There are 9 ways to get from Orlando to Chicago Loop by plane, bus (Flixbus, Greyhound), train (Amtrak), car, bus, 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 Orlando to Chicago Midway International Airport
best- Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane MCO - MDW
4h 44m$194–487Fly Orlando to Chicago O'Hare International Airport
cheapest- Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
4h 57m$74–407Bus
- Take the bus from Orlando Bus Station to Atlanta Bus Stationbus FlixBus N2401 / ...
- Take the bus from Atlanta Bus Station to Chicago Bus Stationbus Greyhound US0100
24h 27m$168–290Train (Amtrak)
- Take the train from Orlando to Chicago Union Stationtrain Floridian
38h 55m$410–1,000Drive 1,106 mi
- Drive from Orlando to Chicago Loopcar 1,106 mi
19h 38m$202–292Bus to Tampa, fly to Chicago Midway International Airport
- Take the bus from Orlando Bus Station to Tampa Bus Stationbus
- Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane TPA - MDW
7h$117–428Fly 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 Millennium Stationtrain
5h 41m$205–790Bus to Tampa, fly to Chicago O'Hare International Airport
- Take the bus from Orlando Bus Station to Tampa Bus Stationbus
- Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane TPA - ORD
7h 19m$157–578Fly Orlando to General Mitchell International Airport, train
- Fly from Orlando (MCO) to General Mitchell International Airport (MKE)plane MCO - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
7h 10m$434–1,166
Orlando to Chicago Loop by bus
Comparing Your Travel Options
The cheapest way to get from Orlando to Chicago Loop is to bus and fly which costs $110 - $430 and takes 7h.
The fastest way to get from Orlando to Chicago Loop is to fly which takes 4h 44m and costs $190 - $490.
No, there is no direct bus from Orlando station to Chicago Loop. However, there are services departing from Orlando Bus Station and arriving at Washington & Lasalle via Atlanta Bus Station and Jefferson & Harrison. The journey, including transfers, takes approximately 24h 27m.
Yes, there is a direct train departing from Orlando and arriving at Chicago Union Station station. Services depart once daily, and operate every day. The journey takes approximately 38h 55m.
The distance between Orlando and Chicago Loop is 1025 miles. The road distance is 1112.4 miles.
The best way to get from Orlando to Chicago Loop without a car is to bus which takes 24h 27m and costs $160 - $290.
It takes approximately 4h 44m to get from Orlando to Chicago Loop, including transfers.
Orlando to Chicago Loop bus services, operated by Flixbus USA, depart from Orlando Bus Station.
Orlando to Chicago Loop train services, operated by Amtrak, depart from Orlando station.
The best way to get from Orlando to Chicago Loop is to fly which takes 4h 44m and costs $190 - $490. Alternatively, you can bus, which costs $160 - $290 and takes 24h 27m, you could also train, which costs $410 - $1,000 and takes 38h 55m.
What companies run services between Orlando, FL, USA and Chicago Loop, IL, USA?
Southwest Airlines and Allegiant Air fly from Orlando (MCO) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, you can take a bus from Orlando Bus Station to Washington & Lasalle via Atlanta Bus Station, Chicago Bus Station, and Jefferson & Harrison in around 24h 27m.
- Website
- southwest.com
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 Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $120–650
Flights from Orlando to General Mitchell International Airport via Nashville
- Ave. Duration
- 4h 30m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $130–650
Flights from Orlando to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 45m
- When
- Saturday
- Estimated price
- $120–650
Flights from Orlando to General Mitchell International Airport via St. Louis
- Ave. Duration
- 4h 40m
- When
- Saturday and Sunday
- Estimated price
- $130–700
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Orlando to Chicago Union Station
- Ave. Duration
- 38h 55m
- Frequency
- Once daily
- Estimated price
- $410–1,000
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $20–50
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Orlando Bus Station to Atlanta Bus Station
- Ave. Duration
- 7h 15m
- Frequency
- Every 4 hours
- Estimated price
- $65–100
- 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
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- 5 times a day
- Estimated price
- $12–19
- Schedules at
- Flixbus USA
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- 5 times a day
- Estimated price
- $12–19
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Orlando to Chicago Loop bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago Loop is 1h behind Orlando. It is currently 5:06 AM in Orlando and 4:06 AM in Chicago Loop.
Orlando to Chicago Loop train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Orlando to Chicago Loop is 1112 miles. It takes approximately 19h 38m to drive from Orlando to Chicago Loop.
Book your Orlando to Chicago Loop train tickets online with Omio.
There are 1286+ hotels available in Chicago Loop.