$27 Cheap flight deals from Chicago (CHI) to Montclair (NYC)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Chicago to Montclair

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Feb 22 - Thu, Mar 5
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$140 Roundtrip, found 1 hour ago
$140
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Feb 22 from O'Hare Intl. to John F. Kennedy Intl., returning Thu, Mar 5, priced at $140 found 1 hour ago
Sat, Feb 21 - Sat, Feb 28
ORD
O'Hare Intl.
EWR
Newark Liberty Intl. Airport
$241 Roundtrip, just found
$241
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Feb 21 from O'Hare Intl. to Newark Liberty Intl. Airport, returning Sat, Feb 28, priced at $241 just found
Sat, Feb 21 - Wed, Mar 4
MDW
Midway Intl.
LGA
LaGuardia
$290 Roundtrip, found 1 day ago
$290
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Feb 21 from Midway Intl. to LaGuardia, returning Wed, Mar 4, priced at $290 found 1 day ago
Sat, Feb 21 - Tue, Feb 24
MDW
Midway Intl.
EWR
Newark Liberty Intl. Airport
$307 Roundtrip, found 6 days ago
$307
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Feb 21 from Midway Intl. to Newark Liberty Intl. Airport, returning Tue, Feb 24, priced at $307 found 6 days ago

Airfares from $27 One Way, $56 Round Trip from Chicago to Montclair

Prices starting at $56 for return flights and $27 for one-way flights to Montclair were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Mar 10 - Tue, Mar 17
ORD
Chicago
EWR
New York
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Mar 10 from Chicago to New York, returning Tue, Mar 17, priced at $56 just found
Fri, May 1 - Tue, May 5
MDW
Chicago
EWR
New York
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, May 1 from Chicago to New York, returning Tue, May 5, priced at $56 found 2 hours ago
Wed, Apr 15 - Fri, Apr 17
ORD
Chicago
JFK
New York
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Chicago to New York, returning Fri, Apr 17, priced at $56 found 2 hours ago
Tue, Mar 10 - Wed, Mar 11
ORD
Chicago
LGA
New York
$68 Roundtrip, found 7 hours ago
$68
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Chicago to New York, returning Wed, Mar 11, priced at $68 found 7 hours ago
Thu, Feb 26 - Wed, Mar 4
MDW
Chicago
LGA
New York
$146 Roundtrip, found 5 days ago
$146
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Chicago to New York, returning Wed, Mar 4, priced at $146 found 5 days ago

Montclair economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
2.5-star property

Hotel St. James

8.8/10 Excellent! (6,546 reviews)

Apr 3 - Apr 5

2 night stay

Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $602, price is now $404 per person
$404
per person
found 1 day ago
Walking distance to many places, perfect location

Reviewed on Feb 13, 2026

Hyatt Regency Jersey City on the Hudson
4.0-star property

Hyatt Regency Jersey City on the Hudson

8.4/10 Very Good! (1,565 reviews)

Mar 26 - Mar 29

3 night stay

Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $611, price is now $405 per person
$405
per person
found 1 day ago
What a wonderful hotel and view very spacious

Reviewed on Jun 13, 2025

The George
4.0-star property

The George

9.4/10 Exceptional! (444 reviews)

Mar 25 - Mar 28

3 night stay

Chicago (CHI) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $758, price is now $512 per person
$512
per person
found 19 hours ago
Beautiful little hotel. Highly recommended.

Reviewed on Aug 25, 2025

Don't see what you're looking for?
See all available trips from Chicago to Montclair
View all trips

More About Flying To Montclair from Chicago

Route Information for Flights from Chicago to Montclair

Origin Airport IATA Code
CHI
Destination Airport IATA Code
NYC
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Montclair

Looking for cheap Chicago to Montclair flights? Orbitz has the cheapest air fares for flights from Chicago to Montclair. Plus, with our cutting-edge mobile tools, travel planning has never been easier or more wallet-friendly.

Mobile Deals and Steals

Orbitz is dedicated to providing low fares on Chicago to Montclair flights. Now you can find the latest deals on-the-go with Orbitz’s mobile apps for iPhone, iPad, Android phones, and tablets. Instantly see discounted rates for hotels, cruises, vacations, and air tickets for a great vacation.

Book Hotels With Confidence

When you’re looking for hotel rooms to go with your bargain flights from Chicago to Montclair, Orbitz provides you descriptions, photos, reviews, and location maps so you know exactly what you are booking. With easy-to-use Orbitz map tools, you can search for nearby hotels on your mobile device.

Access Your Flight Information Anytime

Use the Orbitz app or the mobile Orbitz site, m.orbtiz.com, to see information about your Chicago to Montclair flights anytime you need it. Your itinerary is also sent to your email address for reference. Access updates on your flights from Chicago to Montclair on your mobile device too, including delays and baggage claim details.

Cheap Air Ticket Prices Guaranteed

Orbitz is your number one source for low fares for Chicago to Montclair flights. Our low price guarantee on domestic and international air tickets give you great savings for a perfect trip to Montclair. Need hotels too? You can book them last minute on your mobile phone.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.