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Cheap flights from San José (SJO) to Midway (MDW) from $152

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 5/11. 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.
SJO — MDW
May 10 — May 171
From?
To?
Fri 5/10
Fri 5/17
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 May 5, 2024.

Popular in

December

Cheapest in

August

Round-trip from

$223

One-way from

$152
High demand for flights, 46% potential price rise
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Best time to find cheap flights, 53% potential price drop
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From San José Juan Santamaria Intl to Chicago Midway
Search Deals
One-way flight from San José Juan Santamaria Intl to Chicago Midway
Search Deals

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 17 days in advance, which can save you up to 18% on flights from San José, San José Province to Chicago Midway Airport compared to booking the week you need them. Waiting 17 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $408. For sooner than that we have options available in the next 3 days from $676.

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

Our data shows that August tends to be the cheapest month to fly to Chicago Midway Airport from San José, San José Province. Users have commonly found prices around $499 for the month, but tickets can be as low as $269. Due to multiple factors, prepare for potentially higher prices in March.

When is the cheapest time to fly from San José, San José Province to Chicago Midway Airport (SJO - MDW)?

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 at noon, which can drop the price by up to 2% versus a flight in the morning.

Cheap Frontier flights from San José to Midway

Explore cheap flight options specifically provided by Frontier for the route between San José and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Find some of the cheapest Frontier flights traveling from San José to Chicago. Make sure to check back often as deals are often changing.
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$424
Sun 5/129:16 amSJO - MDW
1 stop28h 23mFrontier
Wed 5/227:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$446
Thu 6/279:19 amSJO - MDW
1 stop28h 15mFrontier
Sat 8/36:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 5/4$674

Cheap Delta flights from San José to Midway

Explore cheap flight options specifically provided by Delta for the route between San José and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 5, 2024.
Some of the lowest-priced Delta flights we've found at this time heading from San José to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Mon 6/37:00 amSJO - MDW
1 stop14h 01mDelta
Sat 6/86:00 amMDW - SJO
1 stop6h 42mDelta
Deal found 5/2$765
Tue 5/287:00 amSJO - MDW
1 stop7h 50mDelta
Tue 6/49:32 amMDW - SJO
2 stops11h 41mDelta
Deal found 5/4$813
Wed 7/177:00 amSJO - MDW
1 stop9h 59mDelta
Fri 8/26:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 5/4$845
Fri 5/317:00 amSJO - MDW
1 stop14h 01mDelta
Fri 6/79:34 amMDW - SJO
2 stops11h 53mDelta
Deal found 5/3$860
Fri 6/77:00 amSJO - MDW
1 stop13h 46mDelta
Tue 6/1110:41 amMDW - SJO
1 stop10h 46mDelta
Deal found 5/3$908
Thu 7/187:00 amSJO - MDW
1 stop9h 59mDelta
Sun 7/216:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 5/4$910
Wed 5/227:00 amSJO - MDW
1 stop7h 50mDelta
Tue 5/286:00 amMDW - SJO
1 stop6h 46mDelta
Deal found 5/3$913
Thu 6/277:00 amSJO - MDW
1 stop13h 46mDelta
Sun 6/306:00 amMDW - SJO
1 stop6h 42mDelta
Deal found 5/3$955
Sun 7/147:00 amSJO - MDW
1 stop9h 59mDelta
Sun 7/216:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 5/3$957

Cheap San José to Midway flights in May & June 2024

Find cheap flight options from San José to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Prices were last updated on May 5, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Fri 5/1712:59 amSJO - MDW
2 stops19h 37mMultiple Airlines
Tue 5/217:35 amMDW - SJO
1 stop26h 11mMultiple Airlines
Deal found 5/3$268
Tue 5/79:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sat 5/114:51 pmMDW - SJO
1 stop16h 55mMultiple Airlines
Deal found 5/4$359
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$424
Sun 5/129:16 amSJO - MDW
1 stop28h 23mFrontier
Wed 5/227:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$446
Tue 5/75:10 amSJO - MDW
2 stops9h 51mMultiple Airlines
Sat 5/114:51 pmMDW - SJO
1 stop16h 55mMultiple Airlines
Deal found 5/4$448
Tue 5/79:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 5/3$485
Wed 5/85:10 amSJO - MDW
2 stops9h 51mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 5/4$542
Mon 5/612:51 amSJO - MDW
2 stops12h 02mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 5/3$560
Sat 5/1810:11 amSJO - MDW
1 stop9h 02mMultiple Airlines
Tue 5/287:35 amMDW - SJO
2 stops12h 15mMultiple Airlines
Deal found 5/4$562

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 2,795,183 searches. Data last updated May 5, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in May and June 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Fri 5/1712:59 amSJO - MDW
2 stops19h 37mMultiple Airlines
Tue 5/217:35 amMDW - SJO
1 stop26h 11mMultiple Airlines
Deal found 5/3$268
Sun 9/89:40 amSJO - MDW
1 stop10h 09mFrontier
Sat 9/1410:00 amMDW - SJO
1 stop23h 25mFrontier
Deal found 5/4$333
Tue 5/79:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sat 5/114:51 pmMDW - SJO
1 stop16h 55mMultiple Airlines
Deal found 5/4$359
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$424
Sun 8/259:40 amSJO - MDW
1 stop10h 09mFrontier
Sat 8/316:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 5/4$432
Sun 5/129:16 amSJO - MDW
1 stop28h 23mFrontier
Wed 5/227:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$446
Tue 5/75:10 amSJO - MDW
2 stops9h 51mMultiple Airlines
Sat 5/114:51 pmMDW - SJO
1 stop16h 55mMultiple Airlines
Deal found 5/4$448
Mon 7/2212:59 amSJO - MDW
2 stops16h 49mMultiple Airlines
Thu 7/252:54 pmMDW - SJO
1 stop22h 51mMultiple Airlines
Deal found 5/4$457
Tue 5/79:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 5/3$485

