Travel within United States is: Fully open. See details.
Rome2rio uses cookies to help personalize content and show you personalised ads. By proceeding, you accept the use of cookies in accordance with our privacy policy. You may opt out of personalised ads at any time. OK

Need a hotel room in Key West?

Book now

There are 6 ways to get from Chicago to Florida Keys by plane, shuttle, 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

Fly Chicago O'Hare to Key West

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

Cheapest

Bus

  1. Take the bus from Chicago IL to Miami FL
  2. Take the bus from Downtown Miami to Key West

Fly Chicago Midway to Key West

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

Fly Chicago Midway to Miami, shuttle

  1. Fly from Chicago Midway (MDW) to Miami (MIA)
  2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FL

Bus via Atlanta

  1. Take the bus from Chicago Amtrak to Atlanta
  2. Take the bus from Atlanta to Miami
  3. Take the bus from Miami to Big Pine Key

Train, bus

  1. Take the train from Chicago Union Station to Washington Union Station
  2. Take the train from Washington Union Station to Miami Amtrak Station
  3. Take the bus from Miami Kendall to Key West

Chicago O'Hare (ORD) to Key West (EYW) flights

167 Weekly Planes
5h 46m Average Duration
$305 Cheapest Price
See schedules
Chicago → Florida Keys
Fully open

Travel safe during COVID-19

Rules to follow in United States

2m

Recommended

Recommended

Travel within United States

Domestic border crossings may be subject to approval, testing and quarantine

COVID-19 help in United States

If you need help, visit the national COVID-19 website or call the COVID-19 Helpline 800-232-4636

Frequently Asked Questions


Yes, travel within United States is currently allowed.

Explore travel options

Domestic travel is not restricted, but some conditions may apply

  • Face masks are recommended
  • There is a social distancing requirement of 2 metres
  • Domestic border crossings may be subject to approval, testing and quarantine

Explore travel options

The national COVID-19 helpline number in Florida Keys is 800-232-4636.

Wearing a face mask on public transport in Florida Keys is recommended.

The social distance requirement in Florida Keys is 2 metres.

Make yourself known to an official member of staff and/or call the national coronavirus helpline number on 800-232-4636.

Last updated: 29 Jun 2022
Exceptions may apply, for full details: Centers for Disease control and prevention (CDC).

We're working around the clock to bring you the latest COVID-19 travel updates.
This information is compiled from official sources. To the best of our knowledge, it is correct as of the last update.
Visit Rome2rio travel advice for general help.

Questions & Answers

The cheapest way to get from Chicago to Florida Keys is to bus which costs $95 - $170 and takes 35h 39m.

More details

The quickest way to get from Chicago to Florida Keys is to fly which costs $340 - $900 and takes 5h 16m.

More details

The distance between Chicago and Florida Keys is 1246 miles.

The best way to get from Chicago to Florida Keys without a car is to bus which takes 35h 39m and costs $95 - $170.

More details

It takes approximately 5h 16m to get from Chicago to Florida Keys, including transfers.

More details

The best way to get from Chicago to Florida Keys is to fly which takes 5h 16m and costs $340 - $900. Alternatively, you can bus, which costs $95 - $170 and takes 35h 39m.

Mode details

The quickest flight from Chicago O'Hare Airport to Key West Airport is the direct flight which takes 3h 9m.

Search flights

Florida Keys is 1h ahead of Chicago. It is currently 5:26 PM in Chicago and 6:26 PM in Florida Keys.

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

Search flights

There are 39+ hotels available in Florida Keys. Prices start at $100 USD per night.

More details

Map of how to get from Chicago to Florida Keys.
Launch map view
  • Distance: 1245.6 miles
  • Duration: 5h 16m

What companies run services between Chicago, IL, USA and Florida Keys, Monroe County, FL, USA?

American Airlines, United Airlines and two other airlines fly from Chicago to Florida Keys hourly. Alternatively, you can take a bus from Chicago to Florida Keys via Miami FL, Downtown Miami, Caroline & Grinnell, Simonton & Dey St., Simonton & Caroline, and Sugarloaf Key - Lower - Opposite Sugarloaf Lodge in around 35h 39m.

