Boston (BOS) to Chicago (ORD) flights
An economy award from Boston (BOS) to Chicago (ORD) starts at 5,500 miles one way with American AAdvantage on American Airlines, plus taxes and fees from $5.60. 4 airlines fly nonstop from Boston (BOS) to Chicago (ORD): American Airlines, Delta Air Lines, JetBlue Airways and United Airlines. The two airports are 864 miles (1,390 km) apart. American Airlines is in oneworld, Delta Air Lines is in SkyTeam and United Airlines is in Star Alliance. There are also 52 ways to fly it with one stop, through Detroit, Buffalo and Rochester and more.
How many miles BOS to ORD costs
Economy, one way, on the nonstop flights, from the Award Flight Pricer's award charts. Ranges run off-peak to peak; "from" is the floor of a dynamic price.
| Program | Economy | Taxes and fees |
|---|---|---|
| American AAdvantageOn American Airlines | 5,500 | $5.60 |
| Alaska Atmos RewardsOn American Airlines | 7,500 | $25.60 |
| Iberia ClubOn American Airlines | 9,000 | $5.60 |
| Qatar Airways Privilege ClubOn JetBlue Airways | 9,000 | $5.60 |
| Air Canada AeroplanOn United Airlines | 10,000 | $33.60 |
| Avianca LifeMilesOn United Airlines | 10,000 | $30.60 |
| Virgin Atlantic Flying ClubOn Delta Air Lines | 11,000 | $5.60 |
| Emirates SkywardsOn United Airlines | 12,000 | $5.60–355.60 |
| Etihad GuestOn American Airlines | 12,000 | $5.60 |
| JAL Mileage BankOn American Airlines | 12,000 | $5.60 |
| Qantas Frequent FlyerOn American Airlines | 13,800 | $5.60 |
| ANA Mileage ClubOn United Airlines | 15,000 | $5.60 |
Business and first class prices, and 9 more programs, are in the Award Flight Pricer. Chart prices need award space on your date, so search it before you transfer points.
Compare every program in the Award Flight PricerAirlines flying nonstop from BOS to ORD
- American Airlinesoneworld · bookable with 9 programsWho books it
- Delta Air LinesSkyTeam · bookable with 8 programsWho books it
- JetBlue AirwaysNot in an alliance · bookable with 2 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book BOS to ORD with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- JetBlue TrueBlueBooks JetBlue Airways, United Airlines
- Singapore Airlines KrisFlyerBooks JetBlue Airways, United Airlines
- Aeromexico RewardsBooks Delta Air Lines
- Air Canada AeroplanBooks United Airlines
- Air France-KLM Flying BlueBooks Delta Air Lines
- Air New Zealand AirpointsBooks United Airlines
- Alaska Atmos RewardsBooks American Airlines
- American AAdvantageBooks American Airlines
- ANA Mileage ClubBooks United Airlines
- Avianca LifeMilesBooks United Airlines
- British Airways ClubBooks American Airlines
- Cathay Pacific Asia MilesBooks American Airlines
- China Eastern Eastern MilesBooks Delta Air Lines
- Delta SkyMilesBooks Delta Air Lines
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- Finnair PlusBooks American Airlines
- Garuda Indonesia GarudaMilesBooks Delta Air Lines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- Korean Air SKYPASSBooks Delta Air Lines
- Lufthansa Miles & MoreBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
- SAS EuroBonusBooks Delta Air Lines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
- Virgin Atlantic Flying ClubBooks Delta Air Lines
BOS to ORD with one stop
52 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Buffalo (BUF)American Airlines the whole way
- Via Rochester (ROC)American Airlines the whole way
- Via Syracuse (SYR)American Airlines the whole way
- Via South Bend (SBN)American Airlines the whole way
- Via Grand Rapids (GRR)Allegiant Air, then American Airlines and United Airlines
- Via Cleveland (CLE)JetBlue Airways and Delta Air Lines, then American Airlines and United Airlines
- Via Toronto (YTZ)Porter Airlines and Air Canada the whole way
- Via Toronto (YYZ)Air Canada the whole way
- Via Pittsburgh (PIT)JetBlue Airways and Delta Air Lines, then American Airlines and United Airlines
- Via New York (LGA)American Airlines and Delta Air Lines the whole way
- Via New York (EWR)United Airlines the whole way
- Via New York (JFK)American Airlines, JetBlue Airways and 1 more the whole way
- Via Milwaukee (MKE)American Airlines the whole way
+1 - Via Middletown (MDT)American Airlines the whole way
BOS to ORD: common questions
How many miles does BOS to ORD cost?
In economy it starts at 5,500 miles one way with American AAdvantage on American Airlines, plus taxes and fees from $5.60. Next cheapest: Alaska Atmos Rewards (7,500), Iberia Club (9,000) and Qatar Airways Privilege Club (9,000). These are award chart prices from the Award Flight Pricer. Programs that price dynamically can cost more on busy dates, so check yours before you transfer points. Business and first class prices are in the pricer too.
Which airlines fly nonstop from BOS to ORD?
American Airlines (oneworld), Delta Air Lines (SkyTeam), JetBlue Airways and United Airlines (Star Alliance) fly nonstop from Boston (BOS) to Chicago (ORD).
How far is Boston from Chicago by plane?
Boston (BOS) and Chicago (ORD) are 864 miles (1,390 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book BOS to ORD award flights?
30 programs can book at least one of the nonstop airlines: JetBlue TrueBlue, Singapore Airlines KrisFlyer, Aeromexico Rewards, Air Canada Aeroplan, Air France-KLM Flying Blue, Air New Zealand Airpoints, Alaska Atmos Rewards, American AAdvantage and 22 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
Where can I connect between Boston and Chicago?
The most direct connections are through Detroit (DTW), Buffalo (BUF), Rochester (ROC), Syracuse (SYR) and South Bend (SBN). On 34 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.