San José del Cabo

$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.
MDW — SJD
Jul 8 — Jul 151
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Cheap flight deals from Midway to San José del Cabo

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José del Cabo (SJD). 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 July 3, 2025.

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
One-way flight from Chicago Midway to San José del Cabo Los Cabos
Highest demand for flights based on searches. 7% potential increase in price ($56 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($34 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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.

This Delta deal was found by Cheapflights users on 7/1. 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.
Mon 8/186:04 amMDW - SJD
1 stop7h 19mDelta
Fri 8/226:10 amSJD - MDW
2 stops13h 34mDelta
Deal found 7/1$400
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
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
This Southwest deal was found by Cheapflights users on 7/1. 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 7/145:15 amMDW - SJD
1 stop5h 35mSouthwest
Wed 7/1611:55 amSJD - MDW
1 stop10h 55mSouthwest
Deal found 7/1$431
This Aeromexico deal was found by Cheapflights users on 7/2. 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.
Fri 9/196:00 amMDW - SJD
2 stops18h 30mAeromexico
Mon 9/227:55 pmSJD - MDW
2 stops23h 41mAeromexico
Deal found 7/2$546

Cheapflights Fare Finder

Customize your flight search to find flights from Midway to San José del Cabo 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 July 3, 2025.
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

Midway

Fly to

San José del Cabo

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

Get insights into the airlines that provide service to San José del Cabo. 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 San José del Cabo. Reviews last updated July 3, 2025.
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.

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.
8.0
Very good

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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.

Overall

8.0

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.2

Entertainment

7.6

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

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?

    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

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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

Discover the top airline that operate flights from Midway to San José del Cabo. 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$543Average$714FlexibilityNo cancel feeOn-time63%

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