Airlines
Delta
Website
delta.com
Flights from Chicago O'Hare to Key West via Atlanta
Ave. Duration
5h 10m
When
Every day
Estimated price
$340 - $850
Flights from Chicago Midway to Key West via Atlanta
Ave. Duration
5h 15m
When
Every day
Estimated price
$390 - $950
Flights from Chicago Midway to Key West via Detroit, Atlanta
Ave. Duration
8h 57m
When
Every day
Estimated price
$420 - $1,100
Flights from Chicago Midway to Miami via Atlanta
Ave. Duration
5h 7m
When
Every day
Estimated price
$190 - $470
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Miami
Ave. Duration
2h 57m
When
Every day
Estimated price
$100 - $380
Flights from Chicago Midway to Miami via Nashville
Ave. Duration
4h 45m
When
Saturday
Estimated price
$100 - $380
Flights from Chicago Midway to Miami via St. Louis
Ave. Duration
5h 5m
When
Saturday
Estimated price
$100 - $380
Flights from Chicago Midway to Miami via Baltimore
Ave. Duration
5h 57m
When
Every day
Estimated price
$100 - $380
Flights from Chicago Midway to Miami via Atlanta
Ave. Duration
5h 45m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$100 - $380
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Key West
Ave. Duration
3h 9m
When
Saturday
Estimated price
$300 - $1,100
Flights from Chicago O'Hare to Key West via Miami
Ave. Duration
5h 12m
When
Every day
Estimated price
$310 - $1,100
Flights from Chicago O'Hare to Key West via Charlotte
Ave. Duration
5h 49m
When
Every day
Estimated price
$310 - $1,100
Flights from Chicago O'Hare to Key West via Dallas/Ft.Worth
Ave. Duration
6h 11m
When
Every day
Estimated price
$340 - $1,200
United Airlines
Website
united.com
Flights from Chicago O'Hare to Key West
Ave. Duration
3h 10m
When
Every day
Estimated price
$300 - $1,100
Flights from Chicago O'Hare to Key West via Washington Dulles
Ave. Duration
5h 51m
When
Saturday
Estimated price
$330 - $1,200
Flights from Chicago Midway to Key West via Tampa
Ave. Duration
4h 45m
When
Saturday
Estimated price
$290 - $900
Flights from Chicago Midway to Key West via Orlando
Ave. Duration
4h 45m
When
Tuesday, Wednesday and Friday
Estimated price
$300 - $900
Silver Airways
Website
silverairways.com
Flights from Chicago Midway to Key West via Tampa
Ave. Duration
4h 45m
When
Saturday
Estimated price
$290 - $900
Flights from Chicago Midway to Key West via Orlando
Ave. Duration
4h 45m
When
Tuesday, Wednesday and Friday
Estimated price
$300 - $900
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
+1 800-872-7245
Website
amtrak.com
Train from Chicago Union Station to Washington Union Station
Ave. Duration
17h 25m
Frequency
Once daily
Estimated price
$80 - $120
Website
Amtrak
Coach Seat
$80 - $120
Premium
$290 - $400
Flexi Coach Seat
$160 - $240
Business Seat
$170 - $250
Train from Washington Union Station to Miami Amtrak Station
Ave. Duration
23h 35m
Frequency
4 times a day
Estimated price
$110 - $160
Website
Amtrak
Coach Seat
$110 - $160
Premium
$350 - $490
Flexi Coach Seat
$230 - $340
Business Seat
$250 - $350
Bus operators
Keys Shuttle
Phone
+1 (888) 765-9997 | (305) 289-9997
Website
keysshuttle.com
Shuttle from Miami, FL - International Airport to Big Pine Key, FL
Ave. Duration
3h
Frequency
4 times a day
Estimated price
$85 - $120
Schedules at
keysshuttle.com
Palmland Bus Lines
Website
palmlandlines.com
Bus from Chicago IL to Miami FL
Ave. Duration
28h 45m
Frequency
Hourly
Estimated price
$80 - $100
Schedules at
palmlandlines.com
Flixbus USA
Phone
(855) 626-8585
Website
flixbus.com
Bus from Downtown Miami to Key West
Ave. Duration
4h 5m
Frequency
Twice daily
Estimated price
$14 - $55
Schedules at
flixbus.com
Adult Standard Purchase
$19 - $55
Adult Advance Purchase
$14 - $20
Bus from Miami Kendall to Key West
Ave. Duration
3h 15m
Frequency
Once daily
Estimated price
$13 - $55
Schedules at
flixbus.com
Adult Standard Purchase
$18 - $55
Adult Advance Purchase
$13 - $19
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 Amtrak to Atlanta
Ave. Duration
16h 50m
Frequency
Twice daily
Estimated price
$75 - $110
Website
greyhound.com
Economy
$75 - $110
Flexible
$110 - $170
Bus from Atlanta to Miami
Ave. Duration
13h 35m
Frequency
3 times a day
Estimated price
$70 - $100
Website
greyhound.com
Economy
$70 - $100
Flexible
$100 - $160
Bus from Miami to Big Pine Key
Ave. Duration
3h 35m
Frequency
Once daily
Estimated price
$20 - $28
Website
greyhound.com
Economy
$20 - $28
Flexible
$35 - $60

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

More Questions & Answers

The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $1 - $5.

More details

ticket