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$162+ Cheap flights from Midway (MDW) to San José (SJO)

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SJO
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Midway to San José

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to San José (SJO). 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 November 21, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

August

Round-trip from

$514
(Kiwi.com)

One-way from

$162
(Kiwi.com)
Provider with most accurate pricing for Chicago Midway-San José Juan Santamaria Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-San José Juan Santamaria Intl flights.
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High demand for flights, 46% potential price rise
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Best time to find cheap flights, 50% potential price drop
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From Chicago Midway to San José Juan Santamaria Intl
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One-way flight from Chicago Midway to San José Juan Santamaria Intl
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Find flight deals from Midway to San José

Cheapest flights from Midway to San José
Explore the most affordable flight options available from Midway to San José. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/28:50 amMDW - SJO
1 stop26h 41mMultiple Airlines
Sat 12/71:24 pmSJO - MDW
2 stops33h 21mMultiple Airlines
Deal found 11/20$514
This Southwest deal was found by Cheapflights users on 11/20. 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.
Wed 12/411:00 amMDW - SJO
1 stop9h 40mSouthwest
Tue 12/109:55 amSJO - MDW
2 stops11h 30mSouthwest
Deal found 11/20$573
This Delta deal was found by Cheapflights users on 11/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:43 pmMDW - SJO
1 stop9h 10mDelta
Tue 12/102:13 pmSJO - MDW
1 stop7h 53mDelta
Deal found 11/21$636
This Gurufare deal was found by Cheapflights users on 11/20. 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 Gurufare is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/182:20 pmMDW - SJO
1 stop19h 58mFrontier
Thu 12/2611:38 amSJO - MDW
1 stop25h 46mFrontier
Deal found 11/20$927

Find flights from Midway to San José within your budget

Customize your flight search to find flights from Midway to San José 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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/2

8:50 am-11:31 am

1 stop26h 41m

San José Juan Santamaria Intl

Sat 12/7

1:24 pm-10:45 pm

2 stops33h 21m

$514

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/26

5:45 am-12:55 pm

1 stop7h 10m

San José Juan Santamaria Intl

Tue 3/4

9:55 am-6:50 pm

2 stops8h 55m

$538

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Mon 12/2

12:43 pm-9:53 pm

1 stop9h 10m

San José Juan Santamaria Intl

Tue 12/10

2:13 pm-10:06 pm

1 stop7h 53m

$636

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 3/8

9:44 pm-8:25 am

1 stop10h 41m

San José Juan Santamaria Intl

Thu 3/13

9:40 am-8:49 pm

1 stop10h 09m

$808

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Sat 1/4

7:55 pm-11:25 am

2 stops15h 30m

San José Juan Santamaria Intl

Sat 1/11

12:27 pm-8:45 am

2 stops20h 18m

$1,248

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Thu 12/5

4:27 pm-12:53 am

2 stops32h 26m

$162

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 1/1

8:25 am-10:18 am

1 stop25h 53m

$208

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Wed 2/26

5:45 am-12:55 pm

1 stop7h 10m

$249

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Tue 12/10

10:38 am-9:57 pm

1 stop11h 19m

$297

ChicagoSan José

MDW - SJO

MDWSJO

Chicago Midway

Fri 3/14

8:39 pm-11:27 am

2 stops15h 48m

$394

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Compare providers for flights from Midway to San José

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 in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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, San José Province 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, San José Province flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José, San José Province flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José, San José Province 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, San José Province 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

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

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

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

Find hourly flight availability from Midway to San José. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 21, 2024.

One of the essential ways to save on airfare from Chicago Midway Airport to San José, San José Province is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the morning could potentially save you up to 25% on airfare.

Rainfall in San José by month

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

In terms of precipitation, rainfall in San José, San José Province ranges from 0.0 - 11.8 inches per month. September is typically the wettest month, when rainfall can reach 11.8 in. February is typically the driest time to visit San José, San José Province when rainfall is around 0.0 in.

Temperature in San José by month

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

If weather is an important factor for your trip to San José, San José Province, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 69.8 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 64.4 F).

Reviews of airlines servicing San José

Get insights into the airlines that provide service to San José. 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. Reviews last updated November 21, 2024.
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Volaris
6.7
Okay
1,287 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Frontier
6.1
Okay
3,539 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Related info for your journey

Find useful and relevant information for your journey from Midway to San José. 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 from Chicago Midway?

    Located just 8.8 mi from the city center, San José Juan Santamaria Intl is the airport most travelers will use when flying to San José from Chicago Midway. Booking flights from Chicago Midway to Juan Santamaria Intl (SJO) 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, San José Province round-trip?

    Our cheapest airline available from Chicago Midway Airport to San José, San José Province is Southwest. Our recent data shows that you can find tickets from as low as $538 on this airline. Additional options worth looking into are Delta and Frontier, starting at $636 and $808 round-trip. Southwest is priced at 32% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Chicago Midway Airport to San José, San José Province one-way?

    $208 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Southwest and Delta, with prices starting from $249 and $297, respectively.

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

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

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

    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.

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

    Yes. Cheapflights offers flight deals from Midway to San José 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, San José Province?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to San José, San José Province (average of $398). Flying from Chicago Midway Airport to San José, San José Province in July is currently the most expensive (average of $532). 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

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to San José flights
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Midway to Liberia flights

Top 2 airlines flying from Midway to San José

Discover the top 2 airlines that operate flights from Midway to San José. 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$479Average$600FlexibilityNo cancel feeOn-time63%
DeltaCheapest$584Average$836FlexibilityNo cancel feeOn-timeN/A
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