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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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$423
(Delta)

One-way from

$163
(Southwest)

Popular in

December

Cheapest in

October

Average price

$912
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. 32% potential increase in price ($373 potential increase over avg. RT price).
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Cheapest flight prices on average. 16% potential price decrease ($111 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 3, 2025.

This Southwest deal was found by Cheapflights users on 11/2. 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.
Tue 12/25:00 amMDW - SJD
2 stops9h 10mSouthwest
Tue 12/911:50 amSJD - MDW
1 stop9h 20mSouthwest
Deal found 11/2$463
This Southwest deal was found by Cheapflights users on 11/2. 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 11/125:25 amMDW - SJD
1 stop7h 45mSouthwest
Sat 11/152:05 pmSJD - MDW
1 stop7h 10mSouthwest
Deal found 11/2$480
This Southwest deal was found by Cheapflights users on 11/2. 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 11/86:20 amMDW - SJD
1 stop6h 40mSouthwest
Tue 11/112:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 11/2$490
This Southwest deal was found by Cheapflights users on 11/3. 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 12/296:05 amMDW - SJD
1 stop7h 25mSouthwest
Thu 1/812:35 pmSJD - MDW
1 stop7h 40mSouthwest
Deal found 11/3$494
This Delta deal was found by Cheapflights users on 11/2. 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.
Tue 11/186:00 amMDW - SJD
1 stop7h 10mDelta
Mon 11/241:15 pmSJD - MDW
1 stop9h 25mDelta
Deal found 11/2$502
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amMDW - SJD
1 stop7h 10mMultiple Airlines
Mon 12/18:20 amSJD - MDW
2 stops27h 44mMultiple Airlines
Deal found 11/3$508
This Southwest deal was found by Cheapflights users on 11/2. 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.
Sun 11/305:50 amMDW - SJD
1 stop6h 50mSouthwest
Sun 12/72:40 pmSJD - MDW
1 stop8h 30mSouthwest
Deal found 11/2$512
This Delta deal was found by Cheapflights users on 11/3. 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.
Mon 11/176:00 amMDW - SJD
1 stop7h 10mDelta
Thu 11/209:32 amSJD - MDW
2 stops13h 08mDelta
Deal found 11/3$523
This Southwest deal was found by Cheapflights users on 11/3. 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 11/177:05 amMDW - SJD
1 stop7h 40mSouthwest
Thu 11/202:40 pmSJD - MDW
2 stops13h 25mSouthwest
Deal found 11/3$528
This Southwest deal was found by Cheapflights users on 11/3. 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 11/88:25 amMDW - SJD
1 stop7h 35mSouthwest
Wed 11/122:40 pmSJD - MDW
1 stop7h 15mSouthwest
Deal found 11/3$530
This Delta deal was found by Cheapflights users on 11/3. 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 11/166:00 amMDW - SJD
1 stop7h 10mDelta
Thu 11/201:15 pmSJD - MDW
1 stop9h 25mDelta
Deal found 11/3$533

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 3, 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

Tue 12/2

5:00 am-1:10 pm

2 stops9h 10m

San José del Cabo Los Cabos

Tue 12/9

11:50 am-10:10 pm

1 stop9h 20m

$463

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/18

6:45 am-2:09 pm

1 stop8h 24m

San José del Cabo Los Cabos

Sun 1/25

1:45 pm-10:26 pm

1 stop7h 41m

$474

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 1/25

5:20 am-1:40 pm

2 stops9h 20m

San José del Cabo Los Cabos

Wed 1/28

2:20 pm-5:05 am

2 stops13h 45m

$512

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 11/30

5:50 am-11:40 am

1 stop6h 50m

San José del Cabo Los Cabos

Sun 12/7

2:40 pm-12:10 am

1 stop8h 30m

$512

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 11/16

6:00 am-12:10 pm

1 stop7h 10m

San José del Cabo Los Cabos

Thu 11/20

9:32 am-11:40 pm

2 stops13h 08m

$533

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 11/12

6:00 am-6:07 pm

2 stops13h 07m

San José del Cabo Los Cabos

Sat 11/15

1:15 pm-11:40 pm

1 stop9h 25m

$548

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 12/5

7:05 am-2:50 pm

2 stops8h 45m

San José del Cabo Los Cabos

Wed 12/10

2:40 pm-5:05 am

2 stops13h 25m

$597

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 12/11

6:20 am-2:50 pm

2 stops9h 30m

San José del Cabo Los Cabos

Fri 12/19

11:50 am-10:50 pm

2 stops10h 00m

$597

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 12/12

9:45 pm-11:20 am

2 stops14h 35m

San José del Cabo Los Cabos

Fri 12/19

11:50 am-9:20 pm

2 stops8h 30m

$597

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 12/9

6:00 am-12:10 pm

1 stop7h 10m

$165

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/1

Showing 1-10 of 18 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

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 $275). 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 3, 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
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Overall

8.0

Boarding

8.1

Comfort

8.0

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 8h 24m. 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 $275). 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

Browse thousands of different options on Cheapflights for your next trip

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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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$545Average$720FlexibilityNo cancel feeOn-time63%

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