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 7 days ago
483 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Oct 26, 2026.)
Today’s best flight deals from Chicago to Boston
Explore current cheapest deals departing from Chicago to Boston
2026-12-03 – 2026-12-07
CHI - Boston
75% AI deal score
$303
$187
Round trip
2026-12-04 – 2026-12-05
CHI - Boston
75% AI deal score
$302
$191
Round trip
2026-11-24 – 2026-11-26
CHI - Boston
45% AI deal score
$243
$234
Round trip
2026-12-02 – 2026-12-07
CHI - Boston
49% AI deal score
$296
$238
Round trip
2027-02-04 – 2027-02-06
CHI - Boston
38% AI deal score
$182
$238
Round trip
2026-12-02 – 2026-12-18
CHI - Boston
44% AI deal score
$241
$240
Round trip
2026-12-12 – 2026-12-18
CHI - Boston
48% AI deal score
$286
$241
Round trip
2026-12-12 – 2026-12-20
CHI - Boston
47% AI deal score
$270
$241
Round trip
2026-12-02 – 2026-12-31
CHI - Boston
43% AI deal score
$231
$241
Round trip
2026-12-02 – 2026-12-20
CHI - Boston
44% AI deal score
$239
$241
Round trip
