Flights from Chicago to Randolph

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.

$121 Roundtrip, found 3 days ago

$121

Roundtrip

found 3 days ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $121 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$121 Roundtrip, found 3 days ago

$121

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $121 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$129 Roundtrip, found 3 days ago

$129

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $129 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$132 Roundtrip, found 3 days ago

$132

Roundtrip

found 3 days ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $132 found 3 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, just found

$137

Roundtrip

just found

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $137 just found

Mon, Oct 20 - Fri, Oct 24

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Oct 20 from O'Hare Intl. to Logan Intl., returning Fri, Oct 24, priced at $137 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$145 Roundtrip, just found

$145

Roundtrip

just found

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $145 just found

Mon, Oct 20 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$147 Roundtrip, found 1 day ago

$147

Roundtrip

found 1 day ago

Select Delta flight, departing Mon, Oct 20 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $147 found 1 day ago

Tue, Oct 14 - Wed, Oct 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$153 Roundtrip, found 2 days ago

$153

Roundtrip

found 2 days ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to Logan Intl., returning Wed, Oct 22, priced at $153 found 2 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, just found

$155

Roundtrip

just found

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $155 just found

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$156 Roundtrip, found 3 days ago

$156

Roundtrip

found 3 days ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $156 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$157 Roundtrip, found 3 days ago

$157

Roundtrip

found 3 days ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $157 found 3 days ago

Wed, Jul 30 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$159 Roundtrip, found 2 days ago

$159

Roundtrip

found 2 days ago

Select United flight, departing Wed, Jul 30 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $159 found 2 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$159 Roundtrip, found 3 days ago

$159

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $159 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$164 Roundtrip, found 3 days ago

$164

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $164 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$164 Roundtrip, found 3 days ago

$164

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $164 found 3 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, just found

$165

Roundtrip

just found

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $165 just found

Sun, Oct 19 - Wed, Oct 22

ORD

O'Hare Intl.

BOS

Logan Intl.

$170 Roundtrip, found 1 day ago

$170

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Logan Intl., returning Wed, Oct 22, priced at $170 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, just found

$172

Roundtrip

just found

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $172 just found

Fri, Sep 12 - Sat, Sep 20

MDW

Midway Intl.

BOS

Logan Intl.

$218 Roundtrip, found 3 days ago

$218

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Fri, Sep 12 from Midway Intl. to Logan Intl., returning Sat, Sep 20, priced at $218 found 3 days ago