Route · ORD → BOS
Flights from Chicago to Boston
The Chicago O'Hare–Boston Logan corridor is one of the busier trunk routes in the northeastern United States, covering roughly 1,389 km great-circle with a typical block time of just over two hours. American, United, and JetBlue carry the bulk of passengers, with narrowbody jets such as the Boeing 737 family and Airbus A320 series handling most departures; Alaska runs a thinner schedule while Spirit offers no-frills fares for budget-conscious travelers. A practical note worth knowing: Boston Logan's Terminal C and Terminal E handle different carriers, so confirm your terminal before heading to the airport, as the inter-terminal walk is not trivial under a tight connection. On the fare side, midweek departures on Tuesdays and Wednesdays typically yield the softest prices, and shoulder periods in January and late September often see reduced demand, making them useful windows for economy travelers willing to be flexible.
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Cheapest dates to fly
Live prices · powered by AviasalesThe calendar below pulls live fares from our search partner for Chicago (ORD) → Boston (BOS). Use the year view… to spot the cheapest week to fly, the day-of-week patterns most travellers miss, and any shoulder-season dips worth shifting your trip around. Prices refresh every few hours, so what you see is what your booking page should look like a moment later — click any date to jump straight to the fare on Aviasales.
Airlines on this route
6 carriersThe 6 carriers we currently track on the Chicago–Boston route, from full-service flag carriers to low-cost competitors. Tap any airline for its full profile, baggage… rules, fleet context, and a live fare search pre-filtered to that carrier — useful if you're loyal to a frequent-flyer programme, want to compare onboard product on the same dates, or are weighing a cheaper one-stop against a pricier nonstop.
Flights from Chicago to Boston
Live schedule · powered by AviasalesBelow is the published weekly schedule for nonstop and one-stop services from Chicago to Boston — the actual flight numbers, departure and arrival times your… booking page will pull from. Use it to plan around departure preferences (early morning vs late evening), see which carriers fly on which weekdays, or pick a connection that lets you sleep in your own bed before a long-haul leg. Click any row to load it directly in the search.
Airport guides
Quick links into the airport profiles at both ends of the route. Each guide covers terminal layout, the airlines that base hubs at ORD and… BOS, the other routes those airports serve, and the ground-transit options most travellers wish they'd read about before landing — the practical context you only really need to know once you've booked, but want to skim before you do.