What this Boston & Chicago page shows
This page compares the full metro areas of Boston (BOS) and Chicago (ORD, MDW) and lists every destination both cities can reach on a nonstop flight: 129 in all, across 38 countries and 7 regions. For each one you can see the flight time and distance from BOS and from CHI, 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 (Toronto has the smallest gap in flight distance here) before opening the full table to sort all 129 shared routes. To filter by month and check live fares, open the Midway app with Boston and Chicago already loaded.
Where you can both fly
Every marker is a destination with nonstop service from both Boston and Chicago. The spread runs from Hyannis close by to Hong Kong 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 BOS and from CHI. When those two legs are close, the trip splits evenly between Boston and Chicago. Open the full table in Midway to sort by either leg or filter by month.
Where in the world
Shared destinations grouped by region — 129 in total across 7 regions.
Year-round or seasonal
63% of these routes fly year-round, with 48 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 Boston and Chicago share?
Boston and Chicago share 129 destinations reachable nonstop from both metros, across 38 countries and 7 regions.
What is the closest place both Boston and Chicago can fly to nonstop?
Hyannis is the closest shared nonstop destination for Boston and Chicago.
Where should travelers from Boston and Chicago meet halfway?
Toronto 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 Boston and Chicago?
Hong Kong is the farthest destination both Boston and Chicago can reach nonstop.
Open Boston and Chicago 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 5, 2026