Cheap Flights from New York to Chicago

The displayed fares were last found on: Sat | 23 April 05:40 AM(EST) . Fares are round trip.

The table above lists New York to Chicago flights for a round-trip flight. The fares are based on a recent trend (date and time mentioned). The cost of plane tickets available with NYC to Chicago flights is inclusive of the base fare, fuel surcharges, airline/airport taxes, and our service fee.

New York to Chicago Flight Information

Departure Airport in NY (Option 1)

LaGuardia Airport

Airport Code: LGA

Location: The airport sits in Queens, New York, U.S.

Hub for: American Airlines and Delta Air Lines

Quick Facts About LGA: Third busiest airport serving the New York City, and 20th in the US.

On Time Performance Ranking in the US

Departure: 27 | Arrival: 29

This is the best departure airport for your flight to Chicago because it has nonstop flights with Spirit, American and United Airlines. This is the busiest and highly competitive route.

Departure Airport Nearby NY (Option 2)

Newark International Airport

Official Name: Newark Liberty International Airport

Airport Code: EWR

Location: The airport straddles the boundary between the cities of Newark and Elizabeth in Essex County and Union County, New Jersey, and the distance from the city center is 23 miles/37 km.

Quick Facts About Newark Airport: The airport serves as the focus city for Frontier Airlines (Low Cost) and is a hub for United Airlines.

On Time Performance Ranking

Departure: 29 | Arrival: 30

Departure Airport in NY (Option 3)

New York International Airport

Official Name: New York Logan International Airport

Airport Code: JFK

Location: New York International Airport sits mostly in East New York and partially in Winthrop, Massachusetts, United States

Quick Facts About New York Airport: The airport serves as the focus city for JetBlue Airways (Low Cost) and American Airlines (Flagship Major airline).

On Time Performance Ranking

Departure: 20 | Arrival: 27

Operating Carriers

Airlines Flights by Stop Departure Airport Arrival Airport Connection Airport
Spirit Airlines (NK) Nonstop LGA ORD Not required
United Airlines (UA) Nonstop LGA ORD Not required
United Airlines (UA) Nonstop EWR ORD Not required
American Airlines (AA) Nonstop LGA ORD Not required
American Airlines (AA) Nonstop EWR ORD Not required
American Airlines (AA) 1-Stop JFK ORD Charlotte (CLT)
United Airlines (UA) 1-Stop EWR ORD Fort Lauderdale (FLL)

Mind the transfer time and connecting airport while booking a connecting flight as the decision has an impact on the travel experience.

Flight Distance and Time

Flight Flight Distance Flight Time
Flight from JFK to  ORD 740 miles/1191 km  2 hours 00 minutes
Flight from LGA to MDW 2,580 miles/4152 km 5 hours, 40 minutes
Flights from JFK to MDW 2,569 miles/4134 km 5 hours 46 minutes
Flight from LGA to ORD 2,569 miles/4134 km 5 hours 38 minutes

Note: The flight time and distance might differ from airlines to airlines based on speed of their airplanes and the route they take. Moreover, the time is only the time spent in air. It excludes the time spent during take-off and landing to the right terminal. Connecting flights have their layover too. So, keep all aspects in mind when you plan your travel.


Tourism Seasons in Chicago


“April to May, September to October”

Chicago witnesses a warm and pleasant weather in April and May. Average low temperature floats around 41.7°F. September to October mark autumn and is the driest part of the year.


“February, July, August”

Majority of the nights in February register temperature below 20°F (-6.7°C). July and August are the hottest months. But it’s not the temperature, rather humidity that plays the foul.


“March, November”

Weather becomes warmer. Mercury leaves the freezing point. The lower limit averages the lows of 30s and 40°F. The number of snowfall days per month stays around 3 to 4.


“December to January”

The number of rainfall days range from 10 to 11 days and snowfall days 6 to 8 per month. The duo make it difficult for visitors to explore the outdoor things. January is the coldest month.

Factors Influencing the Ticket Cost


  • Airfare (USD)

Cheapest months: January, March, April, June and September

Expensive months: November, December, (late booking also triggers ticket cost)

Average month: February, May, August

Data Reference (1)

Day of a Week

  • Airfare (USD)

Cheapest Day: Tuesday, Wednesday, Saturday

Expensive Day: Monday, Friday, Sunday, Thursday

Data Reference (2)

Time of the Day

  • Airfare (USD)

Cheapest time: From 6 in the morning until midnight

Expensive time: From midnight to 6 in the morning

Data Reference (3)


  • Airfare (USD)

Cheapest Airline: JetBlue, American

Expensive Airline: Spirit

Data Reference (4)

Tips on Securing the Lowest Fare

Be flexible with season

February, July and August make up the low season. Expect the lowest or at least below-average fares during the months, provided your travel dates do not clash with any popular event or festival.

Be flexible with month of travel

November marks the costliest month. In the rest of the months, you can expect a cheaper fare.

Be flexible with your day of travel

If you are traveling on a Monday, Friday or a Sunday be ready to pay more. The reason is obvious as this is a domestic flight route and people have intention to use their weekend for leisure and make the most of their working days.

Be flexible with your departure hour

It makes sense to avoid the crowd in the general day hours. If you sacrifice your sleep a bit, you are in for a good savings. Take note of the fare difference between the fare before 6 in the morning and after 6

Be flexible with your carrier

The selection of carrier can make a difference to. Spirit is a low-cost airlines, but its fare is opposed to that characteristic. It’s better to fly with the major airline like American and JetBlue.

Data References

1. Departure date: Last Wednesday every month, fares found on Nov 05, Carrier: American Airlines, Fare Type: Economy. Fares for 11 months because the airline has only 331 days of advance reservation window. October’s fare is an average of the previous two months.
2. Departure date: Week considered: September 21 to 27, 2020. Fares found on November 05. Carrier: American Airlines. Fare Type: Economy.
3. Departure date: Departure Date: September 21, 2020. Fares found on Nov 05. Carrier: American Airlines. Fare Type: Economy.
4. Departure date: Week considered: September 21 to 27, 2020. Fares found on Nov 05. Carrier: American Airlines. Fare Type: Economy.