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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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$417
(Kiwi.com)

One-way from

$145
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$816
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. 7% potential increase in price ($57 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 February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop20h 20mMultiple Airlines
Sun 3/25:49 pmSJD - MDW
1 stop14h 56mMultiple Airlines
Deal found 2/20$417
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 2/277:55 pmMDW - SJD
1 stop21h 28mVolaris
Wed 3/56:19 pmSJD - MDW
1 stop13h 26mVolaris
Deal found 2/20$420
This Delta deal was found by Cheapflights users on 2/20. 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 3/186:00 amMDW - SJD
1 stop9h 05mDelta
Tue 3/2512:37 pmSJD - MDW
1 stop7h 46mDelta
Deal found 2/20$511
This Southwest deal was found by Cheapflights users on 2/20. 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 3/3110:40 pmMDW - SJD
1 stop14h 00mSouthwest
Tue 4/812:30 pmSJD - MDW
2 stops14h 50mSouthwest
Deal found 2/20$533
This Aeromexico deal was found by Cheapflights users on 2/19. 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.
Sat 4/196:04 amMDW - SJD
2 stops14h 13mAeromexico
Thu 4/2412:15 pmSJD - MDW
1 stop8h 11mAeromexico
Deal found 2/19$570

Find flights from Midway to Cabo San Lucas within your budget

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 February 20, 2025.

Fly from

Midway

Fly to

Cabo San Lucas

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/1

8:50 pm-11:20 am

1 stop16h 30m

San José del Cabo Los Cabos

Mon 4/7

9:15 am-10:41 pm

3 stops11h 26m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/2

11:00 am-5:19 pm

1 stop7h 19m

San José del Cabo Los Cabos

Mon 3/10

8:29 am-7:10 pm

1 stop8h 41m

$420

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/18

6:00 am-1:05 pm

1 stop9h 05m

San José del Cabo Los Cabos

Tue 3/25

12:37 pm-10:23 pm

1 stop7h 46m

$511

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 4/6

9:10 am-12:10 pm

Nonstop5h 00m

San José del Cabo Los Cabos

Wed 4/9

11:40 am-8:15 pm

1 stop6h 35m

$541

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 4/19

6:04 am-6:17 pm

2 stops14h 13m

San José del Cabo Los Cabos

Thu 4/24

12:15 pm-10:26 pm

1 stop8h 11m

$570

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 4/2

6:00 am-11:16 am

2 stops31h 16m

$145

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/14

6:15 am-10:56 am

1 stop6h 41m

$153

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 3/15

8:39 pm-7:50 am

1 stop13h 11m

$165

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/25

6:00 am-11:32 am

1 stop7h 32m

$233

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/31

9:00 am-12:00 pm

Nonstop5h 00m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 11 results
1
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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.

Travel insights for flights from Midway to Cabo San Lucas

Get recent, data-driven insights about flights from Midway to Cabo San Lucas including ideal travel times, pricing trends, and more.

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 February 20, 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
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,771 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Volaris
6.7
Okay
1,209 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Food

7.1

Entertainment

7.6

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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?

    $153 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 $165 and $233, respectively.

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

    On average you can expect to pay $795 for a flight from Chicago Midway Airport to Cabo San Lucas. The cheapest flight overall is $618 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $375.

  • 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 2 airlines flying from Midway to Cabo San Lucas

Discover the top 2 airlines 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$496Average$992FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%
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