Fare Guide
Estimated lowest fares found within 7 days
Cheapest Airline
The cheapest airline(s) flying from New York City to Chicago is Spirit Airlines.
Cheapest Month
June
Travel Period: May 2024 - April 2025
The cheapest month(s) to fly from New York City to Chicago is June.
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May 2024
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Jun 2024
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Jul 2024
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Aug 2024
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Sep 2024
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Oct 2024
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Nov 2024
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Dec 2024
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Jan 2025
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Feb 2025
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Mar 2025
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Apr 2025
Cheapest Day of the Week
Tuesday
The cheapest day(s) of the week to fly from New York City to Chicago is Tuesday.
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Sun Sunday
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Mon Monday
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Tue Tuesday
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Wed Wednesday
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Thu Thursday
-
Fri Friday
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Sat Saturday
Cheapest Time
8am
The cheapest time of the day to fly from New York City to Chicago is in the morning.
Early Morning 12:01am - 06:00am
Morning 6:01am - 12:00pm
Afternoon 12:01pm - 6:00pm
Evening 6:01pm to 12:00am
12am
6am
12pm
6pm
Flight Schedules
Last Updated: Tue, 2 Apr, 2024
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Depart
Earliest
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- Earliest
- Latest
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Filter by Airline
All
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Total Duration
- Shortest
- Longest
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Stopover
All
-
Availability
- M
- T
- W
- T
- F
- S
- S
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20:30 - 22:17LGA - ORD
-
20:30 (LGA)New York La Guardia Airport
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22:17 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1705)Boeing 737 800 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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20:55 - 22:38LGA - ORD
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20:55 (LGA)New York La Guardia Airport
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22:38 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1233)Airbus A220 100 Passenger - 2h 43m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
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21:00 - 22:27LGA - ORD
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21:00 (LGA)New York La Guardia Airport
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22:27 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1284)Airbus - 2h 27m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
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21:30 - 22:55LGA - MDW
-
21:30 (LGA)New York La Guardia Airport
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22:55 (MDW)Chicago Midway Airport
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(WN 4967)Boeing 737 700 - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
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21:40 - 23:05LGA - MDW
-
21:40 (LGA)New York La Guardia Airport
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23:05 (MDW)Chicago Midway Airport
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(WN 4967)Boeing 737 700 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
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21:55 - 23:15LGA - MDW
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21:55 (LGA)New York La Guardia Airport
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23:15 (MDW)Chicago Midway Airport
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(WN 4967)Boeing 737 700 - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 700
-
21:59 - 23:42EWR - ORD
-
21:59 (EWR)Newark Liberty International Airport
