There are 7 ways to get from Chicago to Middleburg by plane, taxi, bus (Flixbus, Greyhound), train, car, subway, bus, or bus (Greyhound, Flixbus)
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 Midway International Airport to Gainesville Regional Airport, taxi
best- Fly from Chicago Midway International Airport (MDW) to Gainesville Regional Airport (GNV)plane MDW - GNV
- Take the taxi from Gainesville-Airport-GNV to Middleburgtaxi
6h 34m$238–735Subway to Chicago Midway International Airport, fly to Jacksonville, bus, line 900 bus
cheapest- Take the subway from Roosevelt to Midwaysubway
- Fly from Chicago Midway International Airport (MDW) to Jacksonville (JAX)plane MDW - JAX
- Take the bus from JRTC Bay P to Blanding Blvd + Orange Park Northwaybus
- Take the bus from Blanding Blvd + Orange Park Northway to Circle Kbus
8h 16m$126–714Bus
- Take the bus from Chicago Bus Station to Atlanta Bus Stationbus FlixBus 2512 / ...
- Take the bus from Atlanta Bus Station to Jacksonvillebus FlixBus N2434 / ...
24h 56m$137–368Train, taxi
- Take the train from Chicago Union Station to Jacksonvilletrain Floridian
- Take the taxi from Jacksonville to Middleburgtaxi
35h 25m$498–1,007Drive 1,010.2 mi
- Drive from Chicago to Middleburgcar 1,010.2 mi
18h 17m$185–267Fly Chicago O'Hare International Airport to Jacksonville, bus, line 900 bus
- Fly from Chicago O'Hare International Airport (ORD) to Jacksonville (JAX)plane ORD - JAX
- Take the bus from JRTC Bay P to Blanding Blvd + Orange Park Northwaybus
- Take the bus from Blanding Blvd + Orange Park Northway to Circle Kbus
8h 36m$166–454Bus via Chicago Train Station
- Take the bus from Chicago Train Station to Atlanta Bus Stationbus Greyhound US0100
- Take the bus from Atlanta Bus Station to Jacksonvillebus FlixBus N2434 / ...
26h 36m$174–367
Chicago to Middleburg by bus
Questions & Answers
The cheapest way to get from Chicago to Middleburg is to drive which costs $180 - $270 and takes 18h 17m.
The fastest way to get from Chicago to Middleburg is to fly and taxi which takes 6h 34m and costs $230 - $750.
No, there is no direct bus from Chicago station to Middleburg. However, there are services departing from Chicago Bus Station and arriving at Circle K via Atlanta Bus Station, JRTC Bay P and Blanding Blvd + Orange Park Northway. The journey, including transfers, takes approximately 24h 56m.
The distance between Chicago and Middleburg is 947 miles. The road distance is 1016.1 miles.
The best way to get from Chicago to Middleburg without a car is to bus which takes 24h 56m and costs $130 - $370.
It takes approximately 6h 34m to get from Chicago to Middleburg, including transfers.
Chicago to Middleburg bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Middleburg bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Middleburg is 1h ahead of Chicago. It is currently 9:57 PM in Chicago and 10:57 PM in Middleburg.
Yes, the driving distance between Chicago to Middleburg is 1016 miles. It takes approximately 18h 17m to drive from Chicago to Middleburg.
What companies run services between Chicago, IL, USA and Middleburg, FL, USA?
You can take a bus from Chicago Bus Station to Circle K via Atlanta Bus Station, Jacksonville, JRTC Bay P, and Blanding Blvd + Orange Park Northway in around 24h 56m.
- Website
- delta.com
Flights from Chicago Midway International Airport to Gainesville Regional Airport via Atlanta
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $95–550
Flights from Chicago Midway International Airport to Jacksonville via Atlanta
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $120–700
Flights from Chicago O'Hare International Airport to Jacksonville via Atlanta
- Ave. Duration
- 4h 19m
- When
- Every day
- Estimated price
- $85–460
- Website
- aa.com
Flights from Chicago Midway International Airport to Gainesville Regional Airport via Charlotte
- Ave. Duration
- 4h 20m
- When
- Wednesday
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Jacksonville
- Ave. Duration
- 2h 31m
- When
- Every day
- Estimated price
- $85–460
- Website
- southwest.com
Flights from Chicago Midway International Airport to Jacksonville
- Ave. Duration
- 2h 15m
- When
- Every day
- Estimated price
- $120–700
Flights from Chicago Midway International Airport to Jacksonville via Nashville
- Ave. Duration
- 4h 27m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $120–700
Flights from Chicago Midway International Airport to Jacksonville via St. Louis
- Ave. Duration
- 4h 32m
- When
- Monday, Tuesday, Thursday, Friday, and Sunday
- Estimated price
- $140–750
- Website
- united.com
Flights from Chicago O'Hare International Airport to Jacksonville
- Ave. Duration
- 2h 35m
- When
- Every day
- Estimated price
- $85–460
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Chicago Union Station to Jacksonville
- Ave. Duration
- 34h 45m
- Frequency
- Once daily
- Estimated price
- $420–950
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 888-968-7282
- Website
- transitchicago.com
Subway from Roosevelt to Midway
- Ave. Duration
- 20 min
- Frequency
- Every 10 minutes
- Estimated price
- $2–5
- Website
- https://www.transitchicago.com
- Schedules at
- https://www.transitchicago.com/schedules/
- Adult
- $2–5
- 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
- $85–160
- Schedules at
- flixbus.com
Bus from Atlanta Bus Station to Jacksonville
- Ave. Duration
- 6h 35m
- Frequency
- 3 times a day
- Estimated price
- $45–85
- 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 25m
- Frequency
- 4 times a day
- Estimated price
- $120–240
- Website
- https://www.greyhound.com/
Bus from Atlanta Bus Station to Jacksonville
- Ave. Duration
- 9h 15m
- Frequency
- Once daily
- Estimated price
- $65–130
- Website
- https://www.greyhound.com/
Bus from Chicago Train Station to Atlanta Bus Station
- Ave. Duration
- 16h 5m
- Frequency
- Twice daily
- Estimated price
- $120–240
- Website
- https://www.greyhound.com/
- Phone
- +1 904-630-3100
- Website
- jtafla.com
Bus from JRTC Bay P to Blanding Blvd + Orange Park Northway
- Ave. Duration
- 48 min
- Frequency
- Every 20 minutes
- Estimated price
- $1–3
- Website
- https://www.jtafla.com
Bus from Blanding Blvd + Orange Park Northway to Circle K
- Ave. Duration
- 59 min
- Frequency
- Twice daily
- Estimated price
- $1–3
- Website
- https://www.jtafla.com
- Ave. Duration
- 48 min
- Estimated price
- $75–180
Gainesville Cab Co.
- Phone
- +1 352-371-1515
- Website
- gainesvillemarooncab.com
Cabs 24HR
- Phone
- +1 855-374-8484
- Website
- cab24hr.com
zTrip
- Phone
- +1 904-222-2222
- Website
- ztrip.com
ABC Taxi
- Phone
- +1 904-554-5564
- Website
- abctaxijax.com
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