Flights from Boston to Chicago

Flights

All filters Months and weeks Price Stops Airlines Time Alliances

Cheap one-way flights

If you're planning to travel one-way to Chicago, find the best flight deals available here.
Frontier Airlines
DEPARTURE
BOS - MDW
Sat. Nov 7, 2026
Price per a person from
$110
American Airlines
DEPARTURE
BOS - ORD
Sat. Nov 7, 2026
Price per a person from
$121
Delta Air Lines
DEPARTURE
BOS - ORD
Sat. Nov 7, 2026
Price per a person from
$122
American Airlines
DEPARTURE
BOS - ORD
Wed. Jan 6, 2027
Price per a person from
$121
American Airlines
DEPARTURE
BOS - ORD
Thu. Jan 7, 2027
Price per a person from
$121
Delta Air Lines
DEPARTURE
BOS - ORD
Wed. Jan 6, 2027
Price per a person from
$122
Delta Air Lines
DEPARTURE
BOS - ORD
Thu. Jan 7, 2027
Price per a person from
$122
American Airlines
DEPARTURE
BOS - ORD
Fri. Nov 6, 2026
Price per a person from
$154
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