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Home / Boston — Chicago

Cheap flights Boston — Chicago

Boston (BOS, US) Chicago (MDW, US)
from $91 1 366 km ~2h 6m
Reverse route
How many travellers?
Adults
12+ years
1
Children
2–11 years
0
Infants
under 2
0
Choose your departure date
Cheapest: $91 on 20.11.2026
Prices shown are from searches by other travellers over the last 24 hours. Missing a date? Click any day — we'll find tickets anyway.
November 2026
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December 2026
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January 2027
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Prices found for 14 of 90 days. Prices update as more travellers search. Click any date to search live.
Depart
—
Return
—
Route characteristics
Distance
1 366 km
Flight time
2h 6m
Time difference
-1h
Minimum price
from $91 (20.11.2026)
Average price
$126
Maximum price
$186
Other destinations from Boston
Nantucket
US
Albany
US
Augusta
US
Bar Harbor
US
Hyannis
US
Lebanon
US
Martha's Vineyard
US
Provincetown
US
Rockland
US
Rutland
US
Saranac Lake
US
Dallas
US · Hub
Frequently asked questions about the route Boston — Chicago
How long is the flight from Boston to Chicago?
Approximate flight time — 2h 6m. This is an average for a direct flight. With connections, the time may be longer.
What is the distance from Boston to Chicago?
The straight-line distance — 1 366 km.
How much do flights from Boston to Chicago cost?
The minimum price over 3 months — from $91 on 20.11.2026.
What is the average ticket price?
The average price — $126. Range: $91 — $186.
What is the time difference between Boston and Chicago?
The difference — -1h.
When is the best time to buy tickets?
Optimal — 1–3 months before departure. Check the calendar above — it shows the best dates.
How do I book flights?
Click "View this ticket" on any flight card — you'll be redirected to the booking page with this specific ticket pre-selected.
About the route Boston — Chicago

Flights Boston — Chicago is a popular route. The straight-line distance is 1 366 km. Flight time 2h 6m. Time difference -1h.

The minimum price for the next 3 months — from $91 (20.11.2026). The cheapest dates are highlighted in the calendar above.

The average ticket price — $126, ranging from $91 to $186. Book 1–3 months in advance to get the best deals.

Other destinations in United States from Boston
Nantucket
US
Albany
US
Augusta
US
Bar Harbor
US
Hyannis
US
Lebanon
US
Martha's Vineyard
US
Provincetown
US

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