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Uncover the best deals on Chicago to San Jose flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest MDW - SJO Flights
Useful information for finding best airline tickets from Chicago Midway International to Juan Santamaria International on your next trip.
Cheapest Round Trip Flight
$586
Southwest Airlines
• 2 stops
• 43h 45m
Dec 10 – Dec 17
The cheapest round trip flight from Chicago to San Jose (MDW-SJO-MDW) is currently $586
Fastest Flight
25h 15m
The fastest nonstop flight from Chicago to San Jose (MDW-SJO) takes 25h 15m
Top Airlines Flying from Chicago to San Jose
Latest Flight Deals from Chicago (MDW) to San Jose (SJO)
Compare and book low fare round-trip air tickets from Chicago to San Jose. Ideal for travelers with confirmed return itineraries.
Dec 10 - Dec 17, Economy
Chicago → San Jose
43h 45m
9:55 AM - 12:20 PM • 2 stops
Chicago → San Jose
17h 35m
2:10 PM - 1:05 AM • 2 stops
Southwest Airlines
Dec 10 - Dec 17, Economy
Chicago → San Jose
43h 45m
9:55 AM - 12:20 PM • 2 stops
Chicago → San Jose
17h 35m
2:10 PM - 1:05 AM • 1 stop
Southwest Airlines
Dec 10 - Dec 17, Economy
Chicago → San Jose
40h 50m
11:30 AM - 12:20 PM • 2 stops
Chicago → San Jose
17h 35m
2:10 PM - 1:05 AM • 1 stop
Southwest Airlines
Dec 11 - Dec 18, Economy
Chicago → San Jose
30h 35m
6:30 PM - 1:05 PM • 2 stops
Chicago → San Jose
12h 25m
3:25 PM - 11:10 PM • 1 stop
Southwest Airlines
Dec 11 - Dec 18, Economy
Chicago → San Jose
44h 5m
10:20 AM - 1:05 PM • 2 stops
Chicago → San Jose
12h 25m
3:25 PM - 11:10 PM • 1 stop
Southwest Airlines
FAQs on Chicago to San Jose Flights
What are the airports in Chicago?
ORD,MDW
What’s the most popular airline flying from MDW to SJO?
The most popular airline flying from Chicago to San Jose are
Can I fly from MDW to SJO non-stop?
NO
Which airlines fly nonstop between Chicago and San Jose?
The non-stop flights between Chicago and San Jose are .
What’s the earliest departure time from MDW to SJO Airport?
The earliest flight leaves MDW at 9:55 am and lands in SJO - Juan Santamaria International
What are the airports in San Jose?
SJO
Can I make changes to my Chicago to San Jose flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from MDW to SJO?
Read the fare rules of the Chicago to San Jose air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and San Jose?
operate flights between Chicago and San Jose
How long does a flight from Chicago to San Jose take?
It takes approximately 5 hour to fly non-stop from MDW to SJO, which is 2199.5 miles by air.
Which airlines provide the cheapest flights from Chicago (MDW) to San Jose (SJO) ?
In the past couple of days, the cheapest tickets to SJO from MDW were found on WN : USD 606
Do I need a passport to fly between MDW and SJO?
Yes
What’s the latest departure time from MDW to SJO ?
The last flight leaves MDW at 9:50 pm
Chicago (MDW) to San Jose (SJO): Airport Information
| Origin Airport | Chicago Midway International , Chicago, US |
| Destination Airport | Juan Santamaria International , San Jose, CR |
| Distance | 2200 miles |
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