There are 6 ways to get from Kingston to Chicago by plane, bus or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Kingston to Chicago Midway  •  8 h 47 min

  1. Fly from Kingston (KIN) to Chicago Midway (MDW) KIN - MDW

$223 - $855

5 alternative options

Fly Kingston to Chicago O'Hare  •  9 h 26 min

  1. Fly from Kingston (KIN) to Chicago O'Hare (ORD) KIN - ORD

$283 - $606

Fly Kingston to South Bend, bus  •  10 h 58 min

  1. Fly from Kingston (KIN) to South Bend (SBN) KIN - SBN
  2. Take the bus from South Bend, In to Chicago, Il

$336 - $2,036

Bus to Montego Bay, fly to Chicago Midway  •  10 h 43 min

  1. Take the bus from Kingston to Falmouth
  2. Fly from Montego Bay (MBJ) to Chicago Midway (MDW) MBJ - MDW

$242 - $855

Fly Kingston to Milwaukee, train  •  12 h 30 min

  1. Fly from Kingston (KIN) to Milwaukee (MKE) KIN - MKE
  2. Take the train from Milwaukee Intermodal Station to Chicago Union Station

$238 - $1,042

Bus to Montego Bay, fly to Chicago O'Hare  •  11 h 15 min

  1. Take the bus from Kingston to Falmouth
  2. Fly from Montego Bay (MBJ) to Chicago O'Hare (ORD) MBJ - ORD

$332 - $606

Questions & Answers

The cheapest way to get from Kingston to Chicago is to fly which costs $280 - $650 and takes 9 h 26 min.

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The quickest way to get from Kingston to Chicago is to fly which costs $220 - $900 and takes 8 h 47 min.

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The distance between Kingston and Chicago is 2847 km.

It takes approximately 8 h 47 min to get from Kingston to Chicago, including transfers.

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There is no direct flight from Kingston Airport to Chicago Midway Airport. The quickest flight takes 6 h 25 min and has one stopover.

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Chicago is 1 h behind Kingston. It is currently 7:10 PM in Kingston and 7:10 PM in Chicago.

Spirit Airlines, Caribbean Airlines, JetBlue Airways and two other airlines offer flights from Kingston Airport to Chicago Midway Airport.

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There are 574+ hotels available in Chicago. Prices start at $104 USD per night.

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The best way to get from Kingston to Kingston Airport is to line 98 bus which takes 18 min and costs $1.

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Map of how to get from Kingston to Chicago.
Launch map view
  • Distance: 1779.6 miles
  • Duration: 8 h 47 min

What companies run services between Kingston, Jamaica and Chicago, IL, USA?

Delta, JetBlue Airways and three other airlines fly from Kingston to Chicago 5 times a day.

