$59 Find Cheap Flights from New Haven to Chicago - Compare and Save

Only Avelo Airlines operates flights between New Haven and Chicago.

Flights from New Haven to Chicago usually depart from Tweed-New Haven (HVN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

Only Economy Class is available on flights from New Haven to Chicago.

On this route, nonstop flights are cheaper than layover options on average. Nonstop fares average $225 round-trip, compared to $394 via a layover through Fort Lauderdale (FLL).

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $50–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

Connecting flights from New Haven to Chicago most commonly pass through:

• Orlando (MCO) - 67% of one-stop connections
• Fort Lauderdale (FLL) - 33% of one-stop connections
Together, these airports account for 100% of one-stop bookings on this route.

On the New Haven to Chicago route, being flexible with your departure day can save you up to 70%. Saturday is the cheapest day at $144 round-trip on average, while Tuesday is the most expensive at $474: a $330 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Afternoon is the busiest departure period on New Haven to Chicago flights, with 100% of flights leaving in that window. Morning departures account for 0%, evening flights for 0%, and night flights for 0%.

Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

These are the earliest and latest flight times available from New Haven to Chicago:

• Earliest: departs at 2:40 pm and lands at 5:26 pm
• Latest: departs at 5:10 pm and lands at 7:56 pm.

The flight takes about 2h 46m.

A nonstop flight from New Haven to Chicago takes 2h 46m, covering 762 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $115 to $767. That means the highest observed fare was about 7x higher than the lowest one.

One-way fares from New Haven to Chicago are currently lower than usual. Average one-way flight prices are about $78, which is 25% below the typical average for this route.

Flying via Fort Lauderdale (FLL) gives the shortest average 1-stop total travel time at 13h 05m, compared with 18h 35m via Orlando (MCO).

Chicago is 1 hour behind New Haven (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

· Routes Car & Truck Rentals
· Europcar
· Hertz
· Dollar
· Ace

Near Chicago Midway Airport (MDW) — daily rates from around $32:

· Hertz
· Dollar
· Budget
· Alamo
· Rent-A-Wreck

Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

· Alamo
· Enterprise Rent-A-Car
· Budget
· Avis
· National

Round-trip flights from New Haven to Chicago range from $158 to $302, with an average of $228 over the past 12 months. Anything below $158 counts as a good deal.