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Cheap Flights from Chicago to Boston
CHI → BOS • About 2h 30m nonstop • 4 airlines
Adults
+12 years old
Children
2-11 years old
Infants
Under 2 years
Fares shown are the lowest we have recorded recently on this route and are not a live quote. Run a search above for today's availability, or call (800) 399-8818 and an agent will price it with you.
Flights from Chicago (CHI) to Boston (BOS)
The Chicago to Boston route covers roughly 850 miles and takes about 2h 30m nonstop. 4 airlines compete on it — United Airlines, American Airlines, JetBlue Airways, Southwest Airlines — which keeps fares moving and makes it worth comparing carriers rather than defaulting to the one you usually fly. We have seen one-way fares on this route start around $98.
Boston is the most walkable major city in the United States, and the Freedom Trail threads 16 historic sites across two and a half miles of it. Four hundred years of American history sit within a short stroll of the harbor.
It is also a college town on a massive scale, which keeps the food, the music and the bars considerably younger and cheaper than the historical postcard suggests.
Airlines flying CHI to BOS
- United Airlines
- American Airlines
- JetBlue Airways
- Southwest Airlines
Airports on this route
- Departing: Chicago O'Hare International Airport (ORD)
- Departing: Chicago Midway International Airport (MDW)
- Arriving: Boston Logan International Airport (BOS)
Chicago is served by 2 airports. Fares between them can differ by $50 to $150 on the same dates, so ask us to price all of them before you book.
Best time to fly to Boston
May through October. September and October deliver mild days and New England foliage within an easy drive.
Top things to do in Boston
- Freedom Trail
- Fenway Park
- Boston Common and Public Garden
- Faneuil Hall Marketplace
- Museum of Fine Arts
- North End
- Harvard Square, Cambridge
How to save on Chicago to Boston flights
- Shift your departure by one or two days — midweek departures on this route are consistently cheaper than Friday and Sunday.
- Book four to eight weeks ahead. Last-minute fares on CHI to BOS routinely run double the advance price.
- Compare all 4 carriers rather than checking one airline's own site.
- Logan sits three miles from downtown — the Silver Line bus is free inbound from the airport.
- Avoid the first week of September and graduation weekends in May when the entire city's hotel stock is booked.
- Winter fares are the year's cheapest, but nor'easters cause real disruption in January and February.
About flights from Chicago to Boston
Fares on the CHI to BOS route move with demand, so flexibility is worth more than timing tricks. Shifting your departure by a day or two, flying midweek instead of Friday or Sunday, and booking four to eight weeks ahead all reduce the fare on this route. Chicago is served by 2 airports, so ask us to price all of them — the difference is often significant. Our agents also hold consolidator and unpublished fares that do not appear in online results.
United Airlines, American Airlines, JetBlue Airways, Southwest Airlines all operate on this route. United Airlines typically offers the most frequencies, with American Airlines and JetBlue Airways providing competing schedules. Availability varies by season and by which Chicago airport you depart from, so it is worth comparing all carriers before booking.
A nonstop flight takes about 2h 30m. Itineraries with a connection typically add two to four hours depending on the layover city and the length of the stop.
The two cities are roughly 850 miles apart by air.
Departures leave from Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Arrivals land at Boston Logan International Airport (BOS).
May through October. September and October deliver mild days and New England foliage within an easy drive.