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Flight Deals from New York John F Kennedy Airport to Chicago from $68

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Stops

  • Nonstop
    from $136
  • Up to 1 stop
    $174
  • Up to 2 stops
    $535

Airlines

  • Alaska Airlines
    $584
  • American Airlines
    $201
  • Delta Air Lines
    $177
  • Frontier Airlines
    $202
  • Hawaiian Airlines
    $473
  • JetBlue
    $136

Cabin Class

  • Economy
    $136

Departure Airports

  • New York John F Kennedy Airport
    $136

Arrival Airports

  • Chicago Midway Airport
    $202
  • Chicago O Hare Airport
    $136

Layover Airports

  • Charlotte Douglas International Airport
    $233
  • Cleveland Hopkins International Airport
    $286
  • Denver International Airport
    $239
  • Detroit Metropolitan Airport
    $472
  • General Edward Lawrence Logan International Airport
    $174
  • Harry Reid International Airport
    $227
  • Hartsfield Jackson Atlanta International Airport
    $182
  • Indianapolis International Airport
    $320
  • Minneapolis-St Paul International/Wold-Chamberlain Airport
    $472
  • Nashville International Airport
    $279
  • Orlando International Airport
    $237
  • Pittsburgh International Airport
    $258
  • Raleigh Durham International Airport
    $263
  • Reagan Washington National Airport
    $420
  • Seattle Tacoma International Airport
    $473
  • Tampa International Airport
    $217

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On average save $240 per traveler
JetBlue Logo
JetBlue

05/14/25

JFK
1h 44m
Direct

05/14/25

ORD
JetBlue Logo
JetBlue

05/21/25

ORD
3h 26m
Direct

05/21/25

JFK
$136
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/20/25

JFK
1h 54m
Direct

05/20/25

ORD
JetBlue Logo
JetBlue

05/28/25

ORD
3h 15m
Direct

05/28/25

JFK
$136
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/05/25

JFK
4h 34m
BOS

05/05/25

ORD
JetBlue Logo
JetBlue

05/07/25

ORD
3h 15m
Direct

05/07/25

JFK
$174
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/24/25

JFK
2h 3m
Direct

05/24/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/29/25

ORD
3h 12m
Direct

05/29/25

JFK
$177
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

05/21/25

JFK
6h 37m
BOS

05/21/25

ORD
JetBlue Logo
JetBlue

05/28/25

ORD
3h 15m
Direct

05/28/25

JFK
$177
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/28/25

JFK
1h 51m
Direct

05/28/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/28/25

ORD
6h 52m
ATL

05/28/25

JFK
$182
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/14/25

JFK
2h 9m
Direct

05/14/25

ORD
American Airlines Logo
American Airlines

05/14/25

ORD
3h 6m
Direct

05/14/25

JFK
$201
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/13/25

JFK
2h 9m
Direct

05/13/25

ORD
American Airlines Logo
American Airlines

05/13/25

ORD
3h 6m
Direct

05/13/25

JFK
$201
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/14/25

JFK
5h 26m
ATL

05/14/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/14/25

MDW
8h 51m
ATL

05/14/25

JFK
$202
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/13/25

JFK
7h 41m
ATL

05/13/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/13/25

ORD
6h 47m
ATL

05/14/25

JFK
$202
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/01/25

JFK
21h 5m
TPA

05/02/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/06/25

ORD
6h 47m
ATL

05/07/25

JFK
$217
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/21/25

JFK
11h 51m
LAS

05/21/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/28/25

ORD
9h 12m
ATL

05/29/25

JFK
$227
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/21/25

JFK
2h 9m
Direct

05/21/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
6h 53m
CLT

05/24/25

JFK
$233
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

04/30/25

JFK
25h 17m
MCO

05/01/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/01/25

MDW
7h 4m
ATL

05/02/25

JFK
$237
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/22/25

JFK
13h 18m
MCO

05/22/25

MDW
Frontier Airlines Logo
Frontier Airlines

05/24/25

MDW
13h 3m
ATL

05/25/25

JFK
$237
Free cancellation within 83 hours of booking
Frontier Airlines Logo
Frontier Airlines

