Ducoffs.comAirlines Flying this Route
Ducoffs.com compares full-service and low-cost airlines flying between New York and Chicago in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.
JFK → MDW
Find and Compare the Cheapest Ways to Fly from New York to Chicago
Compare one-way, round-trip and flight + hotel packages from New York to Chicago, a nonstop flight of about 2h, with fares from around 140.
New York to Chicago flight facts
New York to Chicago is a domestic route covering about 729 miles, arriving at Chicago Midway International Airport (MDW) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit.
| Departing from | John F. Kennedy International Airport (JFK) |
|---|---|
| Arriving at | Chicago Midway International Airport (MDW) |
| Distance | 729 miles (1,174 km) |
| Nonstop flight time | About 2h |
| Round-trip fares from | $140 (estimate) |
| Cheapest months | January, February, September |
| Peak season in Chicago | June–August |
| Cheapest hotel months in Chicago | November–April |
| Best time to book | 1 to 3 months ahead |
| Route info updated | October 16, 2026 |
When to visit Chicago
Peak season
June–August
Warm, lakefront festivals
Shoulder season
May & September–October
Mild and comfortable
Off-peak season
November–April
Cold, windy and snowy
Estimated round-trip fares by month, New York to Chicago
| Month | Fares from |
|---|---|
| January | $140 |
| February | $140 |
| March | $190 |
| April | $165 |
| May | $175 |
| June | $210 |
| July | $210 |
| August | $205 |
| September | $140 |
| October | $150 |
| November | $185 |
| December | $185 |
Flying from New York to Chicago
Best Time to Book Flights from New York to Chicago
Fares on this route tend to be lowest in January, February, and September. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.
Average Travel Duration
New York and Chicago are about 729 miles apart. A nonstop flight takes roughly 2h; connecting itineraries usually add 2 to 5 hours.
New York to Chicago flight questions
How can I find the absolute cheapest flight from New York to Chicago?
The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.
What is the cheapest month to fly from New York to Chicago?
Based on typical seasonal demand, January, February, and September tend to offer the lowest fares on this route, with estimated round-trip prices starting around $140. Live prices change daily, so run a search for your exact dates.
How long is the flight from New York to Chicago?
New York and Chicago are about 729 miles apart. A nonstop flight takes roughly 2h, while connecting itineraries usually add 2 to 5 hours depending on the layover.
When are hotels cheapest in Chicago?
Hotel rates in Chicago are usually lowest in November–April, when demand is quieter, and highest during peak season (June–August). Booking your flight and hotel together can save up to 30%.
Which airport do I fly into for Chicago?
This route arrives at Chicago Midway International Airport (MDW). Your search results also show nearby airports when they offer a cheaper or faster option.
How far in advance should I book a flight to Chicago?
For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.
Is it cheaper to bundle flights and hotels together?
Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.
Travel guides for this trip
- PlanningThe Cheapest Months to Fly from Miami, New York, Los Angeles, Chicago, Tampa, Dallas, and AtlantaWhen airfare is lowest from Miami, New York, Los Angeles, Chicago, Tampa, Dallas, and Atlanta, plus the routes that see the biggest seasonal price swings.
- DealsHow to Find Hidden Hotel Deals with Ducoffs TravelTwelve proven ways to pay less for great hotels: smarter dates, bundles, neighborhood swaps, call-in rates, and how to use Ducoffs.com tools to find them.
- PlanningHow to Stretch Your Vacation Days into Longer TripsTurn a few vacation days into long trips by pairing them with public holidays and weekends, and avoid the peak prices that come with holiday travel.