Helping travelers to find the best flight offers
Fly Boston to Chicago with confidence—our search scans over 700 airlines, 50+ travel agencies, and more than 5 top booking systems to uncover the best prices, schedules, and booking terms for your trip. Quickly compare options and lock in the flight that fits your budget and timing, whether you need a nonstop commute or the most flexible fare.
A direct flight is the easiest way to get to your destination. The following airlines operate non-stop flights from Boston to Chicago:
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We keep tight track on airlines' pre-holidays sales and other special offers occurences all the time to let you save maximum amount of funds while traveling to your family or just going out on vacation.
The route Boston — Chicago is served by many carriers — 6 in total, including Southwest Airlines, JetBlue Airways, Air Arabia Abu Dhabi, American Airlines, Frontier Airlines, and Spirit Airlines. This gives passengers wide opportunities: from finding the lowest fare (from $63) to selecting flights by schedule or service class. Our service aggregates data from multiple booking systems so you can compare offers in one place. This saves time and money: no need to check dozens of sites — just pick the right option and book online.
Starting at $63
Starting at $66
Starting at $72
Starting at $78
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Starting at $110
Boston — Chicago
01/01/2026
Departure
Direct flight
WN1432
Starting at $63
Boston — Chicago
12/14/2025
Departure
Direct flight
B6311
Starting at $66
Boston — Chicago
01/10/2026
Departure
Direct flight
WN699
Starting at $72
Boston — Chicago
12/08/2025
Departure
Direct flight
3L3691
Starting at $72
Boston — Chicago
03/05/2026
Departure
Direct flight
AA1283
Starting at $78
Boston — Chicago
01/11/2026
Departure
Direct flight
AA1087
Starting at $79
Boston — Chicago
01/03/2026
Departure
Direct flight
WN1430
Starting at $116
Boston — Chicago
06/21/2026
Departure
Direct flight
B6311
Starting at $118
Boston — Chicago
12/05/2025
Departure
Direct flight
AA4392
Starting at $157
Boston — Chicago
12/22/2025
Departure
Direct flight
AA4413
Starting at $164
Unable to find information about the schedule of direct flights from
Boston Logan International (BOS) is the city’s primary international gateway and a full-service hub for major carriers, while smaller regional airports (notably Worcester and Manchester-Boston nearby) tend to serve low-cost and regional flights. Logan sits on Boston Harbor about 3–5 miles from downtown — typically a 15–30 minute drive depending on traffic — with options including the MBTA Silver Line and Blue Line plus taxis and ride-shares; expect public-transit fares to be modest and road transfers to vary with peak congestion. Travelers usually find Logan convenient for frequent nonstop service and international connections, though terminals can be busy and transfers may take longer during peak hours.
Fly nonstop from Boston to Chicago for the fastest, most convenient way to get between two of America’s liveliest cities—perfect for business trips or a weekend getaway. Direct flights cut travel time and eliminate the hassle of connections, though you may sometimes find cheaper options with stops; if comfort and speed matter, going direct is worth it.
The cheapest one-way flight from Boston to Chicago departs on 01/01/2026, is operated by Southwest Airlines and costs $63
The cheapest roundtrip flight from Boston to Chicago departs on 12/12/2025, is operated by JetBlue Airways and costs $116
Fastest flight from Boston to Chicago takes 2h 45m
There are direct flights on this route 5 days a week: Su, Mo, Th, Fr, and Sa
The distance between Boston and Chicago is 1365km (846 miles). The average flight duration is 2h 55m. There are 110 direct flights from Boston to Chicago. The time difference between Boston and Chicago is 1h. Flights from Boston begin at 5:15 AM. The latest flight from Boston departs at 9:45 PM
Chicago is served by three main airports with distinct roles. O’Hare International (ORD) is the primary international hub and a major transfer point for both legacy and global carriers, typically offering the widest range of routes and frequent premium lounges; it sits about 17 miles northwest of downtown and can take roughly 30–60 minutes by car depending on traffic, with taxi or rideshare fares commonly ranging from moderate to higher during peak times. The Blue Line ‘L’ provides a direct and usually cost-effective express to the Loop in about 40–50 minutes. Midway (MDW) is a smaller, more budget-leaning airport to the southwest, often favored by low-cost and domestic carriers; it’s about 10 miles from downtown and reachable in 20–35 minutes by car or roughly 25–40 minutes via the Orange Line for a lower fare. Pros: ORD offers the most international connectivity and amenities; cons: it can be busy with longer transfer distances. MDW can be quicker for domestic travelers but has fewer long-haul options. Both airports provide shuttle, rental car, and public transit choices, so pick based on schedule, price sensitivity, and preferred balance of convenience versus route variety.
The cheapest flight ticket from Boston to Chicago according to data for the last 48 hours costs $63
Often the best time to buy tickets from Boston to Chicago is 2 months before departure.
Based on statistics over the past years, the lowest prices for flights from Boston to Chicago can be found flying in these months: January, December, March.
The fastest flights from Boston to Chicago start from 2 hours 45 minutes in the air.
The following airlines operate direct flights on the route Boston — Chicago: Southwest Airlines, JetBlue Airways, Air Arabia Abu Dhabi
In different months, ticket prices from Boston to Chicago vary: minimum — $63 (January 2026), maximum — $139 (August 2026). Typically, the flight costs $94–$196.
We couldn't find any special offers for flights from Boston to Chicago