Cheap flights from New York to Chicago

Flights overview

Useful information for finding cheap flights from New York to Chicago and booking your next trip
Cheapest round-trip flights $177
JetBlue Nonstop 3 hr Thu, Aug 13 — Mon, Aug 17
The cheapest round-trip flight from New York to Chicago is currently $177
Cheapest one-way flight $89
United Nonstop 3 hr Wed, Aug 12
The cheapest one-way flight from New York to Chicago is currently $89
Last-minute weekend getaway $329
Frontier 1 stop 8 hr Sat, Jun 6 — Mon, Jun 8
The cheapest last-minute weekend getaway from New York to Chicago is currently $329
Cheapest business class flights $475
American Nonstop 3 hr Sat, Jul 25 — Sun, Jul 26
The cheapest business class round-trip flight from New York to Chicago is currently $475
Fastest flight 2 hr 15 min The fastest nonstop flight from New York to Chicago takes 2 hr 15 min
Nonstop flights Every day There are direct flights on this route every day.

When is the cheapest time to fly?

The cheapest month to fly from New York to Chicago is typically January. The most expensive month to fly is typically June.
January
Cheapest
Typical prices: $65–160
June
Most expensive
Typical prices: $170–260

Popular airlines from New York to Chicago

  • United
    Nonstop
    from $207
    Typical price: $145–285
    188 weekly nonstop flights
    EWR, LGA - ORD Every day
    841 weekly connecting flights
    EWR, LGA - ORD Every day
  • American
    Nonstop
    from $182
    Typical price: $155–290
    126 weekly nonstop flights
    EWR, JFK, LGA - ORD Every day
    911 weekly connecting flights
    EWR, JFK, LGA - ORD Every day
  • Delta
    Nonstop
    from $197
    Typical price: $165–375
    85 weekly nonstop flights
    JFK, LGA - ORD Every day
    2364 weekly connecting flights
    EWR, JFK, LGA - MDW, ORD Every day
  • Southwest
    Nonstop
    from $187
    Typical price: $165–335
    47 weekly nonstop flights
    LGA - MDW Every day
    748 weekly connecting flights
    LGA - MDW, ORD Every day
  • JetBlue
    Nonstop
    from $177
    Typical price: $170–450
    20 weekly nonstop flights
    JFK - ORD Every day
    8 weekly connecting flights
    JFK - ORD Every Mon, Tue, Thu, Fri, Sat, Sun
  • Frontier
    from $258
    Typical price: $115–315
    125 weekly connecting flights
    EWR, JFK, LGA - MDW, ORD Every day

Popular airports near New York

  • John F. Kennedy International Airport (JFK)
    New York United States 38 min 12 mi
  • LaGuardia Airport (LGA)
    New York United States 25 min 8 mi
  • Newark Liberty International Airport (EWR)
    Newark United States 29 min 8 mi
  • New York Stewart International Airport (SWF)
    Newburgh United States 1 hr 27 min 55 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from New York to Chicago

The cheapest flights from New York to Chicago are usually in January. Typical ticket prices in January range from $65 to $160.
The cheapest round-trip flight from New York to Chicago recently found on Google Flights was with JetBlue from $177. The cheapest one-way flight was with United from $89.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from New York to Chicago is $207, flying from Aug 13 to Aug 16.
  • The cheapest American flight from New York to Chicago is $182, flying from Aug 20 to Aug 23.
  • The cheapest Delta flight from New York to Chicago is $197, flying from Aug 20 to Aug 24.
  • The cheapest Southwest flight from New York to Chicago is $187, flying from Aug 20 to Aug 24.
  • The cheapest JetBlue flight from New York to Chicago is $177, flying from Aug 13 to Aug 17.
  • The cheapest Frontier flight from New York to Chicago is $258, flying from Aug 29 to Aug 31.
The cheapest round-trip flight from New York to Chicago starts at $177 from Thu, Aug 13 to Mon, Aug 17. The cheapest one-way flight starts at $89 and departs on Wed, Aug 12.
2 hr 15 min is the shortest flight time from New York to Chicago.
Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
It's easy to use Google Flights to find the cheapest days to fly from New York to Chicago.
Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

You can also turn on price tracking to get alerts if the price changes for a route or flight.
What counts as the best airline for your flights from New York to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from New York to Chicago.

