$216+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Oct 1 — Oct 81
Round-trip
1 adult, Economy
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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
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Cheapest flights from Midway to Cabo San LucasExplore 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 September 1, 2026.
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 September 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Sun 12/66:17 pm -
1 stop13h 27m
Fri 12/117:26 am -
1 stop8h 21m
Deal found 8/31![Multiple Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Fri 10/238:23 pm -
1 stop20h 28m
Fri 12/47:26 am -
1 stop8h 21m
Deal found 8/29![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 8/31. 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 12/69:25 pm -
2 stops15h 15m
Fri 12/112:45 pm -
2 stops9h 20m
Deal found 8/31![Southwest logo]()
$546
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:23 pm -
1 stop20h 28m
Tue 10/133:36 pm -
1 stop25h 28m
Deal found 9/1![Volaris logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/276:17 pm -
1 stop21h 29m
Fri 12/47:26 am -
1 stop8h 21m
Deal found 8/28![Multiple Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 9/1. 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.
Fri 11/65:15 am -
1 stop8h 55m
Tue 11/102:45 pm -
1 stop7h 20m
Deal found 9/1![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 9/1. 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.
Sat 11/147:35 am -
1 stop7h 45m
Tue 11/172:05 pm -
1 stop9h 05m
Deal found 9/1![Southwest logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:30 pm -
2 stops28h 30m
Sat 10/171:20 pm -
1 stop27h 44m
Deal found 8/28![Multiple Airlines logo]()
$577
Best flights from Midway to Cabo San LucasDiscover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
Discover carefully curated flight deals from Midway to Cabo San Lucas that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 1, 2026.
This Southwest deal was found by Cheapflights users on 8/27. 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.
Sat 11/147:35 am -
1 stop7h 45m
Tue 11/172:05 pm -
1 stop9h 05m
Deal found 8/27![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 8/27. 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.
Tue 11/36:05 am -
1 stop8h 05m
Mon 11/93:10 pm -
1 stop13h 30m
Deal found 8/27![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 8/31. 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 10/289:00 am -
1 stop6h 40m
Sun 11/12:45 pm -
2 stops9h 20m
Deal found 8/31![Southwest logo]()
$582
This Southwest deal was found by Cheapflights users on 8/28. 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 10/57:10 am -
1 stop7h 00m
Wed 10/1411:05 am -
2 stops8h 55m
Deal found 8/28![Southwest logo]()
$648
This Southwest deal was found by Cheapflights users on 8/30. 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 10/37:20 am -
1 stop7h 30m
Thu 10/812:15 pm -
1 stop10h 15m
Deal found 8/30![Southwest logo]()
$668
This Southwest deal was found by Cheapflights users on 8/29. 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 10/36:35 am -
2 stops8h 15m
Tue 10/611:05 am -
2 stops9h 15m
Deal found 8/29![Southwest logo]()
$673
This Southwest deal was found by Cheapflights users on 8/29. 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 10/146:05 am -
2 stops9h 35m
Mon 1/1112:00 pm -
2 stops10h 00m
Deal found 8/29![Southwest logo]()
$698
This Southwest deal was found by Cheapflights users on 8/31. 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 10/25:15 am -
2 stops10h 05m
Thu 10/812:15 pm -
2 stops10h 55m
Deal found 8/31![Southwest logo]()
$715
This Southwest deal was found by Cheapflights users on 8/31. 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 10/1510:55 pm -
1 stop14h 25m
Mon 10/191:05 pm -
1 stop13h 25m
Deal found 8/31![Southwest logo]()
$720
This Southwest deal was found by Cheapflights users on 8/28. 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 11/275:20 am -
2 stops9h 55m
Tue 12/111:50 am -
2 stops8h 40m
Deal found 8/28![Southwest logo]()
$725
Last-minute flights from Midway to Cabo San LucasDiscover last-minute flight deals from Midway to Cabo San Lucas. Data last updated September 1, 2026 and is based on user searches.
Discover last-minute flight deals from Midway to Cabo San Lucas. Data last updated September 1, 2026 and is based on user searches.
This Mytrip deal was found by Cheapflights users on 8/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/68:23 pm -
2 stops21h 36m
Sat 9/123:10 pm -
3 stops25h 54m
Deal found 8/28![Volaris logo]()
$589
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/98:23 pm -
1 stop20h 28m
Tue 10/133:36 pm -
1 stop25h 28m
Deal found 9/1![Volaris logo]()
$561
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/103:30 pm -
2 stops28h 30m
Sat 10/171:20 pm -
1 stop27h 44m
Deal found 8/28![Multiple Airlines logo]()
$577
This Southwest deal was found by Cheapflights users on 8/31. 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 10/186:00 am -
1 stop8h 05m
Fri 10/2311:05 am -
1 stop7h 55m
Deal found 8/31![Southwest logo]()
$596
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Fri 10/238:23 pm -
1 stop20h 28m
Fri 12/47:26 am -
1 stop8h 21m
Deal found 8/29![Multiple Airlines logo]()
$524
This Southwest deal was found by Cheapflights users on 8/31. 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 10/286:55 am -
1 stop8h 45m
Sun 11/13:45 pm -
1 stop13h 00m
Deal found 8/31![Southwest logo]()
$582
One-way flights from Midway to Cabo San LucasSearch for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
Search for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated September 1, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:23 pm -
2 stops24h 41m
Deal found 9/1![Volaris logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 8/29. 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.
