What are the cheapest airlines flying from Chicago Midway Airport to San José del Cabo round-trip?

According to our current data, Delta ($400), Southwest ($431), and Aeromexico ($546) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Delta is 43% cheaper than the average price of flights available within the next 90 days to this destination.

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

Travelers seeking maximum savings on their Chicago Midway Airport to San José del Cabo 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.

In terms of precipitation, rainfall in San José del Cabo 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 San José del Cabo when rainfall is around 0.0 in.

If weather is an important factor for your trip to San José del Cabo, 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).

What is the cheapest day to fly round-trip from Chicago Midway Airport to San José del Cabo?

Friday flights are found to be more expensive to fly from Chicago Midway Airport to San José del Cabo. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to San José del Cabo.

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

Travelers have found it’s best to book a flight 50 days in advance to save up to 39% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 50 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago Midway Airport to San José del Cabo 1-2 weeks in advance for as low as $561, or $721 for flights within the next 24 hours.

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

Flights from Chicago Midway Airport to San José del Cabo lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to San José del Cabo in July, with the cheapest ticket starting at $348.

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

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

What airport do you fly into for flights to San José del Cabo from Chicago Midway?

Located just 6.6 mi from the city center, San José del Cabo Los Cabos is the airport most travelers will use when flying to San José del Cabo from Chicago Midway. Booking flights from Chicago Midway to Los Cabos (SJD) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

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

Yes. In addition to deals on Midway to San José del Cabo flights, Cheapflights offers vacation packages that include both flights and hotel.

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

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

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

Yes. Cheapflights offers flight deals from Midway to San José del Cabo by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$148+ Flights from Chicago Midway Airport to San José del Cabo

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Cheap flight deals from Midway to San José del Cabo

Round-trip from	$400 (Delta)
One-way from	$148 (Kiwi.com)
Popular in	November
Cheapest in	August
Average price	$714

From Chicago Midway to San José del Cabo Los Cabos

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One-way flight from Chicago Midway to San José del Cabo Los Cabos

Search Deals

Highest demand for flights based on searches. 7% potential increase in price ($56 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 July 2025

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Find flight deals from Midway to San José del Cabo

Cheapest flights from Midway to San José del Cabo
Explore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Mon 8/186:04 amMDW - SJD

1 stop7h 19mDelta

Fri 8/226:10 amSJD - MDW

2 stops13h 34mDelta

Deal found 7/1

$400

Tue 8/128:39 pmMDW - SJD

1 stop16h 32mMultiple Airlines

Fri 8/157:25 amSJD - MDW

1 stop9h 51mMultiple Airlines

Deal found 7/3

$423

Mon 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

Wed 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

Fri 9/196:00 amMDW - SJD

2 stops18h 30mAeromexico

Mon 9/227:55 pmSJD - MDW

2 stops23h 41mAeromexico

Deal found 7/2

$546

Best flights from Midway to San José del Cabo
Discover carefully curated flight deals from Midway to San José del Cabo that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 3, 2025.

Mon 8/186:04 amMDW - SJD

1 stop7h 19mDelta

Fri 8/226:10 amSJD - MDW

2 stops13h 34mDelta

Deal found 7/1

$400

Tue 8/128:39 pmMDW - SJD

1 stop16h 32mMultiple Airlines

Fri 8/157:25 amSJD - MDW

1 stop9h 51mMultiple Airlines

Deal found 7/3

$423

Mon 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

Wed 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

Fri 9/196:00 amMDW - SJD

2 stops18h 30mAeromexico

Mon 9/227:55 pmSJD - MDW

2 stops23h 41mAeromexico

Deal found 7/2

$546

Last-minute flights from Midway to San José del Cabo
Discover last-minute flight deals from Midway to San José del Cabo. Data last updated July 3, 2025 and is based on user searches.

Fri 7/1112:43 pmMDW - SJD

2 stops11h 17mDelta

Fri 7/186:01 amSJD - MDW

2 stops13h 41mDelta

Deal found 7/1

$884

Sat 7/125:20 amMDW - SJD

1 stop10h 10mSouthwest

Sat 7/1911:55 amSJD - MDW

1 stop7h 05mSouthwest

Deal found 7/3

$511

Sat 7/128:39 pmMDW - SJD

1 stop16h 32mVolaris

Sat 7/194:50 pmSJD - MDW

2 stops24h 26mVolaris

Deal found 7/3

$881

Mon 7/145:15 amMDW - SJD

1 stop5h 35mSouthwest

Wed 7/1611:55 amSJD - MDW

1 stop10h 55mSouthwest

Deal found 7/1

$431

Wed 7/306:00 amMDW - SJD

1 stop7h 22mAeromexico

Wed 8/612:27 pmSJD - MDW

1 stop27h 20mAeromexico

Deal found 7/1

$612

Fri 8/88:39 pmMDW - SJD

2 stops21h 31mVolaris

Mon 8/118:17 pmSJD - MDW

3 stops20h 59mVolaris

Deal found 7/1

$558

Tue 8/128:39 pmMDW - SJD

1 stop16h 32mMultiple Airlines

Fri 8/157:25 amSJD - MDW

1 stop9h 51mMultiple Airlines

Deal found 7/3

$423

Mon 8/186:04 amMDW - SJD

1 stop7h 19mDelta

Fri 8/226:10 amSJD - MDW

2 stops13h 34mDelta

Deal found 7/1

$400

One-way flights from Midway to San José del Cabo
Search for one-way flight options from Midway to San José del Cabo. Find affordable one-way fares based on user searches. Data last updated July 3, 2025.

