
Flights from Chicago to Boston
Cheapest flights from Chicago
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Sep 27 - Wed, Oct 1
ORD
O'Hare Intl.
BOS
Logan Intl.
$91 Roundtrip, found 11 hours ago
$91
Roundtrip
found 11 hours ago

Fri, Sep 26 - Wed, Oct 1
ORD
O'Hare Intl.
BOS
Logan Intl.
$98 Roundtrip, found 11 hours ago
$98
Roundtrip
found 11 hours ago

Fri, Sep 26 - Mon, Sep 29
ORD
O'Hare Intl.
BOS
Logan Intl.
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours ago

Fri, Sep 26 - Sun, Oct 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$105 Roundtrip, found 11 hours ago
$105
Roundtrip
found 11 hours ago

Sun, Sep 28 - Fri, Oct 3
ORD
O'Hare Intl.
BOS
Logan Intl.
$105 Roundtrip, found 8 hours ago
$105
Roundtrip
found 8 hours ago

Wed, Oct 1 - Wed, Oct 1
ORD
O'Hare Intl.
BOS
Logan Intl.
$108 Roundtrip, found 11 hours ago
$108
Roundtrip
found 11 hours ago

Wed, Oct 15 - Mon, Oct 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$114 Roundtrip, found 9 hours ago
$114
Roundtrip
found 9 hours ago

Fri, Sep 26 - Mon, Sep 29
ORD
O'Hare Intl.
BOS
Logan Intl.
$116 Roundtrip, found 14 hours ago
$116
Roundtrip
found 14 hours ago

Fri, Sep 26 - Mon, Sep 29
ORD
O'Hare Intl.
BOS
Logan Intl.
$120 Roundtrip, found 14 hours ago
$120
Roundtrip
found 14 hours ago

Fri, Sep 26 - Mon, Oct 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$121 Roundtrip, found 11 hours ago
$121
Roundtrip
found 11 hours ago

Fri, Sep 26 - Mon, Sep 29
ORD
O'Hare Intl.
BOS
Logan Intl.
$126 Roundtrip, found 14 hours ago
$126
Roundtrip
found 14 hours ago

Wed, Oct 15 - Mon, Oct 20
ORD
O'Hare Intl.
BOS
Logan Intl.
$127 Roundtrip, found 9 hours ago
$127
Roundtrip
found 9 hours ago

Sat, Sep 27 - Sat, Sep 27
ORD
O'Hare Intl.
BOS
Logan Intl.
$137 Roundtrip, found 14 hours ago
$137
Roundtrip
found 14 hours ago

Tue, Aug 5 - Fri, Aug 8
ORD
O'Hare Intl.
BOS
Logan Intl.
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago

Wed, Oct 8 - Wed, Oct 15
ORD
O'Hare Intl.
ORH
Worcester Regional
$212 Roundtrip, found 5 days ago
$212
Roundtrip
found 5 days ago

Tue, Aug 5 - Tue, Aug 12
ORD
O'Hare Intl.
PVD
T.F. Green
$217 Roundtrip, found 4 days ago
$217
Roundtrip
found 4 days ago

Wed, Oct 8 - Thu, Oct 16
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$251 Roundtrip, found 5 days ago
$251
Roundtrip
found 5 days ago

Fri, Sep 26 - Mon, Sep 29
ORD
O'Hare Intl.
BOS
Logan Intl.
$281 Roundtrip, found 14 hours ago
$281
Roundtrip
found 14 hours ago

Sun, Aug 3 - Wed, Aug 13
MDW
Midway Intl.
PVD
T.F. Green
$298 Roundtrip, found 4 days ago
$298
Roundtrip
found 4 days ago

Mon, Aug 4 - Tue, Aug 12
MDW
Midway Intl.
BOS
Logan Intl.
$368 Roundtrip, found 6 days ago
$368
Roundtrip
found 6 days ago