Chicago to Boston flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$209 is $55 (21%) below the usual $264 for Chicago → Boston.
Buy now or wait? We're still learning this route. We have 1 day of prices so far and need about a week to say whether to book or wait.
Not ready to book? Get an email when Chicago → Boston drops below your price.Cheapest round trip by month
Lowest fare found per departure month| Month | Cheapest round trip |
|---|---|
| September 2026 | No fares found yet |
| October 2026 | $209 (cheapest month) |
| November 2026 | $250 |
| December 2026 | No fares found yet |
| January 2027 | No fares found yet |
| February 2027 | No fares found yet |
| March 2027 | No fares found yet |
| April 2027 | $333 |
Cheapest dates in the next 4 months
Round trip, per person-
Oct 19 – 22 3 nights · leave Mon$209 −21% vs usual$209 −21% vs usual Book
Southwest Airlines Nonstop · 2h 20m -
Oct 21 – 24 3 nights · leave Wed$228 −14% vs usual$228 −14% vs usual Book
jetBlue Nonstop · 2h 28m -
Nov 20 – 23 3 nights · leave Fri$250 −5% vs usual$250 −5% vs usual Book
Frontier Airlines 1 stop · 5h 53m -
Nov 17 – 24 7 nights · leave Tue$253$253 Book
Southwest Airlines Nonstop · 2h 20m
-
Nov 21 – 23 2 nights · leave Sat$271$271 Book
Frontier Airlines 1 stop · 5h 53m
-
Oct 20 – 23 3 nights · leave Tue$272$272 Book
jetBlue Nonstop · 2h 55m
-
Oct 21 – 23 2 nights · leave Wed$272$272 Book
Southwest Airlines Nonstop · 2h 20m
-
Oct 25 – 30 5 nights · leave Sun$293 +11% vs usual$293 +11% vs usual Book
United Airlines 1 stop · 2h 17m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Plan the rest of your trip
Boston · Oct 19 – 22Travel insurance · EKTA Airport transfer · Kiwitaxi
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Chicago to Boston: questions
How much is a flight from Chicago to Boston?
The cheapest round trip we have found right now is $209, leaving October 19 and returning October 22. The usual price on this route is about $264, so this fare is 21% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Chicago to Boston?
October 2026, with round trips from $209. The most expensive month in our data is April (from $333). Based on the 3 months ahead we have prices for.
Are there nonstop flights from Chicago to Boston?
Yes. Nonstop from $209 round trip. 54% of the 13 date combinations we track are nonstop.
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 $209, departing October 19 and returning October 22 on a nonstop flight, about 21% below the usual $264. Right now we're following 13 upcoming date combinations on this route. The cheapest month to fly in our data is October, from $209. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.