Cheap Flights from Chicago to Sao Paulo
Cheap Flights from Chicago to Sao Paulo
Looking for cheap flights from Chicago to Sao Paulo? 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 Sao Paulo vary by season, cabin, and date, but available award flights can start around 40,000–44,000 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 Sao Paulo for specific travel dates.
2026-11-30
ORD - GRU
Premium Economy | 2 Stops
From 40,000 Pts + $12
2026-11-10
ORD - GRU
Premium Economy | 2 Stops | 1 left
From 40,000 Pts + $25.6
2026-11-25
ORD - GRU
Premium Economy | 2 Stops | 1 left
From 40,000 Pts + $25.6
2026-11-26
ORD - GRU
Premium Economy | 2 Stops | 6 left
From 40,000 Pts + $25.6
2026-11-24
ORD - GRU
Premium Economy | 1 Stop
From 44,000 Pts + $5.6
2026-12-02
ORD - GRU
Premium Economy | 1 Stop
From 44,000 Pts + $5.6
Chicago to Sao Paulo flight facts
Distance
5,237 mi
8,428 km in a straight line
Estimated flight time
about 11h
In the air, for the straight-line distance
Time difference
+3h
Sao Paulo is 3 hours ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in Sao Paulo
CGH · Congonhas
GRU · Guarulhos - Governador André Franco Montoro Intl
Premium cabin flights from Chicago to Sao Paulo
Premium cabin
2026-11-11
ORD - GRU
Business | 2 Stops | 4 left
From 60,000 Pts + $25.6
Premium cabin
2026-11-13
ORD - GRU
Business | 2 Stops | 3 left
From 60,000 Pts + $25.6
Premium cabin
2026-11-16
ORD - GRU
Business | 2 Stops | 5 left
From 60,000 Pts + $25.6
Premium cabin
2026-12-08
ORD - GRU
Business | 2 Stops | 1 left
From 60,000 Pts + $25.6
Premium cabin
2026-12-24
ORD - GRU
Business | 2 Stops | 1 left
From 60,000 Pts + $25.6
Premium cabin
2026-12-29
ORD - GRU
Business | 2 Stops | 3 left
From 60,000 Pts + $25.6
Selected hotels for your next stay
São Paulo (Brazil)
JW Marriott Hotel Sao Paulo
From Pts or $305
Sao Paulo (Brazil)
Renaissance Sao Paulo Hotel
From Pts or $223
Sao Paulo (Brazil)
Grand Hyatt São Paulo
From Pts or $986
Frequently Asked Questions
The cheapest route from Chicago to Sao Paulo 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 Sao Paulo.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to Sao Paulo.
Chicago and Sao Paulo are about 5,237 miles (8,428 km) apart in a straight line.
Flying the 5,237-mile straight-line distance takes about 11h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
Sao Paulo is 3 hours ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in Sao Paulo: Congonhas (CGH), Guarulhos - Governador André Franco Montoro Intl (GRU).
Travelers searching this route also look at other popular routes into Sao Paulo, plus the return trip when we track it. Fares and award space change daily.
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