Cheapest one-way
C$ 286.33
JetBlue · Nonstop · 2 hr 31 min
One-way tickets on ORD–BOS recently started around C$ 286.33.
Flights from Chicago to Boston
Looking for cheap flights from Chicago to Boston? Fares on the ORD–BOS corridor have started around C$ 286.33; review the latest prices, carriers and travel times here.
Chicago to Boston flights overview
BookingTrolley's most recent fare data for the Chicago to Boston route shows tickets from C$ 286.33. Based on this route's seasonal pattern, fares average roughly C$ 590.47 over the year. Nov tends to be the cheapest month to fly (around C$ 491.83), while Jun is usually the most expensive at about C$ 732.95 — a swing of roughly 49%.
A direct Chicago to Boston flight spans roughly 1,391 km and takes about 2 hr 24 min in the air. BookingTrolley found 4 airlines currently compete on the ORD–BOS corridor, with JetBlue posting one of the lowest fares at C$ 572.66. 4 of them offer nonstop options, which save layover time but can cost more than connecting itineraries.
Frequently asked questions about flying from Chicago to Boston
According to BookingTrolley fare data on the Chicago to Boston route (ORD–BOS), round-trip tickets started at C$ 572.66. Prices are shown in USD for comparison; Canada travellers should confirm the final checkout currency on BookingTrolley.
A nonstop flight from Chicago to Boston takes about 2 hr 24 min in the air on the fastest outbound leg, based on BookingTrolley itinerary data from recent searches. Connecting flights add layover time and can extend total travel to a full day or more.
Recent BookingTrolley comparisons list JetBlue (from C$ 572.66), United Airlines (from C$ 574.03), Delta Air Lines (from C$ 587.73) among the lowest fares on Chicago to Boston. Carrier availability changes with season and sales.
Mid-week departures and shoulder seasons usually cost less. According to BookingTrolley fare data on the Chicago to Boston route (ORD–BOS), round-trip tickets started at C$ 572.66. BookingTrolley helps Canada travellers spot dips before peak travel.
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