What are the cheapest airlines to fly from Chicago Midway Airport to Cabo San Lucas one-way?

$212 is the cheapest one-way deal found within the past few days, from Aeromexico. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $221 and $230, respectively.

What is the cheapest day to fly from Chicago Midway Airport to Cabo San Lucas?

Travelers seeking maximum savings on their Chicago Midway Airport to Cabo San Lucas flight should consider departing on Tuesday mornings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

How far in advance should I book a flight from Chicago Midway Airport to Cabo San Lucas?

To save on the cost of your flight from Chicago Midway Airport to Cabo San Lucas, book at least 50 days before your planned departure. Booking around this time can save you about 34% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $527 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $737.

What is the cheapest month to fly from Chicago Midway Airport to Cabo San Lucas?

Our data shows that July tends to be the cheapest month to fly to Cabo San Lucas from Chicago Midway Airport. Users have commonly found prices around $610 for the month, but tickets can be as low as $352. Due to multiple factors, prepare for potentially higher prices in December.

What is the cheapest time of day to fly from MDW to C4B?

When flying from Chicago Midway Airport to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

$155+ Flights from Chicago Midway Airport to Cabo San Lucas

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1. Tell us where you want to go

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Cheap flight deals from Midway to Cabo San Lucas

Most accurate provider	AranGrant 3 stars
Most trusted provider	AranGrant 3 stars
Round-trip from	$486 (Delta)
One-way from	$155 (Kiwi.com)
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 ($69 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 24, 2025.

Sat 6/76:00 amMDW - SJD

2 stops14h 13mDelta

Sat 6/146:03 amSJD - MDW

2 stops13h 42mDelta

Deal found 4/23

$486

Sun 6/226:00 amMDW - SJD

1 stop6h 40mSouthwest

Fri 6/271:05 pmSJD - MDW

1 stop10h 00mSouthwest

Deal found 4/23

$531

Wed 6/412:48 pmMDW - SJD

2 stops10h 49mAeromexico

Thu 6/56:03 amSJD - MDW

2 stops13h 24mAeromexico

Deal found 4/23

$552

Fri 8/18:39 pmMDW - SJD

1 stop13h 14mVolaris

Mon 8/48:29 amSJD - MDW

1 stop8h 47mVolaris

Deal found 4/23

$558

Fri 8/16:00 amMDW - SJD

2 stops13h 45mMultiple Airlines

Mon 8/48:29 amSJD - MDW

1 stop8h 47mMultiple Airlines

Deal found 4/23

$563

Best flights from Midway to Cabo San Lucas
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 April 24, 2025.

Sat 6/76:00 amMDW - SJD

1 stop7h 43mDelta

Sat 6/146:03 amSJD - MDW

2 stops13h 42mDelta

Deal found 4/23

$486

Sat 5/178:00 amMDW - SJD

1 stop7h 00mSouthwest

Wed 5/2111:40 amSJD - MDW

1 stop9h 10mSouthwest

Deal found 4/23

$516

Wed 6/412:48 pmMDW - SJD

2 stops10h 49mAeromexico

Thu 6/56:03 amSJD - MDW

2 stops13h 24mAeromexico

Deal found 4/23

$552

Fri 8/18:39 pmMDW - SJD

1 stop13h 14mVolaris

Mon 8/48:29 amSJD - MDW

1 stop8h 47mVolaris

Deal found 4/23

$558

Fri 8/16:00 amMDW - SJD

2 stops13h 45mMultiple Airlines

Mon 8/48:29 amSJD - MDW

1 stop8h 47mMultiple Airlines

Deal found 4/23

$563

Last-minute flights from Midway to Cabo San Lucas
Discover last-minute flight deals from Midway to Cabo San Lucas. Data last updated April 24, 2025 and is based on user searches.

