Popular in | June |
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Cheapest in | January |
Round-trip from | $222 |
One-way from | $33 |
Users have found that leaving on a Monday can be a cost-effective option. It’s possible to save up to 42% on your flight compared to booking on days when demand is much higher.
When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 56 days in advance, which can save you up to 96% on flights from New York to Chicago compared to booking the week you need them. Waiting 56 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $281. For sooner than that we have options available in the next 3 days from $423.
Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Chicago. Flights to Chicago from New York in January are about $258 on average during January, but can be found for as low as $86.
It’s typically best to fly out from New York to Chicago in the evening. Doing so could potentially save you 18% on the flight price compared to flying in the afternoon, which is usually more expensive.
Fly from
Fly to
Budget
$60 - $149
Route
Depart
Return
Price
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 9/10
Nonstop2h 39m
Chicago O'Hare Intl
Wed 9/11
Nonstop2h 17m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 9/10
Nonstop2h 39m
Chicago O'Hare Intl
Tue 9/17
Nonstop2h 17m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 7/2
Nonstop2h 38m
Chicago O'Hare Intl
Tue 7/9
Nonstop2h 18m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 9/24
1 stop8h 38m
Chicago O'Hare Intl
Mon 9/30
Nonstop2h 15m
New York LaGuardiaChicago Midway
LGA - MDW
LGAMDW
New York LaGuardia
Wed 9/11
1 stop16h 55m
Chicago Midway
Wed 9/18
1 stop10h 03m
NewarkChicago O'Hare Intl
EWR - ORD
EWRORD
Newark
Wed 8/14
Nonstop2h 37m
Chicago O'Hare Intl
Sat 8/17
Nonstop2h 06m
New York John F Kennedy IntlChicago O'Hare Intl
JFK - ORD
JFKORD
New York John F Kennedy Intl
Wed 7/24
Nonstop2h 53m
Chicago O'Hare Intl
Tue 7/30
Nonstop2h 25m
New York LaGuardiaChicago O'Hare Intl
LGA - ORD
LGAORD
New York LaGuardia
Tue 8/20
Nonstop2h 54m
Chicago O'Hare Intl
Mon 8/26
Nonstop2h 19m
New York LaGuardiaChicago Midway
LGA - MDW
LGAMDW
New York LaGuardia
Mon 7/15
Nonstop2h 25m
Chicago Midway
Wed 7/17
Nonstop2h 10m
CHI Temperature | 23 - 73.4 °F |
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If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Boarding
Entertainment
Crew
Comfort
Overall
Food
Reviews
Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.
Chicago, with its dramatic location along the shores of Lake Michigan, is the professional, business, educational and cultural hub of the Midwest. When in Chicago, you have a wealth of choices, whether you prefer to tour architectural masterpieces, take in the top comedy improv groups in the country, attend a Chicago Cubs game at Wrigley Field, or just get some business done. Not surprisingly, it's easy to find flights between the first and third-largest cities in the United States: New York City and Chicago.
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.
Airline | Cheapest | Average | Flexibility | On-time |
---|---|---|---|---|
Spirit Airlines | Cheapest$40 | Average$153 | FlexibilityNo cancel fee | On-time65% |
JetBlue | Cheapest$79 | Average$329 | FlexibilityNo cancel fee | On-time62% |
Delta | Cheapest$84 | Average$441 | FlexibilityNo cancel fee | On-timeN/A |
American Airlines | Cheapest$116 | Average$277 | FlexibilityNo cancel fee | On-time71% |
United Airlines | Cheapest$117 | Average$285 | FlexibilityNo cancel fee | On-time69% |
Alaska Airlines | Cheapest$146 | Average$278 | FlexibilityNo cancel fee | On-time75% |
4%of flight departures | Early morningMidnight to 6 am |
---|---|
35%of flight departures | Morning6 am to noon |
49%of flight departures | AfternoonNoon to 6 pm |
12%of flight departures | Evening6 pm to midnight |
Sunday | 147daily flights |
---|---|
Monday | 209daily flights |
Tuesday | 191daily flights |
Wednesday | 193daily flights |
Thursday | 187daily flights |
Friday | 204daily flights |
Saturday | 101daily flights |