
$205 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 $510 round trip and $205 one way. Prices and availability subject to change. Additional terms may apply.
SJO From MDW Economy Coach Packages on Similar Airlines


Frequently asked questions
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 $510 to $510, 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 $205. 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 September, 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.
Airport code | Country | Airport name | Number of flights |
---|---|---|---|
ATL | USA | Hartsfield-Jackson Atlanta Intl. | 252 |
DTW | USA | Detroit Metropolitan Wayne County | 156 |
MSP | USA | Minneapolis - St. Paul Intl. | 131 |
SLC | USA | Salt Lake City Intl. | 116 |
SEA | USA | Seattle - Tacoma Intl. | 57 |
LAX | USA | Los Angeles Intl. | 41 |
AMS | NLD | Schiphol | 31 |
YYC | CAN | Calgary Intl. | 26 |
YYZ | CAN | Pearson Intl. | 24 |
JFK | USA | John F. Kennedy Intl. | 23 |
Travelers ❤️ these 🏨 after their flight to San José

Reviewed on Apr 26, 2025

Reviewed on Apr 25, 2025

Reviewed on Apr 26, 2025
Popular Delta Flight Routes from MDW
Top Delta Flight Routes from SJO
Top Flights for Delta originating from MDW
Domestic
- New York to Miami (JFK - MIA)
- Philadelphia to San Juan (PHL - SJU)
- New York to Orlando (JFK - MCO)
- New York to Santiago (JFK - STI)
- New York to Orlando (LGA - MCO)
- New York to Rome (JFK - FCO)
- New York to Orlando (LGA - MCO)
- Chicago to Orlando (ORD - MCO)
- San Juan to Orlando (SJU - MCO)
- San Francisco to Tokyo (SFO - HND)
International
- New York to Montego Bay (JFK - MBJ)
- Newark Liberty Intl. Airport to Miami (EWR - MIA)
- New York to Santiago (JFK - STI)
- New York to San Juan (JFK - SJU)
- Chicago to Orlando (ORD - MCO)
- Seattle to Tokyo (SEA - HND)
- New York to Santo Domingo (JFK - SDQ)
- New York to San Juan (JFK - SJU)
- Newark Liberty Intl. Airport to San Juan (EWR - SJU)
- New York to Rome (JFK - FCO)