Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Earn rewards on top of your airline miles with Orbitz Rewards

Search for flights on more than 400 airlines

Sign up to receive text alerts about your trip

Promo code:
Minimum stay: none
Book Between: 11/14/2018-12/31/2018
Terms & Conditions

Selected fares from New York to Chicago

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

LaGuardia Airport and John F. Kennedy International Airport are the two major airports offering New York to Chicago flights. Carriers land at either Midway Airport or O'Hare International Airport. If you're searching for cheap New York to Chicago flights, consider multiple stops, flexible dates and budget carriers such as JetBlue (flying to O'Hare) and Southwest Airlines or AirTran Airways (flying to Midway).

Carriers with New York to Chicago flights

  • American Airlines
  • AirTran Airways
  • Delta Airlines
  • Frontier Airlines
  • JetBlue Airlines
  • Southwest Airlines
  • Spirit Airlines
  • United Airlines
  • US Airways

Estimated travel times for flights from New York to Chicago

New York to Chicago flights typically take about 2 hours and 15 minutes and cover a distance of approximately more than 700 miles.


Both Chicago airports offer multiple options for transportation after your New York to Chicago flight. Find the taxi stand and shuttle services just outside baggage claim, visit a car rental kiosk or purchase a CTA pass to ride the "L," Chicago's public rail system, to your destination. A single ride costs $2.25, but 1-, 3-, 7- and 30-day unlimited passes can also be purchased. Children under 7 ride free.

Distance from Midway Airport to downtown Chicago: 10 miles
Transit line from Midway Airport to downtown Chicago: Orange (with a commute time of 20-30 minutes)
Distance from O'Hare International Airport to downtown Chicago: 17 miles
Transit line from O'Hare International Airport to downtown Chicago: Blue (with a commute time of 35-40 minutes)

Things to do in Chicago after flights from New York to Chicago

Chicago easily disproves its nickname as the Second City. With historic architecture, a pristine lakeshore, wonderful food and a thriving arts scene, Chicago thrives as a first-rate global destination. Explore these local favorites following flights from New York to Chicago.


  • The Magnificent Mile
  • John Hancock Observatory
  • Navy Pier
  • Millennium Park
  • Grant Park
  • The Art Institute of Chicago
  • The Field Museum
  • Theater District
  • The Board of Trade
  • Willis Tower
  • Adler Planetarium
  • Shedd Aquarium

West Loop

  • Restaurant Row (Randolph Street)


  • Halsted Street

Hyde Park

  • Frank Lloyd Wright's Robie House
  • Museum of Science and Industry
  • Promontory Point
  • University of Chicago


  • Chinatown Square
  • Wentworth Avenue


  • National Museum of Mexican Art
  • Pilsen Murals

Lincoln Park

  • Lincoln Park Zoo
  • Lincoln Park Conservatory
  • North Avenue Beach
  • Steppenwolf Theatre Company
  • Peggy Notebaert Nature Museum
  • Clark Street


  • Boys Town
  • Metro
  • Montrose Harbor


  • Wrigley Field
  • Southport Avenue
  • Music Box Theater


  • Aragon Ballroom
  • The Green Mill
  • The Riviera Theatre
  • Little Saigon


  • The Swedish American Museum Center
  • Clark Street

Rogers Park

  • Loyola Park
  • Loyola University
  • Devon Avenue

Wicker Park/Bucktown

  • Division Street
  • The Polish Museum of America
  • Six Corners
  • Double Door

Getting around Chicago

Chicago is mapped on a grid system. The center is the intersection of State and Madison Streets, with each city block measuring 100 increments.


Metered, garage and pay lots are available throughout the city. Rates vary by location.


Save more with Chicago Flight + Hotel packages

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

*Savings based on all holiday package bookings with Flight + Hotel on from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

Dec 10, 2018

overall fine but no wifi or tv on return flight :(

Nov 21, 2018

I’ve been traveling with the same small perfectly sized carryon backpack type bag for years (fits under the seat in front of me) and never had to to check it in- so I was very surprised that I couldn’t take it onboard and was charged an additional $ the money I saved on my flight with Orbitz was negated. If you get a deal with Orbitz- be sure your carry on is included in the price.

Nov 21, 2018

don't nickel and dime for everyting

Nov 20, 2018

I love Orbitz.

Nov 19, 2018

Air travel is anything but fun. This was relatively painless. One thing that probably isn’t news to Or it’s is that the airlines definitely treat 3rd party booking companies such as yourselves as second class citizens. You do get to fly, but they make it very clear that you are not their top priority. That is a shame, because you are offering a service that not only takes the headache out of the travelers ordeal in making reservations, but streamlines the back end of the airlines’ operations significantly. Orbitz pioneered the simplification and democratization of access to travel. I have tried all of Orbitz’ competitor travel platforms, and Orbitz is consistently the best - especially when things go wrong and a traveler gets stuck by a cancelled, late flight or other airline mishaps. Thank you!

Nov 14, 2018

Amazing staff and pilots and the delta app makes all easy

Nov 11, 2018

Although it departed late. The arrival to Chicago was on time.

Nov 2, 2018

Clean aircraft

Oct 30, 2018

Need better WiFi

Oct 12, 2018

I will never fly Basic Economy again. I can’t believe anyone would. The airlines have made air travel so uncomfortable while ripping us all off it is shameful. I will think long and hard about traveling in the future.