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Cheapest flights from Chicago to Boston
Flaut.Travel was designed and developed by a team dedicated to making the process of searching, comparing and booking airline tickets as easy and convenient as possible. Our service helps travelers to find and buy the cheapest flights from Chicago to Boston. We have connected more than 40 airlines and airline ticketing agencies to help you find the most suitable and affordable flight option.
Remember that on average the ideal time to book flights is 2 months before departure!
A non-stop flight is the most convenient and comfortable way to fly from Chicago to Boston, despite the fact that sometimes flights with transfers can cost significantly less.
Schedule of direct flights from Chicago to Boston
Chicago airports overview
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Boston airports overview
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Frequently asked questions (FAQ)
Answers to questions about the route that travelers are most interested in.
Special offers and sales on air tickets from Chicago to Boston
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.
Alternative routes
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Cheapest one way flight
$89
American Airlines
Direct flight
2h 28m
11/19/2026
The cheapest one-way flight from Chicago to Boston departs on 11/19/2026, is operated by American Airlines and costs $89
Cheapest round trip flight
$183
JetBlue Airways
Direct flight
6 hours
11/03/2026
The cheapest roundtrip flight from Chicago to Boston departs on 11/03/2026, is operated by JetBlue Airways and costs $183
The fastest flight
2h 15m
Fastest flight from Chicago to Boston takes 2h 15m
Direct flights
Several times a week
There are direct flights on this route 6 days a week: Su, Mo, Tu, We, Th, and Sa
Earliest flight
5:15 AM
Latest flight
9:41 PM
Average flight duration
2h 36m
Direct flights count
207
Distance
1365km
Timezone difference
1h
The distance between Chicago and Boston is 1365km (846 miles). The average flight duration is 2h 36m. There are 207 direct flights from Chicago to Boston. The time difference between Chicago and Boston is 1h. Flights from Chicago begin at 5:15 AM. The latest flight from Chicago departs at 9:41 PM
September 2026
Lowest price
on average:
$129
November 2026
Highest price
on average:
$142
Avg Price
The Chicago — Boston route is served by a wide range of airlines: 5 in total, including American Airlines, United Airlines, JetBlue Airways, Southwest Airlines, and Frontier Airlines. Competition among carriers gives passengers the opportunity to find tickets at attractive fares — with prices starting from $89. Our service helps compare all available offers within seconds and choose the most convenient option. You can filter flights by price, departure time, or baggage rules to make your trip as comfortable as possible. With so many airlines, there’s always a chance to catch special promotions and save.
There are most likely no direct flights on the Chicago — Boston route
Chicago is served by two main airports with different roles. O’Hare International (ORD) is the city’s major international and connecting hub, handling a wide mix of legacy and global carriers and often used for long-haul and business routes; fares there can be competitive on hub-to-hub itineraries. It sits about 17–20 miles northwest of downtown; travellers typically take the CTA Blue Line train (around 45–55 minutes, modest fare), taxis or rideshares (35–60 minutes depending on traffic, higher cost), and airport shuttles. Pros: extensive flight choices and frequent services; cons: busy terminals and potential for delays. Midway (MDW) is a smaller, more budget-leaning airport to the southwest, favored by low-cost carriers and for regional flights. It’s roughly 10–12 miles from the Loop and usually quicker to reach—CTA Orange Line trains take about 20–30 minutes for a low fare, while rideshares and taxis are faster but can be pricier during peak times. Pros: compact terminals and shorter walking times; cons: fewer international connections and limited late-night amenities compared with the larger hub.
Boston Logan International (BOS) is New England’s main international gateway and a full-service hub for several legacy carriers, while smaller suburban airports like Manchester‑Boston (MHT) and Providence‑TF Green (PVD) can be used for low‑cost or regional options. Logan sits just across Boston Harbor, typically 3–5 miles (10–20 minutes by car without heavy traffic) from downtown; the MBTA Silver Line, subway connections and taxis/shuttles offer links taking roughly 20–40 minutes with fares usually ranging from free (some airport rides) up to about $3–15 for transit and $25–50+ for taxis/rideshares. Pros: frequent flights, extensive international routes and good public transit; cons: peak‑time congestion and parking costs can be higher, while suburban airports may be cheaper but add ground transport time.
We couldn't find any special offers for flights from Chicago to Boston
What is the cheapest price for flights from Chicago to Boston?
The cheapest flight ticket from Chicago to Boston according to data for the last 48 hours costs $89
When is the best time to buy air tickets on the route Chicago — Boston?
Often the best time to buy tickets from Chicago to Boston is 2 months before departure.
When is the cheapest time of year to fly from Chicago to Boston?
Based on statistics over the past years, the lowest prices for flights from Chicago to Boston can be found flying in these months: September, October, November.
How long does it take to fly from Chicago to Boston?
The fastest flights from Chicago to Boston start from 2 hours 15 minutes in the air.
Which airline can fly direct from Chicago to Boston?
The following airlines operate direct flights on the route Chicago — Boston: American Airlines, United Airlines, JetBlue Airways
The minimum one-way ticket price from Chicago to Boston is $129 (September 2026), while the maximum is $142 (November 2026). On average, a ticket costs $137–$283.
Price dynamics
Tickets from Chicago to Boston cost roughly the same any month. This is convenient: you can plan your trip based on your schedule rather than prices.
Cheaper and more expensive periods
There is a slight difference: it's a bit cheaper in September 2026–October 2026 (averaging $135) and slightly more in October 2026–November 2026 ($142). But overall, the difference is small.
Best time to buy
On this route, you don't need to target specific months — prices are stable. The difference between the cheapest and most expensive period is only 5%. Book whenever it's convenient.
Price predictability
Monthly price variation is just 4.4%. Ticket costs on this route are among the most predictable.
