Flights from Chicago to Middletown

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.

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$90 Roundtrip, found 19 hours ago

$90

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $90 found 19 hours ago

Wed, May 28 - Mon, Jun 2

ORD

O'Hare Intl.

LGA

LaGuardia

$100 Roundtrip, found 16 hours ago

$100

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from O'Hare Intl. to LaGuardia, returning Mon, Jun 2, priced at $100 found 16 hours ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$101 Roundtrip, found 19 hours ago

$101

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $101 found 19 hours ago

Wed, May 28 - Wed, May 28

ORD

O'Hare Intl.

LGA

LaGuardia

$110 Roundtrip, found 16 hours ago

$110

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from O'Hare Intl. to LaGuardia, returning Wed, May 28, priced at $110 found 16 hours ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$111 Roundtrip, found 19 hours ago

$111

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $111 found 19 hours ago

Wed, Jul 30 - Wed, Aug 6

ORD

O'Hare Intl.

EWR

Newark Liberty Intl. Airport

$112 Roundtrip, found 3 days ago

$112

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Jul 30 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Wed, Aug 6, priced at $112 found 3 days ago

Tue, Jun 10 - Fri, Jun 13

ORD

O'Hare Intl.

LGA

LaGuardia

$115 Roundtrip, found 19 hours ago

$115

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Tue, Jun 10 from O'Hare Intl. to LaGuardia, returning Fri, Jun 13, priced at $115 found 19 hours ago

Fri, Jul 11 - Mon, Jul 14

ORD

O'Hare Intl.

LGA

LaGuardia

$120 Roundtrip, found 3 days ago

$120

Roundtrip

found 3 days ago

Select United flight, departing Fri, Jul 11 from O'Hare Intl. to LaGuardia, returning Mon, Jul 14, priced at $120 found 3 days ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$122 Roundtrip, found 19 hours ago

$122

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $122 found 19 hours ago

Mon, Jun 9 - Tue, Jun 10

ORD

O'Hare Intl.

LGA

LaGuardia

$123 Roundtrip, found 19 hours ago

$123

Roundtrip

found 19 hours ago

Select Spirit Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to LaGuardia, returning Tue, Jun 10, priced at $123 found 19 hours ago

Wed, May 28 - Thu, Jun 5

ORD

O'Hare Intl.

LGA

LaGuardia

$125 Roundtrip, found 16 hours ago

$125

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from O'Hare Intl. to LaGuardia, returning Thu, Jun 5, priced at $125 found 16 hours ago

Wed, May 28 - Sat, May 31

ORD

O'Hare Intl.

LGA

LaGuardia

$126 Roundtrip, found 16 hours ago

$126

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Wed, May 28 from O'Hare Intl. to LaGuardia, returning Sat, May 31, priced at $126 found 16 hours ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

LGA

LaGuardia

$128 Roundtrip, found 3 days ago

$128

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to LaGuardia, returning Sat, Jul 5, priced at $128 found 3 days ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

LGA

LaGuardia

$130 Roundtrip, found 3 days ago

$130

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Jul 1 from O'Hare Intl. to LaGuardia, returning Sat, Jul 5, priced at $130 found 3 days ago

Tue, May 27 - Mon, Jun 2

ORD

O'Hare Intl.

LGA

LaGuardia

$135 Roundtrip, found 16 hours ago

$135

Roundtrip

found 16 hours ago

Select Spirit Airlines flight, departing Tue, May 27 from O'Hare Intl. to LaGuardia, returning Mon, Jun 2, priced at $135 found 16 hours ago

Tue, Jul 1 - Sat, Jul 5

ORD

O'Hare Intl.

LGA

LaGuardia

$141 Roundtrip, found 3 days ago

$141

Roundtrip

found 3 days ago

Select American Airlines flight, departing Tue, Jul 1 from O'Hare Intl. to LaGuardia, returning Sat, Jul 5, priced at $141 found 3 days ago

Fri, Jul 11 - Mon, Jul 14

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$150 Roundtrip, found 3 days ago

$150

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Fri, Jul 11 from O'Hare Intl. to John F. Kennedy Intl., returning Mon, Jul 14, priced at $150 found 3 days ago

Tue, Jun 17 - Tue, Jun 24

MDW

Midway Intl.

EWR

Newark Liberty Intl. Airport

$157 Roundtrip, found 1 day ago

$157

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jun 17 from Midway Intl. to Newark Liberty Intl. Airport, returning Tue, Jun 24, priced at $157 found 1 day ago

Tue, May 20 - Thu, May 29

ORD

O'Hare Intl.

JFK

John F. Kennedy Intl.

$220 Roundtrip, found 3 days ago

$220

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, May 20 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, May 29, priced at $220 found 3 days ago

Sun, Jun 22 - Thu, Jun 26

MDW

Midway Intl.

JFK

John F. Kennedy Intl.

$342 Roundtrip, found 1 day ago

$342

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Jun 22 from Midway Intl. to John F. Kennedy Intl., returning Thu, Jun 26, priced at $342 found 1 day ago