There are 10 ways to get from Florida to Chicago by plane, bus (Flixbus, Greyhound), train (Amtrak), 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 Jacksonville to Chicago Midway International Airport
best- Fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW)plane JAX - MDW
4h 56m$104–378Fly Jacksonville to Chicago O'Hare International Airport
cheapest- Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)plane JAX - ORD
5h 24m$64–318Bus
- Take the bus from Jacksonville to Atlanta Bus Stationbus FlixBus 2434 / ...
- Take the bus from Atlanta Bus Station to Chicago Bus Stationbus Greyhound US0100
24h 53m$157–278Train (Amtrak)
- Take the train from Jacksonville to Chicago Union Stationtrain Floridian
36h 36m$382–903Drive 977.4 mi
- Drive from Jacksonville to Chicagocar 977.4 mi
18h 35m$179–258Fly Orlando to Chicago Midway International Airport
- Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane MCO - MDW
5h 5m$194–487Fly Tampa to Chicago Midway International Airport
- Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane TPA - MDW
5h 3m$104–407Fly Fort Lauderdale–Hollywood International Airport to Chicago Midway International Airport
- Fly from Fort Lauderdale–Hollywood International Airport (FLL) to Chicago Midway International Airport (MDW)plane FLL - MDW
5h 11m$154–378Fly Ft. Myers to Chicago Midway International Airport
- Fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW)plane RSW - MDW
6h 18m$106–560Fly Orlando Sanford to South Bend, train
- Fly from Orlando Sanford (SFB) to South Bend (SBN)plane SFB - SBN
- Take the train from South Bend Airport to Van Buren St.train
5h 38m$205–790
Florida to Chicago by bus
Comparing Your Travel Options
The cheapest way to get from Florida to Chicago is to fly which costs $100 - $410 and takes 5h 3m.
The fastest way to get from Florida to Chicago is to fly which takes 4h 56m and costs $100 - $380.
No, there is no direct bus from Florida to Chicago station. However, there are services departing from Newnan St + Ashley St and arriving at Chicago Bus Station via Jacksonville and Atlanta Bus Station. The journey, including transfers, takes approximately 24h 53m.
No, there is no direct train from Florida to Chicago station. However, there are services departing from Jacksonville and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 36h 36m.
The distance between Florida and Chicago is 882 miles. The road distance is 983.1 miles.
The best way to get from Florida to Chicago without a car is to bus which takes 24h 53m and costs $150 - $280.
It takes approximately 4h 56m to get from Florida to Chicago, including transfers.
Florida to Chicago bus services, operated by Flixbus USA, depart from Jacksonville station.
Florida to Chicago train services, operated by Amtrak, depart from Jacksonville station.
The best way to get from Florida to Chicago is to fly which takes 4h 56m and costs $100 - $380. Alternatively, you can bus, which costs $150 - $280 and takes 24h 53m, you could also train, which costs $380 - $950 and takes 36h 36m.
What companies run services between Florida, USA and Chicago, IL, USA?
Southwest Airlines, Frontier Airlines, and Delta fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Newnan St + Ashley St to Chicago Bus Station via JRTC Bay J, Jacksonville, and Atlanta Bus Station in around 24h 53m.
- Website
- southwest.com
Flights from Jacksonville to Chicago Midway International Airport
- Ave. Duration
- 2h 23m
- When
- Every day
- Estimated price
- $70–390
Flights from Jacksonville to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 12m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $75–400
Flights from Jacksonville to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 4h 20m
- When
- Saturday
- Estimated price
- $80–420
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 2h 48m
- When
- Every day
- Estimated price
- $80–430
Flights from Orlando to Chicago Midway International Airport via Louisville
- Ave. Duration
- 4h 15m
- When
- Monday, Thursday, and Friday
- Estimated price
- $80–430
Flights from Orlando to Chicago Midway International Airport via Indianapolis
- Ave. Duration
- 4h 20m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $80–430
Flights from Orlando to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 32m
- When
- Every day
- Estimated price
- $85–430
Flights from Tampa to Chicago Midway International Airport
- Ave. Duration
- 2h 41m
- When
- Every day
- Estimated price
- $85–440
Flights from Tampa to Chicago Midway International Airport via Columbus
- Ave. Duration
- 4h 25m
- When
- Monday, Thursday, and Friday
- Estimated price
- $90–460
Flights from Tampa to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 58m
- When
- Every day
- Estimated price
- $85–440
Flights from Fort Lauderdale–Hollywood International Airport to Chicago Midway International Airport
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $100–550
Flights from Fort Lauderdale–Hollywood International Airport to Chicago Midway International Airport via Tampa
- Ave. Duration
- 6h
- When
- Tuesday and Wednesday
- Estimated price
- $100–550
Flights from Ft. Myers to Chicago Midway International Airport
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $100–550
Flights from Ft. Myers to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 18m
- When
- Tuesday, Wednesday, Sunday, and Saturday
- Estimated price
- $110–550
Flights from Ft. Myers to Chicago Midway International Airport via Columbus
- Ave. Duration
- 5h 27m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $110–600
Flights from Ft. Myers to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 5h 5m
- When
- Monday, Thursday, Friday, and Saturday
- Estimated price
- $110–600
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Jacksonville to Chicago Union Station
- Ave. Duration
- 35h 12m
- Frequency
- Once daily
- Estimated price
- $380–900
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Jacksonville to Atlanta Bus Station
- Ave. Duration
- 6h 40m
- Frequency
- 3 times a day
- Estimated price
- $55–90
- Schedules at
- Flixbus USA
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h 10m
- Frequency
- Twice daily
- Estimated price
- $100–170
- Schedules at
- Flixbus USA
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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Booking & Getting There
Florida to Chicago bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago is 1h behind Florida. It is currently 4:30 PM in Florida and 3:30 PM in Chicago.
Florida to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Florida to Chicago is 983 miles. It takes approximately 18h 35m to drive from Florida to Chicago.
There are 1280+ hotels available in Chicago.




