There are 7 ways to get from Chicago to Looe Key by plane, unknown, bus, train, or shuttle
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 O'Hare International Airport to Key West International Airport, travel
best- Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)ORD - EYW
- Walk from Key West International Airport (EYW) to Looe Key
5h 47mBus, travel
- Take the bus from Chicago Bus Station to Atlanta Bus Station
- Take the bus from Atlanta Bus Station to Miami Airport Station
- Take the bus from Miami Airport Station to Big Pine Key
- Walk from Big Pine Key to Looe Key
34h 21mTrain, shuttle, travel
- Take the train from Chicago Union Station to Hollywood Amtrak Station
- Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FL
- Walk from Big Pine Key, FL to Looe Key
2d 3hFly Chicago Midway International Airport to Key West International Airport, travel
- Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)MDW - EYW
- Walk from Key West International Airport (EYW) to Looe Key
6h 52mFly Chicago O'Hare International Airport to Miami International Airport, shuttle, travel
- Fly from Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA)ORD - MIA
- Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FL
- Walk from Big Pine Key, FL to Looe Key
9h 4mFly Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport, shuttle, travel
- Fly from Chicago Midway International Airport (MDW) to Fort Lauderdale–Hollywood International Airport (FLL)MDW - FLL
- Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FL
- Walk from Big Pine Key, FL to Looe Key
9h 14mFly Chicago Midway International Airport to Miami International Airport, shuttle, travel
- Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)MDW - MIA
- Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FL
- Walk from Big Pine Key, FL to Looe Key
8h 49m
Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW) flights
Questions & Answers
The distance between Chicago and Looe Key is 1302 miles.
The best way to get from Chicago to Looe Key without a car is to bus and travel which takes 34h 21m and costs .
It takes approximately 5h 47m to get from Chicago to Looe Key, including transfers.
Looe Key is 1h ahead of Chicago. It is currently 1:48 AM in Chicago and 2:48 AM in Looe Key.
There are 95+ hotels available in Looe Key.
What companies run services between Chicago, IL, USA and Looe Key, FL, USA?
There is no direct connection from Chicago to Looe Key. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Key West International Airport (EYW), then travel to Looe Key. Alternatively, you can take a bus from Chicago Bus Station to Looe Key via Atlanta Bus Station, Miami Airport Station, and Big Pine Key in around 34h 21m.
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Key West International Airport
- Ave. Duration
- 3h 23m
- When
- Every day
- Estimated price
- $95–470
Flights from Chicago O'Hare International Airport to Miami International Airport
- Ave. Duration
- 3h 7m
- When
- Every day
- Estimated price
- $80–410
Flights from Chicago O'Hare International Airport to Miami International Airport via Jacksonville
- Ave. Duration
- 5h 55m
- When
- Every day
- Estimated price
- $80–410
- Website
- delta.com
Flights from Chicago O'Hare International Airport to Key West International Airport via Atlanta
- Ave. Duration
- 6h 4m
- When
- Every day
- Estimated price
- $95–470
Flights from Chicago Midway International Airport to Key West International Airport via Atlanta
- Ave. Duration
- 5h 37m
- When
- Every day
- Estimated price
- $110–600
- Website
- southwest.com
Flights from Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport
- Ave. Duration
- 2h 57m
- When
- Every day
- Estimated price
- $75–380
Flights from Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport via Tampa
- Ave. Duration
- 5h 13m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $75–390
Flights from Chicago Midway International Airport to Miami International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $100–500
- Website
- united.com
Flights from Chicago O'Hare International Airport to Key West International Airport
- Ave. Duration
- 3h 19m
- When
- Every day
- Estimated price
- $95–470
Flights from Chicago O'Hare International Airport to Miami International Airport
- Ave. Duration
- 3h 14m
- When
- Every day
- Estimated price
- $80–410
- Website
- spirit.com
Flights from Chicago O'Hare International Airport to Key West International Airport via Fort Lauderdale–Hollywood International Airport
- Ave. Duration
- 5h 10m
- When
- Thursday and Sunday
- Estimated price
- $80–400
Flights from Chicago O'Hare International Airport to Miami International Airport
- Ave. Duration
- 3h 5m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $50–290
- Website
- allegiantair.com
Flights from Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport via Asheville
- Ave. Duration
- 4h 22m
- When
- Monday
- Estimated price
- $75–380
Flights from Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport via Knoxville
- Ave. Duration
- 6h
- When
- Monday
- Estimated price
- $75–380
- Website
- flyfrontier.com
Flights from Chicago Midway International Airport to Miami International Airport
- Ave. Duration
- 3h
- When
- Saturday
- Estimated price
- $100–500
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Hollywood Amtrak Station
- Ave. Duration
- 46h 6m
- Frequency
- Once daily
- Estimated price
- $250–550
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- 3 times a day
- Estimated price
- $80–170
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h 15m
- Frequency
- 4 times a day
- Estimated price
- $75–140
- Website
- https://www.greyhound.com/
Bus from Atlanta Bus Station to Miami Airport Station
- Ave. Duration
- 14h 5m
- Frequency
- Twice daily
- Estimated price
- $65–180
- Website
- https://www.greyhound.com/
Bus from Miami Airport Station to Big Pine Key
- Ave. Duration
- 3h 35m
- Frequency
- Twice daily
- Estimated price
- $22–29
- Website
- https://www.greyhound.com/
- Phone
- +1 (305) 289-9997
- groups@keysshuttle.com
- Website
- keysshuttle.com
Shuttle from Miami, FL - International Airport to Big Pine Key, FL
- Ave. Duration
- 3h
- Frequency
- 4 times a day
- Estimated price
- $130–180
- Website
- https://www.keysshuttle.com
Shuttle from Fort Lauderdale, FL - International Airport to Big Pine Key, FL
- Ave. Duration
- 3h 30m
- Frequency
- 4 times a day
- Estimated price
- $150–200
- Website
- https://www.keysshuttle.com
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