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 2,795,183 searches. Data last updated May 5, 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.
Sun 5/129:16 amSJO - MDW
1 stop28h 23mFrontier
Wed 5/227:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 5/4$446
Mon 5/131:42 pmSJO - MDW
1 stop7h 54mMultiple Airlines
Thu 5/167:45 amMDW - SJO
2 stops12h 05mMultiple Airlines
Deal found 5/4$659
Mon 5/131:42 pmSJO - MDW
1 stop7h 54mMultiple Airlines
Thu 5/167:45 amMDW - SJO
2 stops12h 05mMultiple Airlines
Deal found 5/4$671
Mon 5/137:00 amSJO - MDW
1 stop14h 01mDelta
Thu 5/1612:42 pmMDW - SJO
1 stop8h 31mDelta
Deal found 5/4$1,218
Mon 5/137:00 amSJO - MDW
1 stop14h 01mDelta
Wed 5/2212:42 pmMDW - SJO
1 stop8h 31mDelta
Deal found 5/4$1,375

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 2,795,183 searches. Data last updated May 5, 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.
Sat 5/119:36 amSJO - MDW
1 stop12h 20mMultiple Airlines
Deal found 5/4$152
Wed 5/159:36 amSJO - MDW
1 stop27h 10mMultiple Airlines
Deal found 5/4$161
Tue 5/1412:32 pmSJO - MDW
2 stops19h 50mMultiple Airlines
Deal found 5/4$162
Thu 5/169:40 amSJO - MDW
1 stop9h 37mFrontier
Deal found 5/3$167
Wed 5/159:36 amSJO - MDW
2 stops33h 04mMultiple Airlines
Deal found 5/4$174
Sun 6/99:23 amSJO - MDW
1 stop28h 11mFrontier
Deal found 5/4$195
Fri 5/101:42 pmSJO - MDW
1 stop28h 45mMultiple Airlines
Deal found 5/4$197
Mon 5/1312:59 amSJO - MDW
2 stops11h 54mMultiple Airlines
Deal found 5/4$199
Wed 5/155:10 amSJO - MDW
3 stops12h 17mMultiple Airlines
Deal found 5/4$202

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 2,795,183 searches. Data last updated May 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$266 - $765

Route

Depart

Return

Price

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/17

1 stop26h 45m

Chicago Midway

Mon 5/20

1 stop15h 51m

$266

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Fri 5/17

2 stops19h 37m

Chicago Midway

Tue 5/21

1 stop26h 11m

$268

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/16

2 stops12h 42m

Chicago Midway

Mon 5/20

1 stop15h 51m

$380

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 6/2

2 stops12h 42m

Chicago Midway

Thu 6/13

1 stop16h 54m

$387

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 5/19

1 stop28h 25m

Chicago Midway

Wed 5/29

1 stop25h 23m

$424

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Tue 6/18

2 stops12h 17m

Chicago Midway

Sat 6/22

1 stop13h 21m

$425

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 5/12

1 stop28h 23m

Chicago Midway

Wed 5/22

1 stop25h 23m

$446

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 7/22

2 stops16h 49m

Chicago Midway

Thu 7/25

1 stop22h 51m

$457

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Mon 6/3

1 stop14h 01m

Chicago Midway

Sat 6/8

1 stop6h 42m

$765

Flights are sorted by cheapest first

Deals found on 5/3

No data available for this route at this time. Please check back soon.

Average price of flights to Midway by month

Plan your trip from San José to Midway by taking into account the cheapest months to travel. The average price of a one-way flight from San José to Midway is currently $179 while a round-trip flight costs $424. Price data was last updated on April 28, 2024.

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 $140). Flying from San José, San José Province to Chicago Midway Airport in July is currently the most expensive (average of $251). 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.

January

$194

February

$190

March

$219

April

$159

May

$185

June

$235

July

$251

August

$196

September

$157

October

$143

November

$165

December

$140

Temperature and rainfall in Midway by month

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

CHI

Temperature

23 - 73.4 °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 May 5, 2024.
Peruse reviews from past customers who have flown with Frontier 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.
Delta
8.1
Very good
10,838 reviews
Check prices

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.1

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.1
Very good
10,838 reviews
Delta
8.1
Very good
10,838 reviews
Check prices

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.1

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Frontier
6.3
Okay
4,098 reviews
Delta
8.1
Very good
10,838 reviews
Check prices

Comfort

7.9

Crew

8.6

Entertainment

8.0

Boarding

8.2

Food

7.4

Overall

8.1

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 $266, but on average you can expect to pay $575.

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

    There are currently 5+ 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 $424, 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. Check Cheapflights for deals on Delta for as low as $765. Users have found that Frontier is 47% cheaper than the other options available to this destination.

  • 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 5/4.

See more FAQs

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Alternative routes for San José to Midway
See prices for flight routes from nearby airports that may be better suited for you.

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Search flights from San José to Midway by cabin class

Find flights from San José to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from San José to Midway?

Deals for San José to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from San José to Midway?

Millions of users choose and trust Cheapflights to book the best flight deals from San José to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from San José to Midway with no change fees?

Yes! Cheapflights helps users easily find flights from San José to Midway with no change fees.

Can Cheapflights notify me if prices for flights from San José to Midway become cheaper?

Yes! Start tracking prices for San José to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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