Flights from Boston to Chicago

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.

Sat, Nov 22 - Thu, Nov 27

BOS

Logan Intl.

ORD

O'Hare Intl.

$125 Roundtrip, found 2 days ago

$125

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Nov 22 from Logan Intl. to O'Hare Intl., returning Thu, Nov 27, priced at $125 found 2 days ago

Sat, Nov 22 - Tue, Dec 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$131 Roundtrip, found 2 days ago

$131

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Nov 22 from Logan Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $131 found 2 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$137 Roundtrip, found 4 days ago

$137

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 $137 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$149 Roundtrip, found 4 days ago

$149

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $149 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$155 Roundtrip, found 4 days ago

$155

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $155 found 4 days ago

Thu, Nov 27 - Tue, Dec 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$158 Roundtrip, found 2 days ago

$158

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Nov 27 from Logan Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $158 found 2 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$161 Roundtrip, found 4 days ago

$161

Roundtrip

found 4 days ago

Select JetBlue Airways flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $161 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$165 Roundtrip, found 4 days ago

$165

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 $165 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$166 Roundtrip, found 4 days ago

$166

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $166 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$169 Roundtrip, found 4 days ago

$169

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 $169 found 4 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$175 Roundtrip, found 4 days ago

$175

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $175 found 4 days ago

Sun, Nov 23 - Thu, Nov 27

BOS

Logan Intl.

ORD

O'Hare Intl.

$176 Roundtrip, found 2 days ago

$176

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sun, Nov 23 from Logan Intl. to O'Hare Intl., returning Thu, Nov 27, priced at $176 found 2 days ago

Tue, Jul 8 - Sat, Jul 12

BOS

Logan Intl.

ORD

O'Hare Intl.

$177 Roundtrip, found 6 days ago

$177

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Tue, Jul 8 from Logan Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $177 found 6 days ago

Sun, Nov 23 - Tue, Dec 2

BOS

Logan Intl.

ORD

O'Hare Intl.

$178 Roundtrip, found 2 days ago

$178

Roundtrip

found 2 days ago

Select Delta flight, departing Sun, Nov 23 from Logan Intl. to O'Hare Intl., returning Tue, Dec 2, priced at $178 found 2 days ago

Sat, Nov 22 - Wed, Nov 26

BOS

Logan Intl.

ORD

O'Hare Intl.

$181 Roundtrip, found 2 days ago

$181

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Sat, Nov 22 from Logan Intl. to O'Hare Intl., returning Wed, Nov 26, priced at $181 found 2 days ago

Thu, Nov 27 - Thu, Nov 27

BOS

Logan Intl.

ORD

O'Hare Intl.

$186 Roundtrip, found 2 days ago

$186

Roundtrip

found 2 days ago

Select JetBlue Airways flight, departing Thu, Nov 27 from Logan Intl. to O'Hare Intl., returning Thu, Nov 27, priced at $186 found 2 days ago

Thu, Jul 10 - Thu, Jul 17

BOS

Logan Intl.

ORD

O'Hare Intl.

$187 Roundtrip, found 6 days ago

$187

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Jul 10 from Logan Intl. to O'Hare Intl., returning Thu, Jul 17, priced at $187 found 6 days ago

Sun, Sep 7 - Wed, Sep 10

BOS

Logan Intl.

ORD

O'Hare Intl.

$189 Roundtrip, found 4 days ago

$189

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sun, Sep 7 from Logan Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $189 found 4 days ago

Fri, Sep 19 - Sat, Sep 27

BOS

Logan Intl.

MDW

Midway Intl.

$333 Roundtrip, found 2 days ago

$333

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 19 from Logan Intl. to Midway Intl., returning Sat, Sep 27, priced at $333 found 2 days ago

Fri, Jan 16 - Mon, Jan 19

MHT

Manchester-Boston Regional

MDW

Midway Intl.

$1,284 Roundtrip, found 1 day ago

$1,284

Roundtrip

found 1 day ago

Select United flight, departing Fri, Jan 16 from Manchester-Boston Regional to Midway Intl., returning Mon, Jan 19, priced at $1,284 found 1 day ago