There are 3 ways to get from Chicago to Montserrat by plane
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Chicago Midway International Airport to John A. Osborne Airport
best- Fly from Chicago Midway International Airport (MDW) to John A. Osborne Airport (MNI)plane MDW - MNI
20h 16m$324–1,332Fly Chicago O'Hare International Airport to John A. Osborne Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to John A. Osborne Airport (MNI)plane ORD - MNI
11h 54m$214–832Fly Chicago O'Hare International Airport to St Maarten Airport, fly to Montserrat Airport
- Fly from Chicago O'Hare International Airport (ORD) to Princess Juliana International Airport (SXM)plane ORD - SXM
- Fly from St Maarten Airport to Montserrat Airportplane
9h 48m$3,034–3,502
Chicago Midway International Airport (MDW) to John A. Osborne Airport (MNI) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Montserrat is to fly which costs $210 - $850 and takes 11h 54m.
The fastest way to get from Chicago to Montserrat is to fly which takes 9h 48m and costs $3,000 - $3,500.
The distance between Chicago and Montserrat is 3735 km.
It takes approximately 20h 16m to get from Chicago to Montserrat, including transfers.
Montserrat is 1h ahead of Chicago. It is currently 11:28 AM in Chicago and 12:28 PM in Montserrat.
There are 17+ hotels available in Montserrat.
What companies run services between Chicago, IL, USA and Montserrat?
Delta, Montserrat Airways, and three other airlines fly from Chicago Midway International Airport (MDW) to John A. Osborne Airport (MNI) once daily.
- Website
- flymontserrat.com
Flights from Chicago Midway International Airport to John A. Osborne Airport via Atlanta, Antigua
- Ave. Duration
- 19h 33m
- When
- Friday
- Estimated price
- $310–1,300
Flights from Chicago Midway International Airport to John A. Osborne Airport via Charlotte, Antigua
- Ave. Duration
- 19h 15m
- When
- Friday
- Estimated price
- $300–1,300
Flights from Chicago O'Hare International Airport to John A. Osborne Airport via Atlanta, Antigua
- Ave. Duration
- 8h 43m
- When
- Saturday
- Estimated price
- $200–850
Flights from Chicago O'Hare International Airport to John A. Osborne Airport via Charlotte, Antigua
- Ave. Duration
- 9h 10m
- When
- Saturday
- Estimated price
- $190–800
Flights from Chicago O'Hare International Airport to John A. Osborne Airport via Newark, Antigua
- Ave. Duration
- 17h 22m
- When
- Friday
- Estimated price
- $200–850
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Princess Juliana International Airport
- Ave. Duration
- 5h 20m
- When
- Saturday
- Estimated price
- $140–600
Flights from Chicago O'Hare International Airport to Princess Juliana International Airport via Charlotte
- Ave. Duration
- 7h 11m
- When
- Thursday, Friday, and Sunday
- Estimated price
- $140–600
Flights from Chicago O'Hare International Airport to Princess Juliana International Airport via Miami
- Ave. Duration
- 7h 27m
- When
- Every day
- Estimated price
- $150–650
- Website
- fly-winair.sx
Flights from Chicago Midway International Airport to John A. Osborne Airport via Orlando, Princess Juliana International Airport
- Ave. Duration
- 24h 50m
- When
- Monday and Thursday
- Estimated price
- $310–1,300
Flights from Chicago Midway International Airport to John A. Osborne Airport via Baltimore, Princess Juliana International Airport
- Ave. Duration
- 24h 55m
- When
- Monday and Thursday
- Estimated price
- $300–1,300
- Website
- united.com
Flights from Chicago O'Hare International Airport to Princess Juliana International Airport
- Ave. Duration
- 5h 17m
- When
- Saturday
- Estimated price
- $140–600
Want to know more about travelling around the world?
Rome2Rio's Travel Guide series provide vital information for the global traveller. Read our range of informative guides on popular transport routes and companies - including Travelling to the US: What do I need to know?, Need to know: Jadrolinija, and Slovenia: Getting from Ljubljana to Lake Bled - to help you get the most out of your next trip.