Popular airlines from Chicago to New York
Frontier AirlinesFrontier Airlines
American AirlinesAmerican Airlines
Spirit AirlinesSpirit Airlines
DeltaDelta
UnitedUnited
JetBlue AirwaysJetBlue Airways
Southwest AirlinesSouthwest Airlines
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Today's featured flight deals from Chicago to New York
- Chicago (MDW) to New York (LGA).Southwest Airlines, nonstop.Departing on Wed, Dec 31 at 5:55pm from Chicago, arriving at 9:00pm in New York.Returning on Sun, Jan 4 at 9:50pm from New York, arriving at 11:15pm in Chicago.Select Southwest Airlines flight departing on Wed, Dec 31 at 5:55pm from Chicago, returning on Sun, Jan 4 at 9:50pm from New York priced at $37245% less than typical$372
- Chicago (MDW) to New York (LGA).Southwest Airlines, nonstop.Departing on Tue, Jan 20 at 6:05am from Chicago, arriving at 9:10am in New York.Returning on Sat, Jan 24 at 10:37am from New York, arriving at 3:38pm in Chicago.Select Southwest Airlines flight departing on Tue, Jan 20 at 6:05am from Chicago, returning on Sat, Jan 24 at 10:37am from New York priced at $15860% less than typical$158
- Chicago (MDW) to New York (LGA).Southwest Airlines, nonstop.Departing on Tue, Jan 20 at 6:05am from Chicago, arriving at 9:10am in New York.Returning on Sat, Jan 24 at 11:47am from New York, arriving at 4:16pm in Chicago.Select Southwest Airlines flight departing on Tue, Jan 20 at 6:05am from Chicago, returning on Sat, Jan 24 at 11:47am from New York priced at $15860% less than typical$158
- Chicago (MDW) to New York (LGA).Southwest Airlines, nonstop.Departing on Tue, Dec 30 at 8:35am from Chicago, arriving at 11:40am in New York.Returning on Fri, Jan 2 at 4:55pm from New York, arriving at 11:50pm in Chicago.Select Southwest Airlines flight departing on Tue, Dec 30 at 8:35am from Chicago, returning on Fri, Jan 2 at 4:55pm from New York priced at $45140% less than typical$451
- Chicago (ORD) to New York (JFK).American Airlines, nonstop.Departing on Sun, Jan 18 at 11:40am from Chicago, arriving at 2:54pm in New York.Returning on Sun, Jan 25 at 11:00am from New York, arriving at 5:43pm in Chicago.Select American Airlines flight departing on Sun, Jan 18 at 11:40am from Chicago, returning on Sun, Jan 25 at 11:00am from New York priced at $14860% less than typical$148
- Chicago (ORD) to New York (EWR).American Airlines, nonstop.Departing on Wed, Dec 31 at 7:16pm from Chicago, arriving at 10:34pm in New York.Returning on Tue, Jan 6 at 4:30pm from New York, arriving at 6:28pm in Chicago.Select American Airlines flight departing on Wed, Dec 31 at 7:16pm from Chicago, returning on Tue, Jan 6 at 4:30pm from New York priced at $18445% less than typical$184
- Chicago (ORD) to New York (LGA).American Airlines, nonstop.Departing on Fri, Dec 26 at 4:45pm from Chicago, arriving at 7:54pm in New York.Returning on Fri, Jan 2 at 7:20pm from New York, arriving at 9:04pm in Chicago.Select American Airlines flight departing on Fri, Dec 26 at 4:45pm from Chicago, returning on Fri, Jan 2 at 7:20pm from New York priced at $34220% less than typical$342
- Chicago (ORD) to New York (LGA).American Airlines, nonstop.Departing on Fri, Dec 26 at 4:45pm from Chicago, arriving at 7:54pm in New York.Returning on Tue, Dec 30 at 2:16pm from New York, arriving at 6:55pm in Chicago.Select American Airlines flight departing on Fri, Dec 26 at 4:45pm from Chicago, returning on Tue, Dec 30 at 2:16pm from New York priced at $34220% less than typical$342
- Chicago (ORD) to New York (EWR).American Airlines, nonstop.Departing on Wed, Dec 31 at 7:16pm from Chicago, arriving at 10:34pm in New York.Returning on Mon, Jan 5 at 5:59pm from New York, arriving at 7:47pm in Chicago.Select American Airlines flight departing on Wed, Dec 31 at 7:16pm from Chicago, returning on Mon, Jan 5 at 5:59pm from New York priced at $18850% less than typical$188
Cheap Flights from Chicago to New York (CHI-NYC)
Prices were available within the past 7 days and start at $29 for one-way flights and $58 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Find the cheapest month to fly from Chicago (CHI) to New York (NYC)
November is typically the cheapest month to fly
Alternative airports near New York
Prices were available within the past 7 days. Prices and availability are subject to change.
Travel information
Origin airport | Midway Intl. |
|---|---|
Destination airport | Newark Liberty Intl. Airport |
Airlines serving | American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United |
Roundtrip price | $58 |
Distance | 707 mi |
Book with confidence
Chicago to New York Flights
The cheapest times to fly from Chicago to New York
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to New York are during the month of January. You can find some of the cheapest flights from Chicago to New York with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Chicago to New York
Sunday is one of the best days to book for cheap flights from Chicago to New York: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Chicago to New York
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to New York in 2026. You can also book with separate airlines for your outbound and return journeys, from $29 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to New York flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to New York airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
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