$68 Cheap flight deals from New York (NYC) to Skokie (CHI)
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This Weekend's Flight Deals from New York to Skokie
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.
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$267 Roundtrip, found 18 hours ago
$267
Roundtrip
found 18 hours ago
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$373 Roundtrip, found 3 days ago
$373
Roundtrip
found 3 days ago
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$377 Roundtrip, just found
$377
Roundtrip
just found
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$426 Roundtrip, found 21 hours ago
$426
Roundtrip
found 21 hours ago
Airfares from $68 One Way, $135 Round Trip from New York to Skokie
Prices starting at $135 for return flights and $68 for one-way flights to Skokie were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JFK
New York
ORD
Chicago
$135 Roundtrip, just found
$135
Roundtrip
just found
LGA
New York
MDW
Chicago
$137 Roundtrip, found 5 hours ago
$137
Roundtrip
found 5 hours ago
LGA
New York
ORD
Chicago
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
EWR
New York
ORD
Chicago
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
EWR
New York
RFD
Rockford
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Skokie economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,586 reviews)
Aug 26 - Aug 30
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,487, price is now $927 per person
$927
per person
found 1 day ago
Anderson should receive a gold star! So helpful, patient, and has such a great personality. The room was clean on arrival but I did notice housekeeping never cleaned our room during our stay and we had to ask for fresh hand towels every morning. Breakfast was standard and I would definitely like to see an ice machine or at least the juice in the dispenser be cold. The burgers from the bar were good but the pepperoni pizza was very disappointing especially for $22.
Reviewed on Jul 7, 2026
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
9.4/10 Exceptional! (2,566 reviews)
Aug 26 - Aug 30
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $2,049, price is now $1,344 per person
$1,344
per person
found 1 day ago
The hotel was on the pier and
Reviewed on Jul 7, 2026
4.0-star property
Level Chicago Fulton Market
9.2/10 Wonderful! (512 reviews)
Aug 26 - Aug 30
4 night stay
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
United • Roundtrip • Coach
Save 100% on your flight
Price was $1,362, price is now $937 per person
$937
per person
found 1 day ago
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
Skokie packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
9.4/10 Exceptional! (4,586 reviews)
Aug 9 - Aug 12
3 night stay
New York (NYC) to Chicago (ORD)
JetBlue Airways • Roundtrip • PremiumEconomy
Price was $962, price is now $721 per person
$721
per person
found 8 hours ago
Anderson should receive a gold star! So helpful, patient, and has such a great personality. The room was clean on arrival but I did notice housekeeping never cleaned our room during our stay and we had to ask for fresh hand towels every morning. Breakfast was standard and I would definitely like to see an ice machine or at least the juice in the dispenser be cold. The burgers from the bar were good but the pepperoni pizza was very disappointing especially for $22.
Reviewed on Jul 7, 2026
4.5-star property
Pendry Chicago
9.2/10 Wonderful! (1,136 reviews)
Aug 9 - Aug 12
3 night stay
New York (NYC) to Chicago (ORD)
JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,160, price is now $871 per person
$871
per person
found 6 hours ago
The Pendry was absolutely beautiful! The bar, restaurant and cafe on site were amazing and delicious! Also the accessibility to all the attractions we planned to go to was amazing! We were able to walk almost everywhere and the metro was one block away making our trip amazing! We will definitely stay here again! Staff was amazing and friendly especially the doormen!! Loved loved loved!!
Reviewed on Jul 7, 2026
Skokie first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hilton Chicago O'Hare Airport
8.4/10 Very Good! (2,332 reviews)
Aug 16 - Aug 19
3 night stay
New York (JFK) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,109, price is now $922 per person
$922
per person
found 1 day ago
They need to steam clean the carpets, they are sticky and dirty in the room, otherwise everything else was fine.
Reviewed on Jul 7, 2026
5.0-star property
Nobu Hotel Chicago
9.4/10 Exceptional! (879 reviews)
Aug 16 - Aug 19
3 night stay
New York (JFK) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,503, price is now $1,266 per person
$1,266
per person
found 1 day ago
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026
4.0-star property
Level Chicago Fulton Market
9.2/10 Wonderful! (512 reviews)
Aug 16 - Aug 19
3 night stay
New York (JFK) to Chicago (ORD)
American Airlines • Roundtrip • FirstClass
Price was $1,214, price is now $1,035 per person
$1,035
per person
found 1 day ago
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back.
The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.
Reviewed on Jul 2, 2026
More About Flying To Skokie from New York
Route Information for Flights from New York to Skokie
Origin Airport IATA Code | NYC |
|---|---|
Destination Airport IATA Code | CHI |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
New York to Skokie
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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.