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Cabo San Lucas

$163+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
oct. 19 — oct. 261
dom. 10/19
dom. 10/26
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 septiembre 19, 2025.

Round-trip from

$450
(Southwest)

One-way from

$163
(Southwest)

Popular in

December

Cheapest in

October

Average price

$502
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. 21% potential increase in price ($198 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($53 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 19, 2025.

This Southwest deal was found by Cheapflights users on 9/18. 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.
mar. 11/187:05 amMDW - SJD
2 stops8h 45mSouthwest
mar. 11/2511:50 amSJD - MDW
2 stops8h 30mSouthwest
Deal found 9/18$450
This Aeromexico deal was found by Cheapflights users on 9/18. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/216:00 amMDW - SJD
2 stops15h 28mAeromexico
mié. 10/296:00 amSJD - MDW
2 stops14h 14mAeromexico
Deal found 9/18$453
This Delta deal was found by Cheapflights users on 9/16. 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.
mar. 9/306:00 amMDW - SJD
2 stops10h 55mDelta
vie. 10/32:18 pmSJD - MDW
2 stops16h 22mDelta
Deal found 9/16$458
This Southwest deal was found by Cheapflights users on 9/16. 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.
lun. 9/295:45 amMDW - SJD
2 stops9h 05mSouthwest
mié. 10/11:45 pmSJD - MDW
1 stop7h 15mSouthwest
Deal found 9/16$463
This Southwest deal was found by Cheapflights users on 9/18. 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.
lun. 11/177:00 amMDW - SJD
1 stop7h 10mSouthwest
lun. 11/242:05 pmSJD - MDW
1 stop8h 15mSouthwest
Deal found 9/18$466
This Southwest deal was found by Cheapflights users on 9/17. 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.
lun. 10/65:25 amMDW - SJD
2 stops9h 55mSouthwest
vie. 10/1012:50 pmSJD - MDW
1 stop9h 20mSouthwest
Deal found 9/17$468
This Aeromexico deal was found by Cheapflights users on 9/18. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/316:00 amMDW - SJD
1 stop7h 42mAeromexico
sáb. 1/101:40 pmSJD - MDW
1 stop7h 06mAeromexico
Deal found 9/18$477
This Delta deal was found by Cheapflights users on 9/18. 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.
dom. 11/96:00 amMDW - SJD
2 stops13h 07mDelta
mié. 11/129:42 amSJD - MDW
2 stops12h 50mDelta
Deal found 9/18$479
This Southwest deal was found by Cheapflights users on 9/18. 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.
sáb. 10/185:00 amMDW - SJD
1 stop7h 40mSouthwest
mar. 10/2811:15 amSJD - MDW
2 stops10h 20mSouthwest
Deal found 9/18$480
This Delta deal was found by Cheapflights users on 9/18. 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.
mié. 12/316:00 amMDW - SJD
1 stop7h 42mDelta
sáb. 1/101:40 pmSJD - MDW
2 stops18h 10mDelta
Deal found 9/18$482
This Southwest deal was found by Cheapflights users on 9/17. 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.
mar. 10/215:30 amMDW - SJD
2 stops10h 10mSouthwest
mar. 10/2811:15 amSJD - MDW
2 stops10h 50mSouthwest
Deal found 9/17$492

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 septiembre 19, 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

vie. 10/31

6:25 am-11:45 am

1 stop7h 20m

San José del Cabo Los Cabos

mar. 11/4

2:40 pm-10:55 pm

1 stop7h 15m

$450

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 11/2

5:30 am-11:40 am

1 stop7h 10m

San José del Cabo Los Cabos

vie. 11/7

11:50 am-10:00 pm

2 stops9h 10m

$485

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 2/24

6:00 am-12:35 pm

1 stop7h 35m

San José del Cabo Los Cabos

vie. 2/27

1:40 pm-9:46 pm

1 stop7h 06m

$495

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 11/7

5:10 am-1:45 pm

1 stop9h 35m

San José del Cabo Los Cabos

vie. 11/14

11:50 am-9:50 pm

1 stop9h 00m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 11/18

5:00 am-1:10 pm

2 stops9h 10m

San José del Cabo Los Cabos

lun. 11/24

2:05 pm-9:55 pm

1 stop6h 50m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 1/17

6:00 am-6:10 pm

2 stops13h 10m

San José del Cabo Los Cabos

sáb. 1/24

1:40 pm-9:46 pm

1 stop7h 06m

$522

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 12/17

7:00 am-1:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

dom. 12/21

11:50 am-9:20 pm

2 stops8h 30m

$525

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 11/10

9:35 pm-12:10 pm

2 stops15h 35m

San José del Cabo Los Cabos

sáb. 11/15

2:05 pm-5:05 am

2 stops14h 00m

$550

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 12/7

9:40 pm-12:10 pm

2 stops15h 30m

San José del Cabo Los Cabos

dom. 12/14

1:25 pm-1:30 am

1 stop11h 05m

$550

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 10/21

5:15 am-10:20 am

1 stop7h 05m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 16 results
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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
No data available for this route at this time. Please check back soon.

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 septiembre 19, 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
4,242 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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 7h 20m. 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, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cabo San Lucas (average of $437). Flying from Chicago Midway Airport to Cabo San Lucas in March is currently the most expensive (average of $549). 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
O'Hare Intl to Loreto flights
Midway to La Paz 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 septiembre 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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