Cheapest one-way
$ 214.00
Delta Air Lines · Nonstop
One-way tickets on BOS–ORD recently started around $ 214.00.
Flights from Boston to Chicago
Looking for cheap flights from Boston to Chicago? Fares on the BOS–ORD corridor have started around $ 427.00; review the latest prices, carriers and travel times here.
Boston to Chicago flights overview
The lowest fare BookingTrolley recently tracked from Boston to Chicago was $ 427.00. Across the months we have sampled, the typical round-trip fare averages about $ 513.00. Nov tends to be the cheapest month to fly (around $ 427.00), while Jun is usually the most expensive at about $ 636.00 — a swing of roughly 49%.
BOS and ORD sit roughly 1,391 km apart, so total travel time depends on whether you fly nonstop or connect. BookingTrolley found 3 airlines currently compete on the BOS–ORD corridor, with Delta Air Lines posting one of the lowest fares at $ 427.00. 3 of them offer nonstop options, which save layover time but can cost more than connecting itineraries.
Frequently asked questions about flying from Boston to Chicago
Tuesday and Wednesday are typically the cheapest days to fly from Boston to Chicago. According to BookingTrolley fare data on the Boston to Chicago route (BOS–ORD), round-trip tickets started at $ 427.00. United States travellers often save by shifting 3–4 days around their preferred date on BookingTrolley.
The cheapest airlines on Boston to Chicago are Delta Air Lines (from $ 427.00), American Airlines (from $ 448.00), United Airlines (from $ 544.00), according to BookingTrolley's multi-provider comparison priced for the United States market currency when available.
The cheapest flights from Boston to Chicago started at $ 427.00 round trip on a nonstop itinerary on Delta Air Lines, per BookingTrolley data relevant to United States shoppers. Fares fluctuate with demand.
Flight time from Boston to Chicago depends on the airline and on whether the itinerary is nonstop or connecting. BookingTrolley shows a duration only when it is calculated from observed departure and arrival times.
Shoulder season around peak holidays often pairs softer airfares with lighter crowds. According to BookingTrolley fare data on the Boston to Chicago route (BOS–ORD), round-trip tickets started at $ 427.00. BookingTrolley suggests booking 4–8 weeks ahead for routes like Boston to Chicago.
Use BookingTrolley's flexible-date comparison for Boston (BOS) to Chicago (ORD) 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.
Find cheap flights on popular routes
Explore fares from Boston, into Chicago, and on related corridors with BookingTrolley.
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