Wayfli › Boston (BOS) › To Chicago (ORD)
Boston (BOS) to Chicago (ORD) flights
There are direct flights from Boston General Edward Lawrence Logan International Airport to Chicago O'Hare International Airport, sold by 3 airlines (including codeshares): American Airlines, jetBlue and United Airlines. The distance is 1,391 km, about 2h 10m in the air. There are also 21 one-stop options, via airports such as New York, Newark and Toronto.
Live fares for BOS → ORDSee all routes on the map1,391 kmdistance
~2h 10mdirect flight time (estimate)
3direct airlines
21one-stop options
Direct flights from Boston to Chicago
| Route | Airlines (incl. codeshares) | Distance | Time (est.) |
|---|---|---|---|
| BOS → ORD | American Airlines, jetBlue, United Airlines | 1,391 km | ~2h 10m |
Best one-stop connections
Through the biggest hubs first. Times include about 100 minutes to change planes.
| Via | Airlines | Distance | Time (est.) |
|---|---|---|---|
| JFK New York | American Airlines and jetBlue then American Airlines and jetBlue | 1,488 km | ~4h 30m |
| EWR Newark | jetBlue and United Airlines then American Airlines and United Airlines | 1,477 km | ~4h 30m |
| YYZ Toronto | Air Canada and United Airlines then American Airlines and Air Canada | 1,416 km | ~4h 25m |
| IAD Washington | jetBlue and United Airlines then United Airlines | 1,609 km | ~4h 40m |
| PHL Philadelphia | American Airlines and jetBlue then American Airlines and United Airlines | 1,538 km | ~4h 35m |
| YUL Montreal | Air Canada and United Airlines then American Airlines and Air Canada | 1,610 km | ~4h 40m |
| DCA Washington | American Airlines and jetBlue then American Airlines and United Airlines | 1,624 km | ~4h 40m |
| BWI Baltimore | jetBlue and Southwest Airlines then American Airlines and United Airlines | 1,592 km | ~4h 35m |
| CLE Cleveland | United Airlines then American Airlines and United Airlines | 1,410 km | ~4h 25m |
| LGA New York | American Airlines then American Airlines and United Airlines | 1,474 km | ~4h 30m |
| DTW Detroit | jetBlue then American Airlines and United Airlines | 1,391 km | ~4h 20m |
| PIT Pittsburgh | American Airlines and jetBlue then American Airlines and United Airlines | 1,459 km | ~4h 25m |
More from Boston and Chicago
- Chicago (ORD) to Boston (BOS) · return route
- All direct flights from Boston (BOS)
- All direct flights from Chicago (ORD)
- Boston to Istanbul (IST)
- Boston to Amsterdam (AMS)
- Boston to Paris (CDG)
- Boston to Frankfurt (FRA)
- Boston to Dubai (DXB)
- Boston to Beijing (PEK)
- Boston to Dallas-Fort Worth (DFW)
- Boston to Madrid (MAD)
- Boston to Rome (FCO)
- Boston to Munich (MUC)
- Boston to London (LHR)
- Boston to Atlanta (ATL)
- Istanbul (IST) to Chicago
- Amsterdam (AMS) to Chicago
- Paris (CDG) to Chicago
- Frankfurt (FRA) to Chicago
- Dubai (DXB) to Chicago
- Beijing (PEK) to Chicago
- Dallas-Fort Worth (DFW) to Chicago
- Madrid (MAD) to Chicago
- Shanghai (PVG) to Chicago
- Rome (FCO) to Chicago
- Munich (MUC) to Chicago
- London (LHR) to Chicago
Routes come from current airline fares, updated weekly (last update 9 November 2026), plus older schedule data for airports with few recent fares. “Direct” can include a few same-plane flights with a stop. Flight times are estimates from distance. Always check with the airline before booking.