Cheap Flights from Chicago to New York

Cheap Flights from Chicago to New York

Cheap Flights from Chicago to New York
Looking for cheap flights from Chicago to New York? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Chicago to New York vary by season, cabin, and date, but available award flights can start around 4,500 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Chicago to New York for specific travel dates.
2026-11-05
ORD - EWR
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
AS
2026-11-05
ORD - EWR
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
AS
2026-11-05
ORD - EWR
Economy | Non stop | 5 left
From 4,500 Pts + $25.6
AS
2026-11-05
ORD - EWR
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
AS
2026-11-06
ORD - EWR
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
AS
2026-11-06
ORD - EWR
Economy | Non stop | 9+ left
From 4,500 Pts + $25.6
AS
Chicago to New York flight facts
Distance
732 mi
1,178 km in a straight line
Estimated flight time
about 2h
In the air, for the straight-line distance
Time difference
+1h
New York is 1 hour ahead of Chicago.
Airports in Chicago
DPA · Dupage
MDW · Chicago Midway Intl
ORD · Chicago O'Hare Intl
Airports in New York
EWR · Newark Liberty Intl
JFK · John F Kennedy Intl
LGA · La Guardia
Nearby airport alternatives
Flights Chicago - White Plains · White Plains is 28 mi from New York
Flights Chicago - Trenton · Trenton is 55 mi from New York
Flights Milwaukee - New York · Milwaukee is 73 mi from Chicago
Flights Chicago - Allentown · Allentown is 79 mi from New York
Flights South Bend - New York · South Bend is 86 mi from Chicago
Flights Chicago - Philadelphia · Philadelphia is 89 mi from New York
Premium cabin flights from Chicago to New York
Premium cabin
2026-11-05
ORD - JFK
First | 1 Stop | 1 left
From 15,000 Pts + $25.6
AS
Premium cabin
2026-11-05
ORD - JFK
First | 1 Stop | 1 left
From 15,000 Pts + $25.6
AS
Premium cabin
2026-11-05
ORD - LGA
First | 1 Stop | 1 left
From 15,000 Pts + $25.6
AS
Premium cabin
2026-11-05
ORD - JFK
First | Non stop
From 21,500 Pts + $5.6
AA
Premium cabin
2026-11-05
ORD - JFK
First | 1 Stop
From 21,500 Pts + $11.2
AA
Premium cabin
2026-11-05
ORD - JFK
First | Non stop
From 26,500 Pts + $5.6
AA
Selected hotels for your next stay
Thompson Central Park New York
New York (United States)
Thompson Central Park New York
From 20,000 Pts or $418
Home2 Suites by Hilton New Brunswick
New Brunswick, NJ (USA)
Home2 Suites by Hilton New Brunswick
From 40,000 Pts or $120
HGU New York, an SLH Hotel
New York (USA)
HGU New York, an SLH Hotel
From 49,000 Pts or $190
Frequently Asked Questions
The cheapest route from Chicago to New York depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Cheapest Flights to New YorkAward flights to New York
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Chicago to New York.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Chicago to New York.
Chicago and New York are about 732 miles (1,178 km) apart in a straight line.
Flying the 732-mile straight-line distance takes about 2h in the air, estimated from typical cruising speed. Actual travel time depends on the routing; itineraries with connections take longer.
New York is 1 hour ahead of Chicago.
Departures from Chicago: Dupage (DPA), Chicago Midway Intl (MDW), Chicago O'Hare Intl (ORD). Arrivals in New York: Newark Liberty Intl (EWR), John F Kennedy Intl (JFK), La Guardia (LGA).
Travelers searching this route also look at other popular routes into New York, plus the return trip when we track it. Fares and award space change daily.
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