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Los Cabos

$152+ Cheap flights from Midway (MDW) to Los Cabos

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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
1 adult, Economy
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Cheap flight deals from Midway to Los Cabos

Keep the following information in mind while searching for Midway to Los Cabos flight deals. Data was last updated February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$413
(Kiwi.com)

One-way from

$152
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$649
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 Los Cabos
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One-way flight from Chicago Midway to Los Cabos
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Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 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 Los Cabos

Cheapest flights from Midway to Los Cabos
Explore the most affordable flight options available from Midway to Los Cabos. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/23. 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 3/288:39 pmMDW - SJD
1 stop13h 11mMultiple Airlines
Mon 3/311:20 pmSJD - MDW
2 stops22h 28mMultiple Airlines
Deal found 2/23$411
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Mon 3/318:39 pmMDW - SJD
1 stop13h 11mVolaris
Tue 4/88:22 amSJD - MDW
1 stop8h 44mVolaris
Deal found 2/21$413
This Delta deal was found by Cheapflights users on 2/22. 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 3/256:02 amSJD - MDW
2 stops14h 21mDelta
Deal found 2/22$511
This Southwest deal was found by Cheapflights users on 2/22. 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 4/225:50 amMDW - SJD
1 stop7h 40mSouthwest
Tue 4/2911:40 amSJD - MDW
2 stops9h 30mSouthwest
Deal found 2/22$550
This Frontier deal was found by Cheapflights users on 2/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/56:15 amMDW - SJD
1 stop6h 41mFrontier
Sat 7/1212:16 pmSJD - MDW
1 stop10h 11mFrontier
Deal found 2/22$582
This Aeromexico deal was found by Cheapflights users on 2/22. 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.
Mon 3/36:00 amMDW - SJD
1 stop9h 11mAeromexico
Wed 3/51:41 pmSJD - MDW
1 stop7h 39mAeromexico
Deal found 2/22$601

Find flights from Midway to Los Cabos within your budget

Customize your flight search to find flights from Midway to Los Cabos 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 23, 2025.

Fly from

Midway

Fly to

Los Cabos

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 3/28

8:39 pm-7:50 am

1 stop13h 11m

San José del Cabo Los Cabos

Mon 3/31

1:20 pm-1:48 pm

2 stops22h 28m

$411

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 3/31

8:39 pm-7:50 am

1 stop13h 11m

San José del Cabo Los Cabos

Tue 4/8

8:22 am-7:06 pm

1 stop8h 44m

$413

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 3/30

6:00 am-11:28 am

1 stop7h 28m

San José del Cabo Los Cabos

Wed 4/9

12:31 pm-10:21 pm

1 stop7h 50m

$528

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/22

5:50 am-11:30 am

1 stop7h 40m

San José del Cabo Los Cabos

Tue 4/29

11:40 am-11:10 pm

2 stops9h 30m

$550

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 7/5

6:15 am-10:56 am

1 stop6h 41m

San José del Cabo Los Cabos

Sat 7/12

12:16 pm-12:27 am

1 stop10h 11m

$582

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/1

7:50 am-11:16 am

2 stops29h 26m

$152

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 4/5

8:39 pm-11:21 am

1 stop16h 42m

$158

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/25

6:00 am-1:05 pm

1 stop9h 05m

$233

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 11 results
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Best time to book a flight from Midway to Los Cabos

Have a flexible travel schedule? Discover the best time to fly to Los Cabos 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 Los Cabos

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

What is the cheapest month to book a flight from Chicago Midway Airport to Los Cabos?

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $437). Flying from Chicago Midway Airport to Los Cabos 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 Los Cabos by month

Plan your trip to Los Cabos by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Los Cabos 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 Los Cabos when rainfall is around 0.0 in.

Temperature in Los Cabos by month

Plan your trip to Los Cabos by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Los Cabos, 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 Los Cabos

Get insights into the airlines that provide service to Los Cabos. 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 Los Cabos. Reviews last updated February 23, 2025.
To help decide which airline to fly from Chicago to Los Cabos, see what other customers have to say about Southwest, Delta and Aeromexico. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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
1,767 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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
1,207 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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
3,352 reviews
Southwest
8.1
Very good
4,395 reviews

Entertainment

7.6

Food

7.1

Overall

8.1

Boarding

8.2

Crew

8.7

Comfort

8.1

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 Los Cabos. 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 Los Cabos one-way?

    One-way options have recently been found by users for as low as $155 on Frontier. Other airlines that offer cheap prices include Volaris from $158 and Delta from $233 one-way.

  • What are the cheapest flights from Chicago Midway Airport to Los Cabos?

    On average you can expect to pay $795 for a flight from Chicago Midway Airport to Los Cabos. The cheapest flight overall is $618 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $374.

  • Can I find deals for flights from Midway to Los Cabos that include hotel bookings?

    Yes. In addition to deals on Midway to Los Cabos flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Los Cabos?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Los Cabos.

  • Can I find deals for business class flights from Midway to Los Cabos?

    Yes. Cheapflights offers flight deals from Midway to Los Cabos 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 Los Cabos?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Los Cabos (average of $437). Flying from Chicago Midway Airport to Los Cabos 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 Los Cabos

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 Los Cabos

Discover the top 2 airlines that operate flights from Midway to Los Cabos. 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 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$496Average$992FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$543Average$707FlexibilityNo cancel feeOn-time63%
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