Boston to Chicago flights
The cheapest round trip we found from Boston to Chicago is $261 (Dec 4 – 6, 1 stop).
BOS to CHI · 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 | $452 |
| December 2026 | $261 (cheapest month) |
Cheapest dates in the next 4 months
Round trip, per person-
Dec 4 – 6 2 nights · leave Fri$261$261 Book
Frontier Airlines 1 stop · 5h 30m -
Dec 3 – 5 2 nights · leave Thu$307$307 Book
Frontier Airlines 1 stop · 6h 31m
-
Nov 25 – 29 4 nights · leave Wed$452$452 Book
jetBlue Nonstop · 3h 04m -
Nov 27 – 29 2 nights · leave Fri$507$507 Book
Frontier Airlines 2 stops · 6h 30m
Prices change often. The booking site shows the final price before you pay. Other dates? Set an alert
Things to do in Chicago
One Go City pass for Shedd Aquarium, Skydeck Chicago, 360 CHICAGO and more
- All-Inclusive Pass Unlimited Visit as many attractions as you like for 1–5 days from $149 See pass
- Explorer Pass Pick 3–7 of 36 attractions from $109 See pass
- Essentials Pass A few top attractions, chosen as you go from $99 See pass
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
Chicago · Dec 4 – 6Partner links: we may earn a commission if you book, at no extra cost to you.
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Boston to Chicago: questions
How much does a flight from Boston to Chicago cost?
The cheapest round trip we have found right now is $261, leaving December 4 and returning December 6. Prices are per person, economy, in USD.
Which airports do Boston to Chicago flights use?
Boston airports include Logan International (BOS) and Pease Air Force Base (PSM). Chicago airports include O'Hare International (ORD), Chicago Midway International (MDW) and Chicago Rockford International (RFD). The prices on this page cover every airport in both cities (BOS and CHI are the city codes).
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 $261, departing December 4 and returning December 6. The cheapest month to fly in our data is December, from $261. Prices are per person and were correct when found; the final price is set by the airline or booking site when you book.