Boston to Chicago flights
Round trip · Economy · Prices per person in USD
Prices updated
Prices are low right now
$272 is $60 (18%) below the usual $332 for Boston → Chicago.
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 Boston → Chicago 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 | $365 |
| November 2026 | $272 (cheapest month) |
| December 2026 | $332 |
| January 2027 | $334 |
Cheapest dates in the next 4 months
Round trip, per person-
Nov 11 – 15 4 nights · leave Wed$272 −18% vs usual$272 −18% vs usual Book
Southwest Airlines Nonstop · 2h 50m -
Dec 25 – Jan 2, 2027 8 nights · leave Fri$332$332 Book
Southwest Airlines Nonstop · 2h 45m
-
Oct 4 – 7 3 nights · leave Sun$365 +10% vs usual$365 +10% vs usual Book
jetBlue 1 stop · 2h 48m -
Dec 26 – Jan 2, 2027 7 nights · leave Sat$368 +11% vs usual$368 +11% vs usual Book
United Airlines Nonstop · 3h 06m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
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Airport transfer to Chicago
Fixed prices from ORD on KiwitaxiTo see transfer prices here, turn on partner content in .
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Plan the rest of your trip
Chicago · Nov 11 – 15Travel insurance · EKTA Airport transfer · Kiwitaxi
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Good to know
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Boston to Chicago: questions
How much is a flight from Boston to Chicago?
The cheapest round trip we have found right now is $272, leaving November 11 and returning November 15. The usual price on this route is about $332, so this fare is 18% less. Prices are per person, economy, in USD.
What is the cheapest month to fly from Boston to Chicago?
November 2026, with round trips from $272. The most expensive month in our data is October (from $365). Based on the 4 months ahead we have prices for.
About this route
We track round-trip economy fares from Boston (United States) to Chicago (United States) using Travelpayouts / Aviasales data. The cheapest round trip we've found is $272, departing November 11 and returning November 15 on a nonstop flight, about 18% below the usual $332. The cheapest month to fly in our data is November, from $272. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.