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Cabo San Lucas

$193+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$430
(Delta)

One-way from

$193
(Southwest)

Popular in

November

Cheapest in

January

Average price

$700
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. 8% potential increase in price ($70 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($36 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/136:00 amMDW - SJD
1 stop7h 30mDelta
Fri 6/206:03 amSJD - MDW
2 stops13h 42mDelta
Deal found 4/29$430
This Southwest deal was found by Cheapflights users on 4/29. 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.
Tue 7/85:15 amMDW - SJD
1 stop9h 05mSouthwest
Sat 7/1211:55 amSJD - MDW
1 stop7h 05mSouthwest
Deal found 4/29$458
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 5/58:39 pmMDW - SJD
1 stop13h 08mVolaris
Sat 5/108:22 amSJD - MDW
1 stop8h 44mVolaris
Deal found 4/29$495
This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Thu 8/78:39 pmMDW - SJD
1 stop12h 16mMultiple Airlines
Sun 8/108:29 amSJD - MDW
1 stop8h 47mMultiple Airlines
Deal found 4/29$560
This SmartFares deal was found by Cheapflights users on 4/29. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/136:00 amMDW - SJD
1 stop7h 30mAeromexico
Fri 6/2012:35 pmSJD - MDW
1 stop25h 06mAeromexico
Deal found 4/29$592

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 April 29, 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

Fri 6/13

6:00 am-11:30 am

1 stop7h 30m

San José del Cabo Los Cabos

Fri 6/20

6:03 am-9:45 pm

2 stops13h 42m

$430

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 7/20

6:00 am-10:40 am

1 stop6h 40m

San José del Cabo Los Cabos

Fri 7/25

10:05 am-9:55 pm

1 stop9h 50m

$458

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 5/5

8:39 pm-7:47 am

1 stop13h 08m

San José del Cabo Los Cabos

Sat 5/10

8:22 am-7:06 pm

1 stop8h 44m

$495

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 6/10

6:00 am-6:13 pm

2 stops14h 13m

San José del Cabo Los Cabos

Sat 6/14

6:03 am-9:45 pm

2 stops13h 42m

$520

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/3

8:39 pm-7:30 am

1 stop12h 51m

San José del Cabo Los Cabos

Wed 5/7

6:06 am-8:08 pm

2 stops12h 02m

$673

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 6/9

5:15 am-9:05 am

1 stop5h 50m

$193

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 6/16

4:01 pm-8:35 pm

2 stops30h 34m

$197

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/28

12:44 pm-9:51 pm

2 stops11h 07m

$221

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 6/18

9:21 am-1:14 pm

3 stops29h 53m

$389

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 6/23

10:44 pm-7:54 pm

3 stops23h 10m

$523

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 June is currently the most expensive (average of $560). 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.

Rainfall in Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cabo San Lucas ranges from 0.0 - 4.5 inches per month. September is typically the wettest month, when rainfall can reach 4.5 in. March is typically the driest time to visit Cabo San Lucas when rainfall is around 0.0 in.

Temperature in Cabo San Lucas by month

Plan your trip to Cabo San Lucas by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cabo San Lucas, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 66.2 F).

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 April 29, 2025.
See what other customers who have flown with Southwest, Delta and Aeromexico from Chicago to Cabo San Lucas have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Aeromexico
7.5
Good
1,698 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
WestJet
7.2
Good
2,823 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Volaris
6.7
Okay
1,174 reviews
Southwest
8.0
Very good
4,295 reviews

Entertainment

7.6

Boarding

8.2

Comfort

8.0

Food

7.1

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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?

    $193 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and WestJet, with prices starting from $221 and $389, 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 June is currently the most expensive (average of $560). 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
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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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