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Cheap flights from Midway (MDW) to San José (SJO) from $109

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 9/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
MDW — SJO
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
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 June 6, 2024.

Popular in

December

Cheapest in

May

Round-trip from

$383

One-way from

$152
High demand for flights, 41% potential price rise
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Best time to find cheap flights, 66% 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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What is the cheapest day to fly round-trip from Chicago Midway Airport to San José, San José Province?

Leaving on a Tuesday is a viable option for saving on travel. Heavily demanded days of the week can typically drive up the prices you see. Booking your travel for a less competitive day can save up to 164% on the overall cost on flights from Chicago Midway Airport to San José, San José Province.

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

Users have found that booking a flight from Chicago Midway Airport to San José, San José Province at least 34 days early can save you up to 29% on average compared to booking a flight this week. If booking 34 days before your flight isn’t an option for you, users have found flights from Chicago Midway Airport to San José, San José Province for as little as $344 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $584 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago Midway Airport to San José, San José Province?

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to San José, San José Province. Flights to San José, San José Province from Chicago Midway Airport in August are about $541 on average during August, but can be found for as low as $284.

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

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

Cheap Midway to San José flights in June & July 2024

Find cheap flight options from Midway to San José specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to San José in 2024. For more flight deals, be sure to check back very soon.
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Wed 7/1712:55 amSJO - MDW
2 stops11h 43mMultiple Airlines
Deal found 6/6$383
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sat 7/201:40 pmSJO - MDW
1 stop19h 05mMultiple Airlines
Deal found 6/5$407
Sat 6/297:00 amMDW - SJO
1 stop26h 10mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$415
Mon 7/17:30 amMDW - SJO
2 stops17h 39mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$419
Mon 7/112:06 pmMDW - SJO
1 stop25h 39mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$424
Tue 7/21:50 pmMDW - SJO
2 stops11h 19mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$437
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sun 7/211:40 pmSJO - MDW
1 stop20h 25mMultiple Airlines
Deal found 6/5$438
Fri 6/281:11 pmMDW - SJO
1 stop24h 34mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$442
Thu 6/278:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Mon 7/112:32 pmSJO - MDW
2 stops26h 04mMultiple Airlines
Deal found 6/4$444

Midway to San José 2024 flight deals

Discover exclusive flight deals for travel between Midway and San José in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Listed are some of the best fares we've found on flights departing from Chicago to San José in 2024. For more flight deals, be sure to check back very soon.
Wed 8/73:36 pmMDW - SJO
2 stops17h 24mFrontier
Sun 8/119:10 amSJO - MDW
2 stops36h 49mFrontier
Deal found 6/6$344
Wed 8/71:43 pmMDW - SJO
1 stop19h 17mFrontier
Sun 8/119:10 amSJO - MDW
2 stops36h 49mFrontier
Deal found 6/6$349
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 6/4$365
Wed 8/147:27 amMDW - SJO
1 stop25h 58mFrontier
Sun 8/189:40 amSJO - MDW
1 stop24h 15mFrontier
Deal found 6/5$382
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Wed 7/1712:55 amSJO - MDW
2 stops11h 43mMultiple Airlines
Deal found 6/6$383
Fri 9/67:59 pmMDW - SJO
2 stops16h 34mMultiple Airlines
Sun 9/89:40 amSJO - MDW
1 stop10h 09mMultiple Airlines
Deal found 6/6$395
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Sat 7/201:40 pmSJO - MDW
1 stop19h 05mMultiple Airlines
Deal found 6/5$407
Wed 8/287:27 amMDW - SJO
1 stop25h 58mFrontier
Thu 9/59:40 amSJO - MDW
2 stops33h 28mFrontier
Deal found 6/4$414
Sat 6/297:00 amMDW - SJO
1 stop26h 10mMultiple Airlines
Fri 7/121:40 pmSJO - MDW
1 stop17h 05mMultiple Airlines
Deal found 6/5$415

Midway to San José flights leaving soon

Find last-minute flight options from Midway to San José for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Consider one of these great deals we found on last-minute flights from Chicago to San José. Users should examine the flight details to ensure there are no surprises.
Thu 6/206:56 amMDW - SJO
2 stops18h 13mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$461
Sun 6/166:01 pmMDW - SJO
2 stops31h 08mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$516
Thu 6/208:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$541
Sun 6/98:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Tue 6/115:10 amSJO - MDW
2 stops25h 21mMultiple Airlines
Deal found 6/5$551
Sun 6/168:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Sun 6/239:23 amSJO - MDW
1 stop28h 11mMultiple Airlines
Deal found 6/5$580
Sun 6/98:53 pmMDW - SJO
1 stop16h 52mMultiple Airlines
Mon 6/1012:59 amSJO - MDW
2 stops13h 37mMultiple Airlines
Deal found 6/5$589
Fri 6/72:32 pmMDW - SJO
2 stops23h 13mMultiple Airlines
Fri 6/141:42 pmSJO - MDW
1 stop17h 13mMultiple Airlines
Deal found 6/6$603
Thu 6/208:51 pmMDW - SJO
1 stop16h 54mMultiple Airlines
Sat 6/2212:59 amSJO - MDW
2 stops15h 06mMultiple Airlines
Deal found 6/5$642
Fri 6/142:14 pmMDW - SJO
2 stops10h 55mMultiple Airlines
Mon 6/2412:20 pmSJO - MDW
2 stops20h 27mMultiple Airlines
Deal found 6/5$653

