Route · BOS → ORD
Flights from Boston to Chicago
Boston Logan to Chicago O'Hare is one of the busiest short-haul corridors in the northeastern United States, covering roughly 1,389 km with a typical block time of just over two hours. American and United dominate frequency here, operating primarily narrow-body aircraft such as the Airbus A319/A320 family and Boeing 737s, while JetBlue adds competitive pressure with its Mint-equipped A321s on select departures and Spirit serves the price-sensitive end of the market. A practical note worth remembering: Chicago O'Hare spans multiple terminals, and American operates from Terminal 3 while United uses the adjoining Terminal 1, which matters if you're connecting onward. On the fare side, midweek departures on Tuesdays and Wednesdays typically yield lower prices, and late-winter months around January and February often see softened demand, making them among the better windows to book.
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Cheapest dates to fly
Live prices · powered by AviasalesThe calendar below pulls live fares from our search partner for Boston (BOS) → Chicago (ORD). 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 Boston–Chicago 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 Boston to Chicago
Live schedule · powered by AviasalesBelow is the published weekly schedule for nonstop and one-stop services from Boston to Chicago — 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 BOS and… ORD, 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.