$227 Cheap Delta flights from Chicago to San José (MDW to SJO)

Find The Best Day To Fly from Chicago to San José

Amazing Delta MDW to SJO Flight Deals

The cheapest flights to Juan Santamaría Intl. found within the past 7 days were $435 round trip and $227 one way. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 28 - Mon, Dec 15
MDW
Chicago
SJO
San José
$435 Roundtrip, found 5 days ago
$435
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Nov 28 from Chicago to San José, returning Mon, Dec 15, priced at $435 found 5 days ago
Thu, Sep 4 - Mon, Sep 8
MDW
Chicago
SJO
San José
$490 Roundtrip, found 2 days ago
$490
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 4 from Chicago to San José, returning Mon, Sep 8, priced at $490 found 2 days ago

SJO From MDW Economy Coach Packages on Similar Airlines

Price found within the past 48 hours. Click for updated prices.
Si Como No Resort, Spa and Wildlife Refuge

Si Como No Resort, Spa and Wildlife Refuge

3.5 out of 5
Price was $2,245, price is now $912 per person
$912
per person
Oct 11 - Oct 18
just found
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
Vista Suites at Parador

Vista Suites at Parador

2.5 out of 5
Price was $3,723, price is now $1,523 per person
$1,523
per person
Nov 17 - Nov 24
found 3 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to San José (SJO)
Namu Garden Hotel & Spa - Adults Only

Namu Garden Hotel & Spa - Adults Only

4.5 out of 5
Price was $2,540, price is now $1,076 per person
$1,076
per person
Oct 11 - Oct 18
just found
Roundtrip non-stop flight included
Chicago (CHI) to San José (SJO)
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Frequently asked questions

Can I catch a flight from Midway Intl. Airport (MDW) to SJO right now?
For any present SJO travel advice and quarantine requirements, go to the Covid-19 Travel Advisor. Look before you book your flight, so you don't get caught up en route.
What terminal is Delta Air Lines at Chicago Airport?
If you're flying with Delta Air Lines from MDW to Juan Santamaria Intl. Airport (SJO), you should be able to find out the terminal information when you're issued with your ticket. If not, check with your airline.
Are there Delta Air Lines non-stop flights from MDW to SJO?
Delta Air Lines doesn't have direct flights between MDW and Juan Santamaria Intl. Airport, so plan on making at least one stopover. If you're not pushed for time between flights, browse the airport shops while waiting for your connection.
How long is a Delta Air Lines flight from MDW to SJO?
Squeeze in an in-flight snooze and start your vacation well-rested. You'll have plenty of time to do so when traveling with Delta Air Lines between Midway Intl. Airport (MDW) and Juan Santamaria Intl. Airport, with the flight taking around 5 hours and 57 minutes.
How many direct and indirect flights does Delta Air Lines fly from MDW to SJO?
The route is well traveled from Midway Intl. Airport (MDW) to SJO. Delta Air Lines travels between the two at least 7 times per week.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Juan Santamaria Intl. Airport (SJO), please visit our Customer Service Portal.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It's possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Discover our best Delta flight from Chicago MDW to San José SJO 

To find the best deals on flights to Chicago from San José with Delta, just enter your travel dates, filter by Delta, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.  

 

Return flights from Chicago MDW to San José SJO with Delta 

If you’re planning a round trip, booking return flights with Delta is usually the most cost-effective option. With airfares ranging from $435 to $490, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply. 

 

Book one-way Delta flights from Chicago MDW to San José SJO 

A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way Delta flight from Chicago to San José costs from $227. Prices and availability subject to change. Additional terms may apply. 

 

The easy way to find cheap flights to San José SJO from  Chicago MDW with Delta 

To find a cheap Delta flight from Chicago MDW to San José SJO, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference. 

 

How to find our best airfare deals on Delta flights from Chicago MDW to San José SJO 

If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as November, or if you book a flight with a stopover. 

 

Find nonstop flights from Chicago MDW to San José SJO with Delta 

If you’re keen to be on San José soil fast, don’t waste time with a stopover—filter your search results to show direct Delta flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it. 

 

Flexible airline tickets for Delta flights from Chicago MDW to San José SJO 

Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.  

 

There are a lot of reasons to book your flights to San José SJO from  Chicago MDW with Delta on Travelocity 

At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.

Delta Airports
Hop on a(n) Delta flight today by flying to many destinations out of these domestic and international airports:
Airport code
Country
Airport name
Number of flights
ATLUSAHartsfield-Jackson Atlanta Intl.252
DTWUSADetroit Metropolitan Wayne County156
MSPUSAMinneapolis - St. Paul Intl.131
SLCUSASalt Lake City Intl.116
SEAUSASeattle - Tacoma Intl.57
LAXUSALos Angeles Intl.41
AMSNLDSchiphol31
YYCCANCalgary Intl.26
YYZCANPearson Intl.24
JFKUSAJohn F. Kennedy Intl.23

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Hampton by Hilton San Jose Airport

Hampton by Hilton San Jose Airport

3 out of 5
Hwy 1 Airport Blvd, Rio Segundo
This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free ...
Hampton by Hilton San Jose Airport
Courtyard by Marriott San Jose Airport Alajuela

Courtyard by Marriott San Jose Airport Alajuela

3.5 out of 5
Plaza Los Mangos, Radial Francisco J Orlich, Rio Segundo, Alajuela
This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Courtyard by Marriott San Jose Airport Alajuela
Fairfield by Marriott San Jose Airport Alajuela

Fairfield by Marriott San Jose Airport Alajuela

3.5 out of 5
Radial Francisco J. Orlich,, Plaza Los Mangos, Alajuela
This hotel features 2 restaurants and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free airport ...
Fairfield by Marriott San Jose Airport Alajuela
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.