Mon 4/2810:41 pmMDW - SJD

2 stops15h 33mMultiple Airlines

Sat 5/38:22 amSJD - MDW

1 stop8h 44mMultiple Airlines

Deal found 4/23

$645

Mon 4/285:25 amMDW - SJD

1 stop8h 05mSouthwest

Sat 5/310:25 amSJD - MDW

1 stop7h 15mSouthwest

Deal found 4/23

$670

Thu 5/18:39 pmMDW - SJD

1 stop13h 08mVolaris

Mon 5/59:02 pmSJD - MDW

2 stops20h 04mVolaris

Deal found 4/23

$731

Sat 5/36:04 amMDW - SJD

2 stops13h 13mDelta

Sat 5/106:06 amSJD - MDW

2 stops13h 08mDelta

Deal found 4/23

$486

Sat 5/36:04 amMDW - SJD

1 stop7h 06mAeromexico

Sat 5/101:48 pmSJD - MDW

1 stop23h 42mAeromexico

Deal found 4/23

$698

Thu 5/158:39 pmMDW - SJD

1 stop13h 08mVolaris

Sun 5/1812:01 pmSJD - MDW

1 stop29h 05mVolaris

Deal found 4/22

$660

Sat 5/176:00 amMDW - SJD

1 stop7h 43mDelta

Wed 5/216:06 amSJD - MDW

2 stops13h 21mDelta

Deal found 4/23

$486

Sat 5/178:00 amMDW - SJD

1 stop7h 00mSouthwest

Wed 5/2111:40 amSJD - MDW

1 stop9h 10mSouthwest

Deal found 4/23

$516

One-way flights from Midway to Cabo San Lucas
Search for one-way flight options from Midway to Cabo San Lucas. Find affordable one-way fares based on user searches. Data last updated April 24, 2025.

Sun 5/257:45 amMDW - SJD

3 stops26h 55mMultiple Airlines

Deal found 4/23

$155

Sun 5/256:00 amMDW - SJD

1 stop7h 43mAeromexico

Deal found 4/23

$212

Sat 6/286:00 amMDW - SJD

1 stop8h 37mDelta

Deal found 4/24

$221

Fri 8/112:35 pmMDW - SJD

1 stop24h 00mFrontier

Deal found 4/23

$230

Sun 8/176:00 amMDW - SJD

1 stop9h 10mSouthwest

Deal found 4/23

$231

Sat 5/249:59 pmMDW - SJD

1 stop22h 08mVolaris

Deal found 4/23

$294

Cheapflights Fare Finder

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

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/7

6:00 am-12:43 pm

1 stop8h 43m

San José del Cabo Los Cabos

Sat 6/14

6:03 am-9:45 pm

2 stops13h 42m

$486

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 5/17

8:00 am-1:00 pm

1 stop7h 00m

San José del Cabo Los Cabos

Wed 5/21

11:40 am-10:50 pm

1 stop9h 10m

$516

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 6/4

12:48 pm-9:37 pm

2 stops10h 49m

San José del Cabo Los Cabos

Thu 6/5

6:03 am-9:27 pm

2 stops13h 24m

$552

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/1

8:39 pm-7:53 am

1 stop13h 14m

San José del Cabo Los Cabos

Mon 8/4

8:29 am-7:16 pm

1 stop8h 47m

$558

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/1

6:00 am-5:45 pm

2 stops13h 45m

San José del Cabo Los Cabos

Mon 8/4

8:29 am-7:16 pm

1 stop8h 47m

$563

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 5/25

7:45 am-8:40 am

3 stops26h 55m

$155

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 5/25

6:00 am-11:43 am

1 stop7h 43m

$212

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 6/28

6:00 am-12:37 pm

1 stop8h 37m

$221

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/1

12:35 pm-10:35 am

1 stop24h 00m

$230

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 8/17

6:00 am-1:10 pm

1 stop9h 10m

$231

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

Showing 1-10 of 11 results

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

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

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

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

4,286 reviews

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

4,286 reviews

Southwest

8.0

Very good

4,286 reviews

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

7,920 reviews

Southwest

8.0

Very good

4,286 reviews

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

1,700 reviews

Southwest

8.0

Very good

4,286 reviews

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

1,172 reviews

Southwest

8.0

Very good

4,286 reviews

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!

Frontier

6.0

Okay

3,283 reviews

Southwest

8.0

Very good

4,286 reviews

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

What are the cheapest airlines to fly from Chicago Midway Airport to Cabo San Lucas one-way?
$212 is the cheapest one-way deal found within the past few days, from Aeromexico. You may also be able to find cheap deals on Delta and Frontier, with prices starting from $221 and $230, 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

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Midway to Cabo San Lucas

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 airline flying from Midway to Cabo San Lucas

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$545	Average$720	FlexibilityNo cancel fee	On-time63%

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$155+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to Cabo San Lucas with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

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 24, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Midway to Cabo San Lucas

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 April 24, 2025.

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 24, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to Cabo San Lucas that are best for you.

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.

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?

Rainfall in Cabo San Lucas by month

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

Temperature in Cabo San Lucas by month

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

Reviews of airlines servicing Cabo San Lucas

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.

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?

Can I find deals for flights from Midway to Cabo San Lucas that include hotel bookings?

How can I find direct flights from Midway to Cabo San Lucas?

Can I find deals for business class flights from Midway to Cabo San Lucas?

What is the cheapest month to book a flight from Chicago Midway Airport to Cabo San Lucas?

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.

Top airline flying from Midway to Cabo San Lucas

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Travel Smart

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 24, 2025.