There are 9 ways to get from Orlando to Chicago Loop by plane, bus (Flixbus, Greyhound), train (Amtrak), car, train, or bus
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 39m$89–417Bus
- 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 29m$155–335Train (Amtrak)
- Take the train from Orlando to Chicago Union Stationtrain Floridian
38h 55m$500–1,100Drive 1,110.4 mi
- Drive from Orlando to Chicago Loopcar 1,110.4 mi
19h 31m$203–293Fly Orlando to Chicago O'Hare International Airport
- Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
5h 4m$144–477Fly 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
6h 2m$204–738Bus 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$115–522Bus 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 25m$135–732Fly 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 5m$189–821
Orlando to Chicago Loop by bus
Questions & Answers
The cheapest way to get from Orlando to Chicago Loop is to bus which costs $150 - $340 and takes 24h 29m.
The fastest way to get from Orlando to Chicago Loop is to fly which takes 4h 39m and costs $85 - $420.
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 29m.
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 1116.9 miles.
The best way to get from Orlando to Chicago Loop without a car is to bus which takes 24h 29m and costs $150 - $340.
It takes approximately 4h 39m 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 39m and costs $85 - $420. Alternatively, you can bus, which costs $150 - $340 and takes 24h 29m, you could also train, which costs $500 - $1,100 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 29m.
- Website
- southwest.com
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 2h 49m
- When
- Every day
- Estimated price
- $85–410
Flights from Orlando to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 30m
- When
- Monday to Wednesday
- Estimated price
- $90–410
Flights from Tampa to Chicago Midway International Airport
- Ave. Duration
- 2h 41m
- When
- Every day
- Estimated price
- $100–490
Flights from Tampa to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 25m
- When
- Sunday, Tuesday, and Wednesday
- Estimated price
- $100–490
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $160–750
Flights from Orlando to General Mitchell International Airport via Nashville
- Ave. Duration
- 4h 23m
- When
- Every day
- Estimated price
- $160–750
Flights from Orlando to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 38m
- When
- Tuesday to Friday
- Estimated price
- $160–750
Flights from Orlando to General Mitchell International Airport via St. Louis
- Ave. Duration
- 4h 35m
- When
- Tuesday, Wednesday, and Saturday
- Estimated price
- $170–800
- Website
- united.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $65–300
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 10m
- When
- Every day
- Estimated price
- $75–360
- Website
- delta.com
Flights from Orlando to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 59m
- When
- Every day
- Estimated price
- $65–300
Flights from Tampa to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 5h 11m
- When
- Every day
- Estimated price
- $75–360
Flights from Orlando to General Mitchell International Airport via Atlanta
- Ave. Duration
- 4h 31m
- When
- Every day
- Estimated price
- $160–750
Flights from Orlando to General Mitchell International Airport via Detroit
- Ave. Duration
- 4h 45m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $170–800
- Website
- aa.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 11m
- When
- Every day
- Estimated price
- $65–300
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 16m
- When
- Every day
- Estimated price
- $75–360
- Website
- allegiantair.com
Flights from Orlando to Chicago Midway International Airport via Asheville
- Ave. Duration
- 4h 39m
- When
- Monday and Friday
- Estimated price
- $90–410
Flights from Orlando Sanford to South Bend
- Ave. Duration
- 2h 26m
- When
- Monday, Friday, Thursday, Sunday, Wednesday, and Saturday
- Estimated price
- $130–650
- Website
- flyfrontier.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 16m
- When
- Every day
- Estimated price
- $65–300
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 58m
- When
- Tuesday, Thursday, and Sunday
- Estimated price
- $160–750
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Orlando to Chicago Union Station
- Ave. Duration
- 38h 55m
- Frequency
- Once daily
- Estimated price
- $500–1,100
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $25–55
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Millennium Station
- Ave. Duration
- 2h 4m
- 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 Orlando Bus Station to Atlanta Bus Station
- Ave. Duration
- 7h 15m
- Frequency
- Every 4 hours
- Estimated price
- $55–95
- 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
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- Every 4 hours
- Estimated price
- $11–19
- 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 Orlando Bus Station to Atlanta Bus Station
- Ave. Duration
- 10h 10m
- Frequency
- Once 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
- $100–210
- Website
- https://www.greyhound.com/
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 3h 5m
- Frequency
- Once daily
- Estimated price
- $12–24
- Website
- https://www.greyhound.com/
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More Questions & Answers
Orlando to Chicago Loop bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago Loop is 1h behind Orlando. It is currently 9:29 AM in Orlando and 8:29 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 1117 miles. It takes approximately 19h 31m to drive from Orlando to Chicago Loop.
Book your Orlando to Chicago Loop train tickets online with Omio.
There are 1272+ hotels available in Chicago Loop.






