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Cheap flights New York – Chicago

Direct flights from New York to Chicago

Skypicker logo Visit the agent's website for updated prices.
American Airlines logo Visit the airline's website for updated prices. 23 kg (USD 25)
JetBlue Airways logo Visit the airline's website for updated prices. 23 kg (free)
Southwest Airlines Visit the airline's website for updated prices. 22 kg (free)
Spirit Airlines logo Visit the airline's website for updated prices. 18 kg (USD 30)
United Airlines logo Visit the airline's website for updated prices. 23 kg (free)

Selected one-way flight deals

Date Return Route Price
Sorry, we have currently no deals for this route.

Selected round trip flight deals

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Best connecting flights from New York to Chicago

New York → Toronto (YYZ) → Chicago New York → Toronto (YYZ) Toronto (YYZ) → Chicago
via Toronto (YYZ) 1h + 1h ?
New York → Atlanta (ATL) → Chicago New York → Atlanta (ATL) Atlanta (ATL) → Chicago
via Atlanta (ATL) 2h + 1h ?
New York → Toronto (YTZ) → Chicago New York → Toronto (YTZ) Toronto (YTZ) → Chicago
via Toronto (YTZ) 1h + 1h ?
New York → Boston (BOS) → Chicago New York → Boston (BOS) Boston (BOS) → Chicago
via Boston (BOS) 1h + 2h ?
New York → Baltimore (BWI) → Chicago New York → Baltimore (BWI) Baltimore (BWI) → Chicago
via Baltimore (BWI) 1h + 1h ?
New York → Cleveland (CLE) → Chicago New York → Cleveland (CLE) Cleveland (CLE) → Chicago
via Cleveland (CLE) 1h + 1h ?
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Price calendar: best airfares from New York to Chicago

The cheapest airfares are based on one-way flights.

Outbound Inbound

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Airports in New York

New York Newark (EWR) about 24 km from city center
New York - John F. Kennedy (JFK) about 19 km from city center
New York La Guardia (LGA) about 10 km from city center

Airports in Chicago

Chicago Midway International (MDW) about 13 km from city center
Chicago Ohare International (ORD) about 27 km from city center
Route map New York – Chicago

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