There are 5 ways to get from Chicago to Siesta Key by plane, bus (Greyhound, Flixbus), train, bus, 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.
Fly from Chicago Midway International Airport
best- Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane MDW - SRQ
5h 11m$124–659Fly from Chicago O'Hare International Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane ORD - SRQ
5h 39m$80–379Bus
- Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
- Take the bus from Atlanta Bus Station to Tampa Bus Stationbus
- Take the bus from Tampa Bus Station to Sarasota Cattlemen Transfer Centerbus
30h 16m$205–336Train, Amtrak Thruway (Amtrak)
- Take the train from Chicago Union Station to Tampatrain Floridian
- Take the bus from Tampa Union Station to Sarasota Amtrak Bus Stopbus Amtrak Thruway Connecting Service
45h 11mDrive 1,177.2 mi
- Drive from Chicago to Siesta Keycar 1,177.2 mi
20h 59m$195–281
Chicago to Siesta Key by bus
Comparing Your Travel Options
The cheapest way to get from Chicago to Siesta Key is to fly which costs $75 - $380 and takes 5h 39m.
The fastest way to get from Chicago to Siesta Key is to fly which takes 5h 11m and costs $120 - $700.
No, there is no direct bus from Chicago station to Siesta Key. However, there are services departing from Chicago Bus Station and arriving at Ocean Blvd @ Avenida Madera via Atlanta Bus Station, Tampa Bus Station and Cattlemen Transit Station. The journey, including transfers, takes approximately 30h 16m.
The distance between Chicago and Siesta Key is 1069 miles. The road distance is 1184 miles.
The best way to get from Chicago to Siesta Key without a car is to bus which takes 30h 16m and costs $200 - $340.
It takes approximately 5h 11m to get from Chicago to Siesta Key, including transfers.
Chicago to Siesta Key bus services, operated by Greyhound USA, depart from Chicago Bus Station.
The best way to get from Chicago to Siesta Key is to fly which takes 5h 11m and costs $120 - $700. Alternatively, you can bus, which costs $200 - $340 and takes 30h 16m.
Chicago to Siesta Key bus services, operated by Greyhound USA, arrive at Atlanta Bus Station.
Siesta Key is 1h ahead of Chicago. It is currently 3:05 AM in Chicago and 4:05 AM in Siesta Key.
What companies run services between Chicago, IL, USA and Siesta Key, FL, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Ocean Blvd @ Avenida Madera via Atlanta Bus Station, Tampa Bus Station, Sarasota Cattlemen Transfer Center, and Cattlemen Transit Station in around 30h 16m.
- Website
- delta.com
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport via Atlanta
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $120–650
Flights from Chicago O'Hare International Airport to Sarasota–Bradenton International Airport via Atlanta
- Ave. Duration
- 4h 50m
- When
- Every day
- Estimated price
- $75–370
- Website
- southwest.com
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport
- Ave. Duration
- 2h 40m
- When
- Every day
- Estimated price
- $120–650
Flights from Chicago Midway International Airport to Sarasota–Bradenton International Airport via Nashville
- Ave. Duration
- 5h 8m
- When
- Every day
- Estimated price
- $120–650
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Sarasota–Bradenton International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $75–370
- Website
- united.com
Flights from Chicago O'Hare International Airport to Sarasota–Bradenton International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $75–370
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Tampa
- Ave. Duration
- 40h 47m
- Frequency
- Once daily
- Estimated price
- $950–1,600
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h 5m
- Frequency
- 4 times a day
- Estimated price
- $130–200
- Website
- Greyhound
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to Atlanta Bus Station
- Ave. Duration
- 16h
- Frequency
- Twice daily
- Estimated price
- $110–170
- Schedules at
- Flixbus USA
Bus from Atlanta Bus Station to Tampa Bus Station
- Ave. Duration
- 9h 30m
- Frequency
- 5 times a week
- Estimated price
- $80–130
- Schedules at
- Flixbus USA
Bus from Tampa Bus Station to Sarasota Cattlemen Transfer Center
- Ave. Duration
- 1h
- Frequency
- 3 times a day
- Estimated price
- $8–13
- Schedules at
- Flixbus USA
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Bus from Tampa Union Station to Sarasota Amtrak Bus Stop
- Ave. Duration
- 1h 55m
- Frequency
- 4 times a day
- Website
- Amtrak
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.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Need to know: Greyhound
Read the travel guide
Why you should take the train in the US
Read the travel guide
Booking & Getting There
Yes, the driving distance between Chicago to Siesta Key is 1184 miles. It takes approximately 20h 59m to drive from Chicago to Siesta Key.
There are 3326+ hotels available in Siesta Key.