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, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$117 Roundtrip, found 15 hours ago

$117

Roundtrip

found 15 hours ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $117 found 15 hours ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$125 Roundtrip, found 15 hours ago

$125

Roundtrip

found 15 hours ago

Select JetBlue Airways flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $125 found 15 hours ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$129 Roundtrip, found 3 days ago

$129

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $129 found 3 days ago

Tue, Sep 2 - Sat, Sep 6

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 5 days ago

$137

Roundtrip

found 5 days ago

Select United flight, departing Tue, Sep 2 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $137 found 5 days ago

Sun, Jul 13 - Thu, Jul 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 11 hours ago

$137

Roundtrip

found 11 hours ago

Select American Airlines flight, departing Sun, Jul 13 from O'Hare Intl. to Logan Intl., returning Thu, Jul 17, priced at $137 found 11 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, found 2 days ago

$139

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $139 found 2 days ago

Tue, Aug 5 - Thu, Aug 14

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 1 day ago

$145

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Thu, Aug 14, priced at $145 found 1 day ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$147 Roundtrip, found 1 day ago

$147

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $147 found 1 day ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 1 day ago

$149

Roundtrip

found 1 day ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $149 found 1 day ago

Sun, Jul 13 - Thu, Jul 17

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 11 hours ago

$155

Roundtrip

found 11 hours ago

Select United flight, departing Sun, Jul 13 from O'Hare Intl. to Logan Intl., returning Thu, Jul 17, priced at $155 found 11 hours ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 1 day ago

$157

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $157 found 1 day ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$160 Roundtrip, found 1 day ago

$160

Roundtrip

found 1 day ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $160 found 1 day ago

Thu, Aug 7 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$161 Roundtrip, found 1 day ago

$161

Roundtrip

found 1 day ago

Select United flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $161 found 1 day ago

Sat, Aug 23 - Sun, Aug 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 4 days ago

$165

Roundtrip

found 4 days ago

Select United flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Sun, Aug 24, priced at $165 found 4 days ago

Sun, Oct 19 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$169 Roundtrip, found 15 hours ago

$169

Roundtrip

found 15 hours ago

Select Spirit Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $169 found 15 hours ago

Sat, Jul 12 - Sat, Jul 19

ORD

O'Hare Intl.

BOS

Logan Intl.

$210 Roundtrip, found 4 days ago

$210

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Logan Intl., returning Sat, Jul 19, priced at $210 found 4 days ago

Thu, Jun 19 - Fri, Jun 20

MDW

Midway Intl.

BOS

Logan Intl.

$250 Roundtrip, found 2 days ago

$250

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Jun 19 from Midway Intl. to Logan Intl., returning Fri, Jun 20, priced at $250 found 2 days ago

Mon, Jun 30 - Fri, Jul 4

MDW

Midway Intl.

PVD

T.F. Green

$281 Roundtrip, found 1 day ago

$281

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Jun 30 from Midway Intl. to T.F. Green, returning Fri, Jul 4, priced at $281 found 1 day ago

Tue, Jul 29 - Sat, Aug 2

ORD

O'Hare Intl.

MHT

Manchester-Boston Regional

$303 Roundtrip, found 4 days ago

$303

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Tue, Jul 29 from O'Hare Intl. to Manchester-Boston Regional, returning Sat, Aug 2, priced at $303 found 4 days ago

Wed, Jul 9 - Tue, Jul 15

ORD

O'Hare Intl.

PVD

T.F. Green

$303 Roundtrip, found 3 days ago

$303

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Jul 9 from O'Hare Intl. to T.F. Green, returning Tue, Jul 15, priced at $303 found 3 days ago