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There are 8 ways to get from Chicago to Key West by plane, train, bus, ferry or car

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 from Chicago O'Hare  •  6h 11m

  1. Fly from Chicago O'Hare (ORD) to Key West (EYW) ORD - EYW

$264 - $1,209

Cheapest option

Bus  •  41h 16m

  1. Take the bus from Chicago, Il to Atlanta, Ga
  2. Take the bus from Atlanta, Ga to Miami, Fl
  3. Take the bus from Miami, Fl to Key West, Fl

$168 - $240

6 alternative options

Fly from Chicago Midway  •  7h 38m

  1. Fly from Chicago Midway (MDW) to Key West (EYW) MDW - EYW

$314 - $1,508

Train to South Bend, fly  •  10h 53m

  1. Take the train from Van Buren St. to South Bend Airport
  2. Fly from South Bend (SBN) to Key West (EYW) SBN - EYW

$474 - $2,117

Train to Milwaukee, fly  •  9h 12m

  1. Take the train from Chicago Union Station to Milwaukee Intermodal Station
  2. Fly from Milwaukee (MKE) to Key West (EYW) MKE - EYW

$351 - $1,557

Bus, ferry  •  30h 31m

  1. Take the bus from Chicago to Marta Civic Center Station - Nb
  2. Take the bus from Atlanta, GA to Naples, FL
  3. Take the ferry from Marco Island, FL to Key West, FL

$387 - $426

Train, bus, ferry  •  46h 22m

  1. Take the train from Chicago Union Station to Charlottesville Amtrak Station
  2. Take the train from Charlottesville Amtrak Station to Charlotte Amtrak Station
  3. Take the bus from Charlotte, NC to Naples, FL
  4. Take the ferry from Marco Island, FL to Key West, FL

$377 - $508

Drive  •  26h 1m

  1. Drive from Chicago to Key West 1543.3 miles

$150 - $220

Questions & Answers

The cheapest way to get from Chicago to Key West is to drive which costs $150 - $220 and takes 26h 1m.

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The quickest way to get from Chicago to Key West is to fly which costs $260 - $1,300 and takes 6h 11m.

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No, there is no direct bus from Chicago to Key West. However, there are services departing from Chicago, Il and arriving at Flagler & Bertha via Atlanta, Ga, Miami, Fl and Key West International Airport. The journey, including transfers, takes approximately 41h 16m.

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The distance between Chicago and Key West is 1250 miles. The road distance is 1543.3 miles.

Get driving directions

The best way to get from Chicago to Key West without a car is to bus and ferry which takes 30h 31m and costs $380 - $430.

More details

It takes approximately 6h 11m to get from Chicago to Key West, including transfers.

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Chicago to Key West bus services, operated by Greyhound USA, depart from Chicago, Il station.

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The best way to get from Chicago to Key West is to fly which takes 6h 11m and costs $260 - $1,300. Alternatively, you can bus, which costs $160 - $240 and takes 41h 16m.

Mode details

The quickest flight from Chicago O'Hare Airport to Key West Airport is the direct flight which takes 3h 10m.

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Chicago to Key West bus services, operated by Greyhound USA, arrive at Key West, Fl station.

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Map of how to get from Chicago to Key West.
Launch map view
  • Distance: 1250 miles
  • Duration: 6h 11m

What companies run services between Chicago, IL, USA and Key West, FL, USA?

United Airlines, American Airlines and two other airlines fly from Chicago to Key West hourly. Alternatively, you can take a bus from Chicago to Key West via Atlanta, Ga, Miami, Fl, and Key West International Airport in around 41h 16m.

