The Southwest Travel Experience
Long Beach Airport will bring you within three miles of downtown Long Beach, CA. What’re you waiting for?
At Southwest, we know it takes more than great deals on New York airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago to New York the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to LaGuardia Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to New York , know that you wont be surprised at checkout. Low fares and no hidden fees. That’s Transfarency®. And as always, two bags fly free®1. Want the latest news, information, and promotional offers from Southwest? from us. Book your flight today and know that you’ll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
Fly From Chicago To Cleveland Ohio For $102 Round Trip
Hop over to the banks of Lake Eerie this year, where the dusty blues of Muddy Waters, the smooth funk of James Brown, the love songs of Elvis and the booming anthems of Springsteen continue to echo off the waters, having been issuing forth from the doors of Cleveland’s Rock and Roll Hall of Fame since the early 1980s. Flights between these two Midwestern cities are currently amongst the cheapest out of Chicago, with average prices on the route coming in at just $102!
Flights From Chicago To New York City
Businessmen and holiday tourists make up the majority of travelers from Chicago to New York City. New York City harbors a lucrative business district, as well as culturally diverse popular attractions, including fashion shops, museums, theaters, parks and skyscrapers. Cheap flights to NYC are best arranged through Orbitz.com
Chicago, Illinois
Chicago is the largest city in Illinois, serving as an international hub for trade, finance, transportation, telecommunications and industry. The city boasts one of the world’s busiest airports, O’Hare International Airport . It is also served by Chicago Midway Airport .
O’Hare International Airport is situated 17 miles northwest of downtown Chicago and serves direct flights to NYC and other world destinations via such airlines as Delta, Continental, British Airways, American Eagle, Lufthansa and JetBlue. Transportation to the airport is facilitated by the Airport Transit System , airport shuttles and taxis. Economy parking costs a daily minimum of $2 and a maximum that ranges from $9 to $19. The restaurants at O’Hare include America’s Dog, Cafe Zoot, Great American Bagel and Starbucks.
New York
New York is the most populous city in the United States of America, with an estimated population of more than 8 million residents. The city is home to the United Nations Headquarters, making it an important center for international diplomacy. Manhattan, The Bronx, Staten Island, Queens and Brooklyn are the five boroughs that form NYC.
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Connecting Flights Vs Direct Flights From New York City To Chicago
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from New York City to Chicago is $283.
The average price for direct flights from New York City to Chicago is $111.
The chart below shows up to date information regarding non-stop flights from New York City to Chicago.
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Fly From Chicago To Dallas Texas For $164 Round Trip

We know that anyone hitting Dallas’ NorthPark Mall, the city’s colossal Galleria, or even just its collection of bustling downtown bazaars and farmers markets will want as much cash in their pockets as possible, which is why we also love these bargain $164 round trip flights from Chicago’s O’Hare airport to DFW! Cheapest tickets on the route are with American Airlines, closely followed by Spirit and United, while our stats also show that Saturday departures and Wednesday returns could help save fliers up to $80 on their fare.
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Chicago To New York Flights
Book Chicago to New York flight tickets at lowest price. Get best deals on your upcoming Chicago to New York flights only on MakeMyTrip. Also Book New York to Chicago Flights. Currently 84 flights flying from Chicago to New York. To save maximum on flight booking click on below Fare Calendar button and choose your dates.
Chicago to New York-LaGuardia Apt , 1 Dec
United Airlines UA 387 | 319
06:00
New York-LaGuardia Apt, United States
BAGGAGE : CHECK INCABIN
Sorry! Fare rules could not be fetched at the moment.
Sorry! Fare rules could not be fetched at the moment.
Chicago to New York-LaGuardia Apt , 1 Dec
Delta Air Lines DL 551 | 221
06:00
New York-LaGuardia Apt, United States
BAGGAGE : CHECK INCABIN
Sorry! Fare rules could not be fetched at the moment.
Sorry! Fare rules could not be fetched at the moment.