05/24/25

JFK
8h 48m
TPA

05/24/25

ORD
Frontier Airlines Logo
Frontier Airlines

05/27/25

ORD
16h 5m
DEN

05/27/25

JFK
$239
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

JFK
2h 9m
Direct

05/20/25

ORD
American Airlines Logo
American Airlines

05/20/25

ORD
6h 50m
PIT

05/20/25

JFK
$258
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/17/25

JFK
4h 3m
RDU

05/17/25

ORD
American Airlines Logo
American Airlines

05/20/25

ORD
3h 9m
Direct

05/20/25

JFK
$263
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/10/25

JFK
4h 9m
BNA

05/10/25

ORD
American Airlines Logo
American Airlines

05/14/25

ORD
3h 17m
Direct

05/14/25

JFK
$279
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/21/25

JFK
4h 50m
PIT

05/21/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
6h 53m
CLT

05/24/25

JFK
$285
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/22/25

JFK
5h 28m
CLE

05/22/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
3h 17m
Direct

05/27/25

JFK
$286
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/04/25

JFK
5h 53m
CLE

05/04/25

ORD
American Airlines Logo
American Airlines

05/29/25

ORD
3h 19m
Direct

05/29/25

JFK
$296
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/20/25

JFK
5h 17m
BNA

05/20/25

ORD
American Airlines Logo
American Airlines

05/24/25

ORD
6h 53m
CLT

05/24/25

JFK
$311
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/17/25

JFK
5h 5m
IND

05/17/25

ORD
American Airlines Logo
American Airlines

05/27/25

ORD
5h 9m
CLE

05/27/25

JFK
$320
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

05/18/25

JFK
4h 52m
BOS

05/18/25

ORD
American Airlines Logo
American Airlines

05/19/25

ORD
5h 18m
DCA

05/19/25

JFK
$420
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/16/25

JFK
5h 40m
DTW

05/16/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/17/25

ORD
7h 55m
MSP

05/17/25

JFK
$472
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/24/25

JFK
10h 50m
SEA

05/25/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

05/28/25

ORD
14h 42m
SEA

05/29/25

JFK
$473
Free cancellation within 83 hours of booking
Hawaiian Airlines Logo
Hawaiian Airlines

05/27/25

JFK
11h 26m
SEA

05/27/25

ORD
Hawaiian Airlines Logo
Hawaiian Airlines

05/28/25

ORD
12h 1m
SEA

05/29/25

JFK
$523
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

05/05/25

JFK
8h 20m
RDU
ATL

05/05/25

ORD
Delta Air Lines Logo
Delta Air Lines

05/07/25

ORD
8h 15m
MSP

05/07/25

JFK
$535
Free cancellation within 83 hours of booking
Alaska Airlines Logo
Alaska Airlines

05/21/25

JFK
11h 26m
SEA

05/21/25

ORD
Alaska Airlines Logo
Alaska Airlines

05/28/25

ORD
12h 59m
SEA

05/28/25

JFK
$584
Free cancellation within 83 hours of booking

Top Deals on flights from New York John F Kennedy Airport to Chicago

New York City, US (NYC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 27

JFK
1h 54m
Direct

May 27

ORD

as low as

$68

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 20

JFK
2h 9m
Direct

May 20

ORD

as low as

$78

New York City, US (NYC) - Chicago, US (CHI)

 Logo

May 20

JFK
1h 54m
Direct

May 20

ORD

as low as

$84

New York City, US (NYC) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Jun 4

JFK
1h 51m
Direct

Jun 4

ORD

as low as

$88

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 13

JFK
7h 41m
ATL

May 13

ORD

as low as

$103

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 31

JFK
8h 48m
TPA

May 31

ORD

as low as

$103

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 7

JFK
5h 26m
ATL

May 7

MDW

as low as

$103

New York City, US (NYC) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

Jun 7

JFK
12h 26m
MCO

Jun 7

MDW

as low as

$109

New York City, US (NYC) - Chicago, US (CHI)

