Cheap Flight Tickets from Chicago (MDW) to San Jose (SJO), Starting at $445

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

$445

WN Southwest Airlines • 1 stop • 29h 15m

Jan 10 – Jan 16

The cheapest round trip flight from Chicago to San Jose (MDW-SJO-MDW) is currently $445

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Fastest Flight

13h 45m

The fastest nonstop flight from Chicago to San Jose (MDW-SJO) takes 13h 45m

Top Airlines Flying from Chicago to San Jose

Southwest Airlines-WN

Southwest Airlines

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.

Jan 10 - Jan 16, Economy
WN
Chicago → San Jose
29h 15m
7:50 PM - 1:45 PM • 1 stop
WN
Chicago → San Jose
13h 20m
2:45 PM - 10:45 PM • 1 stop
$445
Southwest Airlines
Jan 10 - Jan 16, Economy
WN
Chicago → San Jose
13h 45m
5:20 AM - 1:45 PM • 1 stop
WN
Chicago → San Jose
13h 55m
1:05 PM - 9:40 PM • 1 stop
$445
Southwest Airlines
Jan 09 - Jan 16, Economy
WN
Chicago → San Jose
30h 45m
6:05 PM - 12:50 PM • 2 stops
WN
Chicago → San Jose
13h 20m
2:45 PM - 10:45 PM • 1 stop
$449
Southwest Airlines
Jan 09 - Jan 16, Economy
WN
Chicago → San Jose
34h
5:05 PM - 1:45 PM • 2 stops
WN
Chicago → San Jose
13h 55m
1:05 PM - 9:40 PM • 1 stop
$449
Southwest Airlines
Jan 07 - Jan 18, Economy
WN
Chicago → San Jose
13h 45m
5:20 AM - 1:45 PM • 1 stop
WN
Chicago → San Jose
17h 30m
1:05 PM - 11:55 PM • 2 stops
$449
Southwest Airlines
Jan 09 - Jan 16, Economy
WN
Chicago → San Jose
32h 25m
5:05 PM - 12:50 PM • 2 stops
WN
Chicago → San Jose
13h 55m
1:05 PM - 9:40 PM • 1 stop
$449
Southwest Airlines

Fly from Chicago to San Jose with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to San Jose? Find the biggest savings on one-way and round-trip tickets right here.

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 5:20 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 449
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 7:50 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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