Chicago to Guantanamo Bay Naval Station (ORD–NBW) — Airlines, Schedules & Connections

ORD Airport Page →
1,696 mi airlines charter/private
On-time Some delays Frequent delays
Connecting Flight Schedule 3 1-stop flights Verified 1mo ago
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.

Last scheduled nonstop: Apr 2026.

✦ 1-Stop connections via 3 hubs
NIP Jacksonville ~6h 20m UA → UA Jacksonville (NIP) to Guantanamo Bay Naval Station flights
ATL Atlanta ~6h 46m AAACAF → Atlanta (ATL) to Guantanamo Bay Naval Station flights
IAD Dulles ~6h 54m ACAVAZ → Dulles (IAD) to Guantanamo Bay Naval Station flights
✦ 1-STOP More options, longer trips
✧ 2-STOP Loading... Reach the hardest destinations
Chicago to Guantanamo Bay Naval Station
Connecting service available through multiple hubs.
1 Airlines 1,696 mi 4h 11m nonstop +1h ahead

ORD–NBW had nonstop service from United Airlines, last on the schedule in April 2026. There's no nonstop on it right now, so today you'd fly it with one stop. The connecting options below are sorted by layover. Nonstop, it's about 1,696 miles in 4h 11m.

Also explore ORD Routes NBW Routes ORD Live Flights NBW Live Flights ORD Delays
All flights from Guantanamo Bay Naval Station (NBW) Guantanamo Bay Naval Station to Chicago flights
Carriers on this route

Airline Landscape

Carriers that operated nonstop ORD–NBW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
UA United Airlines 0 – – 72% Star Alliance –
Alliance coverage
Star Alliance: UA (0 flights/wk, 0%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.
Connections

Connection Landscape

1-stop and 2-stop options for ORD to NBW.
1-STOP
One-Stop Connections
3
Hubs
~6h
Fastest
~6h
Longest
NIP ~6h 20m ATL ~6h 46m IAD ~6h 54m
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
1
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
ORD → NBW
72%
Moderate delays possible. Allow buffer time.
Departing
72%
Return
NBW → ORD
96%
Generally reliable. Most flights run on time.
Arriving
96%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. ORD delays →
Know before you go

Travel Essentials

Practical planning for this route.
Time Difference
+1h
Guantanamo Bay Naval Station is 1 hour ahead of Chicago.
ORD: CDT · NBW: CDT

When it's 6:00 PM in Chicago, it's 7:00 PM in Guantanamo Bay Naval Station.
Distance & Flight Time
1,696 mi / 2,730 km
Nonstop flight time is approximately 4h 11m gate to gate.
Visa & Entry

Cuba does not require a visa from US passport holders, but the US restricts travel to Cuba under OFAC regulations. US citizens must qualify under one of 12 authorized travel categories (such as Support for the Cuban People, journalism, or educational activities). General tourism is not permitted. A Cuban Tourist Card is also required, available through airlines or travel agencies for around USD 50 to USD 100.

Passport must be valid for at least 6 months beyond the date of entry. US travelers should document their qualifying category and keep records for at least 5 years. Stays are allowed up to 30 days with one 30-day extension available.

Verify entry requirements with official sources before travel.
Getting to ORD

CTA Blue Line runs 24/7 from downtown Loop stations to O'Hare (45 min, $5). Pace buses serve suburbs. Ride-shares cost $35–55 from downtown depending on traffic; add 30+ minutes during rush hour on the Kennedy Expressway.Economy parking lots E/F connect via ATS people mover. Terminal 5 (international) is separate from Terminals 1–3; allow extra time for inter-terminal transfers.

Facts

ORD–NBW Quick Facts

Key statistics for the Chicago to Guantanamo Bay Naval Station route.
Route details
Distance1,696 mi / 2,730 km
Flight time4h 11m
Time difference+1 hour
Airlines (nonstop)1
1-stop connectionsAvailable
Origin: ORD
Full nameChicago O'Hare International Airport
IATA / ICAOORD / KORD
TimezoneAmerica/Chicago
Passengers/yr80.0M
Elevation680 ft / 207 m
Destination: NBW
Full nameLeeward Point Field
IATA / ICAONBW / MUGM
TimezoneAmerica/Havana
Elevation56 ft / 17 m
FAQ

Frequently Asked Questions

Common questions about ORD to NBW flights.
Nonstop flights from Chicago O'Hare International Airport to Leeward Point Field take about 4h 11m gate to gate. The route covers 1,696 miles.
1 airline operated the nonstop from ORD to NBW: United Airlines. The last scheduled nonstop was in April 2026. There's no nonstop right now, so today you'd fly it with one stop. See the connection options above, ranked by layover.
Not right now. The last scheduled nonstop was in April 2026. You can still fly it with one stop, and the connecting options above are sorted by layover. Nonstop, the hop took about 4h 11m.
Yes, 1-stop connections are available, ranked by layover time.
Guantanamo Bay Naval Station is 1 hour ahead of Chicago.
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 ORD to NBW

Chicago O'Hare International Airport (ORD) and Leeward Point Field (NBW) had nonstop service from United Airlines, last on the schedule in April 2026. The nonstop is dormant right now, so the way to fly it today is one connection, and the options above are sorted by layover.

ORD to NBW Flight Duration and Schedule

Nonstop flight time from ORD to NBW is about 4 hours 11 minutes gate to gate. The route covers a distance of 1,696 miles (2,730 km).

Connecting Options and Alternatives

1-stop connecting options are also available. Two-stop connections are also available via intermediate hubs.