FFL Helper
Chicago CHI
$108
BOS → ORD · United Airlines
FFL Helper / Boston / Chicago / October 2026
BOS → CHI · 2026-10
Boston to Chicago in October 2026
Dated one-way fares from Boston to Chicago in October 2026. Use the calendar to see which days are cheaper.
Lowest this month
$108
Highest this month
$108
Sample fare
$75
Airports
BOS–ORD
Ad. Ticket links are affiliate ads. We may earn a commission if you book. Advertising disclosure
Other months: August 2026 · September 2026 · October 2026 · Full route
October 2026 price calendar
October 2026
From $108
Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
$108
30
31
Dated fares
Booking BOS to CHI in October 2026
This page is only October 2026 on the Boston to Chicago route. Open the full route if you want the next months side by side.
Prices move as seats sell. Confirm the live itinerary before you book Boston to Chicago in October 2026.