Cheap Flights from Chicago to Boston
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Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to Boston
Prices updated 1 day ago
461 airlines compared
80%+ AI score for best value
Fares are subject to change and may not be available for all dates. (Data last updated Sep 14, 2026.)
Today’s best flight deals from Chicago to Boston
Explore current cheapest deals departing from Chicago to Boston
2026-10-17 – 2026-10-24
CHI - Boston
46% AI deal score
$183
$189
Round trip
2026-10-17 – 2026-10-20
CHI - Boston
77% AI deal score
$332
$199
Round trip
2026-10-19 – 2026-10-27
CHI - Boston
44% AI deal score
$174
$202
Round trip
2026-10-21 – 2026-10-22
CHI - Boston
45% AI deal score
$193
$202
Round trip
2026-10-29 – 2026-10-31
CHI - Boston
45% AI deal score
$193
$202
Round trip
2026-10-19 – 2026-10-26
CHI - Boston
43% AI deal score
$183
$216
Round trip
2026-11-02 – 2026-11-09
CHI - Boston
49% AI deal score
$235
$225
Round trip
2026-11-09 – 2026-11-16
CHI - Boston
49% AI deal score
$236
$225
Round trip
2026-11-02 – 2026-11-06
CHI - Boston
41% AI deal score
$132
$229
Round trip
2026-10-23 – 2026-10-28
CHI - Boston
49% AI deal score
$284
$235
Round trip