5,648
7,519
9,765
10,513
Chicago to New York , 1 Dec
Delta Air Lines DL 5493 | CR9
07:00
Sorry! Fare rules could not be fetched at the moment.
Sorry! Fare rules could not be fetched at the moment.
5,648
7,519
9,765
13,506
Chicago to Newark , 1 Dec
United Airlines UA 2164 | 763
07:15
Sorry! Fare rules could not be fetched at the moment.
Sorry! Fare rules could not be fetched at the moment.
Chicago to New York-LaGuardia Apt , 1 Dec
United Airlines UA 3583 | E7W
07:15
New York-LaGuardia Apt, United States
BAGGAGE : CHECK INCABIN
Sorry! Fare rules could not be fetched at the moment.
Sorry! Fare rules could not be fetched at the moment.
Questions We Hear The Most
The average flight time from Chicago to New York is 2 hours 5 minutes.
There are 90 weekly flights from Chicago to New York on Southwest Airlines.
Yes, Southwest flies nonstop from Chicago to New York 4 times per day from Monday through Friday.
Yes, Southwest flies nonstop from Chicago to New York 3 times per day on Saturdays and 5 times per day on Sundays.
To find the lowest fares by day and time to fly Chicago to New York with Southwest, check out our Low Fare Calendar.
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How Can You Get Flights From Chicago To New York
There are certain tricks that you can use if you want to avail yourself cheap flights from Chicago to New York, some of which are listed below:
- You can create a price drop alert so that the portal can notify you about the price drops in a specific airline while planning your trip.
- You can take help from some sort of travel agency to assist you with all that you require.
- Be an early bird and try to book as early as possible to avail cheap flight tickets.
Connecting Flights Vs Direct Flights From Chicago To New York City
Flights between some cities may be significantly cheaper if you choose a multi-stop airline ticket. Although these connecting flights sacrifice some convenience, on average, travelers save 20%-60% when they choose to fly multi-stop versus a direct flight.
The average price for connecting flights from Chicago to New York City is $157.
The average price for direct flights from Chicago to New York City is $125.
The chart below shows up to date information regarding non-stop flights from Chicago to New York City.
Carrier |
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What Is The Cheapest Day To Fly
With the right attitude and flexibility, you can fly for less. Below are the cheapest days to fly:
- Tuesday and WednesdayYou know how most stores are not crowded midweek? Same thing here. Most people opt to depart at the beginning or end of the week.
- Thursday and SaturdayGet a head start on that Friday crowd. This also works on your return flight. Shorten your holiday by a day and increase your savings.
- Monday through ThursdayIf you’re flying internationally, deals are often available when departing these days.
How To Get The Cheapest Flight Ticket From Chicago To New York
Look no further. We’ve gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly from Chicago to New York?
The cheapest time of year to fly to New York from Chicago is August. Most expensive is December
What is the cheapest day to depart Chicago for New York?
Tuesday
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Fly From Chicago To Columbus Ohio For $167 Round Trip
The most costly of our cheapest air fares from Chicago’s O’Hare International Airport still comes in at an attractive $167 round trip, meaning it’s now easier than ever for Illinois locals to make the quick 1.25-hour hop straight across the heartlands of the Midwest. But the good news doesn’t stop there either, because Columbus is consistently rated among the most affordable cities in America, hailed for its wallet-friendly prices and go-getting population of Ohio University students.
One Way Flight From Chicago To New York

Below are the prices of tickets for direct one-way flights from Chicago to New York. The cheapest flight from Chicago to New York starts from $ 32 the departure date for this flight is 02 November 2021.
Flights from Chicago to New York are most popular in August, October, December. During this period, the average price of fly tickets is from $ 58. In the low season in March, April, May, air tickets become cheaper and the average price will be from $ 36 one way.
