Chicago (ORD) to Middletown (MDT) flights
2 airlines fly nonstop from Chicago (ORD) to Middletown (MDT): American Airlines and United Airlines. The two airports are 593 miles (954 km) apart. American Airlines is in oneworld and United Airlines is in Star Alliance. There are also 8 ways to fly it with one stop, through Detroit, Dulles and Philadelphia and more.
Airlines flying nonstop from ORD to MDT
- American Airlinesoneworld · bookable with 9 programsWho books it
- United AirlinesStar Alliance · bookable with 13 programsWho books it
Book ORD to MDT with points
Loyalty programs that can book at least one of the nonstop airlines, from the Award Booking Guide.
- Air Canada AeroplanBooks United Airlines
- 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
- Emirates SkywardsBooks United Airlines
- EVA Air Infinity MileageLandsBooks United Airlines
- Finnair PlusBooks American Airlines
- Iberia ClubBooks American Airlines
- JAL Mileage BankBooks American Airlines
- JetBlue TrueBlueBooks United Airlines
- Lufthansa Miles & MoreBooks United Airlines
- Qantas Frequent FlyerBooks American Airlines
- Qatar Airways Privilege ClubBooks American Airlines
- Singapore Airlines KrisFlyerBooks United Airlines
- TAP Miles&GoBooks United Airlines
- Thai Royal Orchid PlusBooks United Airlines
- Turkish Airlines Miles&SmilesBooks United Airlines
- United MileagePlusBooks United Airlines
ORD to MDT with one stop
8 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 Dulles (IAD)United Airlines the whole way
- Via Philadelphia (PHL)American Airlines the whole way
- Via Charlotte (CLT)American Airlines the whole way
- Via Nashville (BNA)American Airlines and United Airlines, then Allegiant Air
- Via Boston (BOS)American Airlines the whole way
+1 - Via Myrtle Beach (MYR)American Airlines and United Airlines, then Allegiant Air
- Via Atlanta (ATL)Delta Air Lines the whole way+1
ORD to MDT: common questions
Which airlines fly nonstop from ORD to MDT?
American Airlines (oneworld) and United Airlines (Star Alliance) fly nonstop from Chicago (ORD) to Middletown (MDT).
How far is Chicago from Middletown by plane?
Chicago (ORD) and Middletown (MDT) are 593 miles (954 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
Which points programs can book ORD to MDT award flights?
22 programs can book at least one of the nonstop airlines: Air Canada Aeroplan, Air New Zealand Airpoints, Alaska Atmos Rewards, American AAdvantage, ANA Mileage Club, Avianca LifeMiles, British Airways Club, Cathay Pacific Asia Miles and 14 more. Which flights each can book depends on its partners, so check the airline before you transfer points.
How many miles does ORD to MDT cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for ORD to MDT with taxes and fees.
Where can I connect between Chicago and Middletown?
The most direct connections are through Detroit (DTW), Dulles (IAD), Philadelphia (PHL), Charlotte (CLT) and Nashville (BNA). On 6 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.