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Cheap flights from San José (SJO) to Midway (MDW) from $144

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 5/10. 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.
SJO — MDW
May 4 — May 111
From?
To?
Sat 5/4
Sat 5/11
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 April 29, 2024.

Popular in

July

Cheapest in

September

Round-trip from

$222

One-way from

$147
High demand for flights, 45% potential price rise
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Best time to find cheap flights, 69% 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
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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 2,948,547 searches. Data last updated April 29, 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.
Thu 5/169:40 amSJO - MDW
1 stop28h 01mFrontier
Sat 5/187:53 amMDW - SJO
1 stop25h 13mFrontier
Deal found 4/28$281
Thu 8/89:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 8/1412:15 pmMDW - SJO
2 stops21h 10mFrontier
Deal found 4/28$359
Thu 7/189:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 7/247:27 amMDW - SJO
1 stop25h 58mFrontier
Deal found 4/28$364
Thu 7/259:40 amSJO - MDW
1 stop10h 09mFrontier
Sat 8/36:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 4/28$369
Sun 8/119:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 8/1412:15 pmMDW - SJO
2 stops21h 10mFrontier
Deal found 4/28$391
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Sat 6/17:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 4/28$403
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 4/28$415
Sun 8/189:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 8/2812:15 pmMDW - SJO
2 stops21h 10mFrontier
Deal found 4/28$422
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Sat 5/257:53 amMDW - SJO
1 stop25h 13mFrontier
Deal found 4/28$451

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 2,948,547 searches. Data last updated April 29, 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.
Wed 5/221:11 pmSJO - MDW
1 stop7h 50mDelta
Wed 5/296:00 amMDW - SJO
1 stop6h 44mDelta
Deal found 4/28$765
Fri 7/127:00 amSJO - MDW
1 stop9h 59mDelta
Fri 7/191:05 pmMDW - SJO
1 stop8h 03mDelta
Deal found 4/28$808
Thu 5/307:00 amSJO - MDW
1 stop14h 01mDelta
Tue 6/49:32 amMDW - SJO
2 stops11h 41mDelta
Deal found 4/28$813
Tue 10/81:13 pmSJO - MDW
1 stop7h 31mDelta
Tue 10/156:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 4/29$815
Tue 8/201:13 pmSJO - MDW
1 stop7h 34mDelta
Mon 8/266:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 4/28$830
Tue 7/167:00 amSJO - MDW
1 stop13h 41mDelta
Thu 7/1810:11 amMDW - SJO
1 stop10h 57mDelta
Deal found 4/29$860
Sat 8/241:13 pmSJO - MDW
1 stop7h 34mDelta
Sat 8/315:59 pmMDW - SJO
2 stops13h 31mDelta
Deal found 4/28$862
Sat 8/241:13 pmSJO - MDW
1 stop7h 34mDelta
Sat 9/75:59 pmMDW - SJO
2 stops13h 31mDelta
Deal found 4/28$873
Sat 8/241:13 pmSJO - MDW
1 stop7h 34mDelta
Tue 8/276:00 amMDW - SJO
1 stop6h 53mDelta
Deal found 4/28$877

Cheap San José to Midway flights in April & May 2024

Find cheap flight options from San José to Midway specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,948,547 searches. Prices were last updated on April 29, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in April and May 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/169:40 amSJO - MDW
1 stop28h 01mFrontier
Sat 5/187:53 amMDW - SJO
1 stop25h 13mFrontier
Deal found 4/28$281
Thu 5/29:21 amSJO - MDW
1 stop11h 06mFrontier
Sat 5/46:45 amMDW - SJO
1 stop26h 26mFrontier
Deal found 4/28$293
Thu 5/99:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/29$294
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/28$339
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 4/28$347
Wed 5/85:53 amSJO - MDW
2 stops11h 34mMultiple Airlines
Sun 5/125:05 amMDW - SJO
1 stop8h 42mMultiple Airlines
Deal found 4/28$370
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Sat 6/17:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 4/28$403
Tue 5/281:42 pmSJO - MDW
1 stop16h 12mMultiple Airlines
Tue 6/47:05 amMDW - SJO
2 stops12h 50mMultiple Airlines
Deal found 4/29$405
Sun 5/199:16 amSJO - MDW
1 stop28h 25mFrontier
Wed 5/297:53 amMDW - SJO
1 stop25h 23mFrontier
Deal found 4/28$415

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 2,948,547 searches. Data last updated April 29, 2024.
The lowest fares we've come across on flights traveling from San José to Chicago in April and May 2024. If these deals don't appeal to you, be sure to come back soon for more options.
Thu 5/169:40 amSJO - MDW
1 stop28h 01mFrontier
Sat 5/187:53 amMDW - SJO
1 stop25h 13mFrontier
Deal found 4/28$281
Thu 5/29:21 amSJO - MDW
1 stop11h 06mFrontier
Sat 5/46:45 amMDW - SJO
1 stop26h 26mFrontier
Deal found 4/28$293
Thu 5/99:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/29$294
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/28$339
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 4/28$347
Thu 8/89:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 8/1412:15 pmMDW - SJO
2 stops21h 10mFrontier
Deal found 4/28$359
Thu 7/189:40 amSJO - MDW
1 stop10h 09mFrontier
Wed 7/247:27 amMDW - SJO
1 stop25h 58mFrontier
Deal found 4/28$364
Thu 7/259:40 amSJO - MDW
1 stop10h 09mFrontier
Sat 8/36:00 amMDW - SJO
1 stop27h 25mFrontier
Deal found 4/28$369
Wed 5/85:53 amSJO - MDW
2 stops11h 34mMultiple Airlines
Sun 5/125:05 amMDW - SJO
1 stop8h 42mMultiple Airlines
Deal found 4/28$370

