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

Select JetBlue Airways flight, departing Sat, Sep 27 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $91 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

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $98 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

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $98 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

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Sun, Oct 5, priced at $105 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

Select American Airlines flight, departing Sun, Sep 28 from O'Hare Intl. to Logan Intl., returning Fri, Oct 3, priced at $105 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

Select JetBlue Airways flight, departing Wed, Oct 1 from O'Hare Intl. to Logan Intl., returning Wed, Oct 1, priced at $108 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

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $114 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

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $116 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

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $120 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

Select JetBlue Airways flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Oct 6, priced at $121 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

Select United flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $126 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

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $127 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

Select Delta flight, departing Sat, Sep 27 from O'Hare Intl. to Logan Intl., returning Sat, Sep 27, priced at $137 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

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $155 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

Select Delta flight, departing Wed, Oct 8 from O'Hare Intl. to Worcester Regional, returning Wed, Oct 15, priced at $212 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

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to T.F. Green, returning Tue, Aug 12, priced at $217 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

Select American Airlines flight, departing Wed, Oct 8 from O'Hare Intl. to Manchester-Boston Regional, returning Thu, Oct 16, priced at $251 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

Select Frontier Airlines flight, departing Fri, Sep 26 from O'Hare Intl. to Logan Intl., returning Mon, Sep 29, priced at $281 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

Select Delta flight, departing Sun, Aug 3 from Midway Intl. to T.F. Green, returning Wed, Aug 13, priced at $298 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

Select Delta flight, departing Mon, Aug 4 from Midway Intl. to Logan Intl., returning Tue, Aug 12, priced at $368 found 6 days ago