$358 Cheap Delta flights San Juan (SJU) to Chicago (MDW)

View $358 flight on Sun, Jan 11, 2026Opens in a new window

$358 Cheap Delta flights San Juan (SJU) to Chicago (MDW)

Prices were available within the past 7 days and start at $358 for one-way flights and $673 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Delta
Wed, Jun 11 - Sat, Jun 28
SJU
San Juan
MDW
Chicago
$673
Roundtrip
Found 3 days ago
Select Delta flight, departing Wed, Jun 11 from San Juan to Chicago, returning Sat, Jun 28, priced at $673 Found 3 days ago
Delta
Sun, Jun 15 - Wed, Jun 25
SJU
San Juan
MDW
Chicago
$824
Roundtrip
Found 3 days ago
Select Delta flight, departing Sun, Jun 15 from San Juan to Chicago, returning Wed, Jun 25, priced at $824 Found 3 days ago
Delta
Tue, Jun 10 - Sat, Jun 28
SJU
San Juan
MDW
Chicago
$854
Roundtrip
Found 3 days ago
Select Delta flight, departing Tue, Jun 10 from San Juan to Chicago, returning Sat, Jun 28, priced at $854 Found 3 days ago
Delta
Sun, Jun 15 - Tue, Jun 24
SJU
San Juan
MDW
Chicago
$1,005
Roundtrip
Found 3 days ago
Select Delta flight, departing Sun, Jun 15 from San Juan to Chicago, returning Tue, Jun 24, priced at $1,005 Found 3 days ago
Delta
Thu, Jun 12 - Tue, Jun 24
SJU
San Juan
MDW
Chicago
$1,035
Roundtrip
Found 3 days ago
Select Delta flight, departing Thu, Jun 12 from San Juan to Chicago, returning Tue, Jun 24, priced at $1,035 Found 3 days ago
Flights from San Juan (SJU) to Chicago (MDW)
Origin airport
Luis Munoz Marin Intl.
Destination airport
Midway Intl.
Distance
3293 km
Average flight time
4 hours 55 mins