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$181+ Cheap flights from San José (SJO) to Midway (MDW)

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 11/7. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — MDW
Oct 15 — Oct 221
From?
To?
Tue 10/15
Tue 10/22
1 adult, Economy
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Cheap flight deals from San José to Midway

Discover tips and strategies to find the most affordable flight options for your journey from San José (SJO) to Midway (MDW). 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 October 10, 2024.

Popular in

November

Cheapest in

September

Round-trip from

$288
(eDestinos)

One-way from

$181
(Kiwi.com)
High demand for flights, 42% potential price rise
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Best time to find cheap flights, 37% potential price drop
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From San José Juan Santamaria Intl to Chicago Midway
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One-way flight from San José Juan Santamaria Intl to Chicago Midway
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Cheap San José to Midway flights in October & November 2024

Find cheap flight options from San José to Midway specifically for the months of October and November 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Prices were last updated on October 10, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in October and November 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This eDestinos deal was found by Cheapflights users on 10/10. 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.
Tue 11/1212:26 pmSJO - MDW
2 stops34h 26mMultiple Airlines
Sat 11/167:00 amMDW - SJO
2 stops28h 31mMultiple Airlines
Deal found 10/10$290
This Southwest deal was found by Cheapflights users on 10/10. 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.
Tue 11/129:55 amSJO - MDW
2 stops11h 30mSouthwest
Tue 11/199:00 amMDW - SJO
2 stops11h 40mSouthwest
Deal found 10/10$495
This Delta deal was found by Cheapflights users on 10/10. 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.
Tue 11/122:12 pmSJO - MDW
1 stop7h 34mDelta
Sun 11/176:00 amMDW - SJO
1 stop6h 45mDelta
Deal found 10/10$553

San José to Midway 2024 flight deals

Discover exclusive flight deals for travel between San José and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,713,696 searches. Data last updated October 10, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in October and November 2024. If these deals don't appeal to you, be sure to come back soon for more options.
This eDestinos deal was found by Cheapflights users on 10/10. 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.
Tue 11/1212:26 pmSJO - MDW
2 stops34h 26mMultiple Airlines
Sat 11/167:00 amMDW - SJO
2 stops28h 31mMultiple Airlines
Deal found 10/10$290
This Southwest deal was found by Cheapflights users on 10/10. 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.
Tue 11/129:55 amSJO - MDW
2 stops11h 30mSouthwest
Tue 11/199:00 amMDW - SJO
2 stops11h 40mSouthwest
Deal found 10/10$495
This Delta deal was found by Cheapflights users on 10/10. 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.
Tue 11/122:12 pmSJO - MDW
1 stop7h 34mDelta
Sun 11/176:00 amMDW - SJO
1 stop6h 45mDelta
Deal found 10/10$553

San José to Midway flights leaving soon

Find last-minute flight options from San José to Midway 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 2,713,696 searches. Data last updated October 10, 2024.
Have a look at some of the last-minute flights available departing from San José to Chicago. It's wise to confirm all flight details are correct before booking.
This Kiwi.com deal was found by Cheapflights users on 10/10. 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.
Thu 10/1712:27 pmSJO - MDW
2 stops20h 20mMultiple Airlines
Mon 10/213:48 pmMDW - SJO
1 stop21h 56mMultiple Airlines
Deal found 10/10$489
This Southwest deal was found by Cheapflights users on 10/10. 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.
Thu 10/179:00 amSJO - MDW
1 stop7h 50mSouthwest
Mon 10/216:15 amMDW - SJO
1 stop7h 30mSouthwest
Deal found 10/10$562
This Delta deal was found by Cheapflights users on 10/10. 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.
Sat 10/191:13 pmSJO - MDW
1 stop7h 25mDelta
Wed 10/236:00 amMDW - SJO
1 stop6h 48mDelta
Deal found 10/10$1,242

One-way flights to Midway from San José

Search for one-way flight options from San José to Midway. 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 2,713,696 searches. Data last updated October 10, 2024.
Take a look at some of the best available options we've come across on one-way flights from San José to Chicago. Users needing a return flight from San José to Chicago should utilize the search form above.
This Kiwi.com deal was found by Cheapflights users on 10/9. 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.
Thu 11/712:26 pmSJO - MDW
1 stop30h 57mMultiple Airlines
Deal found 10/9$181
This Kiwi.com deal was found by Cheapflights users on 10/8. 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 10/1612:27 pmSJO - MDW
2 stops20h 20mVolaris
Deal found 10/8$298
This Southwest deal was found by Cheapflights users on 10/8. 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 10/169:00 amSJO - MDW
1 stop9h 50mSouthwest
Deal found 10/8$308
This eDestinos deal was found by Cheapflights users on 10/9. 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.
Sat 1/1810:40 amSJO - MDW
2 stops34h 19mFrontier
Deal found 10/9$344
This Delta deal was found by Cheapflights users on 10/9. 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.
Tue 12/37:00 amSJO - MDW
2 stops10h 02mDelta
Deal found 10/9$452

