HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cabo San Lucas

$145+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Cabo San Lucas with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 29, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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 2/36:14 pm
MDW
-
SJD
2 stops15h 26m
Delta
Tue 2/109:35 am
SJD
-
MDW
2 stops11h 47m
Delta
Deal found 1/27$477
This Southwest deal was found by Cheapflights users on 1/28. 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 2/277:50 am
MDW
-
SJD
1 stop6h 35m
Southwest
Tue 3/312:00 pm
SJD
-
MDW
1 stop9h 55m
Southwest
Deal found 1/28$478
This Delta deal was found by Cheapflights users on 1/28. 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 5/710:35 am
MDW
-
SJD
2 stops13h 50m
Delta
Wed 5/1311:36 am
SJD
-
MDW
1 stop8h 09m
Delta
Deal found 1/28$480
This Delta deal was found by Cheapflights users on 1/28. 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 2/196:40 pm
MDW
-
SJD
2 stops15h 00m
Delta
Tue 2/244:56 pm
SJD
-
MDW
2 stops15h 10m
Delta
Deal found 1/28$482
This eDestinos deal was found by Cheapflights users on 1/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/137:54 pm
MDW
-
SJD
2 stops38h 31m
Multiple Airlines
Fri 3/203:20 pm
SJD
-
MDW
3 stops22h 05m
Multiple Airlines
Deal found 1/27$485
This Southwest deal was found by Cheapflights users on 1/27. 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 3/115:55 am
MDW
-
SJD
1 stop7h 05m
Southwest
Wed 3/1810:35 am
SJD
-
MDW
Nonstop3h 55m
Southwest
Deal found 1/27$487
This Southwest deal was found by Cheapflights users on 1/28. 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 3/89:30 am
MDW
-
SJD
Nonstop4h 55m
Southwest
Fri 3/132:30 pm
SJD
-
MDW
1 stop12h 05m
Southwest
Deal found 1/28$488
This Southwest deal was found by Cheapflights users on 1/28. 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 2/235:55 am
MDW
-
SJD
1 stop6h 45m
Southwest
Mon 3/22:05 pm
SJD
-
MDW
1 stop9h 20m
Southwest
Deal found 1/28$490
This Delta deal was found by Cheapflights users on 1/28. 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 3/2310:45 am
MDW
-
SJD
2 stops13h 44m
Delta
Thu 3/262:19 pm
SJD
-
MDW
2 stops20h 10m
Delta
Deal found 1/28$501
This Delta deal was found by Cheapflights users on 1/27. 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 3/97:20 pm
MDW
-
SJD
1 stop16h 24m
Delta
Sat 3/142:19 pm
SJD
-
MDW
1 stop17h 37m
Delta
Deal found 1/27$502
This Delta deal was found by Cheapflights users on 1/27. 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 3/66:40 pm
MDW
-
SJD
2 stops15h 00m
Delta
Fri 3/132:46 pm
SJD
-
MDW
2 stops19h 43m
Delta
Deal found 1/27$506
This Delta deal was found by Cheapflights users on 1/28. 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 2/276:00 am
MDW
-
SJD
1 stop9h 09m
Delta
Tue 3/34:56 pm
SJD
-
MDW
2 stops15h 10m
Delta
Deal found 1/28$507

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$478
(Southwest)

One-way from

$145
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$475
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. 14% potential increase in price ($123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($65 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
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

Fri 2/27

7:50 am-1:25 pm

1 stop6h 35m

San José del Cabo Los Cabos

Tue 3/3

12:00 pm-10:55 pm

1 stop9h 55m

$478

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Thu 2/19

6:40 pm-8:40 am

2 stops15h 00m

San José del Cabo Los Cabos

Tue 2/24

9:35 am-10:33 pm

2 stops11h 58m

$482

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/23

5:55 am-11:40 am

1 stop6h 45m

San José del Cabo Los Cabos

Mon 3/2

2:05 pm-12:25 am

1 stop9h 20m

$490

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/23

10:45 am-10:29 pm

2 stops13h 44m

San José del Cabo Los Cabos

Thu 3/26

2:19 pm-12:29 pm

2 stops20h 10m

$501

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/10

6:00 am-10:29 pm

2 stops18h 29m

San José del Cabo Los Cabos

Sat 3/14

2:19 pm-9:56 am

1 stop17h 37m

$502

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/9

6:00 am-10:29 pm

2 stops18h 29m

San José del Cabo Los Cabos

Sat 3/14

2:19 pm-9:56 am

1 stop17h 37m

$502

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 3/7

11:45 am-10:30 am

2 stops23h 45m

San José del Cabo Los Cabos

Sat 3/14

2:19 pm-12:29 pm

2 stops20h 10m

$506

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 5/26

10:35 am-10:25 pm

2 stops13h 50m

San José del Cabo Los Cabos

Tue 6/2

6:00 am-9:45 pm

2 stops13h 45m

$513

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/2

10:43 am-10:25 pm

2 stops13h 42m

San José del Cabo Los Cabos

Sat 5/9

11:36 am-9:45 pm

1 stop8h 09m

$525

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/16

6:00 am-12:46 pm

1 stop8h 46m

San José del Cabo Los Cabos

Tue 5/19

6:00 am-9:45 pm

2 stops13h 45m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 20 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 $1,112). 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 January 29, 2026.
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
4,267 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

8.0

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 6h 35m. 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 $696 for a flight from Chicago Midway Airport to Cabo San Lucas. The cheapest flight overall is $564 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $433.

  • 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 $1,112). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$485Average$697FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.