$29 Cheap flight deals from Chicago (CHI) to Massapequa (NYC)
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This Weekend's Flight Deals from Chicago to Massapequa
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.
MDW
Midway Intl.
EWR
Newark Liberty Intl. Airport
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
ORD
O'Hare Intl.
LGA
LaGuardia
$238 Roundtrip, found 1 hour ago
$238
Roundtrip
found 1 hour ago
MDW
Midway Intl.
LGA
LaGuardia
$298 Roundtrip, found 10 hours ago
$298
Roundtrip
found 10 hours ago
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$322 Roundtrip, found 4 hours ago
$322
Roundtrip
found 4 hours ago
Airfares from $29 One Way, $72 Round Trip from Chicago to Massapequa
Prices starting at $72 for return flights and $29 for one-way flights to Massapequa were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
MDW
Chicago
EWR
New York
$72 Roundtrip, just found
$72
Roundtrip
just found
ORD
Chicago
EWR
New York
$99 Roundtrip, just found
$99
Roundtrip
just found
ORD
Chicago
LGA
New York
$104 Roundtrip, found 1 hour ago
$104
Roundtrip
found 1 hour ago
MDW
Chicago
LGA
New York
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
ORD
Chicago
JFK
New York
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Massapequa economy flight packages
Price found within the past 48 hours. Click for updated prices.
2.5-star property
Candlewood Suites New York City-Times Square by IHG
8.6/10 Excellent! (1,827 reviews)
Jun 5 - Jun 9
4 night stay
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Delta • Coach
Newark Liberty Intl. Airport (EWR) to Chicago (CHI)
Spirit Airlines • Coach
Save 100% on your flight
Price was $942, price is now $566 per person
$566
per person
found 1 day ago
The A/C make terrible noise all night
Reviewed on Mar 17, 2026
5.0-star property
1 Hotel Central Park
9/10 Wonderful! (1,003 reviews)
May 20 - May 24
4 night stay
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,000, price is now $1,143 per person
$1,143
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
4.0-star property
Hotel Riu Plaza Manhattan Times Square
9/10 Wonderful! (3,411 reviews)
May 20 - May 24
4 night stay
Chicago (CHI) to Newark Liberty Intl. Airport (EWR)
Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,390, price is now $841 per person
$841
per person
found 1 day ago
Got in early, Checked in early, left the bags and went to visit World Trade One . room was available at 2 PM.
It was a short 24 hour trip to New York , so essentially room was needed just ro sleep in it, It was great, the view from the second highest floor in hotel was nice .
Reviewed on Feb 5, 2026
Massapequa business class flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Night Hotel Broadway
7.2/10 Good! (2,893 reviews)
May 26 - May 31
5 night stay
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,342, price is now $982 per person
$982
per person
found 12 hours ago
EVERYONE VERY NICE AND HELPFUL AND CARING! WOULD STAY HERE AGAIN!
CLEAN ROOM AND VERY NICE AREA
Reviewed on Nov 28, 2025
4.0-star property
Hotel Riu Plaza Manhattan Times Square
9/10 Wonderful! (3,411 reviews)
May 26 - May 31
5 night stay
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $1,839, price is now $1,281 per person
$1,281
per person
found 12 hours ago
Got in early, Checked in early, left the bags and went to visit World Trade One . room was available at 2 PM.
It was a short 24 hour trip to New York , so essentially room was needed just ro sleep in it, It was great, the view from the second highest floor in hotel was nice .
Reviewed on Feb 5, 2026
5.0-star property
WestHouse New York
8.4/10 Very Good! (1,003 reviews)
May 26 - May 31
5 night stay
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $1,691, price is now $1,193 per person
$1,193
per person
found 12 hours ago
Nice hotel with excellent breakfast: dynamite view from terrace, friendly staff.
Spacious Room was well equipped, with safe, luxury bathroom, vanity, fridge, excellent king bed, great sheets , occasional chair, closet, bench, etc.
no coffee in room but coffee/cappuccino etc is on 23rd floor breakfast room most of the day.
Rooms have nice art deco decor though showing a little wear
Reviewed on Nov 27, 2025
Massapequa first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza New York Times Square
9/10 Wonderful! (2,951 reviews)
Jun 6 - Jun 9
3 night stay
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
American Airlines • Non-stop • FirstClass
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Price was $1,466, price is now $1,080 per person
$1,080
per person
found 5 hours ago
Beautiful room and great customer service
Reviewed on Feb 7, 2026
5.0-star property
1 Hotel Central Park
9/10 Wonderful! (1,003 reviews)
May 26 - May 31
5 night stay
Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
American Airlines • FirstClass
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,773, price is now $1,774 per person
$1,774
per person
found 2 hours 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
2.0-star property
LGA AIRPORT
10/10 Exceptional! (2 reviews)
Jun 6 - Jun 9
3 night stay
Chicago (ORD) to New York (JFK)
American Airlines • Non-stop • FirstClass
New York (JFK) to Chicago (ORD)
Frontier Airlines • Non-stop • FirstClass
Save 100% on your flight
Price was $5,436, price is now $4,031 per person
$4,031
per person
found 5 hours ago
More About Flying To Massapequa from Chicago
Route Information for Flights from Chicago to Massapequa
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | NYC |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Massapequa
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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.