Mon 9/288:23 pm -
1 stop18h 03m
Deal found 8/29![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 9/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:23 pm -
2 stops45h 36m
Deal found 9/1![Volaris logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/246:17 pm -
1 stop22h 43m
Deal found 8/28![Multiple Airlines logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/136:17 pm -
1 stop22h 41m
Deal found 8/28![Multiple Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 8/31. 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.
Sun 9/278:23 pm -
1 stop18h 03m
Deal found 8/31![Multiple Airlines logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sun 11/16:17 pm -
1 stop13h 30m
Deal found 8/30![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sun 2/286:17 pm -
1 stop24h 02m
Deal found 8/30![Multiple Airlines logo]()
$234
This Mytrip deal was found by Cheapflights users on 8/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:23 pm -
2 stops21h 36m
Deal found 8/27![Volaris logo]()
$235
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 September 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $511 (Kiwi.com) |
One-way from | $216 (Kiwi.com) |
Popular in | August |
Cheapest in | January |
Average price | $641 |
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 7,457,451 searches. Data last updated September 1, 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
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sat 11/14
7:35 am-2:20 pm
1 stop7h 45m
San José del Cabo Los Cabos
Tue 11/17
2:05 pm-12:10 am
1 stop9h 05m
$571
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Tue 11/3
6:05 am-1:10 pm
1 stop8h 05m
San José del Cabo Los Cabos
Mon 11/9
3:10 pm-5:40 am
1 stop13h 30m
$582
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Wed 10/28
9:00 am-1:40 pm
1 stop6h 40m
San José del Cabo Los Cabos
Sun 11/1
2:45 pm-1:05 am
2 stops9h 20m
$582
Quickest round-trip
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Mon 10/5
7:10 am-12:10 pm
1 stop7h 00m
San José del Cabo Los Cabos
Wed 10/14
11:05 am-10:00 pm
2 stops8h 55m
$648
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sat 10/3
7:20 am-12:50 pm
1 stop7h 30m
San José del Cabo Los Cabos
Thu 10/8
12:15 pm-12:30 am
1 stop10h 15m
$668
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Sat 10/3
6:35 am-12:50 pm
2 stops8h 15m
San José del Cabo Los Cabos
Tue 10/6
11:05 am-10:20 pm
2 stops9h 15m
$673
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Wed 10/14
6:05 am-1:40 pm
2 stops9h 35m
San José del Cabo Los Cabos
Mon 1/11
12:00 pm-11:00 pm
2 stops10h 00m
$698
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Fri 10/2
5:15 am-1:20 pm
2 stops10h 05m
San José del Cabo Los Cabos
Thu 10/8
12:15 pm-1:10 am
2 stops10h 55m
$715
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Thu 10/15
10:55 pm-11:20 am
1 stop14h 25m
San José del Cabo Los Cabos
Mon 10/19
1:05 pm-4:30 am
1 stop13h 25m
$720
ChicagoSan José del Cabo
MDW Chicago Midway - SJD San José del Cabo Los Cabos
MDWSJD
Chicago Midway
Fri 11/27
5:20 am-2:15 pm
2 stops9h 55m
San José del Cabo Los Cabos
Tue 12/1
11:50 am-9:30 pm
2 stops8h 40m
$725
Showing 1-10 of 17 resultsSorted by cheapest first
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.
MDW-SJD
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
MDW-C4B
MDW-SJD
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 September 1, 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.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentSarah,Aug 2024
MDW - AUS
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.
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Alternative routes for Midway to Cabo San Lucas
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Complete your trip
Complete your trip to Cabo San Lucas by adding a car rental and/or hotel reservation to your travel itinerary.
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Midway and Cabo San Lucas flights
Browse other Midway and Cabo San Lucas flight options. Last updated on September 1, 2026.
Other flights from Midway
Browse through other flights departing from Midway. Flights are based on user searches made on Cheapflights and were last updated on September 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Midway to Cabo San Lucas flights
Consider these flights traveling from Midway to Cabo San Lucas.
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 7,457,451 searches. Data last updated September 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$475 | Average$696 | FlexibilityNo cancel fee | On-time63% |