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Where To Buy Cheap Flights From Chicago To New York City
The best way to find a great deal on airfare is to search multiple sites. When you run a search on FareCompare, we search multiple sites and fare sources all at once so you don’t have to – which is why we think FareCompare is the best place to find cheap tickets. Airlines can adjust prices for tickets from Chicago to New York City based on the day and time that you decide to book your flight. We have collected data from all airlines, and have found that Tuesdays, Wednesdays, and Saturdays are often the best days to book flights. If you’d like to learn more, read our article about the best time to buy airline tickets.
What Are The Best Hotels To Stay In New York
Here is a list of all the best hotels that you can choose to stay in New York.
- New York City – Times Square
- Holiday Inn Express New York City Times Square
- Holiday Inn Express Manhattan Times Square South
- Holiday Inn Express New York City – Chelsea
- Holiday Inn Manhattan 6th Ave – Chelsea
- Holiday Inn NYC – Lower East Side
- Holiday Inn Express & Suites Jersey City – Holland Tunnel
- Holiday Inn New York City – Wall Street
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Find The Ideal Flight To Chicago
With Jetcost you can find and compare the best available offers for flights to Chicago, but it doesn’t end there! Improve your search by selecting the characteristics of your flight: use the filters to find only flights to Chicago that meet your needs. Whether you only want direct flights or tickets of a specific airline, Jetcost will find the best deals for you according to your specific needs. All in one search! Book your cheap flight to Chicago now and save money.
What Are The Reasons To Choose Flycoair For Your Flights From Chicago To New York Trip
Flycoair is a virtual travel agency that can assist you with all your requirements regarding your trip via cheap flights from chicago to new york. The below mentioned are reasons you can check if you want to make your travel a convenient and hassle-free experience for yourself and your flight mates.
- The travel agency notifies you about the best methods to make your travel cheaper and convenient.
- It helps you make sure that you avail all the facilities that add to the amount you have paid for your tickets.
- It helps you to know the best time to book cheap flight tickets with any particular airline.
Sometimes, it also tells you to get through the struggle of finding what you can do to make your trip memorable or what all activities you can do at a particular place.
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Essential Travel Information: Chicago To New York Newark
Our travel information panel above gives useful information about:
- The distance between Chicago and New York Newark
- The time it takes to fly to New York Newark from Chicago
- The airlines with the cheapest flights from Chicago to New York Newark
- The airlines which fly direct to New York Newark from Chicago.
Low Cost Flights From New York To Chicago
LowCostClub will always do a comparison of airfares from New York to Chicago with several airlines . They will always provide you with all available options so that you can find the cheapest flight to Chicago apart from allowing you to choose where you want to do your bookings. Here, there are also special offers for air tickets from New York to Chicago. Last week, for instance, the cheapest round-trip prices stood at $70 while the cheapest one-way price that was available within the last week cost $29
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One Way Flights Vs Round Trip Flights From New York City To Chicago
We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from New York City to Chicago. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.
The average price for one way flights from New York City to Chicago is $129.
The average price for round trip flights from New York City to Chicago is $191.
Which Direct Flight Route Between New York City And Chicago Is Cheapest

You’ll typically find cheaper flights when departing from LaGuardia than from JFK, though prices do fluctuate seasonally and even daily. Landing at O’Hare in Chicago is typically a cheaper choice than looking for a flight to Midway.Whether you’re traveling for business or vacation, Chicago is a friendly, welcoming town that combines high-end urban style with Midwestern hospitality. Take a cruise down the Chicago River to marvel at the architecture of this city’s startling skyscrapers, or head to the suburbs to explore some of Frank Lloyd Wright’s greatest designs. The Art Institute of Chicago is home to some of the greatest Impressionist paintings in the world, and the Magnificent Mile along Michigan Avenue satisfies even the most demanding shopper. Finish a day in Chicago with uproarious laughter at one of the many improv performances around town.Your visit to Chicago can combine business and fun seamlessly. Just remember to bundle up against the wind that sweeps off Lake Michigan during all seasons. To find a cheap flight to Chicago from NYC at the perfect time of day, use our smart search engine.
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