What this Chicago & São Paulo page shows
This page compares the full metro areas of Chicago (ORD, MDW) and São Paulo (GRU, CGH, VCP) and lists every destination both cities can reach on a nonstop flight: 35 in all, across 20 countries and 7 regions. For each one you can see the flight time and distance from CHI and from GRU, so the trade-off between the two legs is clear at a glance.
Use the map to see how far the options spread, then check the meet-in-the-middle pick (Bogotá has the smallest gap in flight distance here) before opening the full table to sort all 35 shared routes. To filter by month and check live fares, open the Midway app with Chicago and São Paulo already loaded.
Where you can both fly
Every marker is a destination with nonstop service from both Chicago and São Paulo. The spread runs from Toronto close by to Dubai at the far edge, so you can gauge whether a short hop or a long-haul meet-up makes more sense.
All shared destinations
Each row is a destination both cities reach nonstop. The two right-hand columns give the flight time and distance from CHI and from GRU. When those two legs are close, the trip splits evenly between Chicago and São Paulo. Open the full table in Midway to sort by either leg or filter by month.
Where in the world
Shared destinations grouped by region — 35 in total across 7 regions.
Year-round or seasonal
74% of these routes fly year-round, with 9 running only in certain seasons. If your meet-up date is flexible you have the full set to choose from; if it is fixed, lean toward the year-round destinations so you are not counting on a route that may not be flying that month.
Related Routes
Frequently asked questions
How many nonstop destinations do Chicago and São Paulo share?
There are 35 destinations both Chicago and São Paulo reach without a connection, spanning 20 countries in 7 regions.
What is the closest place both Chicago and São Paulo can fly to nonstop?
Toronto is the closest shared nonstop destination for Chicago and São Paulo.
Where should travelers from Chicago and São Paulo meet halfway?
Bogotá is the most balanced shared destination, with the smallest difference in flight distance from the two cities.
What is the farthest shared nonstop destination from Chicago and São Paulo?
Dubai is the farthest destination both Chicago and São Paulo can reach nonstop.
Open Chicago and São Paulo in Midway
Filter by month, distance, flight time, country and region, see prices from each city, and send the link to your group.
Last updated: October 6, 2026