- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Plan, book, fly with confidence
Cheap Flights from Chicago to Mayagüez (CHI-SJU)
Prices were available within the past 7 days and start at $62 for one-way flights and $137 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Mon, Aug 26 - Tue, Aug 27
ORD
Chicago
SJU
San Juan
$137 Roundtrip, just found
$137
Roundtrip
just found
Tue, Aug 27 - Wed, Aug 28
ORD
Chicago
SJU
San Juan
$149 Roundtrip, just found
$149
Roundtrip
just found
Thu, Jun 6 - Wed, Jun 12
MDW
Chicago
SJU
San Juan
$238 Roundtrip, found 10 hours ago
$238
Roundtrip
found 10 hours ago
Wed, Aug 21 - Wed, Aug 21
ORD
Chicago
SJU
San Juan
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Sat, Jul 20 - Tue, Aug 6
ORD
Chicago
SJU
San Juan
$276 Roundtrip, found 6 hours ago
$276
Roundtrip
found 6 hours ago
Wed, Sep 25 - Tue, Oct 8
ORD
Chicago
BQN
Aguadilla
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Expedia's Latest Trends
Flights
Flights from Las Vegas to AnaheimFlights from Seattle to MauiFlights from Maui to HonoluluFlights from Providence to BentonvilleFlights from Philadelphia to AnaheimFlights from New York to Yellowstone National ParkFlights from San Francisco to South Lake TahoeFlights from Los Angeles to ShenyangFlights from Honolulu to MauiFlights from Chicago to South Lake TahoeFlights from Los Angeles to San Miguel de AllendeFlights from Boston to ProvidencialesFlights from New York to NormanFlights from Denver to BentonvilleFlights from Orlando to GatlinburgFlights from Seattle to EntebbeFlights from New York to Machu PicchuFlights from Phoenix to AnaheimFlights from Chicago to AnaheimFlights from Denver to AnaheimFlights from Houston to BentonvilleFlights from Spokane to MauiFlights from Los Angeles to Machu PicchuFlights from Anchorage to MauiFlights from Seattle to AnaheimFlights from Las Vegas to MauiFlights from Minneapolis - St. Paul to AnaheimFlights from Los Angeles to Paradise IslandFlights from Houston to AnaheimFlights from Boston to Anaheim
*Available to One Key members.