One-way flights to San José from Midway

Search for one-way flight options from Midway to San José. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Some of the best available deals we've found on one-way flights from Chicago to San José. Users needing a return flight from Chicago to San José should utilize the search form above.
Tue 9/1012:34 pmMDW - SJO
2 stops23h 59mMultiple Airlines
Deal found 6/6$109
Tue 9/1710:00 amMDW - SJO
2 stops26h 33mMultiple Airlines
Deal found 6/5$118
Mon 9/169:44 pmMDW - SJO
2 stops14h 49mMultiple Airlines
Deal found 6/5$126
Wed 9/188:13 pmMDW - SJO
3 stops28h 02mMultiple Airlines
Deal found 6/5$129
Wed 9/189:44 pmMDW - SJO
1 stop11h 41mFrontier
Deal found 6/5$152
Sun 9/155:54 amMDW - SJO
2 stops13h 56mMultiple Airlines
Deal found 6/5$167
Sun 7/149:04 pmMDW - SJO
1 stop16h 41mMultiple Airlines
Deal found 6/6$169
Sat 9/219:44 pmMDW - SJO
2 stops14h 49mMultiple Airlines
Deal found 6/5$177
Thu 9/192:45 pmMDW - SJO
2 stops21h 48mMultiple Airlines
Deal found 6/5$183

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$344 - $653

Route

Depart

Return

Price

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/7

2 stops17h 24m

San José Juan Santamaria Intl

Sun 8/11

2 stops36h 49m

$344

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/7

1 stop19h 17m

San José Juan Santamaria Intl

Sun 8/11

2 stops36h 49m

$349

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/28

1 stop25h 58m

San José Juan Santamaria Intl

Thu 9/5

1 stop24h 15m

$365

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Wed 8/14

1 stop25h 58m

San José Juan Santamaria Intl

Sun 8/18

1 stop24h 15m

$382

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 7/14

1 stop16h 41m

San José Juan Santamaria Intl

Wed 7/17

2 stops11h 43m

$383

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Fri 9/6

2 stops16h 34m

San José Juan Santamaria Intl

Sun 9/8

1 stop10h 09m

$395

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 7/14

1 stop16h 41m

San José Juan Santamaria Intl

Sat 7/20

1 stop19h 05m

$407

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sat 6/29

1 stop26h 10m

San José Juan Santamaria Intl

Fri 7/12

1 stop17h 05m

$415

Chicago MidwaySan José Juan Santamaria Intl

MDW - SJO

MDWSJO

Chicago Midway

Sun 11/24

1 stop15h 08m

San José Juan Santamaria Intl

Mon 12/2

1 stop14h 44m

$653

Flights are sorted by cheapest first

Deals found on 6/6

What is the cheapest day to fly from Chicago Midway Airport to San José, San José Province?

Use this chart to determine the cheapest time to fly round-trip from Midway to San José. Price data was last updated on June 2, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago Midway Airport to San José, San José Province flight should consider departing on Thursday mornings when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

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.

Temperature and rainfall in San José by month

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

SJO

Temperature

64.4 - 69.8 °F

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 June 6, 2024.
To help decide which airline to fly from Chicago to San José, see what other customers have to say about Frontier and Delta. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Frontier
6.2
Okay
3,985 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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 1 airline.

  • Can I find flights from Chicago Midway Airport to San José, San José Province for under $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to San José, San José Province for under $400. The cheapest flight booked recently is on Frontier for just $344, but on average you can expect to pay $417.

  • Are there last-minute flights available from Chicago Midway Airport to San José, San José Province for under $500?

    There are currently 20+ open flights from Chicago Midway Airport to San José, San José Province within the next 7 days for less than $500.

  • What is the cheapest airline to fly 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 Frontier. Our recent data shows that you can find tickets from as low as $344 on this airline. Frontier is priced at 59% lower than the current average price of a flight leaving 3 months from now.

  • What does MDW to SJO mean?

    MDW and SJO are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. MDW to SJO refers to a flight route from Chicago Midway Airport to San José Juan Santamaria Intl Airport.

  • Can I find deals for flights from Midway to San José that include extra baggage allowance?

    The amount of baggage you can bring on your Midway to San José flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Midway to San José with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to San José flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Midway to San José that allow pets onboard?

    Many airlines flying from Midway to San José offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Midway to San José?

    Yes, you can often find last-minute deals on Midway to San José flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago Midway Airport to San José, San José Province flight deals updated?

    The Chicago Midway Airport to San José, San José Province flight deals you see on this page were last updated on 6/6.

  • 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 $383). Flying from Chicago Midway Airport to San José, San José Province in July is currently the most expensive (average of $519). 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
See prices for flight routes from nearby airports that may be better suited for you.

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Top airline flying from Midway to San José

Discover the top airline 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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$729Average$836FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to San José by cabin class

Find flights from Midway to San José, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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