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# Chicago → Sao Paulo · Business return from US$2,431
- URL: https://atthepointyend.com/chicago-sao-paulo-business-return-from-us-2-431/
- Published: 2026-08-18T11:37:56.000Z
- Updated: 2026-08-18T11:54:08.000Z
- Description: Business return to Sao Paulo from US$2,431, well below typical. Checked against live availability.
- Author: At The Pointy End
- Tags: #deal, north-america, south-america, United States, Brazil, business

**Well below the usual price** for this route. You're looking at **Business class** from **US$2,431 return** with ![](https://www.google.com/s2/favicons?domain=avianca.com&sz=32)Avianca. *All prices in US dollars.*

*✓ We confirmed this fare was bookable on 17 Aug. Prices move, so always check the live fare before you book.*

![Chicago to Sao Paulo route map](https://storage.ghost.io/c/b4/3a/b43afb32-9ba5-4930-9546-430122c7e305/content/images/2026/08/map-ord-gru-atpe-71bf70a7e340bab4.png)

### The deal at a glance

| **Route**        | Chicago (ORD) → Sao Paulo (GRU)                                         |
| ---------------- | ----------------------------------------------------------------------- |
| **Cabin**        | Business class                                                          |
| **Trip**         | Return                                                                  |
| **Flights**      | 2 stops · ORD-BOG-GRU                                                   |
| **Airline**      | ![](https://www.google.com/s2/favicons?domain=avianca.com&sz=32)Avianca |
| **Travel dates** | 26 discounted departure days found between 1 Oct and 30 Oct             |
| **Book by**      | While it lasts                                                          |
| **Distance**     | \~8,428 km · \~10.5h flying each way                                    |

**The fare we priced:** depart 4 Oct, return 14 Oct. That exact itinerary was live at the price above when we checked.

**Cheapest departure days in the window:** 4 Oct, 6 Oct, 9 Oct, 11 Oct, 27 Oct, 28 Oct. Prices vary by day; flexible dates find the best fare.

[Check this US$2,431 fare →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fus.trip.com%2Fflights%2Fshowfarefirst%3Fdcity%3Dchi%26dairport%3Dord%26acity%3Dsao%26aairport%3Dgru%26ddate%3D2026-10-04%26rdate%3D2026-10-14%26triptype%3Drt%26class%3Dc%26lowpricesource%3Dsearchform%26quantity%3D1%26searchboxarg%3Dt%26nonstoponly%3Doff%26locale%3Den-US%26curr%3DUSD%26Allianceid%3D9230425%26SID%3D323960127%26trip%5Fsub1%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Fweb&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=flight&ref=atthepointyend.com)   
*Opens the live fare on the booking site. You always see the current price before you book. We may earn a commission if you book, at no extra cost to you.*

Fares like this appear and disappear on their own schedule: [get free email alerts](#/portal/signup) the moment we find the next one.

### Make it a trip

Booked the fare? The rest of Sao Paulo, sorted. We may earn a commission on these, which never affects which deals we publish.

Where to stay

Hotels in Sao Paulo

[Search →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fus.trip.com%2Fhotels%2Flist%3FcityId%3D415%26searchType%3DCT%26checkin%3D2026-10-04%26checkout%3D2026-10-14%26crn%3D1%26adult%3D2%26Allianceid%3D9230425%26SID%3D323960127%26trip%5Fsub1%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Fhotel&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=hotels&ref=atthepointyend.com) 

via Trip.com

Things to do

Tours and tickets

[Search →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fwww.klook.com%2Fsearch%2F%3Fquery%3DSao%2BPaulo%26aid%3D128430%26aff%5Fadid%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Ftours&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=tours&ref=atthepointyend.com) 

via Klook

Airport transfer

Private or shared

[Search →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fwww.trip.com%2Fairport-transfers%2F%3FAllianceid%3D9230425%26SID%3D323960127%26trip%5Fsub1%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Ftransfer&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=transfer&ref=atthepointyend.com) 

via Trip.com

Car hire

Compare local rates

[Search →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Ftp.media%2Fr%3Fmarker%3D749879%26trs%3D549325%26p%3D5996%26u%3Dhttps%253A%252F%252Fgetrentacar.com%26campaign%5Fid%3D222%26sub%5Fid%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Fcar&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=car&ref=atthepointyend.com) 

via GetRentacar

### Why it's a deal

$2,431 in business class is well below what this route normally goes for up front. We only see availability at the moment we check, so if the dates work for you, the button shows whether the price is still there.

