New Haven to Chicago (HVN–MDW) — Airlines, Schedules & Connections

HVN Airport Page →
769 mi airlines charter/private ~1/wk
On-time Some delays Frequent delays
Connecting Flight Schedule 22 1-stop flights Verified 3w ago
Charter / private route. No scheduled airline service — operated by charter & private aviation.
Nonstop Charter / private 1-Stop 2-Stop Hide separate tickets Hide overnight Hide codeshares
  Flight Airline AC Dep Arr Dur OTP Sched  
✈ Nonstop

No flights match your filters.

No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.

✦ 1-Stop connections via 10 hubs
BWI Baltimore 4h 5m XP → WN Baltimore (BWI) to Chicago flights
RDU Raleigh/Durham 4h 45m MXXP → LXJWN Raleigh/Durham (RDU) to Chicago flights
BNA Nashville 5h 5m XP → WN Nashville (BNA) to Chicago flights
ATL Atlanta 5h 14m XP → AFAMDL Atlanta (ATL) to Chicago flights
MYR Myrtle Beach 5h 35m XP → WN Myrtle Beach (MYR) to Chicago flights
TPA Tampa 6h 20m XP → WN Tampa (TPA) to Chicago flights
MCO Orlando 6h 23m MXXP → WN Orlando (MCO) to Chicago flights
ORF Norfolk 6h 46m MX → WN Norfolk (ORF) to Chicago flights
RIC Richmond 6h 49m MX → LXJWN Richmond (RIC) to Chicago flights
CHS Charleston 6h 57m MXXP → EJAWN Charleston (CHS) to Chicago flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
New Haven to Chicago
Flown by charter / private operators — no scheduled airline service.
769 mi 2h 2m nonstop -1h behind

HVN–MDW has no scheduled airline service; it is flown by charter / private operators. 1-stop connecting options are also available.

Also explore HVN Routes MDW Routes HVN Live Flights MDW Live Flights MDW Delays
All flights from Chicago (MDW) Chicago to New Haven flights
Connections

Connection Landscape

1-stop and 2-stop options for HVN to MDW.
1-STOP
One-Stop Connections
22
Hubs
~4h
Fastest
~17h
Longest
BWI ~4h 5m PHL ~4h 15m ALB ~4h 20m IND ~4h 33m RDU ~4h 45m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1,108
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.
Reliability

On-Time Performance

What to expect at each end of your journey.
Outbound
HVN → MDW
80%
Generally reliable. Most flights run on time.
Arriving
80%
Return
MDW → HVN
100%
Generally reliable. Most flights run on time.
Departing
100%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. MDW delays →
Alternatives

Other ways to reach Chicago from New Haven

Nearby airports with service to Chicago Midway International Airport.
Metric HVN→MDW ISP→MDW HPN→MDW
Distance from HVN – 34 mi 45 mi
Nonstop airlines – 1 11
Weekly flights ~1 1 3
Flight time 2h 2m 1h 59m 1h 37m
Islip (ISP) to Chicago flights · White Plains (HPN) to Chicago flights · Hartford (BDL) to Chicago flights
Airports within 200 miles of HVN with service to Chicago Midway International Airport.
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind New Haven.
HVN: EDT · MDW: CDT

When it's 6:00 PM in New Haven, it's 5:00 PM in Chicago.
Distance & Flight Time
769 mi / 1,237 km
Nonstop flight time is approximately 2h 2m gate to gate.
Facts

HVN–MDW Quick Facts

Key statistics for the New Haven to Chicago route.
Route details
Distance769 mi / 1,237 km
Flight time2h 2m
Time difference-1 hour
Airlines (nonstop)Charter / private
Weekly flights~1 out
1-stop connectionsAvailable
Origin: HVN
Full nameTweed New Haven Airport
IATA / ICAOHVN / KHVN
TimezoneAmerica/New_York
Passengers/yr1.2M
Elevation12 ft / 4 m
Destination: MDW
Full nameChicago Midway International Airport
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m
FAQ

Frequently Asked Questions

Common questions about HVN to MDW flights.
Nonstop flights from Tweed New Haven Airport to Chicago Midway International Airport take about 2h 2m gate to gate. The route covers 769 miles.
Yes, 1-stop connections are available, ranked by layover time. Common connecting points include Baltimore/Washington International Thurgood Marshall, Raleigh-Durham and Nashville.
Chicago is 1 hour behind New Haven.
Yes, return flights from MDW to HVN are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include ISP, HPN and BDL. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from HVN to MDW

Tweed New Haven Airport (HVN) and Chicago Midway International Airport (MDW) are connected through multiple connecting hub airports.

HVN to MDW Flight Duration and Schedule

Nonstop flight time from HVN to MDW is about 2 hours 2 minutes gate to gate. The route covers a distance of 769 miles (1,237 km).

Connecting Options and Alternatives

1-stop connecting options are also available, commonly via Baltimore/Washington International Thurgood Marshall, Raleigh-Durham and Nashville. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Islip (ISP), White Plains (HPN) and Hartford (BDL).