Flights from Boston to Countryside

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Cheapest flights from Boston

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.

United
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select United flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $117 found 4 days ago
Delta
Tue, Jun 17 - Tue, Jun 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 17 from Logan Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $117 found 1 day ago
JetBlue Airways
Sat, Sep 20 - Fri, Sep 26
BOS
Logan Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Sep 20 from Logan Intl. to O'Hare Intl., returning Fri, Sep 26, priced at $125 found 1 day ago
United
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 7 hours ago
$125
Roundtrip
found 7 hours ago
Select United flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $125 found 7 hours ago
American Airlines
Sat, Sep 20 - Wed, Sep 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Sep 20 from Logan Intl. to O'Hare Intl., returning Wed, Sep 24, priced at $125 found 1 day ago
JetBlue Airways
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$131 Roundtrip, found 7 hours ago
$131
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $131 found 7 hours ago
Delta
Thu, Sep 18 - Tue, Sep 23
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Sep 18 from Logan Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $135 found 1 day ago
JetBlue Airways
Tue, Jul 8 - Fri, Jul 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Fri, Jul 11, priced at $137 found 1 hour ago
American Airlines
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 7 hours ago
$141
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $141 found 7 hours ago
Delta
Sat, Sep 20 - Wed, Sep 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Sep 20 from Logan Intl. to O'Hare Intl., returning Wed, Sep 24, priced at $145 found 1 day ago
Delta
Tue, Jun 17 - Tue, Jun 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 17 from Logan Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $147 found 1 day ago
United
Sat, Sep 20 - Wed, Sep 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select United flight, departing Sat, Sep 20 from Logan Intl. to O'Hare Intl., returning Wed, Sep 24, priced at $148 found 1 day ago
United
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 7 hours ago
$149
Roundtrip
found 7 hours ago
Select United flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $149 found 7 hours ago
Frontier Airlines
Fri, Sep 19 - Sat, Sep 27
BOS
Logan Intl.
MDW
Midway Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Sep 19 from Logan Intl. to Midway Intl., returning Sat, Sep 27, priced at $154 found 1 day ago
American Airlines
Tue, Jun 17 - Tue, Jun 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 17 from Logan Intl. to O'Hare Intl., returning Tue, Jun 24, priced at $157 found 1 day ago
United
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 7 hours ago
$159
Roundtrip
found 7 hours ago
Select United flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $159 found 7 hours ago
United
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$160 Roundtrip, found 7 hours ago
$160
Roundtrip
found 7 hours ago
Select United flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $160 found 7 hours ago
JetBlue Airways
Sun, Sep 7 - Wed, Sep 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 7 hours ago
$161
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $161 found 7 hours ago
Spirit Airlines
Sat, Sep 20 - Wed, Sep 24
BOS
Logan Intl.
ORD
O'Hare Intl.
$167 Roundtrip, found 1 day ago
$167
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Sep 20 from Logan Intl. to O'Hare Intl., returning Wed, Sep 24, priced at $167 found 1 day ago
United
Sun, Jun 22 - Sun, Jun 22
MHT
Manchester-Boston Regional
MDW
Midway Intl.
$1,835 Roundtrip, found 13 hours ago
$1,835
Roundtrip
found 13 hours ago
Select United flight, departing Sun, Jun 22 from Manchester-Boston Regional to Midway Intl., returning Sun, Jun 22, priced at $1,835 found 13 hours ago