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 - Tue, Oct 21

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Tue, Oct 21, priced at $137 found 1 day ago

Sat, Oct 11 - Tue, Oct 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 7 hours ago

$137

Roundtrip

found 7 hours ago

Select Delta flight, departing Sat, Oct 11 from O'Hare Intl. to Logan Intl., returning Tue, Oct 28, priced at $137 found 7 hours ago

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$143 Roundtrip, found 20 hours ago

$143

Roundtrip

found 20 hours ago

Select American Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $143 found 20 hours ago

Wed, Oct 15 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, found 3 days ago

$145

Roundtrip

found 3 days ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $145 found 3 days ago

Mon, Oct 20 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$147 Roundtrip, found 4 days ago

$147

Roundtrip

found 4 days ago

Select Delta flight, departing Mon, Oct 20 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $147 found 4 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$149 Roundtrip, found 13 hours ago

$149

Roundtrip

found 13 hours ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $149 found 13 hours ago

Tue, Oct 14 - Wed, Oct 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$153 Roundtrip, found 6 days ago

$153

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Wed, Oct 22, priced at $153 found 6 days ago

Sat, Oct 11 - Mon, Oct 27

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 7 hours ago

$155

Roundtrip

found 7 hours ago

Select Delta flight, departing Sat, Oct 11 from O'Hare Intl. to Logan Intl., returning Mon, Oct 27, priced at $155 found 7 hours ago

Mon, Oct 13 - Sat, Oct 18

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 13 hours ago

$165

Roundtrip

found 13 hours ago

Select United flight, departing Mon, Oct 13 from O'Hare Intl. to Logan Intl., returning Sat, Oct 18, priced at $165 found 13 hours ago

Wed, Oct 15 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, found 3 days ago

$167

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $167 found 3 days ago

Sun, Oct 19 - Wed, Oct 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$170 Roundtrip, found 4 days ago

$170

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Logan Intl., returning Wed, Oct 22, priced at $170 found 4 days ago

Sat, Aug 9 - Sat, Aug 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$171 Roundtrip, found 1 day ago

$171

Roundtrip

found 1 day ago

Select United flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Sat, Aug 16, priced at $171 found 1 day ago

Wed, Oct 15 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, found 3 days ago

$172

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $172 found 3 days ago

Fri, Oct 17 - Mon, Oct 27

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 7 hours ago

$173

Roundtrip

found 7 hours ago

Select Delta flight, departing Fri, Oct 17 from O'Hare Intl. to Logan Intl., returning Mon, Oct 27, priced at $173 found 7 hours ago

Wed, Oct 15 - Wed, Oct 29

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 3 days ago

$175

Roundtrip

found 3 days ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Wed, Oct 29, priced at $175 found 3 days ago

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 20 hours ago

$177

Roundtrip

found 20 hours ago

Select American Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $177 found 20 hours ago

Sat, Aug 9 - Sat, Aug 16

ORD

O'Hare Intl.

BOS

Logan Intl.

$208 Roundtrip, found 1 day ago

$208

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Sat, Aug 16, priced at $208 found 1 day ago

Thu, Sep 11 - Tue, Sep 16

ORD

O'Hare Intl.

PVD

T.F. Green

$217 Roundtrip, found 5 days ago

$217

Roundtrip

found 5 days ago

Select United flight, departing Thu, Sep 11 from O'Hare Intl. to T.F. Green, returning Tue, Sep 16, priced at $217 found 5 days ago

Thu, Aug 7 - Sat, Aug 16

MDW

Midway Intl.

BOS

Logan Intl.

$218 Roundtrip, found 3 days ago

$218

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Aug 7 from Midway Intl. to Logan Intl., returning Sat, Aug 16, priced at $218 found 3 days ago

Sat, Oct 11 - Wed, Oct 15

ORD

O'Hare Intl.

PVC

Provincetown Municipal

$625 Roundtrip, found 13 hours ago

$625

Roundtrip

found 13 hours ago

Select JetBlue Airways flight, departing Sat, Oct 11 from O'Hare Intl. to Provincetown Municipal, returning Wed, Oct 15, priced at $625 found 13 hours ago