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San José del Cabo

$116+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJD
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$423
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$563
Provider with most accurate pricing for Chicago Midway-San José del Cabo Los Cabos flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San José del Cabo Los Cabos flights.
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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
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High demand for flights, 10% potential price rise
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Best time to find cheap flights, 5% potential price drop
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Average for round-trip flights in January 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 January 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 1/14. 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.
Wed 2/197:55 pmMDW - SJD
1 stop20h 20mMultiple Airlines
Mon 2/245:08 pmSJD - MDW
1 stop14h 37mMultiple Airlines
Deal found 1/14$423
This Kiwi.com deal was found by Cheapflights users on 1/15. 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.
Wed 2/1911:00 amMDW - SJD
1 stop7h 19mVolaris
Wed 2/266:19 pmSJD - MDW
1 stop13h 26mVolaris
Deal found 1/15$424
This Cheapflightsfares deal was found by Cheapflights users on 1/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:40 amMDW - SJD
1 stop27h 44mFrontier
Sat 3/810:44 amSJD - MDW
1 stop12h 33mFrontier
Deal found 1/15$476
This eDestinos deal was found by Cheapflights users on 1/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/106:00 amMDW - SJD
1 stop7h 36mAeromexico
Fri 2/141:41 pmSJD - MDW
1 stop7h 39mAeromexico
Deal found 1/15$515
This Delta deal was found by Cheapflights users on 1/16. 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.
Sun 2/236:00 amMDW - SJD
2 stops12h 27mDelta
Thu 2/276:02 amSJD - MDW
2 stops15h 18mDelta
Deal found 1/16$538
This Southwest deal was found by Cheapflights users on 1/15. 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 3/35:20 amMDW - SJD
1 stop7h 20mSouthwest
Fri 3/72:00 pmSJD - MDW
Nonstop4h 00mSouthwest
Deal found 1/15$573

Find flights from Midway to San José del Cabo within your budget

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 January 16, 2025.

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Route

Depart

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Price

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 2/19

7:55 pm-3:15 pm

1 stop20h 20m

San José del Cabo Los Cabos

Mon 2/24

5:08 pm-8:45 am

1 stop14h 37m

$423

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Wed 2/19

11:00 am-5:19 pm

1 stop7h 19m

San José del Cabo Los Cabos

Wed 2/26

6:19 pm-8:45 am

1 stop13h 26m

$424

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/28

6:40 am-9:24 am

1 stop27h 44m

San José del Cabo Los Cabos

Sat 3/8

10:44 am-12:17 am

1 stop12h 33m

$476

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Mon 2/10

6:00 am-12:36 pm

1 stop7h 36m

San José del Cabo Los Cabos

Fri 2/14

1:41 pm-10:20 pm

1 stop7h 39m

$515

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 2/23

6:00 am-5:27 pm

2 stops12h 27m

San José del Cabo Los Cabos

Thu 2/27

6:02 am-10:20 pm

2 stops15h 18m

$538

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sun 3/30

5:25 am-12:50 pm

1 stop9h 25m

San José del Cabo Los Cabos

Wed 4/2

1:00 pm-7:00 pm

Nonstop4h 00m

$548

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 4/8

6:40 am-2:50 pm

3 stops34h 10m

$116

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Sat 1/25

7:55 pm-4:23 pm

1 stop21h 28m

$145

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Fri 2/28

8:14 pm-9:24 am

2 stops14h 10m

$158

ChicagoSan José del Cabo

MDW - SJD

MDWSJD

Chicago Midway

Tue 3/18

6:00 am-2:47 pm

2 stops10h 47m

$251

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 11 results
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Compare providers for flights from Midway to San José del Cabo

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to San José del Cabo in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-San José del Cabo flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-San José del Cabo flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José del Cabo flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José del Cabo flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-San José del Cabo flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Travel insights for flights from Midway to San José del Cabo

Get recent, data-driven insights about flights from Midway to San José del Cabo including ideal travel times, pricing trends, and more.

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 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 San José del Cabo by month

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

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.

Temperature in San José del Cabo by month

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

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).

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 January 16, 2025.
Read through reviews of airlines operating flights from Chicago to San José del Cabo, such as Aeromexico and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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
3,435 reviews
Southwest
8.1
Very good
4,659 reviews

Comfort

8.1

Entertainment

7.7

Overall

8.1

Food

7.2

Crew

8.7

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 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 2 different airlines.

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

    According to our current data, Volaris ($424), Frontier ($476), and Aeromexico ($515) offers the cheapest pricing from Chicago Midway Airport to San José del Cabo. Volaris is 40% 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 Volaris ($145), Frontier ($158), and Delta ($251).

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

    On average you can expect to pay $775 for a flight from Chicago Midway Airport to San José del Cabo. The cheapest flight overall is $382 while the most popular route, (Chicago Midway - San José del Cabo Los Cabos) is currently priced at $380.

  • 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 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.

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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.
O'Hare Intl 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 San José del Cabo

Discover the top 2 airlines 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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$496Average$749FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$563Average$850FlexibilityNo cancel feeOn-time63%
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