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23:42 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1393)Boeing 737 800 - 2h 43m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
06:00 - 07:31EWR - ORD
-
06:00 (EWR)Newark Liberty International Airport
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07:31 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 320)Boeing 737 800 - 2h 31m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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06:00 - 07:25LGA - ORD
-
06:00 (LGA)New York La Guardia Airport
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07:25 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2684)Airbus - 2h 25m
- Direct
-
- M
- T
- W
- T
- F
- S
- -
- Airbus
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06:00 - 07:42LGA - ORD
-
06:00 (LGA)New York La Guardia Airport
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07:42 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1275)Airbus A220 100 Passenger - 2h 42m
- Direct
-
- M
- T
- W
- T
- F
- -
- -
- Airbus A220 100 Passenger
-
06:00 - 07:59LGA - ORD
-
06:00 (LGA)New York La Guardia Airport
-
07:59 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 462)Airbus - 2h 59m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
06:07 - 07:40EWR - ORD
-
06:07 (EWR)Newark Liberty International Airport
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07:40 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2919)Boeing 737 800 - 2h 33m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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06:30 - 07:55LGA - MDW
-
06:30 (LGA)New York La Guardia Airport
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07:55 (MDW)Chicago Midway Airport
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(WN 4920)Boeing 737 800 - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 800
-
06:30 - 07:55LGA - MDW
-
06:30 (LGA)New York La Guardia Airport
-
07:55 (MDW)Chicago Midway Airport
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(WN 4920)Boeing 737 Max 8 Passenger - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 Max 8 Passenger
-
06:30 - 07:54LGA - ORD
-
06:30 (LGA)New York La Guardia Airport
-
07:54 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2684)Airbus - 2h 24m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Airbus
-
07:00 - 08:24LGA - ORD
-
07:00 (LGA)New York La Guardia Airport
-
08:24 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 219)Airbus - 2h 24m
- Direct
-
- M
- T
- W
- T
- F
- S
- -
- Airbus
-
07:10 - 08:35LGA - MDW
-
07:10 (LGA)New York La Guardia Airport
-
08:35 (MDW)Chicago Midway Airport
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(WN 4920)Boeing 737 800 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
07:15 - 08:45EWR - ORD
-
07:15 (EWR)Newark Liberty International Airport
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08:45 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2323)Boeing 737 800 - 2h 30m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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07:30 - 09:15LGA - ORD
-
07:30 (LGA)New York La Guardia Airport
-
09:15 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1681)Airbus A220 100 Passenger - 2h 45m
- Direct
-
- M
- T
- W
- T
- F
- -
- -
- Airbus A220 100 Passenger
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07:30 - 09:11LGA - ORD
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07:30 (LGA)New York La Guardia Airport
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09:11 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 660)Boeing 737 800 - 2h 41m
- Direct
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- M
- T
- W
- T
- F
- -
- -
- Boeing 737 800
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07:32 - 09:15EWR - ORD
-
07:32 (EWR)Newark Liberty International Airport
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09:15 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 1627)Boeing 737 800 - 2h 43m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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08:00 - 09:37LGA - ORD
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08:00 (LGA)New York La Guardia Airport
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09:37 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1788)Airbus - 2h 37m
