to Chicago Midway Airport were last updated today.
How old do you have to be to fly from Los Cabos to Chicago Midway Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Los Cabos to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Los Cabos to Chicago Midway Airport?
momondo data reveals that the most frequently booked plane model on the route from Los Cabos to Chicago Midway Airport is Boeing 737 MAX 8, representing 16.46% of all bookings. The subsequent popular models are Boeing 737-800 at 10.71%, Boeing 737-800 Passenger/BBJ2 (winglets) at 10.50%, and Airbus A321neo at 8.36%.

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 Los Cabos to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Los Cabos.

Can I find flights from Los Cabos to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Los Cabos which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Los Cabos to Chicago?

Once you have performed a search for Los Cabos to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Los Cabos to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Los Cabos and alert you when they change.