JetBlue Logo
JetBlue

May 20

JFK
6h 37m
BOS

May 20

ORD

as low as

$119

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 20

JFK
5h 14m
BNA

May 20

ORD

as low as

$125

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Jul 26

JFK
4h 12m
DCA

Jul 26

ORD

as low as

$128

New York City, US (NYC) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 3

JFK
4h 25m
CVG

Aug 3

ORD

as low as

$128

Frequently Asked Questions

What is the typical flight duration from New York John F Kennedy Airport to Chicago?
The flight from New York John F Kennedy Airport to Chicago typically takes between 2 to 3 hours, depending on factors such as weather, air traffic, and the flight path. Direct flights usually complete the journey quicker, while connecting flights may add extra time. It’s advisable to give yourself additional time for boarding and security checks at the airports. Planning ahead with airline schedules can help optimize your travel day and ensure you have a smooth transition between the two major cities.
Are there any direct flights from New York John F Kennedy Airport to Chicago?
Yes, direct flights are available from New York John F Kennedy Airport to Chicago. These flights generally take about 2 to 3 hours and offer the convenience of reaching the destination without layovers. However, availability can depend on the time of year and the airline’s schedule. Travelers should consider booking early, as direct flights tend to fill up quickly, especially during peak seasons. Fares can range approximately from $150 to $400, so comparing different airlines and booking options is highly recommended.
What are the best transportation options from Chicago airport to downtown or popular tourist attractions?
For transportation from Chicago’s airport to downtown and other tourist areas, several options are available. Taxis and rideshares like Uber or Lyft provide convenient door-to-door service with costs typically ranging from $30 to $50. Alternatively, the CTA Blue Line offers a cost-effective train service, with fares around $5 to $10 and a travel time of about 45 minutes to an hour. Car rentals are also an option if you plan to explore further. By reviewing current schedules and fares, visitors can select the option that best fits their itinerary and budget.
What are the must-see attractions in Chicago for travelers arriving from New York John F Kennedy Airport?
Key attractions in Chicago include the iconic Millennium Park with its Cloud Gate sculpture, the historic Willis Tower Skydeck, and the vibrant Navy Pier. The Art Institute of Chicago offers a rich cultural experience, while the riverwalk and surrounding neighborhoods provide unique local charm. These sites offer a mix of modern and historic experiences characteristic of the city. Visitors from New York should allocate time to explore these diverse landmarks and enjoy the local culinary scene, which adds a delightful layer to the substantial cultural heritage Chicago proudly offers.
Which local dishes should travelers from New York John F Kennedy Airport try when visiting Chicago?
Travelers visiting Chicago should indulge in its renowned culinary specialties. Deep-dish pizza, celebrated for its thick, buttery crust and generous layers of cheese and toppings, is a must-try. The Chicago-style hot dog, served with pickle, sport peppers, and relish on a poppy seed bun, offers a local twist on a classic diner meal. Additionally, the Italian beef sandwich and Garrett Popcorn provide unique flavor experiences. Prices generally range from $10 to $30 per meal, allowing visitors to enjoy authentic local dishes without overspending while discovering new tastes.
What are the best family-friendly activities in Chicago for travelers from New York John F Kennedy Airport?
Chicago offers a variety of family-friendly activities that cater to all age groups. The Shedd Aquarium, Field Museum, and Lincoln Park Zoo are excellent choices, providing educational yet entertaining experiences for kids and adults alike. Outdoor spaces such as parks and interactive children’s museums also contribute to a well-rounded visit. With ticket prices generally ranging from $15 to $40 per person, families can tailor their itinerary based on interests and budget. Exploring these attractions ensures that visitors from New York experience a mix of adventure, learning, and fun throughout their stay.
Are there any budget-friendly hotels in Chicago for visitors from New York John F Kennedy Airport?
Yes, several budget-friendly hotel options are available throughout Chicago. Many accommodations offer competitive rates ranging from $70 to $150 per night, often including amenities such as free Wi-Fi and breakfast. Neighborhoods with efficient public transit connections and proximity to popular attractions are ideal for cost-conscious travelers. Reviews often highlight these hotels for their cleanliness and convenience. It’s advisable for visitors traveling from New York to compare deals and book in advance, especially during peak tourist seasons, to secure the best rates and locations that suit both their budget and travel itinerary.
What are the top cultural experiences in Chicago for visitors from New York John F Kennedy Airport?
