Route information
- Data Nov 2026 – Oct 2027
Data covers November 2026–October 2027. Across all six months with calendar prices, November 2026 is the cheapest (20,000 points); July 2027 is the priciest (38,000).
ORDGRU
Chicago to Sao Pauloaward flights
Compare 10 loyalty programs for Chicago to Sao Paulo award flights, with economy seats from 20,000 points.
From
ORD
ORD
To
GRU
GRU
Depart
Route snapshot
Chicago to Sao Paulo shows nonstop award space on United Airlines. Across the 10 programs pricing it, economy starts at 20,000 points through American AAdvantage. More programs mean more ways to overpay, since the same seat can cost very different amounts depending on the program. The tables below compare ORD–GRU pricing across all 10 programs.
- Route
- ORD to GRU
- Direct service
- 161 direct award flights
- Airlines with award availability
- 11
- Best economy price
- From 20,000 pts
- Best premium economy price
- From 33,000 pts
- Best business price
- From 57,500 pts
- Best first class price
- From 60,000 pts
Award pricing comparison
Best one-way award prices per airline over the next 12 months.
| Airline | Economy | Premium economy | Business | First |
|---|---|---|---|---|
 American AirlinesAA | 20,000Lowest | 33,000Lowest | 57,500Lowest | 60,000Lowest |
 AviancaAV | 27,990pts | Not available | 60,000pts | Not available |
 Copa AirlinesCM | 28,000pts | Not available | 100,000pts | Not available |
 KLMKL | 29,000pts | 90,000pts | 288,000pts | Not available |
 GolG3 | 30,000pts | 40,000pts | Not available | Not available |
 DeltaDL | 36,000pts | 155,000pts | 480,000pts | 420,000pts |
 AeromexicoAM | 38,062pts | 96,000pts | 86,000pts | Not available |
 Air CanadaAC | 40,000pts | 74,000pts | 95,800pts | Not available |
 United AirlinesUA | 40,000pts | 55,000pts | 212,900pts | 179,300pts |
 LATAMLA | 48,500pts | Not available | 119,000pts | Not available |
Lowest in each cabin—No award seats foundPoints, one-way. Live award pricing from FlightFlyer data, computed 10/31/2026. Prices vary by date and availability.
Award pricing by month
When award seats between Chicago and Sao Paulo price cheapest over the next year.
Cheapest monthNovember 2026 · 20,000 pts
CheapestNext 12 months| Month | Cheapest award (points) |
|---|---|
| Nov 2026 | 20,000 |
| Dec 2026 | 26,000 |
| Jan 2027 | 27,990 |
| Feb 2027 | 37,000 |
| Mar 2027 | No award data |
| Apr 2027 | No award data |
| May 2027 | No award data |
| Jun 2027 | No award data |
| Jul 2027 | 38,000 |
| Aug 2027 | 22,000 |
| Sep 2027 | No award data |
| Oct 2027 | No award data |
Nov, Aug, Dec currently price cheapest on this route, with awards from 20,000 pts one-way based on recent award data.
Airlines with award seats on this route
8 airlines with award seats between Chicago and Sao Paulo, nonstop or connecting.
American AirlinesAAAir CanadaACAeromexicoAMAviancaAVCopa AirlinesCMDeltaDLGolG3United AirlinesUARoute notes
What to know before booking Chicago to Sao Paulo with points.
About this route
Chicago to Sao Paulo is served by American Airlines, Air Canada, Air France and 8 more, offering multiple options for award travelers. Compare 10 loyalty programs to find the best value for your points. Award prices start from 20,000 points in economy. Use our search tool to check real-time award availability on this route.
Chicago–Sao Paulo Flights
This route runs from Chicago's O'Hare International Airport (ORD) to Sao Paulo (GRU). Nonstop award space in the data comes from a single airline: United Airlines. Less than 1% of the award options in the data are nonstop, so most results connect.
Best Ways to Book With Points & Miles
Booking Chicago–Sao Paulo with points starts with the cabin, then the program. The economy floor connects once; an economy nonstop on United Airlines costs more. The connection changes airports in New York, from LaGuardia (LGA) to John F. Kennedy (JFK), so leave time to get between them. Taxes and fees on the cheapest economy seat run about $6, below the route's typical economy taxes. Stepping up costs about 1.7 times the economy points for premium economy and about 2.9 times for business.
Best Points & Miles Programs
American AAdvantage wins economy at 20,000 points, premium economy at 33,000, and business class at 57,500. The premium-economy routing changes airports between Newark and New York, from Newark (EWR) to John F. Kennedy (JFK), so allow transfer time. Alaska Atmos Rewards' 60,000-point first-class fare connects; treat it as mixed-cabin until each segment's cabin checks out. The other eight programs include Air France-KLM Flying Blue, Air Canada Aeroplan, and Delta SkyMiles.
Airlines & Routing Options
The data has one nonstop award carrier on Chicago–Sao Paulo: United Airlines. Its Star Alliance membership means alliance partners can sell that seat too, not only United MileagePlus. The cheaper connecting awards in the data change planes in Miami, New York, and Mexico City.
Alternative Airports & Routes
Neither Chicago nor Sao Paulo shows a same-metro alternate airport in the data, so the main airports are the ones to watch. Out of Chicago, Aruba (9,000 points) and Athens (9,500) are cheaper redemptions at last check. When saver space runs out, a few days of date flexibility is the main lever.
Booking tips
- 1Search flexible dates first, since saver award seats can appear on scattered days.
- 2Compare partner programs before transferring points, since the same seat can price very differently.
- 3Check both direct and connecting options when direct award seats are limited.
- 4Book early for peak travel periods, when saver space disappears fastest.
- 5Recheck availability often, since airlines may release more award seats closer to departure.
Similar routes
Alternative corridors travelers consider alongside Chicago to Sao Paulo.
ORDYYZChicago to Toronto
From 1,883 ptsBusiness 9,000 pts
ORDFLLChicago to Fort Lauderdale
From 5,500 ptsBusiness 29,000 pts
ORDLAXChicago to Los Angeles
From 5,700 ptsBusiness 25,500 pts
ORDMUCChicago to Munich
From 6,293 ptsBusiness 55,000 pts
ORDSEAChicago to Seattle
From 6,900 ptsBusiness 30,000 pts
ORDJFKChicago to New York
From 7,500 ptsBusiness 25,000 pts
FAQ
Frequently Asked Questions
Common questions travelers ask about the Chicago to Sao Paulo route.
At last check, the economy floor is 20,000 points one-way through American AAdvantage, with one stop. That itinerary changes airports in New York, from LaGuardia to JFK, so allow time for the transfer. With 10 programs pricing the route, it pays to check several. The pricing table above breaks the price down by cabin.