- Direct
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- M
- T
- W
- T
- F
- S
- -
- Airbus
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08:10 - 10:05JFK - ORD
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08:10 (JFK)New York John F. Kennedy International Airport
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10:05 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 2206)Airbus A220 100 Passenger - 2h 55m
- Direct
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- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
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08:11 - 09:59JFK - ORD
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08:11 (JFK)New York John F. Kennedy International Airport
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09:59 (ORD)Chicago O'Hare International Airport
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JetBlue Airways (B6 1105)Embraer Emb E90 - 2h 48m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Embraer Emb E90
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08:15 - 09:35LGA - MDW
-
08:15 (LGA)New York La Guardia Airport
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09:35 (MDW)Chicago Midway Airport
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(WN 3139)Boeing 737 800 - 2h 20m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
-
08:20 - 09:57EWR - ORD
-
08:20 (EWR)Newark Liberty International Airport
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09:57 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1793)Boeing 737 800 - 2h 37m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
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08:50 - 10:40LGA - ORD
-
08:50 (LGA)New York La Guardia Airport
-
10:40 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1263)Airbus A220 100 Passenger - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
-
08:50 - 10:40LGA - ORD
-
08:50 (LGA)New York La Guardia Airport
-
10:40 (ORD)Chicago O'Hare International Airport
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Delta Air Lines (DL 1210)Airbus A220 100 Passenger - 2h 50m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Airbus A220 100 Passenger
-
09:00 - 10:29LGA - ORD
-
09:00 (LGA)New York La Guardia Airport
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10:29 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 623)Airbus - 2h 29m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
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09:00 - 10:35LGA - MDW
-
09:00 (LGA)New York La Guardia Airport
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10:35 (MDW)Chicago Midway Airport
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(WN 3137)Boeing 737 700 - 2h 35m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
09:00 - 10:47EWR - ORD
-
09:00 (EWR)Newark Liberty International Airport
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10:47 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 2038)Boeing 737 Max 9 Passenger - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 Max 9 Passenger
-
09:04 - 11:10JFK - ORD
-
09:04 (JFK)New York John F. Kennedy International Airport
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11:10 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 2819)Boeing 737 800 - 3h 06m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
09:25 - 10:55LGA - MDW
-
09:25 (LGA)New York La Guardia Airport
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10:55 (MDW)Chicago Midway Airport
-
(WN 3137)Boeing 737 700 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
09:50 - 11:45LGA - ORD
-
09:50 (LGA)New York La Guardia Airport
-
11:45 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2562)Airbus A220 100 Passenger - 2h 55m
- Direct
-
- M
- T
- W
- T
- F
- -
- -
- Airbus A220 100 Passenger
-
10:00 - 11:45EWR - ORD
-
10:00 (EWR)Newark Liberty International Airport
-
11:45 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1796)Boeing 737 800 - 2h 45m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
10:00 - 11:43LGA - ORD
-
10:00 (LGA)New York La Guardia Airport
-
11:43 (ORD)Chicago O'Hare International Airport
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United Airlines (UA 1310)Airbus - 2h 43m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
10:30 - 12:09LGA - ORD
-
10:30 (LGA)New York La Guardia Airport
-
