Cheap Flights from Chicago to Boston
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Boston
Prices updated 2 days ago
451 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Aug 17, 2026.)
Today’s best flight deals from Chicago to Boston
Explore current cheapest deals departing from Chicago to Boston
2026-10-13 – 2026-10-20
CHI - Boston
76% AI deal score
$277
$156
Round trip
2026-10-28 – 2026-10-31
CHI - Boston
79% AI deal score
$291
$156
Round trip
2026-10-21 – 2026-10-28
CHI - Boston
78% AI deal score
$281
$156
Round trip
2026-11-11 – 2026-11-18
CHI - Boston
75% AI deal score
$236
$156
Round trip
2026-11-11 – 2026-11-17
CHI - Boston
75% AI deal score
$236
$156
Round trip
2026-09-01 – 2026-09-02
CHI - Boston
78% AI deal score
$274
$159
Round trip
2026-10-01 – 2026-10-05
CHI - Boston
66% AI deal score
$177
$161
Round trip
2026-11-09 – 2026-11-11
CHI - Boston
75% AI deal score
$244
$161
Round trip
2026-11-07 – 2026-11-09
CHI - Boston
48% AI deal score
$151
$161
Round trip
2026-09-22 – 2026-09-23
CHI - Boston
48% AI deal score
$153
$163
Round trip
