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Cabo San Lucas

$151+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
ene. 26 — feb. 21
dom. 1/26
dom. 2/2
1 adult, Economy
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Cheap flight deals from Midway to Cabo San Lucas

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cabo San Lucas (C4B). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 21, 2025.

Round-trip from

$416
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$563
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 ($68 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 January 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 enero 21, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
sáb. 2/227:55 pmMDW - SJD
1 stop12h 35mMultiple Airlines
mar. 3/47:57 pmSJD - MDW
1 stop11h 48mMultiple Airlines
Deal found 1/21$419
This Mytrip deal was found by Cheapflights users on 1/21. 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.
dom. 2/237:55 pmMDW - SJD
1 stop12h 36mVolaris
dom. 3/24:10 pmSJD - MDW
2 stops15h 35mVolaris
Deal found 1/21$433
This FlightHub deal was found by Cheapflights users on 1/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/286:40 amMDW - SJD
1 stop27h 44mFrontier
sáb. 3/810:44 amSJD - MDW
1 stop12h 33mFrontier
Deal found 1/21$476
This Southwest deal was found by Cheapflights users on 1/21. 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.
dom. 3/210:35 pmMDW - SJD
1 stop14h 05mSouthwest
lun. 3/101:00 pmSJD - MDW
Nonstop4h 00mSouthwest
Deal found 1/21$529
This Delta deal was found by Cheapflights users on 1/21. 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.
mar. 3/46:00 amMDW - SJD
1 stop7h 36mDelta
mar. 3/1112:42 pmSJD - MDW
1 stop7h 41mDelta
Deal found 1/21$538
This Aeromexico deal was found by Cheapflights users on 1/21. 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.
jue. 2/276:00 amMDW - SJD
1 stop9h 11mAeromexico
mar. 3/41:41 pmSJD - MDW
1 stop7h 39mAeromexico
Deal found 1/21$563

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 enero 21, 2025.

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Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

sáb. 2/1

7:55 pm-7:30 am

1 stop12h 35m

San José del Cabo Los Cabos

mar. 2/11

5:08 pm-8:45 am

1 stop14h 37m

$416

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 2/7

7:55 pm-10:42 am

1 stop15h 47m

San José del Cabo Los Cabos

mié. 2/12

4:10 pm-8:45 am

2 stops15h 35m

$417

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

dom. 3/2

10:35 pm-11:40 am

1 stop14h 05m

San José del Cabo Los Cabos

lun. 3/10

1:00 pm-7:00 pm

Nonstop4h 00m

$529

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mar. 3/4

6:00 am-12:36 pm

1 stop7h 36m

San José del Cabo Los Cabos

mar. 3/11

12:42 pm-10:23 pm

1 stop7h 41m

$538

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 2/10

6:00 am-2:11 pm

1 stop9h 11m

San José del Cabo Los Cabos

sáb. 2/15

1:41 pm-10:20 pm

1 stop7h 39m

$593

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 3/7

6:40 am-9:24 am

1 stop27h 44m

San José del Cabo Los Cabos

sáb. 3/15

9:44 am-12:17 am

1 stop12h 33m

$640

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 2/26

6:00 am-3:15 pm

2 stops34h 15m

$151

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

vie. 2/28

8:14 pm-9:24 am

2 stops14h 10m

$158

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

lun. 5/12

8:39 pm-7:33 am

1 stop12h 54m

$176

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

mié. 4/2

6:00 am-1:05 pm

1 stop9h 05m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 11 results
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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 enero 21, 2025.
See what other customers who have flown with 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
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Aeromexico
7.5
Good
1,849 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Volaris
6.7
Okay
1,249 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Overall

8.1

Food

7.2

Entertainment

7.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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?

    $158 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 $176 and $251, respectively.

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

    On average you can expect to pay $775 for a flight from Chicago Midway Airport to Cabo San Lucas. The cheapest flight overall is $382 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $373.

  • 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
O'Hare Intl to Loreto flights
Midway to La Paz 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 enero 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$496Average$749FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$734FlexibilityNo cancel feeOn-time63%
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