12:09 (ORD)Chicago O'Hare International Airport
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American Airlines (AA 327)Boeing 737 800 - 2h 39m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:00 - 12:40LGA - ORD
-
11:00 (LGA)New York La Guardia Airport
-
12:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2320)Airbus - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
11:04 - 12:40EWR - ORD
-
11:04 (EWR)Newark Liberty International Airport
-
12:40 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1872)Boeing 737 800 - 2h 36m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:10 - 12:35LGA - MDW
-
11:10 (LGA)New York La Guardia Airport
-
12:35 (MDW)Chicago Midway Airport
-
(WN 6011)Boeing 737 700 - 2h 25m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
11:19 - 13:06EWR - ORD
-
11:19 (EWR)Newark Liberty International Airport
-
13:06 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1027)Boeing 737 800 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
11:30 - 18:15EWR - ORD
-
11:30 (EWR)Newark Liberty International Airport
-
18:15 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 661)Boeing 737 800 - 7h 45m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:00 - 13:29LGA - ORD
-
12:00 (LGA)New York La Guardia Airport
-
13:29 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2352)Airbus - 2h 29m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
12:05 - 14:07JFK - ORD
-
12:05 (JFK)New York John F. Kennedy International Airport
-
14:07 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 4955)Canadair Regional - 3h 02m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Canadair Regional
-
12:30 - 14:00LGA - MDW
-
12:30 (LGA)New York La Guardia Airport
-
14:00 (MDW)Chicago Midway Airport
-
(WN 6011)Boeing 737 700 - 2h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 700
-
12:30 - 14:00LGA - MDW
-
12:30 (LGA)New York La Guardia Airport
-
14:00 (MDW)Chicago Midway Airport
-
(WN 6011)Boeing 737 800 - 2h 30m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
-
12:30 - 14:21LGA - ORD
-
12:30 (LGA)New York La Guardia Airport
-
14:21 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 1435)Airbus A220 100 Passenger - 2h 51m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
-
12:40 - 14:20LGA - ORD
-
12:40 (LGA)New York La Guardia Airport
-
14:20 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 386)Boeing 737 800 - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
12:45 - 14:10LGA - MDW
-
12:45 (LGA)New York La Guardia Airport
-
14:10 (MDW)Chicago Midway Airport
-
(WN 6011)Boeing 737 800 - 2h 25m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 800
-
12:58 - 18:44EWR - ORD
-
12:58 (EWR)Newark Liberty International Airport
-
18:44 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1947)Airbus - 6h 46m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Airbus
-
13:00 - 14:38LGA - ORD
-
13:00 (LGA)New York La Guardia Airport
-
14:38 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1338)Airbus - 2h 38m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
13:15 - 14:50EWR - ORD
-
13:15 (EWR)Newark Liberty International Airport
-
14:50 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 323)Boeing 737 800 - 2h 35m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:00 - 15:30LGA - MDW
-
14:00 (LGA)New York La Guardia Airport
-
15:30 (MDW)Chicago Midway Airport
-
(WN 3139)Boeing 737 800 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
14:00 - 15:41LGA - ORD
-
14:00 (LGA)New York La Guardia Airport
-
15:41 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2649)Airbus - 2h 41m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
14:20 - 16:04LGA - ORD
-
14:20 (LGA)New York La Guardia Airport
-
16:04 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2871)Airbus A220 100 Passenger - 2h 44m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
-
14:25 - 15:50LGA - MDW
-
14:25 (LGA)New York La Guardia Airport
-
15:50 (MDW)Chicago Midway Airport
-
(WN 3139)Boeing 737 Max 8 Passenger - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
14:30 - 16:21LGA - ORD
-
14:30 (LGA)New York La Guardia Airport
-
16:21 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2824)Boeing 737 800 - 2h 51m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:35 - 16:10EWR - ORD
-
14:35 (EWR)Newark Liberty International Airport
-
