Chicago to Boston in October 2026
Round trips departing in October · Economy · Prices per person in USD
Prices updated
Typical in October
$293
Median of 9 date combinations
Usual on this route
$264
October's cheapest is 21% less
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 October fares drop below your price.October 2026 by departure day
Cheapest round trip leaving that day| Mon | Tue | Wed | Thu | Fri | Sat | Sun |
|---|---|---|---|---|---|---|
| 1 | 2 $373 | 3 | 4 | |||
| 5 $393 | 6 $369 | 7 | 8 | 9 | 10 | 11 |
| 12 | 13 | 14 | 15 | 16 $347 | 17 | 18 |
| 19 $209 | 20 $272 | 21 $228 | 22 | 23 | 24 | 25 $293 |
| 26 | 27 | 28 | 29 | 30 | 31 |
Empty days: no round trip found for that departure date yet. Green = cheapest third of the month.
Cheapest dates in October 2026
Round trip, per person-
Oct 19 – 22 3 nights · leave Mon$209Southwest Airlines Nonstop · 2h 20mBook
-
Oct 21 – 24 3 nights · leave Wed$228jetBlue Nonstop · 2h 28mBook
-
Oct 20 – 23 3 nights · leave Tue$272jetBlue Nonstop · 2h 55mBook
-
Oct 21 – 23 2 nights · leave Wed$272Southwest Airlines Nonstop · 2h 20mBook
-
Oct 25 – 30 5 nights · leave Sun$293United Airlines 1 stop · 2h 17mBook
-
Oct 16 – 18 2 nights · leave Fri$347United Airlines 1 stop · 2h 30mBook
-
Oct 6 – 18 12 nights · leave Tue$369United Airlines 1 stop · 2h 23mBook
-
Oct 2 – 6 4 nights · leave Fri$373Southwest Airlines Nonstop · 2h 20mBook
-
Oct 5 – 18 13 nights · leave Mon$393Southwest Airlines 1 stop · 2h 20mBook
Prices change often. The booking site shows the final price before you pay.
Cheapest by trip length
2–4 nights
$209
Oct 19 – 22 · 6 options
5–7 nights
$293
Oct 25 – 30 · 1 option
8–14 nights
$369
Oct 6 – 18 · 2 options
Good to know for October
Nonstop flights
Nonstop from $209
56% of the 9 date combinations we track are nonstop.
Airlines with cheap fares
3 airlines
Most often: Southwest Airlines, United Airlines, jetBlue.
October vs other months
Cheapest round trip 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 |
Chicago to Boston in October: questions
What's the cheapest date to fly from Chicago to Boston in October 2026?
Leaving Monday, October 19 and returning Thursday, October 22 (3 nights) for $209 round trip on Southwest Airlines, the cheapest of the 9 date combinations we track that month.
How much is a round trip from Chicago to Boston in October 2026?
From $209. Half of the 9 date combinations we track are under $293. Prices are per person in USD and change often.