Cheap flights from Chicago O'Hare to Boston Logan from $119
Updated 2026-07-25
864 miles great-circle distance, typically flown in 2h 08m with 5 airlines operating direct service from Chicago O'Hare (ORD) to Boston Logan (BOS). Fares on this corridor stay relatively stable across the year — booking 4–8 weeks ahead and choosing a midweek departure typically secures the best price.
Flying from Chicago O'Hare
Chicago O'Hare is one of America's two busiest hubs and the home base for both United and American — Terminals 1 and 2 belong to United, Terminal 3 to American, and Terminal 5 handles all international arrivals. The CTA Blue Line runs from a station at the airport to downtown Loop in around 45 minutes for $5. Winter weather drives chronic delays from late November through February, so build in connection padding through ORD between Thanksgiving and President's Day.
Arriving in Boston
Boston Logan is 3 miles from downtown Boston — the closest big-city airport in the country to its city centre. The Silver Line bus runs free for arriving passengers from each terminal directly to South Station in 15 minutes. Fares to Boston peak around college move-in (late August), graduation (May) and during the Marathon (April); January and February are cheapest, though weather disruption is significant.
Who flies ORD to BOS?
| Airline | IATA | Flight time | Cabin |
| United Airlines | UA | 2h 08m | Economy |
| American Airlines | AA | 2h 08m | Economy |
| Spirit Airlines | NK | 2h 08m | Economy |
| Frontier Airlines | F9 | 2h 08m | Economy |
| Delta Air Lines | DL | 2h 08m | Economy |
5 carriers fly direct on this corridor. Frequencies vary by season — summer and winter holiday peaks see additional flights.
Chicago to Boston FAQs
Direct flights from Chicago O'Hare (ORD) to Boston Logan (BOS) take approximately 2h 08m for the 864-mile journey, plus 30–60 minutes of taxi, climb and descent. Total airport-to-airport time depends on cruise winds and air-traffic queueing on approach.
5 carriers operate direct service from Chicago O'Hare (ORD) to Boston Logan (BOS): United Airlines, American Airlines, Spirit Airlines, Frontier Airlines and Delta Air Lines. Frequencies vary by season and carrier — United Airlines typically operates the highest weekly count on this corridor.
No — United States is domestic travel for US citizens. A US passport is not required for the 50 states, DC or US territories (Puerto Rico, US Virgin Islands, Guam, American Samoa, Northern Mariana Islands), though Real ID-compliant ID is required at TSA from May 2025.
Boston Logan (BOS) is the primary international airport for Boston. Allow 30–60 minutes for the ground transfer by train, express bus, taxi or rideshare depending on traffic and time of day. See the airport's official website for current train and shuttle timetables.