By clicking, I agree to the terms

New York to Chicago Flights

Flight only Hotel only Flight + Hotel

Flight type

Round-trip One-way
Age of children at time of trip

We will search for applicable airfare discounts. Must have 1 adult for each infant in lap

Selected fares from New York to Chicago

Departure Arrival Travel dates Round-trip
NYC CHI Wed, Oct 22 - Tue, Oct 28 $181
NYC CHI Wed, Oct 22 - Sat, Oct 25 $195
NYC CHI Wed, Oct 22 - Tue, Oct 28 $207
NYC CHI Tue, Nov 11 - Wed, Nov 12 $226
NYC CHI Mon, Oct 20 - Wed, Oct 22 $227
NYC CHI Tue, Nov 11 - Wed, Nov 12 $231
NYC CHI Tue, Nov 11 - Wed, Nov 12 $231
NYC CHI Sat, Oct 25 - Thu, Oct 30 $360
NYC CHI Tue, Oct 21 - Fri, Oct 24 $590
NYC CHI Wed, Mar 4 - Thu, Mar 5 $1,579

New York and Chicago airports and terminals

Airports in New York NY, US
map of airports in New York
  • 1

    LaGuardia Airport (LGA)

    Distance from City Center: 6.1 miles

    Terminals and carriers for flights from LGA to CHI

    Terminal Carriers
    Terminal B American Airlines, US Airways, United Airlines
  • 2

    JFK Airport (JFK)

    Distance from City Center: 13.1 miles

    Terminals and carriers for flights from JFK to CHI

    Terminal Carriers
    Terminal 2 Delta Air Lines
    Terminal 5 jetBlue
    Terminal 8 American Airlines, US Airways
  • 3

    Newark Airport (EWR)

    Distance from City Center: 10.5 miles

Back to menu Return to top

Airports in Chicago IL, US
map of airports in Chicago
  • 1

    Midway Airport (MDW)

    Distance from City Center: 9.5 miles

  • 2

    O'Hare Airport (ORD)

    Distance from City Center: 15.1 miles

    Terminals and carriers for flights from NYC to ORD

    Terminal Carriers
    Terminal 1 US Airways, United Airlines
    Terminal 2 Delta Air Lines, US Airways, United Airlines
    Terminal 3 American Airlines, US Airways, jetBlue
Back to menu Return to top

Cheap flights from New York to Chicago

Sun Mon Tue Wed Thu Fri Sat
1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22
$181
23 24 25
26 27 28 29 30 31

Highlighted price = Cheapest round-trip flights

Prices are round trip per person (conditions apply)

Featured Chicago Airport Hotels

Hotel only $139

Hilton Chicago O'Hare Airport

4 stars
3.9 / 5 123 reviews

O'Hare International Airport Map

Park & Fly - Includes up to 3 nights valet parking

...This O'Hare airport hotel is located in Terminal 2 and is within walking distance to all O'Hare Airport's domestic terminals.... More

Hotel only $137

Holiday Inn Express & Suites CHICAGO-MIDWAY AIRPORT

3 stars
4.1 / 5 42 reviews

6500 South Cicero Avenue Map

Exceptional Hotel Near Chicago Midway Airport Searching for hotels near the best sights in downtown Chicago?... More

Hotel only $144

Hilton Garden Inn Chicago/Midway Airport

3 stars
3.6 / 5 14 reviews

6530 S. Cicero Avenue Map

Complimentary wired and Wi-Fi Internet Access

...Advance Purchase Rate online!The Hilton Garden Inn Chicago Midway Airport in Chicago is located on the Midway Hotel Center campus just two blocks south of the Chicago Midway Airport and the... More

Hotel only $135

Hampton Inn Chicago-Midway Airport

2 stars
3.8 / 5 17 reviews

6540 S. Cicero Ave. Map

Free On The HouseT hot breakfast, Wi-Fi

...And no matter what time your flight got in or is going out, we're here to pick you up or drop you off.... land here and let your vacation take off...welcome to the Hampton Inn Chicago-Midway... More

Hotel only $179

Chicago Marriott Midway

3 stars
3.7 / 5 7 reviews

6520 South Cicero Avenue Map

Rate includes breakfast

...WiFi-equipped guest rooms at our Chicago Midway Airport hotel are recently renovated and offer soundproof windows, 32" flat-screen TVs and room service.... Perfect for business travel and... More

Hotel only $109

Sheraton Chicago O’Hare Airport Hotel

4 stars
4.0 / 5 109 reviews

6501 N. Mannheim Road Map

Save 40% on your stay

...Complimentary shuttle service to and from O'Hare Airport is available 24 hours a day.... Our all-suite hotel is conveniently located minutes from O'Hare International Airport, Donald E. Stephens... More

October

Cheapest weekend flights in October from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Thu, Oct 30 New York (LGA) Chicago (ORD) Spirit Airlines $205
Earn $2.05
Return Sat, Nov 1 Chicago (ORD) New York (LGA) Spirit Airlines

Lowest roundtrip airfare in October from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Oct 22 New York (LGA) Chicago (ORD) Frontier Airlines $181
Earn $1.81
Return Tue, Oct 28 Chicago (ORD) New York (LGA) Frontier Airlines

Best one-week trip in October from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Oct 28 New York (LGA) Chicago (ORD) Spirit Airlines $195
Earn $1.95
Return Tue, Nov 4 Chicago (ORD) New York (LGA) Spirit Airlines
Back to menu Return to top

November

Cheapest weekend flights in November from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 1 New York (LGA) Chicago (ORD) Spirit Airlines $205
Earn $2.05
Return Mon, Nov 3 Chicago (ORD) New York (LGA) Spirit Airlines

