Cheap Flights from San Juan to Chicago
Cheap Flights from San Juan to Chicago
Looking for cheap flights from San Juan to Chicago? 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 San Juan to Chicago vary by season, cabin, and date, but available award flights can start around 8,900–15,000 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 San Juan to Chicago for specific travel dates.
2026-12-02
SJU - ORD
Economy | 1 Stop | 9+ left
From 8,900 Pts + $5.6
2026-11-22
SJU - ORD
Economy | 1 Stop | 9+ left
From 11,900 Pts + $5.6
2026-11-13
SJU - ORD
Economy | Non stop | 9+ left
From 12,500 Pts + $25.6
2026-12-04
SJU - ORD
Economy | Non stop | 5 left
From 12,500 Pts + $25.6
2026-11-22
SJU - ORD
Economy | 1 Stop | 9+ left
From 15,000 Pts + $125
2026-12-02
SJU - ORD
Economy | 1 Stop | 9+ left
From 15,000 Pts + $125
San Juan to Chicago 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
Chicago is 2 hours behind San Juan.
Airports in San Juan
SJU · Luis Munoz Marin Intl
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Nearby airport alternatives
Flights St. Thomas - Chicago · St. Thomas is 68 mi from San Juan
Flights San Juan - Madison · Madison is 111 mi from Chicago
Flights Punta Cana - Chicago · Punta Cana is 155 mi from San Juan
Flights San Juan - Springfield · Springfield is 167 mi from Chicago
Premium cabin flights from San Juan to Chicago
Premium cabin
2026-12-02
SJU - ORD
First | 1 Stop | 2 left
From 52,000 Pts + $5.6
Premium cabin
2026-11-22
SJU - ORD
First | 1 Stop | 2 left
From 80,600 Pts + $5.6
Premium cabin
2026-12-01
SJU - ORD
First | 1 Stop | 6 left
From 95,300 Pts + $5.6
Premium cabin
2026-11-30
SJU - ORD
First | 1 Stop | 1 left
From 107,800 Pts + $5.6
Premium cabin
2026-11-10
SJU - ORD
Business | 1 Stop | 3 left
From 35,000 Pts + $25.6
Premium cabin
2026-11-11
SJU - ORD
Business | 1 Stop | 1 left
From 35,000 Pts + $25.6
Selected hotels for your next stay
Chicago (United States)
Chicago Athletic Association
From 15,000 Pts or $236
Chicago (USA)
ACME Hotel Chicago, Outset Collection by Hilton
From 28,000 Pts or $75
Chicago, IL (USA)
Waldorf Astoria Chicago
From 95,000 Pts or $407
Frequently Asked Questions
The cheapest route from San Juan to Chicago 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 San Juan to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from San Juan to Chicago.
San Juan and Chicago 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.
Chicago is 2 hours behind San Juan.
Departures from San Juan: Luis Munoz Marin Intl (SJU). Arrivals in Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD).
Travelers searching this route also look at other popular routes into Chicago, plus the return trip when we track it. Fares and award space change daily.
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