There are 5 ways to get from Siesta Key to Chicago by plane, bus (Flixbus, Greyhound), car, 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 to Chicago Midway International Airport
best- Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane SRQ - MDW
5h$134–708Fly to Chicago O'Hare International Airport
cheapest- Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane SRQ - ORD
5h 34m$114–608Bus
- Take the bus from Sarasota Cattlemen Transfer Center to Tampa Bus Stationbus
- Take the bus from Tampa Bus Station to Atlanta Bus Stationbus
- Take the bus from Atlanta Bus Station to Chicago Bus Stationbus
29h 43m$178–308Drive, train (Amtrak)
- Drive from Siesta Key to Tampacar
- Take the train from Tampa to Chicago Union Stationtrain Floridian
42h 14m$471–1,115Drive 1,178.4 mi
- Drive from Siesta Key to Chicagocar 1,178.4 mi
21h$216–311
Siesta Key to Chicago by bus
Comparing Your Travel Options
The cheapest way to get from Siesta Key to Chicago is to bus which costs $170 - $310 and takes 29h 43m.
The fastest way to get from Siesta Key to Chicago is to fly which takes 5h and costs $130 - $750.
No, there is no direct bus from Siesta Key to Chicago station. However, there are services departing from Ocean Blvd @ Avenida Madera NB and arriving at Chicago Bus Station via Downtown Transfer Station, Sarasota Cattlemen Transfer Center, Tampa Bus Station and Atlanta Bus Station. The journey, including transfers, takes approximately 29h 43m.
The distance between Siesta Key and Chicago is 1068 miles. The road distance is 1185.3 miles.
The best way to get from Siesta Key to Chicago without a car is to bus which takes 29h 43m and costs $170 - $310.
It takes approximately 5h to get from Siesta Key to Chicago, including transfers.
Siesta Key to Chicago bus services, operated by Flixbus USA, depart from Sarasota Cattlemen Transfer Center station.
The best way to get from Siesta Key to Chicago is to fly which takes 5h and costs $130 - $750. Alternatively, you can bus, which costs $170 - $310 and takes 29h 43m.
Siesta Key to Chicago bus services, operated by Flixbus USA, arrive at Tampa Bus Station.
Chicago is 1h behind Siesta Key. It is currently 3:58 AM in Siesta Key and 2:58 AM in Chicago.
What companies run services between Siesta Key, FL, USA and Chicago, IL, USA?
Southwest Airlines flies from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW) 3 times a day. Alternatively, you can take a bus from Ocean Blvd @ Avenida Madera NB to Chicago Bus Station via Main St @ Lemon Ave, Downtown Transfer Station, Cattlemen Transit Station, Sarasota Cattlemen Transfer Center, Tampa Bus Station, and Atlanta Bus Station in around 29h 43m.
- Website
- southwest.com
Flights from Sarasota–Bradenton International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 44m
- When
- Every day
- Estimated price
- $130–700
Flights from Sarasota–Bradenton International Airport to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 22m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $140–700
Flights from Sarasota–Bradenton International Airport to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 4h 45m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $150–700
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Tampa to Chicago Union Station
- Ave. Duration
- 40h 56m
- Frequency
- Once daily
- Estimated price
- $460–1,100
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Sarasota Cattlemen Transfer Center to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- 3 times a day
- Estimated price
- $9–15
- Schedules at
- Flixbus USA
Bus from Tampa Bus Station to Atlanta Bus Station
- Ave. Duration
- 8h 15m
- Frequency
- Once daily
- Estimated price
- $65–110
- Schedules at
- Flixbus USA
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h 10m
- Frequency
- Twice daily
- Estimated price
- $100–160
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Yes, the driving distance between Siesta Key to Chicago is 1185 miles. It takes approximately 21h to drive from Siesta Key to Chicago.
There are 1284+ hotels available in Chicago.