FFL Helper

FFL Helper / Boston / Chicago

BOS → CHI

Boston (BOS) to Chicago (CHI)

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

Lowest fare $91
Distance 849 mi
Flight time 9h 41m
Airports BOS–MDW
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By month: October 2026 from $134 · November 2026 from $91 · December 2026 from $171

Price calendar

October 2026

From $134 · up to $160

Mon
Tue
Wed
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Sun
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2
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23 $160 24 $159 25 $159 26 $158 27 $152 28 $138 29 $155 30 $145 31 $134

November 2026

From $91 · up to $192

Mon
Tue
Wed
Thu
Fri
Sat
Sun
1 $192 2 $165 3 $135 4 $123 5 $151 6 $178 7 $117 8 $116 9 $116 10 $116 11 $116 12 $116 13 $116 14 $116 15 $115 16 $103 17 $103 18 $103 19 $103 20 $91
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Upcoming dates

Chicago CHI

$91

Nov 20, 11:06am · 9h 41m · 1 stop

BOS → MDW · Frontier Airlines

Tickets

Chicago CHI

$115

Nov 15, 3:21pm · 3h 15m · 0 stops

BOS → ORD · American 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.