Airlines
Delta
Website
delta.com
Flights from Chicago O'Hare to Key West via Atlanta
Ave. Duration
5h 33m
When
Every day
Estimated price
$260 - $1,200
Flights from Chicago Midway to Key West via Atlanta
Ave. Duration
5h 33m
When
Every day
Estimated price
$310 - $1,500
Flights from Chicago Midway to Key West via Detroit, Atlanta
Ave. Duration
9h 26m
When
Every day
Estimated price
$330 - $1,500
Flights from South Bend to Key West via Atlanta
Ave. Duration
6h 47m
When
Every day
Estimated price
$460 - $2,100
Flights from South Bend to Key West via Detroit, Atlanta
Ave. Duration
8h 39m
When
Every day
Estimated price
$490 - $2,200
Flights from South Bend to Key West via Minneapolis, Atlanta
Ave. Duration
9h 25m
When
Every day
Estimated price
$550 - $2,400
Flights from Milwaukee to Key West via Atlanta
Ave. Duration
5h 50m
When
Every day
Estimated price
$320 - $1,500
Flights from Milwaukee to Key West via Minneapolis, Atlanta
Ave. Duration
8h 25m
When
Every day
Estimated price
$380 - $1,600
Flights from Milwaukee to Key West via Detroit, Atlanta
Ave. Duration
8h 40m
When
Every day
Estimated price
$340 - $1,500
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Key West
Ave. Duration
3h 19m
When
Saturday
Estimated price
$280 - $1,200
Flights from Chicago O'Hare to Key West via Miami
Ave. Duration
5h 33m
When
Every day
Estimated price
$290 - $1,200
Flights from Chicago O'Hare to Key West via Charlotte
Ave. Duration
6h 19m
When
Every day
Estimated price
$290 - $1,200
Flights from Chicago O'Hare to Key West via Dallas/Ft.Worth
Ave. Duration
6h 27m
When
Every day
Estimated price
$340 - $1,400
Flights from Chicago O'Hare to Key West via Philadelphia
Ave. Duration
6h 41m
When
Saturday
Estimated price
$340 - $1,300
Flights from South Bend to Key West via Charlotte
Ave. Duration
8h 43m
When
Every day
Estimated price
$500 - $2,100
Flights from South Bend to Key West via Dallas/Ft.Worth
Ave. Duration
9h 24m
When
Every day
Estimated price
$600 - $2,400
Flights from Milwaukee to Key West via Charlotte
Ave. Duration
5h 35m
When
Every day
Estimated price
$360 - $1,500
Flights from Milwaukee to Key West via Philadelphia
Ave. Duration
8h 10m
When
Saturday
Estimated price
$400 - $1,600
Flights from Milwaukee to Key West via Dallas/Ft.Worth
Ave. Duration
9h 27m
When
Every day
Estimated price
$420 - $1,600
Flights from Milwaukee to Key West via Chicago O'Hare, Miami
Ave. Duration
7h 31m
When
Every day
Estimated price
$360 - $1,500
United Airlines
Website
united.com
Flights from Chicago O'Hare to Key West
Ave. Duration
3h 10m
When
Monday, Thursday and Saturday
Estimated price
$290 - $1,300
Flights from Chicago Midway to Key West via Orlando
Ave. Duration
4h 55m
When
Saturday
Estimated price
$370 - $1,500
Flights from South Bend to Key West via Chicago O'Hare
Ave. Duration
6h 10m
When
Monday, Thursday and Saturday
Estimated price
$500 - $2,300
Flights from Milwaukee to Key West via Chicago O'Hare
Ave. Duration
5h 10m
When
Monday, Thursday and Saturday
Estimated price
$360 - $1,600
Silver Airways
Website
silverairways.com
Flights from Chicago Midway to Key West via Orlando
Ave. Duration
4h 55m
When
Saturday
Estimated price
$370 - $1,500
Train operators
South Shore Line
Phone
+1 219-926-5744
Website
nictd.com
Train from Van Buren St. to South Bend Airport
Ave. Duration
2h 25m
Frequency
5 times a day
Estimated price
$12 - $14
Schedules at
nictd.com
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
+1 215-856-7924
Website
amtrak.com
Train from Chicago Union Station to Milwaukee Intermodal Station
Ave. Duration
1h 29m
Frequency
Every 4 hours
Estimated price
$27 - $40
Website
amtrak.com
Coach Seat
$27 - $40
Premium
$180 - $260
Flexi Coach Seat
$40 - $60
Business Seat
$35 - $55
Train from Chicago Union Station to Charlottesville Amtrak Station
Ave. Duration
20h 25m
Frequency
3 times a week
Estimated price
$85 - $120
Website
amtrak.com
Coach Seat
$85 - $120
Premium
$300 - $410
Flexi Coach Seat
$160 - $250
Business Seat
$180 - $260
Train from Charlottesville Amtrak Station to Charlotte Amtrak Station
Ave. Duration
5h 28m
Frequency
Once daily
Estimated price
$40 - $60
Website
amtrak.com
Coach Seat
$40 - $60
Premium
$210 - $300
Flexi Coach Seat
$70 - $110
Business Seat
$70 - $110
Bus operators
La Cubana
Phone
+1 305-541-1700
Website
lacubanabus.com
Bus from Atlanta, GA to Naples, FL
Ave. Duration
10h 30m
Frequency
3 times a week
Estimated price
$159
Schedules at
lacubanabus.com
Bus from Charlotte, NC to Naples, FL
Ave. Duration
14h
Frequency
3 times a week
Estimated price
$100 - $160
Schedules at
lacubanabus.com
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 Chicago, Il to Atlanta, Ga
Ave. Duration
15h 45m
Frequency
4 times a day
Estimated price
$70 - $110
Website
greyhound.com
Economy
$70 - $110
Flexible
$110 - $160
Bus from Atlanta, Ga to Miami, Fl
Ave. Duration
17h 55m
Frequency
4 times a day
Estimated price
$70 - $100
Website
greyhound.com
Economy
$70 - $100
Flexible
$110 - $160
Bus from Miami, Fl to Key West, Fl
Ave. Duration
4h 30m
Frequency
Twice daily
Estimated price
$22 - $35
Website
greyhound.com
Economy
$22 - $35
Flexible
$40 - $65
Ferry operators
Key West Express
Phone
+1 239-463-5733
Website
keywestexpress.net
Ferry from Marco Island, FL to Key West, FL
Ave. Duration
3h
Frequency
Once daily
Estimated price
$95
Book at
Key West Express

Want to know more about travelling around United States

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More Questions & Answers

Key West is 1h ahead of Chicago. It is currently 12:17 PM in Chicago and 1:17 PM in Key West.

Yes, the driving distance between Chicago to Key West is 1543 miles. It takes approximately 26h 1m to drive from Chicago to Key West.

Get driving directions

United Airlines, Delta and American Airlines offer flights from Chicago O'Hare Airport to Key West Airport.

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There are 340+ hotels available in Key West. Prices start at $142 USD per night.

More details

The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 43m and costs $2 - $5.

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