$147 Cheap flight deals from Chicago (CHI) to Monroe (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 Monroe

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.

Sat, Jan 31 - Wed, Feb 4
ORD
O'Hare Intl.
HPN
Westchester County
$447 Roundtrip, found 1 hour ago
$447
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jan 31 from O'Hare Intl. to Westchester County, returning Wed, Feb 4, priced at $447 found 1 hour ago
Sat, Jan 31 - Sat, Feb 7
MDW
Midway Intl.
HPN
Westchester County
$447 Roundtrip, found 1 hour ago
$447
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jan 31 from Midway Intl. to Westchester County, returning Sat, Feb 7, priced at $447 found 1 hour ago

Airfares from $147 One Way, $319 Round Trip from Chicago to Monroe

Prices starting at $319 for return flights and $147 for one-way flights to Monroe 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, Feb 24 - Tue, Mar 3
ORD
Chicago
HPN
White Plains
$319 Roundtrip, found 4 days ago
$319
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Feb 24 from Chicago to White Plains, returning Tue, Mar 3, priced at $319 found 4 days ago
Tue, Feb 24 - Mon, Mar 2
ORD
Chicago
HPN
White Plains
$323 Roundtrip, found 4 days ago
$323
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Feb 24 from Chicago to White Plains, returning Mon, Mar 2, priced at $323 found 4 days ago
Wed, Feb 25 - Tue, Mar 3
ORD
Chicago
HPN
White Plains
$327 Roundtrip, found 4 days ago
$327
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 25 from Chicago to White Plains, returning Tue, Mar 3, priced at $327 found 4 days ago
Wed, Apr 1 - Wed, Apr 8
ORD
Chicago
HPN
White Plains
$329 Roundtrip, found 6 days ago
$329
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Apr 1 from Chicago to White Plains, returning Wed, Apr 8, priced at $329 found 6 days ago
Mon, Feb 23 - Tue, Mar 3
ORD
Chicago
HPN
White Plains
$333 Roundtrip, found 4 days ago
$333
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Feb 23 from Chicago to White Plains, returning Tue, Mar 3, priced at $333 found 4 days ago

Monroe economy flight packages

Price found within the past 48 hours. Click for updated prices.
Mountain Springs Lake Resort
3.5-star property

Mountain Springs Lake Resort

9.6/10 Exceptional! (234 reviews)

Mar 2 - Mar 4

2 night stay

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

Frontier Airlines • Coach

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

Spirit Airlines • Coach
Price was $395, price is now $250 per person
$250
per person
found 1 day ago
Even though every cabin was occupied it was very peaceful and quiet

Reviewed on Aug 1, 2021

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

8.8/10 Excellent! (1,000 reviews)

Mar 22 - Mar 27

5 night stay

Chicago (CHI) to New York (JFK)

Frontier Airlines • Coach

New York (JFK) to Chicago (CHI)

Spirit Airlines • Coach
Price was $2,732, price is now $1,707 per person
$1,707
per person
found 1 day ago
The hotel is beautiful looking forward to visiting again.

Reviewed on Feb 21, 2023

The Inn At Fox Hollow Hotel
4.0-star property

The Inn At Fox Hollow Hotel

9.2/10 Wonderful! (1,002 reviews)

Feb 27 - Mar 1

2 night stay

Chicago (CHI) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $524, price is now $331 per person
$331
per person
found 1 day ago
Very nice and clean large rooms

Reviewed on Jan 21, 2025

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

Monroe first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel
4.0-star property

Sheraton New York Times Square Hotel

7.4/10 Good! (5,413 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $1,649, price is now $1,103 per person
$1,103
per person
found 1 day ago
The room is too old, best location

Reviewed on Jan 25, 2026

Mandarin Oriental, New York
5.0-star property

Mandarin Oriental, New York

9.2/10 Wonderful! (591 reviews)

Mar 1 - Mar 4

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,138, price is now $1,583 per person
$1,583
per person
found 1 day ago
Beautiful common areas, extremely professional staff, biggest hotel bathroom ever! Bed was very comfy

Reviewed on Dec 10, 2025

1 Hotel Central Park
5.0-star property

1 Hotel Central Park

9/10 Wonderful! (1,001 reviews)

Mar 1 - Mar 4

3 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Price was $1,667, price is now $1,280 per person
$1,280
per person
found 1 day ago
We have traditionally always stayed in the theater district area however more recently the area has changed. More homeless, dirtier and just not as enjoyable for us. We decided to stay more uptown in the central park area and the Orbitz site recommended the 1 Hotel Central Park. From the moment we checked in it was truly like a zen feeling and experience. Less hustle and bustle checking in, the staff was super friendly, attentive and helpful in every way from the check to the concierge. The room was modern (in a zen way), mini bar was stocked with wines, drinks and snacks. A coffee pod machine as well. The restaurant Jams, was excellent for breakfast and always packed! We HIGHLY recommend staying here and as a matter of fact tyhis will be our new go to staying in NYC.

Reviewed on Jul 13, 2025

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

More About Flying To Monroe from Chicago

Route Information for Flights from Chicago to Monroe

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

Chicago to Monroe

Orbitz can provide you with the greatest deals on a wide range of Chicago to Monroe flights. Orbitz offers guaranteed low prices and offers you the convenience of cutting-edge mobile tools thus providing you with your best travel experience ever.

Mobile Apps for Chicago to Monroe Flights

You can use our mobile app to find the cheapest prices for flights from Chicago to Monroe. With this cutting-edge technology, you can check up on your flight’s status, gate number and luggage claim handling, and reserve exclusive deals on top hotels at short notice.

Loyalty Rewarded

For travelers who regularly book Chicago to Monroe flights, our frequent flyer program offers even more low-cost air tickets. You will be able to store your miles in your personal Orbitz account and add them with ease to your future reservations.

Trouble-Free Traveling With Flight Alerts

Orbitz will not only provide you with the assistance that you require when purchasing flights from Chicago to Monroe but will ensure that you remain fully updated on any flight delays, changes or disruptions by providing free alerts. Your Chicago to Monroe flights alerts can be sent directly to your phone or email. You can also opt for these alerts to be sent to your family and friends so that everyone is kept informed of your travel plans.

 Budget Flying Made Simple

Finding cheap flights from Chicago to Monroe is easy with Orbitz. You can pick and choose airlines for your international flights to create inexpensive yet convenient travel arrangements.

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.