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Cabo San Lucas

$148+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$400
(Delta)

One-way from

$148
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$714
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. 7% potential increase in price ($56 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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 8/186:04 amMDW - SJD
1 stop7h 19mDelta
Fri 8/226:10 amSJD - MDW
2 stops13h 34mDelta
Deal found 7/1$400
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Tue 8/128:39 pmMDW - SJD
1 stop16h 32mMultiple Airlines
Fri 8/157:25 amSJD - MDW
1 stop9h 51mMultiple Airlines
Deal found 7/3$423
This Southwest deal was found by Cheapflights users on 7/1. 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 7/145:15 amMDW - SJD
1 stop5h 35mSouthwest
Wed 7/1611:55 amSJD - MDW
1 stop10h 55mSouthwest
Deal found 7/1$431
This Aeromexico deal was found by Cheapflights users on 7/2. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/196:00 amMDW - SJD
2 stops18h 30mAeromexico
Mon 9/227:55 pmSJD - MDW
2 stops23h 41mAeromexico
Deal found 7/2$546

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 July 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

Mon 8/18

6:04 am-11:23 am

1 stop7h 19m

San José del Cabo Los Cabos

Fri 8/22

6:10 am-9:44 pm

2 stops13h 34m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 8/12

8:39 pm-11:11 am

1 stop16h 32m

San José del Cabo Los Cabos

Fri 8/15

7:25 am-7:16 pm

1 stop9h 51m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 7/14

5:15 am-8:50 am

1 stop5h 35m

San José del Cabo Los Cabos

Wed 7/16

11:55 am-12:50 am

1 stop10h 55m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 9/19

6:00 am-10:30 pm

2 stops18h 30m

San José del Cabo Los Cabos

Mon 9/22

7:55 pm-9:36 pm

2 stops23h 41m

$546

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/8

8:39 pm-4:10 pm

2 stops21h 31m

San José del Cabo Los Cabos

Mon 8/11

8:17 pm-7:16 pm

3 stops20h 59m

$558

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/1

7:45 am-2:00 pm

2 stops32h 15m

$148

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/15

12:35 pm-10:35 am

1 stop24h 00m

$168

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/11

8:39 pm-11:11 am

1 stop16h 32m

$170

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 9/23

6:00 am-2:49 pm

2 stops10h 49m

$179

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 9/20

11:00 am-11:30 am

2 stops26h 30m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 $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.

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 July 3, 2025.
Read through reviews of airlines operating flights from Chicago Midway Airport to Cabo San Lucas, such as Southwest, Delta, and Aeromexico. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Aeromexico
7.5
Good
1,718 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Volaris
6.7
Okay
1,171 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Comfort

8.0

Entertainment

7.6

Boarding

8.2

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Cabo San Lucas one-way?

    $168 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Volaris and Delta, with prices starting from $170 and $179, respectively.

  • 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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