San José

$208+ Cheap flights from Midway (MDW) to San José (SJO)

MDW — SJO
Dec 9 — Dec 161
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Cheap flight deals from Midway to San José

Cheapest flights from Midway to San José

Sat 11/286:00 am -
1 stop16h 15m
Mon 12/77:00 am -
1 stop15h 54m
Deal found 11/7$459
Sat 11/286:00 am -
1 stop16h 15m
Sun 12/67:00 am -
2 stops11h 01m
Deal found 11/7$463
Sat 11/1411:27 am -
1 stop10h 48m
Fri 11/202:37 pm -
1 stop8h 17m
Deal found 11/4$493
Sat 11/286:00 am -
1 stop16h 15m
Wed 12/27:00 am -
1 stop9h 16m
Deal found 11/7$506
Sat 11/1411:27 am -
1 stop10h 48m
Sat 11/217:00 am -
1 stop9h 18m
Deal found 11/6$523
Wed 11/115:20 am -
1 stop7h 55m
Tue 11/172:15 pm -
1 stop8h 55m
Deal found 11/6$544
Wed 11/111:05 pm -
1 stop9h 10m
Tue 11/172:37 pm -
1 stop8h 17m
Deal found 11/5$553
Mon 11/98:15 pm -
2 stops17h 00m
Wed 11/111:20 pm -
1 stop8h 00m
Deal found 11/6$579

Find flight deals from Midway to San José

Most accurate provider

Ovago
3 stars

Most trusted provider

Ovago
3 stars

Round-trip from

$450
(Delta)

One-way from

$208
(Southwest)

Popular in

December

Cheapest in

February

Average price

$557
Provider with most accurate pricing for Chicago Midway-San José Juan Santamaria Intl flight deals.
Provider most trusted by Cheapflights users for Chicago Midway-San José Juan Santamaria Intl flights.
From Chicago Midway to San José Juan Santamaria Intl
One-way flight from Chicago Midway to San José Juan Santamaria Intl
Highest demand for flights based on searches. 1% potential increase in price ($9 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in November 2026

Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to San José that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Wed 2/24

5:20 am-1:45 pm

1 stop8h 25m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$208

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 3/15

9:10 am-7:40 pm

2 stops11h 30m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$328

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Tue 12/1

5:20 am-1:15 pm

1 stop7h 55m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$375

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 12/7

5:20 am-1:15 pm

1 stop7h 55m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$413

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Fri 1/22

6:00 am-12:58 pm

1 stop6h 58m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$425

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sat 12/5

6:00 am-10:17 pm

1 stop16h 17m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$425

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 11/30

6:00 am-10:15 pm

1 stop16h 15m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$425
Quickest round-trip

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Thu 2/25

6:00 am-12:45 pm

1 stop6h 45m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$435

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Mon 2/1

6:00 am-9:49 pm

1 stop15h 49m

San José Juan Santamaria Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$435

ChicagoSan José

MDW Chicago Midway - SJO San José Juan Santamaria Intl

MDWSJO

Chicago Midway

Sun 1/24

6:00 am-9:49 pm

1 stop15h 49m

San José Juan Santamaria Intl

Tue 2/2

7:00 am-11:55 pm

1 stop16h 55m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/8

Showing 1-10 of 21 resultsSorted by cheapest first
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Compare providers for flights from Midway to San José

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*
OvagoPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 flights, users find the pricing of Ovago to be most consistent on Cheapflights vs. Ovago Users can find the same prices on Chicago Midway Airport-San José flight deals on Cheapflights vs. Ovago >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-San José flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-San José flights, Cheapflights users trust Ovago the most. Ovago 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 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

Reviews of airlines servicing San José

Read through reviews of airlines operating flights from Chicago Midway Airport to San José, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Crew

8.6

Entertainment

7.5

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Patricia,Oct 2026

DAL - TPA

I love flying southwest, Both flights were packed full full - so not room for all carry one and bags had to be checked but still good flights.

Related info for your journey

  • 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.

  • How long is the flight from Chicago Midway Airport to San José?

    Delta and Southwest can get you from Chicago Midway Airport to San José in just under 8h 25m. Your travel time can differ by up to 7h 24m. The distance from Chicago Midway Airport to San José is about 2206 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to San José round-trip?

    Flying on Southwest is currently your cheapest option to San José, with prices starting at $521.

  • 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.

See more FAQs

Traveling to a place near San José?

Book flights to San José if you plan to visit one of these locations
Alajuela
Heredia
Dominical
Manuel Antonio

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Alternative routes for Midway to San José

Top airline flying from Midway to San José

AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$521Average$813FlexibilityNo cancel feeOn-time63%

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