Chicago is well-known for its vibrant cultural scene offering experiences that blend art, history, and live entertainment. The Art Institute of Chicago houses impressive collections and is complemented by local theater productions and music festivals throughout the year. Architectural tours, especially river cruises that showcase historic landmarks, provide an insightful look into the city’s evolution. Costs for these experiences typically range from free admissions at galleries on certain days to between $20 and $50 for guided tours. Visitors can enrich their journey from New York by embracing the city’s dynamic cultural offerings.
What are the customs requirements for travelers flying from New York John F Kennedy Airport to Chicago?
This information is not applicable to Chicago or New York John F Kennedy Airport, as both are domestic travel hubs within the United States. Since the journey remains within U.S. borders, travelers do not have to worry about customs procedures. However, it is important to carry valid identification, such as a driver’s license or passport, as required by TSA guidelines for security screening. Always double-check current travel regulations before departure, ensuring a seamless and hassle-free transition between the two major cities.
What are the best seasonal travel tips for visiting Chicago from New York John F Kennedy Airport?
Seasonal travel to Chicago offers unique experiences throughout the year. In winter, the city hosts festive holiday markets and ice skating rinks, while spring and summer bring outdoor festivals, river cruises, and architectural boat tours. In fall, the crisp air and colorful foliage enhance park visits and city walks. Weather-appropriate clothing is essential, with activity costs varying from $10 to $50. Visitors from New York should check local event calendars and weather forecasts ahead of time, allowing for advanced planning to enjoy the seasonal offerings and tailor their itinerary to the best experiences available.
Is there a specific time of year when Chicago is best visited by travelers from New York John F Kennedy Airport?
Yes, many travelers agree that late spring through early fall is the best time to visit Chicago. This period offers comfortably warm weather, ranging from about 60°F to 80°F, which is ideal for exploring outdoor attractions and engaging in city-wide festivals. These months provide ample daylight for sightseeing and dining al fresco. Although winter brings a unique charm with holiday events, colder temperatures and unpredictable weather can make extensive outdoor touring less comfortable. Planning your visit during these milder months helps ensure a well-rounded and enjoyable travel experience from New York.
What are the unique airport amenities in Chicago for travelers arriving from New York John F Kennedy Airport?
Chicago’s premier airports, including O’Hare and Midway, offer a range of amenities that enhance the overall travel experience. These facilities feature diverse dining options, duty-free shopping, free Wi-Fi, and dedicated business lounges. Additional services such as shower facilities, quiet rooms, and local art displays add a touch of local culture. With amenities often available for a nominal fee—ranging from complimentary services to costs between $10 and $30—these features ensure comfort and convenience. This focus on traveler well-being provides a welcoming stopover for guests arriving from New York.
What are the best rideshare options from Chicago airport to downtown?
For rideshare options from Chicago’s airports to downtown, both Uber and Lyft are excellent choices. These services offer a variety of ride types, from standard to premium options, ensuring cost flexibility. Fares generally range between $25 and $45, depending on factors such as time of day, distance, and traffic conditions. Rideshare apps provide real-time tracking, allowing travelers to monitor their ride status. Planning ahead and scheduling rides during off-peak hours may also reduce costs. This door-to-door service is convenient for visitors seeking a seamless transition from the airport to the vibrant heart of the city.
Are there any seasonal events in Chicago that travelers from New York John F Kennedy Airport should not miss?
Yes, Chicago boasts a range of seasonal events that are highly recommended for visitors. During summer, events like the Taste of Chicago and various outdoor music festivals attract large crowds with extensive food and cultural showcases. In the winter months, holiday markets, ice skating rinks, and festive light displays create a magical atmosphere. Autumn ushers in art fairs and community celebrations that highlight the city's dynamic cultural spirit. Ticket prices for these events can range from free entry to about $50, so visitors from New York should check local listings in advance and secure tickets early for popular events.
What are the most affordable dining options in Chicago for travelers from New York John F Kennedy Airport?
Chicago offers a wealth of affordable dining options that provide both local flavor and value for money. Budget-friendly spots include neighborhood diners, food trucks, and casual eateries serving dishes like deep-dish pizza and Chicago-style hot dogs. Meals typically cost between $8 and $20, making it easy to enjoy authentic local cuisine without overspending. Additionally, many restaurants offer daily specials and happy hour promotions that further reduce costs. Travelers should utilize food review apps and local guides to discover hidden gems that capture the city's culinary spirit while keeping meals both delicious and affordable.