16:10 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1689)Boeing 737 800 - 2h 35m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:59 - 16:46EWR - ORD
-
14:59 (EWR)Newark Liberty International Airport
-
16:46 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1840)Boeing 737 800 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
14:59 - 18:34EWR - ORD
-
14:59 (EWR)Newark Liberty International Airport
-
18:34 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2144)Airbus - 4h 35m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
15:00 - 16:34LGA - ORD
-
15:00 (LGA)New York La Guardia Airport
-
16:34 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2075)Airbus - 2h 34m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
15:20 - 17:21JFK - ORD
-
15:20 (JFK)New York John F. Kennedy International Airport
-
17:21 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2207)Airbus A220 100 Passenger - 3h 01m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus A220 100 Passenger
-
15:30 - 17:00LGA - MDW
-
15:30 (LGA)New York La Guardia Airport
-
17:00 (MDW)Chicago Midway Airport
-
(WN 127)Boeing 737 700 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 700
-
15:30 - 17:00LGA - MDW
-
15:30 (LGA)New York La Guardia Airport
-
17:00 (MDW)Chicago Midway Airport
-
(WN 127)Boeing 737 800 - 2h 30m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Boeing 737 800
-
15:30 - 17:00LGA - MDW
-
15:30 (LGA)New York La Guardia Airport
-
17:00 (MDW)Chicago Midway Airport
-
(WN 127)Boeing 737 Max 8 Passenger - 2h 30m
- Direct
-
- -
- -
- -
- -
- -
- -
- S
- Boeing 737 Max 8 Passenger
-
15:54 - 17:45JFK - ORD
-
15:54 (JFK)New York John F. Kennedy International Airport
-
17:45 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2226)Boeing 737 800 - 2h 51m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
16:00 - 17:41LGA - ORD
-
16:00 (LGA)New York La Guardia Airport
-
17:41 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1258)Airbus - 2h 41m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
16:10 - 17:50LGA - ORD
-
16:10 (LGA)New York La Guardia Airport
-
17:50 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 527)Boeing 737 800 - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
16:35 - 18:00LGA - MDW
-
16:35 (LGA)New York La Guardia Airport
-
18:00 (MDW)Chicago Midway Airport
-
(WN 5302)Boeing 737 Max 8 Passenger - 2h 25m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
16:40 - 18:10LGA - MDW
-
16:40 (LGA)New York La Guardia Airport
-
18:10 (MDW)Chicago Midway Airport
-
(WN 5302)Boeing 737 800 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
16:55 - 18:53LGA - ORD
-
16:55 (LGA)New York La Guardia Airport
-
18:53 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 2662)Airbus A220 100 Passenger - 2h 58m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
-
16:59 - 18:46EWR - ORD
-
16:59 (EWR)Newark Liberty International Airport
-
18:46 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 2113)Boeing 737 800 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
17:00 - 18:40LGA - ORD
-
17:00 (LGA)New York La Guardia Airport
-
18:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 451)Airbus - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
17:01 - 19:03JFK - ORD
-
17:01 (JFK)New York John F. Kennedy International Airport
-
19:03 (ORD)Chicago O'Hare International Airport
-
JetBlue Airways (B6 605)Embraer Emb E90 - 3h 02m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Embraer Emb E90
-
17:25 - 18:55LGA - MDW
-
17:25 (LGA)New York La Guardia Airport
-
18:55 (MDW)Chicago Midway Airport
-
(WN 5323)Boeing 737 Max 8 Passenger - 2h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- -
- Boeing 737 Max 8 Passenger
-
17:45 - 19:43LGA - ORD
-
17:45 (LGA)New York La Guardia Airport
-
19:43 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 1004)Airbus A220 100 Passenger - 2h 58m
- Direct
-
- -
- -
- -
- -
- -
- S
- -
- Airbus A220 100 Passenger
-
18:00 - 19:49LGA - ORD
-
18:00 (LGA)New York La Guardia Airport
-
19:49 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1906)Airbus - 2h 49m
- Direct
-
- M
- T
- W
- T
- F
- -
- -
- Airbus
-
18:01 - 19:40EWR - ORD
-
18:01 (EWR)Newark Liberty International Airport
-
19:40 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1688)Airbus - 2h 39m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Airbus
-
18:25 - 20:12EWR - ORD
-
18:25 (EWR)Newark Liberty International Airport
-
