Cheap Flights from Chicago to San Juan
Cheap Flights from Chicago to San Juan
Looking for cheap flights from Chicago to San Juan? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to San Juan vary by season, cabin, and date, but available award flights can start around 14,300–15,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to San Juan for specific travel dates.
2026-12-31
ORD - SJU
Economy | 1 Stop | 9+ left
From 14,300 Pts + $5.6
2026-11-24
ORD - SJU
Economy | 1 Stop | 9+ left
From 15,000 Pts + $48.6
2026-12-22
ORD - SJU
Economy | 1 Stop | 4 left
From 15,000 Pts + $48.6
2026-11-22
ORD - SJU
Economy | 2 Stops | 4 left
From 15,000 Pts + $125
2026-12-10
ORD - SJU
Economy | 2 Stops | 9+ left
From 15,000 Pts + $125
2026-12-13
ORD - SJU
Economy | 2 Stops | 9+ left
From 15,000 Pts + $125
Chicago to San Juan flight facts
Distance
2,072 mi
3,335 km in a straight line
Estimated flight time
about 4h 45m
In the air, for the straight-line distance
Time difference
+2h
San Juan is 2 hours ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in San Juan
SJU · Luis Munoz Marin Intl
Nearby airport alternatives
Flights Chicago - St. Thomas · St. Thomas is 68 mi from San Juan
Flights Milwaukee - San Juan · Milwaukee is 73 mi from Chicago
Flights Chicago - Aguadilla · Aguadilla is 74 mi from San Juan
Flights South Bend - San Juan · South Bend is 86 mi from Chicago
Flights Madison - San Juan · Madison is 111 mi from Chicago
Flights Grand Rapids - San Juan · Grand Rapids is 142 mi from Chicago
Premium cabin flights from Chicago to San Juan
Premium cabin
2026-11-21
ORD - SJU
First | 1 Stop
From 43,600 Pts + $29
Premium cabin
2026-11-19
ORD - SJU
First | 1 Stop | 6 left
From 98,300 Pts + $5.6
Premium cabin
2026-11-20
ORD - SJU
First | 1 Stop | 2 left
From 103,300 Pts + $5.6
Premium cabin
2026-11-21
ORD - SJU
First | 1 Stop | 5 left
From 112,800 Pts + $5.6
Premium cabin
2026-11-10
ORD - SJU
Business | Non stop | 8 left
From 25,000 Pts + $25.6
Premium cabin
2026-11-06
ORD - SJU
Business | 1 Stop | 3 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
San Juan (Puerto Rico)
Olive Boutique Hotel(SLH)
From 90,000 Pts or $371
San Juan (Puerto Rico)
Sheraton Puerto Rico Resort & Casino
From Pts or $387
San Juan (Puerto Rico)
San Juan Marriott Resort & Stellaris Casino
From Pts or $509
Frequently Asked Questions
The cheapest route from Chicago to San Juan depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to San Juan.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to San Juan.
Chicago and San Juan are about 2,072 miles (3,335 km) apart in a straight line.
Flying the 2,072-mile straight-line distance takes about 4h 45m in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
San Juan is 2 hours ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in San Juan: Luis Munoz Marin Intl (SJU).
Travelers searching this route also look at other popular routes into San Juan, plus the return trip when we track it. Fares and award space change daily.
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