Mon 9/17:45 amMDW - SJD

2 stops32h 15mMultiple Airlines

Deal found 7/1

$148

Fri 8/1512:35 pmMDW - SJD

1 stop24h 00mFrontier

Deal found 7/3

$168

Mon 8/118:39 pmMDW - SJD

1 stop16h 32mVolaris

Deal found 7/3

$170

Tue 9/236:00 amMDW - SJD

1 stop7h 25mDelta

Deal found 7/3

$179

Sat 9/2011:00 amMDW - SJD

2 stops26h 30mAeromexico

Deal found 7/2

$185

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/18

6:04 am-11:23 am

1 stop7h 19m

San José del Cabo Los Cabos

Fri 8/22

6:10 am-9:44 pm

2 stops13h 34m

$400

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 8/12

8:39 pm-11:11 am

1 stop16h 32m

San José del Cabo Los Cabos

Fri 8/15

7:25 am-7:16 pm

1 stop9h 51m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 7/14

5:15 am-8:50 am

1 stop5h 35m

San José del Cabo Los Cabos

Wed 7/16

11:55 am-12:50 am

1 stop10h 55m

$431

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 9/19

6:00 am-10:30 pm

2 stops18h 30m

San José del Cabo Los Cabos

Mon 9/22

7:55 pm-9:36 pm

2 stops23h 41m

$546

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/8

8:39 pm-4:10 pm

2 stops21h 31m

San José del Cabo Los Cabos

Mon 8/11

8:17 pm-7:16 pm

3 stops20h 59m

$558

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 9/1

7:45 am-2:00 pm

2 stops32h 15m

$148

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 8/15

12:35 pm-10:35 am

1 stop24h 00m

$168

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 8/11

8:39 pm-11:11 am

1 stop16h 32m

$170

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 9/23

6:00 am-2:49 pm

2 stops10h 49m

$179

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 9/20

11:00 am-11:30 am

2 stops26h 30m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Best time to book a flight from Midway to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo 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 San José del Cabo

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

Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $437). Flying from Chicago Midway Airport to San José del Cabo in March is currently the most expensive (average of $549). 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.

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from Chicago Midway Airport to San José del Cabo to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Southwest

8.0

Very good

4,266 reviews

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Delta

8.0

Very good

7,982 reviews

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Aeromexico

7.5

Good

1,718 reviews

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Volaris

6.7

Okay

1,171 reviews

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Frontier

5.9

Fair

3,286 reviews

Southwest

8.0

Very good

4,266 reviews

Reviews

1 / 20

8.0

Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Related info for your journey

What airport do you fly into for flights to San José del Cabo from Chicago Midway?
Located just 6.6 mi from the city center, San José del Cabo Los Cabos is the airport most travelers will use when flying to San José del Cabo from Chicago Midway. Booking flights from Chicago Midway to Los Cabos (SJD) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.
What are the cheapest airlines flying from Chicago Midway Airport to San José del Cabo round-trip?
According to our current data, Delta ($400), Southwest ($431), and Aeromexico ($546) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Delta is 43% cheaper than the average price of flights available within the next 90 days to this destination.
What are the cheapest airlines to fly from Chicago Midway Airport to San José del Cabo one-way?
The cheapest airlines for a one-way flight from Chicago Midway Airport to San José del Cabo are Frontier ($168), Volaris ($170), and Delta ($179).
Can I find deals for flights from Midway to San José del Cabo that include hotel bookings?
Yes. In addition to deals on Midway to San José del Cabo flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Midway to San José del Cabo?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to San José del Cabo.
Can I find deals for business class flights from Midway to San José del Cabo?
Yes. Cheapflights offers flight deals from Midway to San José del Cabo 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 San José del Cabo?
Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to San José del Cabo (average of $437). Flying from Chicago Midway Airport to San José del Cabo in March is currently the most expensive (average of $549). 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

Top airline flying from Midway to San José del Cabo

Airline	Cheapest	Average	Flexibility	On-time
Southwest	Cheapest$543	Average$714	FlexibilityNo cancel fee	On-time63%

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$148+ Cheap flights from Midway (MDW) to San José del Cabo (SJD)

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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Midway to San José del Cabo with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Midway to San José del Cabo

Round-trip from

One-way from

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Cheapest in

Average price

Find flight deals from Midway to San José del Cabo

Cheapest flights from Midway to San José del CaboExplore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Explore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Midway to San José del Cabo

Have a flexible travel schedule? Discover the best time to fly to San José del Cabo from Midway with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to San José del Cabo

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

Reviews of airlines servicing San José del Cabo

Peruse reviews from past customers who have flown with Southwest, Delta, and Aeromexico from Chicago Midway Airport to San José del Cabo to help guide your decision. You can also see how each airline stacks up 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 San José del Cabo. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly into for flights to San José del Cabo from Chicago Midway?

What are the cheapest airlines flying from Chicago Midway Airport to San José del Cabo round-trip?

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

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

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

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

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

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 San José del Cabo

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Midway to San José del Cabo

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Cheapest flights from Midway to San José del Cabo
Explore the most affordable flight options available from Midway to San José del Cabo. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.