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 38 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 37 min

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

$283 - $606

Bus to Montego Bay, fly to Chicago Midway  •  10 h 45 min

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

$233 - $830

Bus to Montego Bay, fly to Chicago O'Hare  •  11 h 6 min

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

$323 - $581

Fly Kingston to South Bend, bus  •  11 h 8 min

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

$386 - $2,336

Fly Kingston to Milwaukee, train  •  12 h 26 min

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

$241 - $1,077

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

Delta, Caribbean Airlines and two other airlines fly from Kingston to Chicago 3 times a day.

Airlines
Delta
Website
delta.com
Flights from Kingston to Chicago Midway via Atlanta
Ave. Duration
6 h 16 min
When
Every day
Estimated price
$230 - $1,500
Flights from Kingston to Chicago O'Hare via Atlanta
Ave. Duration
6 h 33 min
When
Every day
Estimated price
$210 - $1,400
Flights from Kingston to Chicago O'Hare via Atlanta, Covington
Ave. Duration
8 h 23 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $1,400
Flights from Montego Bay to Chicago Midway via Atlanta
Ave. Duration
7 h 10 min
When
Every day
Estimated price
$220 - $1,400
Flights from Montego Bay to Chicago O'Hare via Atlanta
Ave. Duration
6 h 55 min
When
Every day
Estimated price
$200 - $1,300
Flights from Kingston to South Bend via Atlanta
Ave. Duration
6 h 36 min
When
Monday to Friday
Estimated price
$370 - $2,300
Flights from Kingston to South Bend via Atlanta, Detroit
Ave. Duration
8 h 41 min
When
Monday to Friday
Estimated price
$390 - $2,400
Flights from Kingston to Milwaukee via Atlanta
Ave. Duration
6 h 56 min
When
Every day
Estimated price
$260 - $1,600
Flights from Kingston to Milwaukee via Atlanta, Covington
Ave. Duration
11 h 38 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$260 - $1,600
American Airlines
Website
aa.com
Flights from Kingston to Chicago O'Hare via Miami
Ave. Duration
7 h 24 min
When
Every day
Estimated price
$310 - $1,200
Flights from Montego Bay to Chicago O'Hare
Ave. Duration
4 h 39 min
When
Saturday
Estimated price
$170 - $1,100
Flights from Montego Bay to Chicago O'Hare via Charlotte
Ave. Duration
6 h 50 min
When
Every day
Estimated price
$180 - $1,100
Flights from Montego Bay to Chicago O'Hare via Miami
Ave. Duration
7 h 6 min
When
Every day
Estimated price
$170 - $1,100
Flights from Montego Bay to Chicago O'Hare via Philadelphia
Ave. Duration
7 h 25 min
When
Every day
Estimated price
$210 - $1,200
Southwest Airlines
Website
southwest.com
Flights from Kingston to Chicago Midway via Fort Lauderdale
Ave. Duration
6 h 37 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $850
Flights from Montego Bay to Chicago Midway
Ave. Duration
4 h 10 min
When
Monday, Wednesday, Friday, Saturday and Sunday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Orlando
Ave. Duration
5 h 40 min
When
Monday to Friday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Baltimore
Ave. Duration
6 h 30 min
When
Every day
Estimated price
$230 - $850
Flights from Montego Bay to Chicago Midway via Fort Lauderdale
Ave. Duration
6 h 47 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $800
Flights from Montego Bay to Chicago Midway via Houston Hobby Apt
Ave. Duration
7 h 45 min
When
Sunday
Estimated price
$250 - $900
United Airlines
Website
united.com
Flights from Kingston to Chicago O'Hare via Panama City
Ave. Duration
9 h
When
Monday, Wednesday, Thursday and Friday
Estimated price
$380 - $1,300
Flights from Montego Bay to Chicago O'Hare
Ave. Duration
4 h 20 min
When
Saturday
Estimated price
$190 - $1,100
Flights from Montego Bay to Chicago O'Hare via Washington Dulles
Ave. Duration
6 h 31 min
When
Saturday
Estimated price
$210 - $1,200
Flights from Kingston to Milwaukee via Toronto
Ave. Duration
9 h 20 min
When
Tuesday
Estimated price
$210 - $1,000
JetBlue Airways
Website
jetblue.com
Flights from Kingston to Chicago O'Hare via New York JFK
Ave. Duration
9 h 7 min
When
Every day
Estimated price
$270 - $1,100
Spirit Airlines
Website
spirit.com
Flights from Kingston to Chicago O'Hare via Fort Lauderdale
Ave. Duration
8 h 18 min
When
Every day
Estimated price
$180 - $650
Copa Airlines
Website
copaair.com
Flights from Kingston to Chicago O'Hare via Panama City
Ave. Duration
9 h
When
Monday, Wednesday, Thursday and Friday
Estimated price
$380 - $1,300
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
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Milwaukee Intermodal Station Amtrak to Chicago Union Station Amtrak
Ave. Duration
1 h 29 min
Frequency
Every 4 hours
Estimated price
$28 - $60
Website
amtrak.com
Coach Seat
$28 - $45
Flexi Coach Seat
$50 - $75
Business Coach Seat
$40 - $60
Room
$150 - $210
Bus operators
Knutsford Express Ltd
Phone
1876 971 1822
Email
info@knutsfordexpress.com
Website
knutsfordexpress.com
Bus from Kingston to Montego Bay Airport
Ave. Duration
4 h
Frequency
Every 4 hours
Estimated price
$20 - $26
Schedules at
knutsfordexpress.com
Book at
knutsfordexpress.com
Greyhound USA
Phone
+1 214-849-8100
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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Questions & Answers

The distance between Kingston and Chicago is 2847 km.

The cheapest way to get from Kingston to Chicago is to bus and fly which costs $320 - $600 and takes 11 h 6 min.

The quickest way to get from Kingston to Chicago is to fly which takes 8 h 38 min and costs $220 - $900.

It takes approximately 8 h 38 min to get from Kingston to Chicago, including transfers.