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.
Fly Chicago Midway to Key West
-
Fly from Chicago Midway (MDW) to Key West (EYW)
Fly Chicago Midway to Miami, shuttle
-
Fly from Chicago Midway (MDW) to Miami (MIA)
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Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FL
Bus via Atlanta
-
Take the bus from Chicago Amtrak to Atlanta
-
Take the bus from Atlanta to Miami
-
Take the bus from Miami to Big Pine Key
Train, bus
-
Take the train from Chicago Union Station to Washington Union Station
-
Take the train from Washington Union Station to Miami Amtrak Station
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Take the bus from Miami Kendall to Key West
Chicago O'Hare (ORD) to Key West (EYW) flights
Travel safe during COVID-19
Rules to follow in United States
2m
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 optionsDomestic 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
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.
The quickest way to get from Chicago to Florida Keys is to fly which costs $340 - $900 and takes 5h 16m.
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.
It takes approximately 5h 16m to get from Chicago to Florida Keys, including transfers.
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.
The quickest flight from Chicago O'Hare Airport to Key West Airport is the direct flight which takes 3h 9m.
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.
There are 39+ hotels available in Florida Keys. Prices start at $100 USD per night.
- 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.
- 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
- 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
- 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
- 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
- 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
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
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- 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
- Website
- palmlandlines.com
Bus from Chicago IL to Miami FL
- Ave. Duration
- 28h 45m
- Frequency
- Hourly
- Estimated price
- $80 - $100
- Schedules at
- palmlandlines.com
- 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 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
- 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.
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The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 42 min and costs $1 - $5.