
Flight Deals from New York City to Chicago Midway Airport from $84
Top flight deals from leading airlines:







... and +100s more
Save up to 50% on select flights with Priceline
Save an average of $240 per person when bundling your flight and hotel together with Priceline
If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference
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Price Drop Deals Near You
Stops
- Up to 1 stop$142
- Up to 2 stops$725
Airlines
- Delta Air Lines$142
- Frontier Airlines$313
- United Airlines$725
Cabin Class
- Economy$142
Departure Airports
- New York John F Kennedy Airport$227
- New York LaGuardia Airport$313
- Newark Liberty Airport$142
Arrival Airports
- Chicago Midway Airport$142
Layover Airports
- Denver International Airport$960
- Detroit Metropolitan Airport$142
- Hartsfield Jackson Atlanta International Airport$176
- Minneapolis-St Paul International/Wold-Chamberlain Airport$151
- Orlando International Airport$333
- Raleigh Durham International Airport$1120
- Washington Dulles Airport$725
Best Price. GUARANTEED.
Exclusively for Priceline Members
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We'll refund the difference if you find a lower price.
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Top Deals on flights from New York City to Chicago Midway Airport
New York City, US (NYC) - Chicago, US (CHI)

Jul 16
Jul 16
as low as
New York City, US (NYC) - Chicago, US (CHI)

Jul 8
Jul 8
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New York City, US (NYC) - Chicago, US (CHI)

Jul 9
Jul 9
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New York City, US (NYC) - Chicago, US (CHI)

Jul 22
Jul 22
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New York City, US (NYC) - Chicago, US (CHI)

Jul 14
Jul 14
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New York City, US (NYC) - Chicago, US (CHI)

Jul 10
Jul 10
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New York City, US (NYC) - Chicago, US (CHI)

Jul 7
Jul 7
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New York City, US (NYC) - Chicago, US (CHI)

Jul 4
Jul 5
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New York City, US (NYC) - Chicago, US (CHI)

Jul 1
Jul 1
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New York City, US (NYC) - Chicago, US (CHI)

Jun 30
Jul 1
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New York City, US (NYC) - Chicago, US (CHI)

Jul 24
Jul 24
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New York City, US (NYC) - Chicago, US (CHI)

Jul 21
Jul 21
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