Cheap Flight Deals From Kingston (KIN) to Chicago (CHI) Starting at $189

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Airfares from $189 One Way, $341 Round Trip from Kingston to Chicago

Prices starting at $341 for return flights and $189 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

More About Flying To Chicago from Kingston

Route Information for Flights from Kingston to Chicago

Origin Airport IATA Code KIN
Destination Airport IATA Code CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Traveling from Kingston to Chicago

Kingston Airport Information

The primary airport serving the Kingston, Jamaica area is the Norman Manley International Airport, located on the Palisadoes peninsula in Kingston harbor, 17 miles from the city center. Those looking for cheap flights from Kingston will have their choice of destinations as over 130 international fights depart from the airport on a weekly basis. Several international carriers, including British Airways, Air Canada, Virgin Atlantic and Delta, are available for flights, with most airlines offering online reservations through Orbitz.com. A second airport is available in town, the Tinson Pen Aerodrome, which only provides domestic flights to Montego Bay.

Parking at the Norman Manley International Airport

Parking is available at the Norman Manley airport for a tiered fee. Each hour is about $1.70 up to three hours. From there the service is offered at a discount with a fee of only about $7 for every 24-hour period.

Transportation to Norman Manley International

Official Jamaica Union of Travelers Association taxis provide transportation to the airport from the city center. The cost for the taxi ride is about $22, with the trip taking about 30 minutes to complete. Airport shuttles are also available, providing large passenger vans that will pick you up from your Kingston location. The cost varies, as all passengers in the shuttle picked up from the same general area share it.

Breakfast Before Leaving

Food at the airport is available from a variety of restaurants including the Blue Moon Café, Island Deli, Island Grill and Tastee. If you have time before arriving at the airport, the Knutsford Court Hotel on Chelsea Ave. serves a delicious sunrise buffet breakfast, featuring an international cuisine with a Caribbean touch. The available dishes should provide you with a tasty send-off before catching one of the cheap flights from Kingston.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Am I able to catch a flight from Kingston to Chicago now?
Our Covid-19 Travel Advisor will help you with questions about current travel restrictions and quarantine requirements when catching a flight from Kingston to Chicago.
What is the shortest flight from Kingston to Chicago?
The shortest flight time from Kingston to Chicago is 4 hours and 51 minutes, which gives you loads of time to enjoy a drink or lose yourself in a gripping novel.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.