In terms of nonstop flights, United is the most popular. United offers 188 nonstop flights and 841 connecting flights per week. United flies from Newark Liberty International Airport (EWR) , LaGuardia Airport (LGA) to Chicago O'Hare International Airport (ORD) .

In terms of flights, Delta is the most popular. Delta offers 85 nonstop flights and 2,364 connecting flights per week. Delta flies from Newark Liberty International Airport (EWR) , John F. Kennedy International Airport (JFK) , LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .

Other popular airlines flying from New York to Chicago are:
  • American offers 126 nonstop flights and 911 connecting flights per week. American flies from Newark Liberty International Airport (EWR) , John F. Kennedy International Airport (JFK) , LaGuardia Airport (LGA) to Chicago O'Hare International Airport (ORD) .
  • Southwest offers 47 nonstop flights and 748 connecting flights per week. Southwest flies from LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
  • JetBlue offers 20 nonstop flights and 8 connecting flights per week. JetBlue flies from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD) .
  • Frontier offers 125 connecting flights per week. Frontier flies from Newark Liberty International Airport (EWR) , John F. Kennedy International Airport (JFK) , LaGuardia Airport (LGA) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
The number of connecting flights refers to distinct flights with at least one stop between New York and Chicago.
The cheapest round-trip flight from New York to Chicago recently found on Google Flights was with JetBlue from $177. The cheapest one-way flight was with United from $89.

Some of the cheapest round-trip deals we found with different airlines:
  • The cheapest United flight from New York to Chicago is $207, flying from Aug 13 to Aug 16.
  • The cheapest American flight from New York to Chicago is $182, flying from Aug 20 to Aug 23.
  • The cheapest Delta flight from New York to Chicago is $197, flying from Aug 20 to Aug 24.
  • The cheapest Southwest flight from New York to Chicago is $187, flying from Aug 20 to Aug 24.
  • The cheapest JetBlue flight from New York to Chicago is $177, flying from Aug 13 to Aug 17.
  • The cheapest Frontier flight from New York to Chicago is $258, flying from Aug 29 to Aug 31.
United, American, Delta, JetBlue and Southwest fly direct from New York to Chicago.
  • There are 188 United direct flights from New York to Chicago per week. Flights are available every day.
  • There are 126 American direct flights from New York to Chicago per week. Flights are available every day.
  • There are 85 Delta direct flights from New York to Chicago per week. Flights are available every day.
  • There are 47 Southwest direct flights from New York to Chicago per week. Flights are available every day.
  • There are 20 JetBlue direct flights from New York to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
The cheapest last-minute deal between New York and Chicago at price $329 is offered by Frontier from Sat, Jun 6 to Mon, Jun 8.
United, American, Delta, JetBlue and Southwest fly direct from New York to Chicago.
  • There are 188 United direct flights from New York to Chicago per week. Flights are available every day.
  • There are 126 American direct flights from New York to Chicago per week. Flights are available every day.
  • There are 85 Delta direct flights from New York to Chicago per week. Flights are available every day.
  • There are 47 Southwest direct flights from New York to Chicago per week. Flights are available every day.
  • There are 20 JetBlue direct flights from New York to Chicago per week. Flights are available every day.
Use the Stops filter while searching for flights, to see only nonstop options in your results.
There are direct flights from New York to Chicago on a daily basis.
The cheapest direct (nonstop) round-trip flights between New York and Chicago start at $177 from Thu, Aug 13 to Mon, Aug 17 with JetBlue.
It's easy to find nonstop flights with Google Flights! Once you've searched for flights from New York to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
The cheapest business class round-trip flights between New York and Chicago start at $475 from Sat, Jul 25 to Sun, Jul 26 with American.
The cheapest economy class round-trip flights between New York and Chicago start at $177 from Thu, Aug 13 to Mon, Aug 17.
To book business class trips from New York to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

You can also adjust the trip type to view one-way fares.
The best last-minute getaway deal for the next weekend between New York and Chicago starts at $329 from Sat, Jun 6 to Mon, Jun 8 with Frontier.
The cheapest last-minute deal between New York and Chicago at price $329 is offered by Frontier from Sat, Jun 6 to Mon, Jun 8.
To find last-minute flight deals from New York to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

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