20:12 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1232)Boeing 737 800 - 2h 47m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
18:30 - 20:11LGA - ORD
-
18:30 (LGA)New York La Guardia Airport
-
20:11 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 2041)Boeing 737 800 - 2h 41m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
18:50 - 20:20LGA - MDW
-
18:50 (LGA)New York La Guardia Airport
-
20:20 (MDW)Chicago Midway Airport
-
(WN 6052)Boeing 737 700 - 2h 30m
- Direct
-
- M
- -
- -
- T
- F
- -
- S
- Boeing 737 700
-
18:55 - 20:49LGA - ORD
-
18:55 (LGA)New York La Guardia Airport
-
20:49 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 1004)Airbus A220 100 Passenger - 2h 54m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus A220 100 Passenger
-
18:55 - 20:57JFK - ORD
-
18:55 (JFK)New York John F. Kennedy International Airport
-
20:57 (ORD)Chicago O'Hare International Airport
-
Delta Air Lines (DL 5118)Canadair Regional - 3h 02m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Canadair Regional
-
19:00 - 20:40LGA - ORD
-
19:00 (LGA)New York La Guardia Airport
-
20:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1981)Airbus - 2h 40m
- Direct
-
- M
- T
- W
- T
- F
- -
- S
- Airbus
-
19:30 - 21:00LGA - MDW
-
19:30 (LGA)New York La Guardia Airport
-
21:00 (MDW)Chicago Midway Airport
-
(WN 6052)Boeing 737 800 - 2h 30m
- Direct
-
- -
- T
- W
- -
- -
- -
- -
- Boeing 737 800
-
19:57 - 21:27EWR - ORD
-
19:57 (EWR)Newark Liberty International Airport
-
21:27 (ORD)Chicago O'Hare International Airport
-
American Airlines (AA 1691)Boeing 737 800 - 2h 30m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
-
19:57 - 21:40EWR - ORD
-
19:57 (EWR)Newark Liberty International Airport
-
21:40 (ORD)Chicago O'Hare International Airport
-
United Airlines (UA 1234)Boeing 737 800 - 2h 43m
- Direct
-
- M
- T
- W
- T
- F
- S
- S
- Boeing 737 800
Connecting Flights
-
06:00 - 07:30LGA - BNA09:00 - 10:45BNA - ORD
-
06:00 (LGA)New York La Guardia Airport09:00 (BNA)Nashville Airport
-
07:30 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
-
(WN 603)Boeing 737 Max 8 Passenger (WN 510)Boeing 737 700 - 5h 45m (1h 30m)
- BNA Nashville 1h 30m
-
- M
- -
- -
- T
- F
- -
- -
-
06:00 - 07:30LGA - BNA09:00 - 10:45BNA - ORD
-
06:00 (LGA)New York La Guardia Airport09:00 (BNA)Nashville Airport
-
07:30 (BNA)Nashville Airport10:45 (ORD)Chicago O'Hare International Airport
-
(WN 603)Boeing 737 800 (WN 510)Boeing 737 700 - 5h 45m (1h 30m)
- BNA Nashville 1h 30m
-
- -
- T
- W
- -
- -
- -
- -
-
06:00 - 07:30LGA - BNA09:15 - 10:50BNA - MDW
-
06:00 (LGA)New York La Guardia Airport09:15 (BNA)Nashville Airport
-
07:30 (BNA)Nashville Airport10:50 (MDW)Chicago Midway Airport
-
(WN 603)Boeing 737 800 (WN 2119)Boeing 737 700 - 5h 50m (1h 45m)
- BNA Nashville 1h 45m
-
- -
- -
- -
- -
- -
- S
- -
-
07:00 - 09:25LGA - ATL10:40 - 11:35ATL - MDW
-
07:00 (LGA)New York La Guardia Airport10:40 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:25 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:35 (MDW)Chicago Midway Airport
-
(WN 254)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 5h 35m (1h 15m)
- ATL Atlanta 1h 15m
-
- -
- -
- -
- -
- -
- S
- -
-
07:15 - 09:45LGA - ATL10:45 - 11:40ATL - MDW
-
07:15 (LGA)New York La Guardia Airport10:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
09:45 (ATL)Atlanta Hartsfield-Jackson Intl Airport11:40 (MDW)Chicago Midway Airport
-
(WN 254)Boeing 737 Max 8 Passenger (WN 5518)Boeing 737 Max 8 Passenger - 5h 25m (1h)
- ATL Atlanta 1h
-
- M
- -
- -
- T
- F
- -
- -
-
09:35 - 11:10LGA - BNA12:30 - 14:15BNA - ORD
-
09:35 (LGA)New York La Guardia Airport12:30 (BNA)Nashville Airport
-
11:10 (BNA)Nashville Airport14:15 (ORD)Chicago O'Hare International Airport
-
(WN 606)Boeing 737 700 (WN 3623)Boeing 737 700 - 5h 40m (1h 20m)
- BNA Nashville 1h 20m
-
- M
- -
- -
- T
- F
- -
- -
-
11:00 - 13:35LGA - ATL14:35 - 15:25ATL - MDW
-
11:00 (LGA)New York La Guardia Airport14:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
13:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport15:25 (MDW)Chicago Midway Airport
-
(WN 5822)Boeing 737 Max 8 Passenger (WN 1751)Boeing 737 Max 8 Passenger - 5h 25m (1h)
- ATL Atlanta 1h
-
- M
- -
- -
- T
- F
- -
- -
-
11:25 - 13:35LGA - MCI15:10 - 16:30MCI - MDW
-
11:25 (LGA)New York La Guardia Airport15:10 (MCI)Kansas City International Airport
-
