Flights to Roosevelt Roads from Chicago - ￥24,150

View ￥24,150 flight on Thu, Oct 9, 2025Opens in a new window

Popular airlines from Chicago to Roosevelt Roads

  • American Airlines

    American Airlines

  • United

    United

  • Delta

    Delta

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago to Roosevelt Roads (CHI-SJU)

Prices were available within the past 7 days and start at ￥24,150 for one-way flights and ￥42,100 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, Oct 9 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥42,100 Roundtrip, found 15 hours ago
￥42,100
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Oct 9 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥42,100 found 15 hours ago
American Airlines
Fri, Oct 10 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥46,130 Roundtrip, found 15 hours ago
￥46,130
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Oct 10 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥46,130 found 15 hours ago
American Airlines
Thu, Oct 9 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥46,800 Roundtrip, found 15 hours ago
￥46,800
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Thu, Oct 9 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥46,800 found 15 hours ago
American Airlines
Fri, Oct 10 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥47,470 Roundtrip, found 15 hours ago
￥47,470
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Oct 10 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥47,470 found 15 hours ago
Delta
Fri, Oct 10 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥47,600 Roundtrip, found 15 hours ago
￥47,600
Roundtrip
found 15 hours ago
Select Delta flight, departing Fri, Oct 10 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥47,600 found 15 hours ago
United
Fri, Oct 10 - Sat, Oct 11
ORD
Chicago
SJU
San Juan
￥53,530 Roundtrip, found 15 hours ago
￥53,530
Roundtrip
found 15 hours ago
Select United flight, departing Fri, Oct 10 from Chicago to San Juan, returning Sat, Oct 11, priced at ￥53,530 found 15 hours ago

Find the cheapest month to fly from Chicago (CHI) to San Juan (SJU)

January is typically the cheapest month to fly

From ￥18,470 - ￥62,890 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.