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
5h 2m$124–658Fly Orlando to Chicago Midway International Airport
cheapest- Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane MCO - MDW
5h$84–427Bus
- 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$147–363Train (Amtrak)
- Take the train from Jacksonville to Chicago Union Stationtrain Floridian
36h 36m$442–953Drive 981.8 mi
- Drive from Jacksonville to Chicagocar 981.8 mi
18h 27m$180–259Fly Jacksonville to Chicago O'Hare International Airport
- Fly from Jacksonville (JAX) to Chicago O'Hare International Airport (ORD)plane JAX - ORD
5h 31m$99–558Fly Tampa to Chicago Midway International Airport
- Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane TPA - MDW
5h 10m$99–487Fly 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$104–558Fly Ft. Myers to Chicago Midway International Airport
- Fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW)plane RSW - MDW
6h 18m$126–660Fly 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
6h 2m$204–788
Florida to Chicago by bus
Questions & Answers
The cheapest way to get from Florida to Chicago is to bus which costs $140 - $370 and takes 24h 53m.
The fastest way to get from Florida to Chicago is to fly which takes 5h and costs $80 - $430.
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.
The distance between Florida and Chicago is 882 miles. The road distance is 987.5 miles.
The best way to get from Florida to Chicago without a car is to bus which takes 24h 53m and costs $140 - $370.
It takes approximately 5h 2m to get from Florida to Chicago, including transfers.
Florida to Chicago bus services, operated by Flixbus USA, depart from Jacksonville station.
The best way to get from Florida to Chicago is to fly which takes 5h 2m and costs $120 - $700. Alternatively, you can bus, which costs $140 - $370 and takes 24h 53m, you could also train, which costs $440 - $1,000 and takes 36h 36m.
Florida to Chicago bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago is 1h behind Florida. It is currently 4:58 AM in Florida and 3:58 AM in Chicago.
What companies run services between Florida, USA and Chicago, IL, USA?
Southwest Airlines, Delta, and Frontier Airlines fly from Jacksonville (JAX) to Chicago Midway International Airport (MDW) every 3 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 25m
- When
- Every day
- Estimated price
- $120–650
Flights from Jacksonville to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h
- When
- Tuesday, Wednesday, Saturday, and Sunday
- Estimated price
- $120–650
Flights from Jacksonville to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 4h 57m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $130–700
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $80–420
Flights from Orlando to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 33m
- When
- Tuesday, Wednesday, Sunday, and Saturday
- Estimated price
- $85–420
Flights from Tampa to Chicago Midway International Airport
- Ave. Duration
- 2h 40m
- When
- Every day
- Estimated price
- $95–480
Flights from Tampa to Chicago Midway International Airport via Columbus
- Ave. Duration
- 4h 15m
- When
- Saturday
- Estimated price
- $100–550
Flights from Tampa to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 20m
- When
- Saturday
- Estimated price
- $95–490
Flights from Tampa to Chicago Midway International Airport via Louisville
- Ave. Duration
- 4h 25m
- When
- Saturday
- Estimated price
- $95–480
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
- 5h 5m
- When
- Saturday, Monday, Thursday, and Friday
- Estimated price
- $110–550
Flights from Ft. Myers to Chicago Midway International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $120–650
Flights from Ft. Myers to Chicago Midway International Airport via Columbus
- Ave. Duration
- 4h 50m
- When
- Saturday
- Estimated price
- $130–650
Flights from Ft. Myers to Chicago Midway International Airport via St. Louis
- Ave. Duration
- 5h 5m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $140–650
Flights from Ft. Myers to Chicago Midway International Airport via Nashville
- Ave. Duration
- 5h 52m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $130–650
Flights from Ft. Myers to Chicago Midway International Airport via Indianapolis
- Ave. Duration
- 5h 35m
- When
- Sunday
- Estimated price
- $120–650
- Website
- delta.com
Flights from Jacksonville to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $120–650
Flights from Jacksonville to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 52m
- When
- Every day
- Estimated price
- $100–550
Flights from Ft. Myers to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 5h 37m
- When
- Every day
- Estimated price
- $120–650
- Website
- allegiantair.com
Flights from Fort Lauderdale–Hollywood International Airport to Chicago Midway International Airport via Knoxville
- Ave. Duration
- 4h 50m
- When
- Thursday and Sunday
- Estimated price
- $100–550
Flights from Orlando Sanford to South Bend
- Ave. Duration
- 2h 29m
- When
- Thursday, Sunday, Monday, Friday, Wednesday, and Saturday
- Estimated price
- $130–700
- Website
- united.com
Flights from Jacksonville to Chicago O'Hare International Airport
- Ave. Duration
- 2h 53m
- When
- Every day
- Estimated price
- $95–550
- Website
- aa.com
Flights from Jacksonville to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $95–550
- Website
- flyfrontier.com
Flights from Jacksonville to Chicago Midway International Airport via Atlanta
- Ave. Duration
- 4h 34m
- When
- Every day
- Estimated price
- $120–650
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Jacksonville to Chicago Union Station
- Ave. Duration
- 35h 12m
- Frequency
- Once daily
- Estimated price
- $440–950
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Jacksonville to Atlanta Bus Station
- Ave. Duration
- 6h 40m
- Frequency
- 3 times a day
- Estimated price
- $50–85
- Schedules at
- flixbus.com
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- Twice daily
- Estimated price
- $95–160
- 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 Jacksonville to Atlanta Bus Station
- Ave. Duration
- 8h 45m
- Frequency
- Twice daily
- Estimated price
- $60–130
- Website
- https://www.greyhound.com/
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h
- Frequency
- 4 times a day
- Estimated price
- $110–230
- Website
- https://www.greyhound.com/
Want to know more about travelling around United States
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More Questions & Answers
Yes, the driving distance between Florida to Chicago is 988 miles. It takes approximately 18h 27m to drive from Florida to Chicago.
There are 784+ hotels available in Chicago.






