Flights from Chicago to Rochester

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.

Wed, Oct 15 - Fri, Oct 17

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 Fri, Oct 17, priced at $137 just found

Wed, Oct 15 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, just found

$137

Roundtrip

just found

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 just found

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$137 Roundtrip, found 19 hours ago

$137

Roundtrip

found 19 hours ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $137 found 19 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$139 Roundtrip, just found

$139

Roundtrip

just found

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

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$150 Roundtrip, just found

$150

Roundtrip

just found

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $150 just found

Tue, Aug 5 - Fri, Aug 8

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Fri, Aug 8, priced at $155 found 1 day ago

Tue, Aug 5 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$155 Roundtrip, found 1 day ago

$155

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $155 found 1 day ago

Tue, Jul 22 - Mon, Jul 28

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 5 days ago

$165

Roundtrip

found 5 days ago

Select Spirit Airlines flight, departing Tue, Jul 22 from O'Hare Intl. to Logan Intl., returning Mon, Jul 28, priced at $165 found 5 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

BOS

Logan Intl.

$165 Roundtrip, found 19 hours ago

$165

Roundtrip

found 19 hours ago

Select United flight, departing Sat, Oct 18 from O'Hare Intl. to Logan Intl., returning Thu, Oct 23, priced at $165 found 19 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$167 Roundtrip, just found

$167

Roundtrip

just found

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $167 just found

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$172 Roundtrip, just found

$172

Roundtrip

just found

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

Sat, Aug 9 - Tue, Aug 12

ORD

O'Hare Intl.

BOS

Logan Intl.

$173 Roundtrip, found 1 day ago

$173

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Tue, Aug 12, priced at $173 found 1 day ago

Thu, Aug 7 - Wed, Aug 13

ORD

O'Hare Intl.

BOS

Logan Intl.

$175 Roundtrip, found 1 day ago

$175

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Wed, Aug 13, priced at $175 found 1 day ago

Thu, Aug 7 - Sun, Aug 10

ORD

O'Hare Intl.

BOS

Logan Intl.

$176 Roundtrip, found 1 day ago

$176

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Thu, Aug 7 from O'Hare Intl. to Logan Intl., returning Sun, Aug 10, priced at $176 found 1 day ago

Sat, Aug 9 - Mon, Aug 11

ORD

O'Hare Intl.

BOS

Logan Intl.

$177 Roundtrip, found 1 day ago

$177

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sat, Aug 9 from O'Hare Intl. to Logan Intl., returning Mon, Aug 11, priced at $177 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

BOS

Logan Intl.

$193 Roundtrip, just found

$193

Roundtrip

just found

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Logan Intl., returning Mon, Oct 20, priced at $193 just found

Thu, Sep 11 - Tue, Sep 16

ORD

O'Hare Intl.

PVD

T.F. Green

$243 Roundtrip, found 1 day ago

$243

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Sep 11 from O'Hare Intl. to T.F. Green, returning Tue, Sep 16, priced at $243 found 1 day ago

Mon, Jun 30 - Tue, Jul 1

MDW

Midway Intl.

PVD

T.F. Green

$281 Roundtrip, found 4 days ago

$281

Roundtrip

found 4 days ago

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

Thu, Jul 10 - Sat, Jul 19

MDW

Midway Intl.

BOS

Logan Intl.

$284 Roundtrip, found 16 hours ago

$284

Roundtrip

found 16 hours ago

Select Frontier Airlines flight, departing Thu, Jul 10 from Midway Intl. to Logan Intl., returning Sat, Jul 19, priced at $284 found 16 hours ago

Sat, Jul 5 - Wed, Jul 9

ORD

O'Hare Intl.

HYA

Barnstable Municipal

$333 Roundtrip, found 6 days ago

$333

Roundtrip

found 6 days ago

Select American Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Barnstable Municipal, returning Wed, Jul 9, priced at $333 found 6 days ago