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Cabo San Lucas

$134+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Aeromexico deal was found by Cheapflights users on 12/16. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:00 amMDW - SJD
1 stop7h 47mAeromexico
Wed 12/311:52 pmSJD - MDW
1 stop7h 30mAeromexico
Deal found 12/16$522
This Delta deal was found by Cheapflights users on 12/15. 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
Tue 12/231:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 12/15$533
This Delta deal was found by Cheapflights users on 12/16. 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.
Tue 12/306:00 amMDW - SJD
1 stop7h 47mDelta
Wed 1/71:45 pmSJD - MDW
1 stop7h 22mDelta
Deal found 12/16$562
This Southwest deal was found by Cheapflights users on 12/15. 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 12/225:00 amMDW - SJD
1 stop6h 55mSouthwest
Thu 12/252:05 pmSJD - MDW
1 stop7h 05mSouthwest
Deal found 12/15$572
This Southwest deal was found by Cheapflights users on 12/15. 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.
Thu 12/185:30 amMDW - SJD
1 stop10h 20mSouthwest
Tue 12/2311:50 amSJD - MDW
2 stops8h 30mSouthwest
Deal found 12/15$573
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/256:00 amMDW - SJD
1 stop7h 47mDelta
Sun 12/281:52 pmSJD - MDW
1 stop7h 30mDelta
Deal found 12/16$578
This Delta deal was found by Cheapflights users on 12/16. 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.
Wed 12/316:00 amMDW - SJD
1 stop7h 47mDelta
Wed 1/71:45 pmSJD - MDW
1 stop7h 22mDelta
Deal found 12/16$596
This Aeromexico deal was found by Cheapflights users on 12/17. 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 Aeromexico is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amMDW - SJD
1 stop9h 10mAeromexico
Mon 1/51:45 pmSJD - MDW
1 stop7h 22mAeromexico
Deal found 12/17$607
This Southwest deal was found by Cheapflights users on 12/16. 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.
Wed 12/247:05 amMDW - SJD
1 stop7h 40mSouthwest
Mon 12/2911:50 amSJD - MDW
2 stops8h 30mSouthwest
Deal found 12/16$617
This Southwest deal was found by Cheapflights users on 12/15. 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.
Fri 12/195:00 amMDW - SJD
1 stop9h 45mSouthwest
Sun 12/212:40 pmSJD - MDW
1 stop9h 30mSouthwest
Deal found 12/15$618

Find 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 December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$480
(Delta)

One-way from

$134
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$1,293
Provider with most accurate pricing for Chicago (CHI)-San José del Cabo Los Cabos flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-San José del Cabo Los Cabos flights.
Search Deals
From Chicago Midway to Cabo San Lucas
Search Deals
One-way flight from Chicago Midway to Cabo San Lucas
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($216 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 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

Sun 3/1

6:15 am-1:55 pm

1 stop8h 40m

San José del Cabo Los Cabos

Fri 3/6

1:35 pm-6:30 pm

Nonstop3h 55m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/26

6:00 am-5:36 pm

2 stops12h 36m

San José del Cabo Los Cabos

Fri 1/30

6:05 am-10:22 pm

2 stops15h 17m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 1/21

6:00 am-5:41 pm

2 stops12h 41m

San José del Cabo Los Cabos

Tue 1/27

6:05 am-10:22 pm

2 stops15h 17m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/16

7:20 pm-9:45 am

1 stop16h 25m

San José del Cabo Los Cabos

Wed 3/18

12:40 pm-10:29 pm

1 stop7h 49m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/17

6:35 pm-5:41 pm

2 stops25h 06m

San José del Cabo Los Cabos

Tue 3/24

1:50 pm-8:50 am

1 stop17h 00m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/3

6:00 am-5:37 pm

2 stops12h 37m

San José del Cabo Los Cabos

Fri 3/6

6:05 am-10:42 pm

2 stops15h 37m

$500

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/17

6:35 pm-10:40 am

2 stops18h 05m

San José del Cabo Los Cabos

Fri 3/20

2:30 pm-12:29 pm

2 stops19h 59m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 3/11

6:30 am-5:41 pm

2 stops13h 11m

San José del Cabo Los Cabos

Tue 3/24

8:40 am-10:29 pm

2 stops11h 49m

$505

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 1/19

12:57 pm-1:06 pm

2 stops25h 09m

$206

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 2/24

5:05 am-11:40 am

1 stop7h 35m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 17 results
1
2

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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Cabo San Lucas (average of $471). Flying from Chicago Midway Airport to Cabo San Lucas in February is currently the most expensive (average of $800). 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 December 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
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 40m. 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.

  • What are the cheapest flights from Chicago Midway Airport to Cabo San Lucas?

    On average you can expect to pay $585 for a flight from Chicago Midway Airport to Cabo San Lucas. The cheapest flight overall is $467 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $427.

  • 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Cabo San Lucas (average of $471). Flying from Chicago Midway Airport to Cabo San Lucas in February is currently the most expensive (average of $800). 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$485Average$707FlexibilityNo cancel feeOn-time63%

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