FFL Helper

FFL Helper / Boston / Chicago

BOS → CHI

Boston to Chicago

Compare one-way fares for flights from Boston to Chicago.

Lowest fare $75
Distance 849 mi
Flight time 2h 58m
Airports BOS–ORD
Search this route

Ad. Ticket links are affiliate ads. We may earn a commission if you book. Advertising disclosure

By month: August 2026 from $75 · September 2026 from $92 · October 2026 from $96

Price calendar

August 2026

From $75 · up to $138

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 $138 25 $75 26 $129 27 $124 28 $119 29 $119 30 $119 31 $120

September 2026

From $92 · up to $136

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1
2 $129 3 $136 4 $132 5 $132 6 $132 7 $128 8 $129 9 $129 10 $129 11 $129 12 $129 13 $129 14 $129 15 $129 16 $129 17 $129 18 $129 19 $129 20 $130 21 $124 22 $92 23 $104 24 $104 25 $104 26 $115
27
28
29
30

Upcoming dates

Chicago CHI

$75

Aug 25, 6:42pm · 2h 58m · 0 stops

BOS → ORD · United Airlines

Tickets

Chicago CHI

$92

Sep 22, 12:52pm · 6h 31m · 1 stop

BOS → ORD · Frontier Airlines

Tickets

Chicago CHI

$96

Oct 03, 12:54pm · 6h 29m · 1 stop

BOS → ORD · Frontier Airlines

Tickets

About this route

This calendar shows dated one-way fares from Boston to Chicago. Use it to see which days are cheaper before you search tickets.

Flight time and airport codes on this page are for the sample itinerary we have on file. Always confirm the live routing when you book Boston to Chicago.