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 2,948,547 searches. Data last updated April 29, 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.
Thu 5/99:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/29$294
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/28$339
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 4/28$347
Wed 5/85:53 amSJO - MDW
2 stops11h 34mMultiple Airlines
Sun 5/125:05 amMDW - SJO
1 stop8h 42mMultiple Airlines
Deal found 4/28$370
Thu 5/99:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Sun 5/127:13 pmMDW - SJO
2 stops15h 49mMultiple Airlines
Deal found 4/29$422
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Sun 5/127:13 pmMDW - SJO
2 stops15h 49mMultiple Airlines
Deal found 4/28$440
Sun 5/59:36 amSJO - MDW
1 stop12h 45mMultiple Airlines
Thu 5/92:44 pmMDW - SJO
2 stops10h 20mMultiple Airlines
Deal found 4/28$450
Sat 5/412:51 amSJO - MDW
2 stops13h 57mMultiple Airlines
Thu 5/95:16 pmMDW - SJO
1 stop16h 30mMultiple Airlines
Deal found 4/28$466
Sat 5/412:51 amSJO - MDW
2 stops13h 57mMultiple Airlines
Sun 5/126:31 pmMDW - SJO
1 stop15h 50mMultiple Airlines
Deal found 4/28$484

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 2,948,547 searches. Data last updated April 29, 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.
Fri 5/109:36 amSJO - MDW
2 stops36h 05mMultiple Airlines
Deal found 4/28$144
Thu 5/99:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Deal found 4/29$147
Tue 5/79:36 amSJO - MDW
1 stop12h 50mMultiple Airlines
Deal found 4/28$152
Mon 5/612:51 amSJO - MDW
2 stops14h 10mMultiple Airlines
Deal found 4/28$161
Thu 5/169:40 amSJO - MDW
1 stop28h 01mFrontier
Deal found 4/28$162
Thu 5/169:40 amSJO - MDW
1 stop28h 01mFrontier
Deal found 4/27$163
Thu 5/301:42 pmSJO - MDW
1 stop21h 38mMultiple Airlines
Deal found 4/28$170
Fri 8/231:45 pmSJO - MDW
1 stop18h 28mMultiple Airlines
Deal found 4/28$176
Wed 5/2912:59 amSJO - MDW
2 stops22h 47mMultiple Airlines
Deal found 4/28$182

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 2,948,547 searches. Data last updated April 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$278 - $765

Route

Depart

Return

Price

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/9

1 stop12h 50m

Chicago Midway

Sun 5/12

1 stop8h 42m

$278

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/16

1 stop28h 01m

Chicago Midway

Sat 5/18

1 stop25h 13m

$281

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 8/8

1 stop10h 09m

Chicago Midway

Wed 8/14

2 stops21h 10m

$359

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 7/18

1 stop10h 09m

Chicago Midway

Wed 7/24

1 stop25h 58m

$364

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 7/25

1 stop10h 09m

Chicago Midway

Sat 8/3

1 stop27h 25m

$369

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Thu 5/9

1 stop12h 50m

Chicago Midway

Sun 5/12

2 stops15h 49m

$382

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Sun 8/11

1 stop10h 09m

Chicago Midway

Wed 8/14

2 stops21h 10m

$391

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/15

2 stops11h 34m

Chicago Midway

Wed 5/22

1 stop26h 32m

$424

San José Juan Santamaria IntlChicago Midway

SJO - MDW

SJOMDW

San José Juan Santamaria Intl

Wed 5/22

1 stop7h 50m

Chicago Midway

Wed 5/29

1 stop6h 44m

$765

Flights are sorted by cheapest first

Deals found on 4/28

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 $162 while a round-trip flight costs $401. Price data was last updated on April 21, 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 $254). 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

$254

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 April 29, 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
10,913 reviews
Check prices

Food

7.4

Comfort

7.9

Overall

8.1

Entertainment

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,913 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Food

7.4

Comfort

7.9

Overall

8.1

Entertainment

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Frontier
6.3
Okay
4,123 reviews
Delta
8.1
Very good
10,913 reviews
Check prices

Food

7.4

Comfort

7.9

Overall

8.1

Entertainment

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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 $278, but on average you can expect to pay $422.

  • Are there last-minute flights available from San José, San José Province to Chicago Midway Airport for under $300?

    There are currently 18+ open flights from San José, San José Province to Chicago Midway Airport within the next 7 days for less than $300.

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

    Currently priced at $281, 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 64% 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 4/29.

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.
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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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