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Cabo San Lucas

$140+ Cheap flights from Midway (MDW) to Cabo San Lucas, Mexico

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Cheap flight deals from Midway to Cabo San Lucas

Keep the following information in mind while searching for Midway to Cabo San Lucas flight deals. Data was last updated November 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$385
(Delta)

One-way from

$140
(Mytrip)

Popular in

December

Cheapest in

October

Average price

$773
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
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From Chicago Midway to Cabo San Lucas
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One-way flight from Chicago Midway to Cabo San Lucas
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Highest demand for flights based on searches. 35% potential increase in price ($440 potential increase over avg. RT price).
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Cheapest flight prices on average. 15% potential price decrease ($109 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Midway to Cabo San Lucas

Cheapest flights from Midway to Cabo San Lucas
Explore the most affordable flight options available from Midway to Cabo San Lucas. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 18, 2025.

This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/249:50 amMDW - SJD
2 stops23h 55mDelta
Mon 12/291:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 11/17$385
This Southwest deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/298:10 amMDW - SJD
Nonstop4h 50mSouthwest
Tue 12/211:50 amSJD - MDW
1 stop9h 20mSouthwest
Deal found 11/18$406
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/286:00 amMDW - SJD
2 stops13h 10mDelta
Sat 12/61:15 pmSJD - MDW
1 stop9h 32mDelta
Deal found 11/18$410
This Southwest deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/197:00 amMDW - SJD
1 stop7h 10mSouthwest
Wed 11/261:25 pmSJD - MDW
1 stop7h 10mSouthwest
Deal found 11/18$449
This Southwest deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:15 amMDW - SJD
1 stop7h 35mSouthwest
Sat 12/2011:30 amSJD - MDW
2 stops9h 20mSouthwest
Deal found 11/18$450
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amMDW - SJD
1 stop7h 47mDelta
Wed 12/313:15 pmSJD - MDW
1 stop16h 50mDelta
Deal found 11/17$460
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amMDW - SJD
1 stop7h 47mDelta
Sun 12/284:35 pmSJD - MDW
2 stops17h 31mDelta
Deal found 11/18$465
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/176:00 amMDW - SJD
1 stop7h 10mDelta
Fri 12/261:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 11/17$468
This Delta deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:00 amMDW - SJD
1 stop7h 10mDelta
Thu 12/254:35 pmSJD - MDW
2 stops15h 14mDelta
Deal found 11/17$473
This Southwest deal was found by Cheapflights users on 11/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/85:35 amMDW - SJD
2 stops8h 35mSouthwest
Fri 12/1211:50 amSJD - MDW
2 stops9h 10mSouthwest
Deal found 11/17$485
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:00 amMDW - SJD
1 stop7h 10mDelta
Fri 12/129:32 amSJD - MDW
2 stops13h 15mDelta
Deal found 11/18$490

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Cabo San Lucas 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, Cheapflights users made 2,558,603 searches. Data last updated November 18, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Cabo San Lucas that are best for you.

Fly from

Midway

Fly to

Cabo San Lucas

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 11/29

7:45 am-1:10 pm

1 stop6h 25m

San José del Cabo Los Cabos

Tue 12/2

11:50 am-10:10 pm

1 stop9h 20m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Sat 12/6

1:15 pm-11:47 pm

1 stop9h 32m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 11/28

5:30 am-2:50 pm

1 stop10h 20m

San José del Cabo Los Cabos

Tue 12/2

2:05 pm-10:10 pm

1 stop7h 05m

$410

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

6:00 am-12:40 pm

1 stop7h 40m

San José del Cabo Los Cabos

Sat 1/31

6:05 am-10:22 pm

2 stops15h 17m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 1/8

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Fri 1/16

1:45 pm-10:07 pm

1 stop7h 22m

$422

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/5

5:31 pm-8:40 am

2 stops16h 09m

San José del Cabo Los Cabos

Sat 1/10

1:45 pm-10:07 pm

1 stop7h 22m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

5:59 pm-8:40 am

2 stops15h 41m

San José del Cabo Los Cabos

Sun 1/25

4:32 pm-8:52 am

2 stops15h 20m

$427

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 1/23

6:00 am-2:09 pm

1 stop9h 09m

San José del Cabo Los Cabos

Mon 2/2

1:45 pm-10:22 pm

1 stop7h 37m

$452

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 1/23

6:54 pm-11:30 am

1 stop17h 36m

$154

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 12/17

6:00 am-12:10 pm

1 stop7h 10m

$167

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 17 results
1
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Best time to book a flight from Midway to Cabo San Lucas

Have a flexible travel schedule? Discover the best time to fly to Cabo San Lucas from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Cabo San Lucas

What is the cheapest month to book a flight from Chicago Midway Airport to Cabo San Lucas?

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Cabo San Lucas (average of $393). Flying from Chicago Midway Airport to Cabo San Lucas in February is currently the most expensive (average of $793). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Cabo San Lucas

Get insights into the airlines that provide service to Cabo San Lucas. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cabo San Lucas. Reviews last updated November 18, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cabo San Lucas, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Midway to Cabo San Lucas. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago Midway Airport to Cabo San Lucas?

    There are many flights that can get you from Chicago Midway Airport to Cabo San Lucas in 6h 25m. Fly via Southwest or Delta to get the fastest option. The distance between Chicago Midway Airport and Cabo San Lucas is about 1804 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Cabo San Lucas that include hotel bookings?

    Yes. In addition to deals on Midway to Cabo San Lucas flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cabo San Lucas?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cabo San Lucas.

  • Can I find deals for business class flights from Midway to Cabo San Lucas?

    Yes. Cheapflights offers flight deals from Midway to Cabo San Lucas by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Cabo San Lucas?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Cabo San Lucas (average of $393). Flying from Chicago Midway Airport to Cabo San Lucas in February is currently the most expensive (average of $793). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Midway to Cabo San Lucas

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to San José del Cabo flights
Midway to San José del Cabo flights
O'Hare Intl to La Paz flights
Midway to La Paz flights
O'Hare Intl to Loreto flights

Top airline flying from Midway to Cabo San Lucas

Discover the top airline that operate flights from Midway to Cabo San Lucas. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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