Find flights from San José to Midway within your budget

Customize your flight search to find flights from San José to Midway 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 2,713,696 searches. Data last updated October 10, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$288 - $553

Route

Depart

Return

Price

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 11/5

2 stops31h 21m

Chicago Midway

Tue 11/12

2 stops18h 45m

$288

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sat 1/18

1 stop24h 15m

Chicago Midway

Fri 1/24

1 stop11h 41m

$383

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 11/8

1 stop11h 00m

Chicago Midway

Sun 11/10

1 stop7h 35m

$507

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 11/12

1 stop7h 34m

Chicago Midway

Sun 11/17

1 stop6h 45m

$553

Flights are sorted by cheapest first

Deals found on 10/9

Best time to book a flight from San José to Midway

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

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

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

Find hourly flight availability from San José to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 10, 2024.

When flying from San José, San José Province to Chicago Midway Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the morning, which can drop the price by up to 32% versus a flight at noon.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 10, 2024.
Peruse reviews from past customers who have flown with Southwest and Delta from San José to Chicago to help guide your decision. 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
8.2
Very good
5,203 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.2

Boarding

8.3

Reviews

1 / 10

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

Southwest
8.2
Very good
5,203 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.2

Boarding

8.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,963 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.2

Boarding

8.3

Reviews

1 / 10

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

Volaris
6.7
Okay
1,323 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.2

Boarding

8.3

Reviews

1 / 10

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

Frontier
6.1
Okay
3,645 reviews
Southwest
8.2
Very good
5,203 reviews

Comfort

8.1

Crew

8.7

Entertainment

7.7

Food

7.2

Overall

8.2

Boarding

8.3

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 San José to Midway. 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 from for flights from San José to Chicago Midway?

    San José Juan Santamaria Intl (SJO), located 8.8 mi from the city center, is the airport you fly out of when you book flights from San José to Chicago Midway. 0 airlines have flights from Juan Santamaria Intl to Chicago Midway on a regular basis. Booking flights from San José Juan Santamaria Intl to Chicago Midway should not be difficult; the airport handles an average of 0 outbound flights to Chicago Midway per day.

  • Can I find flights from San José, San José Province to Chicago Midway Airport for under $300 on Cheapflights?

    Yes, there are multiple flights from San José, San José Province to Chicago Midway Airport for under $300. The cheapest flight booked recently is on Multiple Airlines for just $288, but on average you can expect to pay $432.

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

    There are currently 3+ open flights from San José, San José Province to Chicago Midway Airport within the next 7 days for less than $500.

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

    Currently priced at $383, Frontier will fly you from San José, San José Province to Chicago Midway Airport and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and Delta - these airlines can fly you to your destination from $507 and $553, respectively. Users have found that Frontier is 61% cheaper than the other options available to this destination.

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

    $298 is the cheapest one-way deal found within the past few days, from Volaris. You may also be able to find cheap deals on Southwest and Frontier, with prices starting from $308 and $344, respectively.

  • What does SJO to MDW mean?

    This is defined as San José Juan Santamaria Intl Airport (SJO) and Chicago Midway Airport (MDW). Codes like Chicago Midway Airport are often used to just call airports uniquely.

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

    The amount of baggage you can bring on your San José to Midway 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 San José to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter San José to Midway 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 San José to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from San José to Midway 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 San José to Midway that allow pets onboard?

    Many airlines flying from San José to Midway 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 San José to Midway?

    Yes, you can often find last-minute deals on San José to Midway 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 San José, San José Province to Chicago Midway Airport flight deals updated?

    The San José, San José Province to Chicago Midway Airport flight deals you see on this page were last updated on 10/10.

  • What is the cheapest month to book a flight from San José, San José Province to Chicago Midway Airport?

    Currently, December is the cheapest month in which you can book a flight from San José, San José Province to Chicago Midway Airport (average of $142). Flying from San José, San José Province to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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