Flights from Montauk to Chicago

Cheapest flights from Montauk

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, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$92 Roundtrip, found 1 day ago

$92

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $92 found 1 day ago

Tue, Aug 19 - Wed, Aug 20

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$97 Roundtrip, found 14 hours ago

$97

Roundtrip

found 14 hours ago

Select JetBlue Airways flight, departing Tue, Aug 19 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Aug 20, priced at $97 found 14 hours ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$97 Roundtrip, found 1 day ago

$97

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $97 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$112 Roundtrip, found 1 day ago

$112

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $112 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$115 Roundtrip, found 1 day ago

$115

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $115 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$117 Roundtrip, found 1 day ago

$117

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $117 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$117 Roundtrip, found 1 day ago

$117

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $117 found 1 day ago

Tue, Aug 19 - Thu, Aug 21

JFK

John F. Kennedy Intl.

ORD

O'Hare Intl.

$120 Roundtrip, found 14 hours ago

$120

Roundtrip

found 14 hours ago

Select JetBlue Airways flight, departing Tue, Aug 19 from John F. Kennedy Intl. to O'Hare Intl., returning Thu, Aug 21, priced at $120 found 14 hours ago

Sat, Aug 16 - Tue, Aug 19

LGA

LaGuardia

ORD

O'Hare Intl.

$122 Roundtrip, found 14 hours ago

$122

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sat, Aug 16 from LaGuardia to O'Hare Intl., returning Tue, Aug 19, priced at $122 found 14 hours ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$122 Roundtrip, found 1 day ago

$122

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $122 found 1 day ago

Fri, Jun 27 - Fri, Jun 27

EWR

Newark Liberty Intl. Airport

ORD

O'Hare Intl.

$122 Roundtrip, found 6 days ago

$122

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Fri, Jun 27 from Newark Liberty Intl. Airport to O'Hare Intl., returning Fri, Jun 27, priced at $122 found 6 days ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$127 Roundtrip, found 1 day ago

$127

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $127 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$130 Roundtrip, found 1 day ago

$130

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $130 found 1 day ago

Wed, Jul 9 - Wed, Jul 23

LGA

LaGuardia

ORD

O'Hare Intl.

$132 Roundtrip, found 1 day ago

$132

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 9 from LaGuardia to O'Hare Intl., returning Wed, Jul 23, priced at $132 found 1 day ago

Tue, Aug 19 - Wed, Aug 20

LGA

LaGuardia

ORD

O'Hare Intl.

$137 Roundtrip, found 14 hours ago

$137

Roundtrip

found 14 hours ago

Select Delta flight, departing Tue, Aug 19 from LaGuardia to O'Hare Intl., returning Wed, Aug 20, priced at $137 found 14 hours ago

Tue, Aug 19 - Fri, Aug 22

LGA

LaGuardia

ORD

O'Hare Intl.

$140 Roundtrip, found 14 hours ago

$140

Roundtrip

found 14 hours ago

Select American Airlines flight, departing Tue, Aug 19 from LaGuardia to O'Hare Intl., returning Fri, Aug 22, priced at $140 found 14 hours ago

Sat, Jun 14 - Sat, Jun 21

EWR

Newark Liberty Intl. Airport

MDW

Midway Intl.

$250 Roundtrip, found 6 days ago

$250

Roundtrip

found 6 days ago

Select Delta flight, departing Sat, Jun 14 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, Jun 21, priced at $250 found 6 days ago

Sun, Jun 15 - Tue, Jun 17

EWR

Newark Liberty Intl. Airport

MDW

Midway Intl.

$258 Roundtrip, found 6 days ago

$258

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Sun, Jun 15 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Jun 17, priced at $258 found 6 days ago

Sat, Aug 16 - Tue, Aug 19

LGA

LaGuardia

MDW

Midway Intl.

$347 Roundtrip, found 14 hours ago

$347

Roundtrip

found 14 hours ago

Select Frontier Airlines flight, departing Sat, Aug 16 from LaGuardia to Midway Intl., returning Tue, Aug 19, priced at $347 found 14 hours ago

Sat, Jul 12 - Thu, Jul 17

JFK

John F. Kennedy Intl.

MDW

Midway Intl.

$452 Roundtrip, found 4 days ago

$452

Roundtrip

found 4 days ago

Select Delta flight, departing Sat, Jul 12 from John F. Kennedy Intl. to Midway Intl., returning Thu, Jul 17, priced at $452 found 4 days ago