13:35 (MCI)Kansas City International Airport16:30 (MDW)Chicago Midway Airport
-
(WN 5728)Boeing 737 700 (WN 3150)Boeing 737 800 - 6h 05m (1h 35m)
- MCI Kansas City 1h 35m
-
- M
- -
- -
- T
- F
- -
- -
-
12:55 - 15:25LGA - ATL17:05 - 18:00ATL - MDW
-
12:55 (LGA)New York La Guardia Airport17:05 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
15:25 (ATL)Atlanta Hartsfield-Jackson Intl Airport18:00 (MDW)Chicago Midway Airport
-
(WN 5822)Boeing 737 Max 8 Passenger (WN 5042)Boeing 737 Max 8 Passenger - 6h 05m (1h 40m)
- ATL Atlanta 1h 40m
-
- -
- -
- -
- -
- -
- S
- -
-
13:00 - 14:45LGA - STL15:50 - 16:55STL - MDW
-
13:00 (LGA)New York La Guardia Airport15:50 (STL)St Louis Lambert Intl Airport
-
14:45 (STL)St Louis Lambert Intl Airport16:55 (MDW)Chicago Midway Airport
-
(WN 4667)Boeing 737 700 (WN 3242)Boeing 737 700 - 4h 55m (1h 05m)
- STL Saint Louis 1h 05m
-
- M
- -
- -
- T
- F
- -
- -
-
14:00 - 15:35LGA - BNA17:00 - 18:35BNA - MDW
-
14:00 (LGA)New York La Guardia Airport17:00 (BNA)Nashville Airport
-
15:35 (BNA)Nashville Airport18:35 (MDW)Chicago Midway Airport
-
(WN 608)Boeing 737 800 (WN 2261)Boeing 737 800 - 5h 35m (1h 25m)
- BNA Nashville 1h 25m
-
- M
- -
- -
- T
- F
- -
- -
-
14:05 - 15:35LGA - BNA16:45 - 18:20BNA - MDW
-
14:05 (LGA)New York La Guardia Airport16:45 (BNA)Nashville Airport
-
15:35 (BNA)Nashville Airport18:20 (MDW)Chicago Midway Airport
-
(WN 608)Boeing 737 Max 8 Passenger (WN 2261)Boeing 737 Max 8 Passenger - 5h 15m (1h 10m)
- BNA Nashville 1h 10m
-
- -
- T
- W
- -
- -
- -
- -
-
14:25 - 16:10LGA - STL17:10 - 18:15STL - MDW
-
14:25 (LGA)New York La Guardia Airport17:10 (STL)St Louis Lambert Intl Airport
-
16:10 (STL)St Louis Lambert Intl Airport18:15 (MDW)Chicago Midway Airport
-
(WN 6172)Boeing 737 800 (WN 3244)Boeing 737 800 - 4h 50m (1h)
- STL Saint Louis 1h
-
- -
- -
- -
- -
- -
- S
- -
-
15:30 - 17:20LGA - STL18:25 - 19:30STL - MDW
-
15:30 (LGA)New York La Guardia Airport18:25 (STL)St Louis Lambert Intl Airport
-
17:20 (STL)St Louis Lambert Intl Airport19:30 (MDW)Chicago Midway Airport
-
(WN 6172)Boeing 737 700 (WN 5687)Boeing 737 800 - 5h (1h 05m)
- STL Saint Louis 1h 05m
-
- -
- -
- -
- -
- -
- -
- S
-
16:55 - 19:25LGA - ATL20:35 - 21:30ATL - MDW
-
16:55 (LGA)New York La Guardia Airport20:35 (ATL)Atlanta Hartsfield-Jackson Intl Airport
-
19:25 (ATL)Atlanta Hartsfield-Jackson Intl Airport21:30 (MDW)Chicago Midway Airport
-
(WN 256)Boeing 737 Max 8 Passenger (WN 5960)Boeing 737 800 - 5h 35m (1h 10m)
- ATL Atlanta 1h 10m
-
- M
- -
- -
- T
- F
- -
- -
-
19:55 - 21:40LGA - STL22:50 - 23:55STL - MDW
-
19:55 (LGA)New York La Guardia Airport22:50 (STL)St Louis Lambert Intl Airport
-
21:40 (STL)St Louis Lambert Intl Airport23:55 (MDW)Chicago Midway Airport
-
(WN 1486)Boeing 737 Max 8 Passenger (WN 3244)Boeing 737 800 - 5h (1h 10m)
- STL Saint Louis 1h 10m
-
- -
- -
- -
- -
- -
- -
- S
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What’s the fastest flight time from New York City to Chicago?
The fastest flight time for direct flights from New York City to Chicago is 2 hours 20 minutes. Check latest flight schedules & prices on Wego.
What’s the most popular airline flying from New York City to Chicago?
The most popular airline flying from New York City to Chicago is American Airlines. Find the latest flight deals on Wego.
How far is Chicago from New York City?
The flight distance between New York City and Chicago is 1144km. Check all available flights on Wego.
When is the earliest and latest flight of the day?
The earliest flight of the day departs at 06:00. The last flight of the day departs at 20:30. See the full list of flight times on Wego.
How many airlines offer direct flights from New York City to Chicago?
There are 5 airlines that offer direct flights from New York City to Chicago. Find out the list of airlines on Wego.
All Airports in New York City
Newark Liberty International Airport
All Airports in Chicago
Popular Airlines flying from New York City to Chicago
Popular destinations from Chicago
Popular destinations from New York City
Popular Hotels in Chicago
- Clarion Inn Elmhurst - Oak Brook near I-88, I-290, I-294
- The Royal Sonesta Chicago Downtown
- Club Quarters Hotel, Central Loop, Chicago
- The Ritz-Carlton, Chicago
- Fairmont Chicago at Millennium Park Gold Experience
- Swissôtel Chicago
- Pendry Chicago
- Hotel Felix Chicago
- Hotel Saint Clair
- Best Western River North Hotel