Chicago to Boston flights
The cheapest round trip we found from Chicago to Boston is $271 (Dec 11 – 13, 1 stop), 6% below the usual $287.
CHI to BOS · Round trip · Economy · Prices per person in USD · Price found (1 day ago)
Cheapest found
Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| November 2026 | $281 |
| December 2026 | $271 (cheapest month) |
Cheapest dates in the next 4 months
Round trip, per person-
Dec 11 – 13 2 nights · leave Fri$271 −6% vs usual$271 −6% vs usual Book
Frontier Airlines 1 stop · 6h 06m -
Nov 22 – 27 5 nights · leave Sun$281$281 Book
Frontier Airlines 1 stop · 6h 10m
-
Dec 23 – 27 4 nights · leave Wed$293$293 Book
American Airlines 1 stop · 2h 35m -
Nov 20 – 22 2 nights · leave Fri$300 +5% vs usual$300 +5% vs usual Book
Southwest Airlines Nonstop · 2h 20m -
Nov 26 – 30 4 nights · leave Thu$308 +7% vs usual$308 +7% vs usual Book
Frontier Airlines 1 stop · 6h 01m
-
Nov 25 – 29 4 nights · leave Wed$441 +54% vs usual$441 +54% vs usual Book
Southwest Airlines 1 stop · 2h 15m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
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Go City prices checked Oct 23, 2026; the final price is on Go City. Partner links: we may earn a commission if you book, at no extra cost to you.
Plan the rest of your trip
Boston · Dec 11 – 13Partner links: we may earn a commission if you book, at no extra cost to you.
Good to know
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Flights to Boston from other cities
All flights to Boston Flying the other way? Boston to Chicago from $261
Chicago to Boston: questions
How much does a flight from Chicago to Boston cost?
The cheapest round trip we have found right now is $271, leaving December 11 and returning December 13. The usual price on this route is about $287, so this fare is 6% less. Prices are per person, economy, in USD.
Which airports do Chicago to Boston flights use?
Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). Boston airports include Logan International (BOS) and Pease Air Force Base (PSM). The prices on this page cover every airport in both cities (CHI and BOS are the city codes).
About this route
We track round-trip economy fares from Chicago (United States) to Boston (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $271, departing December 11 and returning December 13, about 6% below the usual $287. Right now we're following 6 upcoming date combinations on this route. The cheapest month to fly in our data is December, from $271. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.