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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
$177
Southwest Airlines
• 2 stops
• 19h 5m
Aug 06 – Aug 09
The cheapest round trip flight from Chicago to San Jose (MDW-SJO-MDW) is currently $177
Fastest Flight
10h 44m
The fastest nonstop flight from Chicago to San Jose (MDW-SJO) takes 10h 44m
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.
Aug 06 - Aug 09, Economy
Chicago → San Jose
19h 5m
7:55 AM - 6:40 PM • 2 stops
Chicago → San Jose
15h 30m
9:00 AM - 7:30 PM • 2 stops
Southwest Airlines
Aug 06 - Aug 09, Economy
Chicago → San Jose
19h 5m
7:55 AM - 6:40 PM • 2 stops
Chicago → San Jose
17h 15m
12:35 PM - 12:10 AM • 1 stop
Southwest Airlines
Aug 06 - Aug 09, Economy
Chicago → San Jose
23h 30m
5:30 AM - 6:40 PM • 2 stops
Chicago → San Jose
15h 30m
9:00 AM - 7:30 PM • 2 stops
Southwest Airlines
Aug 06 - Aug 09, Economy
Chicago → San Jose
15h 10m
10:30 AM - 6:40 PM • 2 stops
Chicago → San Jose
18h 40m
9:00 AM - 9:20 PM • 1 stop
Southwest Airlines
Aug 06 - Aug 09, Economy
Chicago → San Jose
20h 15m
7:25 AM - 6:40 PM • 1 stop
Chicago → San Jose
29h 10m
12:35 PM - 7:25 AM • 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 5:30 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 177
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 10:30 am
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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