[![Chicago to Sao Paulo Business class fare on Google Flights](https://storage.ghost.io/c/b4/3a/b43afb32-9ba5-4930-9546-430122c7e305/content/images/2026/08/gf-proof-atpe-71bf70a7e340bab4.png)](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fus.trip.com%2Fflights%2Fshowfarefirst%3Fdcity%3Dchi%26dairport%3Dord%26acity%3Dsao%26aairport%3Dgru%26ddate%3D2026-10-04%26rdate%3D2026-10-14%26triptype%3Drt%26class%3Dc%26lowpricesource%3Dsearchform%26quantity%3D1%26searchboxarg%3Dt%26nonstoponly%3Doff%26locale%3Den-US%26curr%3DUSD%26Allianceid%3D9230425%26SID%3D323960127%26trip%5Fsub1%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Fweb&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=flight&ref=atthepointyend.com)

Fare spotted on Google Flights on 17 Aug. Tap to check the current price, which may have moved since.

### Fare rules & what to check

Before booking, confirm the essentials:

- **Baggage & seat**: what's included at this fare
- **Changes & refunds**: discounted premium fares are often non-refundable
- **Routing**: long layovers or a different return path

### Price in your currency

USD2,431

EUR2,101

GBP1,795

AUD3,432

CAD3,373

BRL12,601

*Converted 2026-08-17\. Rates move, so treat it as a guide.*

Paying in another currency? [Get a free multi-currency travel card](https://www.revolut.com/en-AU/?ref=atthepointyend.com) and spend at great exchange rates while you travel.

### How to book

[Check this US$2,431 fare →](https://go.atthepointyend.com/go/l?u=https%3A%2F%2Fus.trip.com%2Fflights%2Fshowfarefirst%3Fdcity%3Dchi%26dairport%3Dord%26acity%3Dsao%26aairport%3Dgru%26ddate%3D2026-10-04%26rdate%3D2026-10-14%26triptype%3Drt%26class%3Dc%26lowpricesource%3Dsearchform%26quantity%3D1%26searchboxarg%3Dt%26nonstoponly%3Doff%26locale%3Den-US%26curr%3DUSD%26Allianceid%3D9230425%26SID%3D323960127%26trip%5Fsub1%3Datpe%5Fatpe-71bf70a7e340bab4%5Fnorth-america%5Fweb&k=deal&i=atpe-71bf70a7e340bab4&c=web&p=flight&ref=atthepointyend.com)   
*Opens the live fare on the booking site. You always see the current price before you book. We may earn a commission if you book, at no extra cost to you.*

*No fixed sale end date. The price was live when we checked; the button always opens the current fare.*

### Where to stay in Sao Paulo

Over a million hotels on Trip.com, with prices in your currency and free cancellation on many rooms.

Destination

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Rooms1234

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**Data the moment you land in Sao Paulo.**A Saily eSIM installs before you fly: no roaming bill, no airport SIM queue.

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**Flying out of Chicago often?** Our Chicago departure guide tracks every live business and first class fare leaving Chicago: who flies where, what each route normally costs, and when it’s cheapest. [See every business class deal from Chicago →](https://atthepointyend.com/business-class-from-chicago/) 

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### Share this deal

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*At The Pointy End earns a commission if you book through our links, at no extra cost to you. It never affects which deals we post. Prices and availability change, so always confirm before booking.*

Cover photo by [Agustin Diaz Gargiulo](https://unsplash.com/@agustindiazg?utm%5Fsource=at%5Fthe%5Fpointy%5Fend&utm%5Fmedium=referral) on [Unsplash](https://unsplash.com/?utm%5Fsource=at%5Fthe%5Fpointy%5Fend&utm%5Fmedium=referral).