Lowest roundtrip airfare in November from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Sat, Nov 8 New York (LGA) Chicago (ORD) Spirit Airlines $195
Earn $1.95
Return Tue, Nov 11 Chicago (ORD) New York (LGA) Spirit Airlines

Best one-week trip in November from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Nov 4 New York (LGA) Chicago (ORD) Spirit Airlines $195
Earn $1.95
Return Tue, Nov 11 Chicago (ORD) New York (LGA) Spirit Airlines
Back to menu Return to top

December

Cheapest weekend flights in December from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Fri, Dec 5 New York (LGA) Chicago (ORD) Spirit Airlines $205
Earn $2.05
Return Sat, Dec 6 Chicago (ORD) New York (LGA) Spirit Airlines

Lowest roundtrip airfare in December from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Tue, Dec 2 New York (LGA) Chicago (ORD) Spirit Airlines $195
Earn $1.95
Return Wed, Dec 10 Chicago (ORD) New York (LGA) Spirit Airlines

Best one-week trip in December from New York to Chicago

Travel dates Departure Arrival Stops: Round-trip
Leave Wed, Dec 3 New York (LGA) Chicago (ORD) Spirit Airlines $195
Earn $1.95
Return Wed, Dec 10 Chicago (ORD) New York (LGA) Spirit Airlines
Back to menu Return to top

Travel from New York to Chicago

Flights from New York to Chicago are popular with both business and pleasure travelers. Incorporated as a city in 1837, Chicago has grown in leaps and bounds to become an international hub for finance, commerce, telecommunication and transportation. With the help of Orbitz.com, you can easily book your flight to Chicago.

New York City

Manhattan, The Bronx, Brooklyn, Queens and Staten Island are the five boroughs that form New York City (NYC). The city is served by three airports-John F. Kennedy International Airport (JFK), Newark Liberty International Airport (EWR) and LaGuardia Airport (LGA). Traveling from Midtown by taxi takes between 45 and 60 minutes to JFK, between 20 and 35 minutes to LaGuardia and between 35 and 50 minutes to Newark. Taxis charge approximately $69-75 from Manhattan to Newark and a flat rate of $45 from Manhattan to JFK. Taking a taxi from Manhattan to LaGuardia costs approximately $30.

Short-term parking for 30 minutes or less at all three airports costs $3. Long-term parking at LaGuardia costs $66 for the first 48 hours. At Newark and JFK, long-term parking costs $18 for the first 24 hours.

Brooklyn Deli, McDonald's, Ruby's Diner and Java Moon Café are just some of the restaurants that you will find at Newark. For quick bites at JFK, visit McDonald's, JikJi Café or Sbarro restaurants. Auntie Anne's and Dunkin' Donuts restaurants are just some of the eateries available at LaGuardia.

Chicago, Illinois

Located in northeastern Illinois on the shores of Lake Michigan, Chicago is colloquially referred to as the City of Big Shoulders, the Windy City and the Second City. It is the third most populous city in the Unites States of America, with more than 2.7 million residents. It is also an international hub for transportation, finance, industry and commerce.

Touring Chicago

Chicago O'Hare International Airport, also known as O'Hare Field or O'Hare Airport, is a major airport located approximately 17 miles northwest of downtown Chicago. You can take a taxi, bus or train from the airport to downtown. Depending on traffic, a taxi will take 30-45 minutes to get to downtown from the airport and charge approximately $35-$45.

Chicago experiences a humid continental climate with hot, humid summers and cold winters. January, the coldest month, experiences a mean low temperature of 14.3 degrees Fahrenheit. July is the warmest month, with an average high temperature of 83.5 degrees Fahrenheit. Summer and fall are the best times to visit, as there are many outdoor activities to engage in.

The Art Institute of Chicago, located 2.5 miles from the city's center, is home to some of the world's great art collections, including the popular artwork American Gothic. Other popular sites that you should visit include the Museum of Science and Industry, the Chicago Cultural Center and the Oriental Institute Museum.

Bag Great Chicago Vacation Deals

In addition to being an international hub for finance, trade and industry, Chicago is also home to numerous tourist attractions. You can easily book a cheap flight from New York to Chicago today using Orbitz.com.

Interesting facts about flights from New York to Chicago

    • 61 direct flights are operating from New York to Chicago today.
    • Today's average time for a direct flight is 2h 34m.
    • American Airlines flight 303 (1:00 AM GMT, Boeing 737-800 Passenger) is today's earliest available flight from New York to Chicago.
    • jetBlue flight 105 (4:45 PM GMT, Embraer 190) is today's latest available flight from New York to Chicago.
    • Today's shortest direct flight from New York to Chicago (American Airlines flight 303, Boeing 737-800 Passenger) takes 2h 20m.
    • Today's longest direct flight from New York to Chicago (Delta Air Lines flight 2928, Canadair Regional Jet 900) takes 2h 54m.
    • Flights from JFK Airport (JFK), LaGuardia Airport (LGA), Newark Airport (EWR) to Midway Airport (MDW), O'Hare Airport (ORD) are available for this route.

Aircraft options between New York and Chicago

Equipment Carrier
Boeing 737-700 Passenger United Airlines, US Airways
Embraer 170 United Airlines, US Airways
Boeing 757-200 Passenger United Airlines, US Airways
Airbus Industrie A319 United Airlines, US Airways
Boeing 737-800 Passenger American Airlines, US Airways, United Airlines
McDonnell Douglas MD-80 American Airlines, US Airways
Canadair Regional Jet 700 Delta Air Lines
Embraer 190 jetBlue
Canadair Regional Jet 900 Delta Air Lines
McDonnell Douglas MD-83 American Airlines, US Airways
Airbus Industrie A320 United Airlines, jetBlue, US Airways
Embraer 175 United Airlines