Cheapest one-way
$ 209.00
JetBlue · Nonstop · 2 hr 31 min
One-way tickets on ORD–BOS recently started around $ 209.00.
Flights from Chicago to Boston
Compare Chicago to Boston flights on BookingTrolley, where the lowest tracked fare was $ 209.00. Check airlines, nonstop options and the cheapest months to fly.
Chicago to Boston flights overview
BookingTrolley's most recent fare data for the Chicago to Boston route shows tickets from $ 209.00. Based on this route's seasonal pattern, fares average roughly $ 431.00 over the year. Nov tends to be the cheapest month to fly (around $ 359.00), while Jun is usually the most expensive at about $ 535.00 — 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 $ 418.00. 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
Tuesday and Wednesday are typically the cheapest days to fly from Chicago to Boston. According to BookingTrolley fare data on the Chicago to Boston route (ORD–BOS), round-trip tickets started at $ 418.00. United States travellers often save by shifting 3–4 days around their preferred date on BookingTrolley.
The cheapest airlines on Chicago to Boston are JetBlue (from $ 418.00), United Airlines (from $ 419.00), Delta Air Lines (from $ 429.00), according to BookingTrolley's multi-provider comparison priced for the United States market currency when available.
The cheapest flights from Chicago to Boston started at $ 418.00 round trip on a nonstop itinerary on JetBlue, per BookingTrolley data relevant to United States shoppers. Fares fluctuate with demand.
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.
Shoulder season around peak holidays often pairs softer airfares with lighter crowds. According to BookingTrolley fare data on the Chicago to Boston route (ORD–BOS), round-trip tickets started at $ 418.00. BookingTrolley suggests booking 4–8 weeks ahead for routes like Chicago to Boston.
Use BookingTrolley's flexible-date comparison for Chicago (ORD) to Boston (BOS) to see which days cost least. Avoiding Friday–Sunday peaks is one of the fastest ways for United States travellers to cut the ticket price.
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