Airlines
Delta
Website
delta.com
Flights from Kingston to Chicago Midway via Atlanta
Ave. Duration
6 h 25 min
When
Monday, Tuesday, Thursday, Friday, Saturday and Sunday
Estimated price
$230 - $1,500
Flights from Kingston to Chicago Midway via New York JFK, Detroit
Ave. Duration
11 h 8 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$280 - $1,700
Flights from Kingston to Chicago O'Hare via Atlanta
Ave. Duration
6 h 20 min
When
Monday, Tuesday, Thursday, Friday, Saturday and Sunday
Estimated price
$210 - $1,400
Flights from Kingston to Chicago O'Hare via New York JFK
Ave. Duration
11 h 21 min
When
Every day
Estimated price
$250 - $1,500
Flights from Kingston to Chicago O'Hare via Atlanta, Covington
Ave. Duration
9 h 29 min
When
Monday, Tuesday, Thursday, Friday and Sunday
Estimated price
$210 - $1,400
Flights from Kingston to South Bend via Atlanta
Ave. Duration
6 h 26 min
When
Monday, Tuesday, Thursday, Friday, Saturday and Sunday
Estimated price
$370 - $2,300
Flights from Kingston to South Bend via Atlanta, Detroit
Ave. Duration
8 h 42 min
When
Monday, Tuesday, Thursday, Friday and Sunday
Estimated price
$390 - $2,400
Flights from Kingston to South Bend via New York JFK, Detroit
Ave. Duration
10 h 42 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$430 - $2,600
Flights from Montego Bay to Chicago Midway via Atlanta
Ave. Duration
6 h 59 min
When
Every day
Estimated price
$220 - $1,400
Flights from Kingston to Milwaukee via Atlanta
Ave. Duration
7 h 3 min
When
Monday, Tuesday, Thursday, Friday, Saturday and Sunday
Estimated price
$260 - $1,600
Flights from Kingston to Milwaukee via Atlanta, Covington
Ave. Duration
10 h 54 min
When
Monday, Tuesday, Thursday, Friday and Sunday
Estimated price
$260 - $1,600
Flights from Kingston to Milwaukee via New York JFK, Detroit
Ave. Duration
10 h 54 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$300 - $1,800
Flights from Kingston to Milwaukee via New York JFK, Boston
Ave. Duration
11 h 57 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$320 - $1,900
Flights from Montego Bay to Chicago O'Hare via Atlanta
Ave. Duration
6 h 37 min
When
Every day
Estimated price
$200 - $1,300
Flights from Montego Bay to Chicago O'Hare via Detroit
Ave. Duration
7 h 25 min
When
Saturday
Estimated price
$210 - $1,300
Flights from Montego Bay to Chicago O'Hare via New York JFK
Ave. Duration
8 h 20 min
When
Every day
Estimated price
$240 - $1,500
Southwest Airlines
Website
southwest.com
Flights from Kingston to Chicago Midway via Fort Lauderdale
Ave. Duration
6 h 44 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $850
Flights from Montego Bay to Chicago Midway
Ave. Duration
4 h
When
Monday, Wednesday, Friday and Sunday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Orlando
Ave. Duration
6 h
When
Saturday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Baltimore
Ave. Duration
6 h 35 min
When
Sunday
Estimated price
$230 - $850
Flights from Montego Bay to Chicago Midway via Fort Lauderdale
Ave. Duration
7 h 5 min
When
Saturday and Sunday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Houston Hobby Apt
Ave. Duration
8 h 20 min
When
Monday and Friday
Estimated price
$250 - $900
Flights from Kingston to Milwaukee via Fort Lauderdale
Ave. Duration
7 h 6 min
When
Sunday
Estimated price
$240 - $900
American Airlines
Website
aa.com
Flights from Kingston to Chicago O'Hare via Miami
Ave. Duration
7 h 16 min
When
Every day
Estimated price
$310 - $1,200
Flights from Kingston to South Bend via Miami, Charlotte
Ave. Duration
13 h 21 min
When
Every day
Estimated price
$320 - $2,000
Flights from Montego Bay to Chicago O'Hare
Ave. Duration
4 h 23 min
When
Saturday and Sunday
Estimated price
$170 - $1,100
Flights from Montego Bay to Chicago O'Hare via Miami
Ave. Duration
7 h 8 min
When
Every day
Estimated price
$170 - $1,100
Flights from Montego Bay to Chicago O'Hare via Charlotte
Ave. Duration
6 h 34 min
When
Every day
Estimated price
$180 - $1,100
Flights from Montego Bay to Chicago O'Hare via Philadelphia
Ave. Duration
8 h 7 min
When
Monday, Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$210 - $1,200
JetBlue Airways
Website
jetblue.com
Flights from Kingston to Chicago O'Hare via Fort Lauderdale
Ave. Duration
6 h 55 min
When
Every day
Estimated price
$220 - $950
Flights from Kingston to Chicago O'Hare via New York JFK
Ave. Duration
9 h 16 min
When
Every day
Estimated price
$270 - $1,100
United Airlines
Website
united.com
Flights from Kingston to Chicago O'Hare via Panama City
Ave. Duration
8 h 55 min
When
Monday, Wednesday, Thursday and Friday
Estimated price
$380 - $1,300
Flights from Kingston to Milwaukee via Toronto
Ave. Duration
9 h 20 min
When
Tuesday
Estimated price
$210 - $1,000
Flights from Montego Bay to Chicago O'Hare
Ave. Duration
4 h 19 min
When
Every day
Estimated price
$190 - $1,100
Air Canada
Website
aircanada.com
Flights from Kingston to Milwaukee via Toronto
Ave. Duration
9 h 20 min
When
Tuesday
Estimated price
$210 - $1,000
Flights from Montego Bay to Chicago O'Hare via Toronto
Ave. Duration
8 h 7 min
When
Every day
Estimated price
$900 - $1,500
Flights from Montego Bay to Chicago O'Hare via Montreal
Ave. Duration
8 h 23 min
When
Friday
Estimated price
$900 - $1,500
Copa Airlines
Website
copaair.com
Flights from Kingston to Chicago O'Hare via Panama City
Ave. Duration
8 h 55 min
When
Monday, Wednesday, Thursday and Friday
Estimated price
$380 - $1,300
Spirit Airlines
Website
spirit.com
Flights from Kingston to Chicago O'Hare via Fort Lauderdale
Ave. Duration
12 h 4 min
When
Monday, Thursday, Friday, Saturday and Sunday
Estimated price
$180 - $650
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Milwaukee Intermodal Station to Chicago Union Station
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$25
Website
amtrak.com
Coach Seat
$25
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from South Bend, In to Chicago, Il
Ave. Duration
1 h 10 min
Frequency
Every 3 hours
Estimated price
$15 - $35
Website
greyhound.com
Economy
$15 - $23
Flexible
$27 - $35

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