Flights from Chicago to New Canaan

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, Jun 4 - Sat, Jun 14

ORD

O'Hare Intl.

LGA

LaGuardia

$90 Roundtrip, found 4 days ago

$90

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to LaGuardia, returning Sat, Jun 14, priced at $90 found 4 days ago

Sat, Nov 15 - Tue, Nov 18

ORD

O'Hare Intl.

LGA

LaGuardia

$100 Roundtrip, found 9 hours ago

$100

Roundtrip

found 9 hours ago

Select Spirit Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to LaGuardia, returning Tue, Nov 18, priced at $100 found 9 hours ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

LGA

LaGuardia

$101 Roundtrip, found 4 days ago

$101

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to LaGuardia, returning Wed, Jun 11, priced at $101 found 4 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$109 Roundtrip, found 1 day ago

$109

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $109 found 1 day ago

Wed, Nov 12 - Sat, Nov 15

ORD

O'Hare Intl.

LGA

LaGuardia

$110 Roundtrip, found 9 hours ago

$110

Roundtrip

found 9 hours ago

Select Spirit Airlines flight, departing Wed, Nov 12 from O'Hare Intl. to LaGuardia, returning Sat, Nov 15, priced at $110 found 9 hours ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

LGA

LaGuardia

$111 Roundtrip, found 4 days ago

$111

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to LaGuardia, returning Wed, Jun 11, priced at $111 found 4 days ago

Wed, Jun 4 - Thu, Jun 12

ORD

O'Hare Intl.

LGA

LaGuardia

$115 Roundtrip, found 4 days ago

$115

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Wed, Jun 4 from O'Hare Intl. to LaGuardia, returning Thu, Jun 12, priced at $115 found 4 days ago

Tue, Jun 24 - Wed, Jun 25

ORD

O'Hare Intl.

LGA

LaGuardia

$117 Roundtrip, found 1 day ago

$117

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 24 from O'Hare Intl. to LaGuardia, returning Wed, Jun 25, priced at $117 found 1 day ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

LGA

LaGuardia

$122 Roundtrip, found 4 days ago

$122

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to LaGuardia, returning Wed, Jun 11, priced at $122 found 4 days ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$123 Roundtrip, found 6 days ago

$123

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $123 found 6 days ago

Sat, Jun 21 - Wed, Jun 25

ORD

O'Hare Intl.

LGA

LaGuardia

$125 Roundtrip, found 1 day ago

$125

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Wed, Jun 25, priced at $125 found 1 day ago

Wed, May 28 - Sat, May 31

ORD

O'Hare Intl.

LGA

LaGuardia

$126 Roundtrip, found 6 days ago

$126

Roundtrip

found 6 days ago

Select Spirit Airlines flight, departing Wed, May 28 from O'Hare Intl. to LaGuardia, returning Sat, May 31, priced at $126 found 6 days ago

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

LGA

LaGuardia

$129 Roundtrip, found 4 days ago

$129

Roundtrip

found 4 days ago

Select American Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to LaGuardia, returning Wed, Jun 11, priced at $129 found 4 days ago

Sat, Nov 15 - Tue, Nov 18

ORD

O'Hare Intl.

LGA

LaGuardia

$133 Roundtrip, found 9 hours ago

$133

Roundtrip

found 9 hours ago

Select Spirit Airlines flight, departing Sat, Nov 15 from O'Hare Intl. to LaGuardia, returning Tue, Nov 18, priced at $133 found 9 hours ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$135 Roundtrip, found 1 day ago

$135

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $135 found 1 day ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$137 Roundtrip, found 1 day ago

$137

Roundtrip

found 1 day ago

Select United flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $137 found 1 day ago

Sun, Jun 8 - Wed, Jun 11

ORD

O'Hare Intl.

LGA

LaGuardia

$138 Roundtrip, found 4 days ago

$138

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Jun 8 from O'Hare Intl. to LaGuardia, returning Wed, Jun 11, priced at $138 found 4 days ago

Sat, Jun 21 - Tue, Jun 24

ORD

O'Hare Intl.

LGA

LaGuardia

$147 Roundtrip, found 1 day ago

$147

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Jun 21 from O'Hare Intl. to LaGuardia, returning Tue, Jun 24, priced at $147 found 1 day ago

Mon, Jun 16 - Thu, Jun 26

MDW

Midway Intl.

LGA

LaGuardia

$195 Roundtrip, found 1 day ago

$195

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Jun 16 from Midway Intl. to LaGuardia, returning Thu, Jun 26, priced at $195 found 1 day ago

Tue, Jun 17 - Tue, Jun 24

ORD

O'Hare Intl.

HPN

Westchester County

$297 Roundtrip, found 10 hours ago

$297

Roundtrip

found 10 hours ago

Select Delta flight, departing Tue, Jun 17 from O'Hare Intl. to Westchester County, returning Tue, Jun 24, priced at $297 found 10 hours ago