There are 9 ways to get from Orlando to Chicago 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 46m$194–497Fly Orlando to Chicago O'Hare International Airport
cheapest- Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
5h 7m$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 15m$165–300Train (Amtrak)
- Take the train from Orlando to Chicago Union Stationtrain Floridian
38h 55m$900–1,500Drive 1,105.1 mi
- Drive from Orlando to Chicagocar 1,105.1 mi
19h 37m$202–292Fly 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 40m$195–740Bus 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
6h 57m$116–429Bus 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 26m$156–579Fly 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 6m$459–1,191
Orlando to Chicago by bus
Comparing Your Travel Options
The cheapest way to get from Orlando to Chicago is to bus and fly which costs $110 - $430 and takes 6h 57m.
The fastest way to get from Orlando to Chicago is to fly which takes 4h 46m and costs $190 - $500.
No, there is no direct bus from Orlando station to Chicago station. However, there are services departing from Orlando Bus Station and arriving at Chicago Bus Station via Atlanta Bus Station. The journey, including transfers, takes approximately 24h 15m.
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 is 1024 miles. The road distance is 1111.6 miles.
The best way to get from Orlando to Chicago without a car is to bus which takes 24h 15m and costs $160 - $300.
It takes approximately 4h 46m to get from Orlando to Chicago, including transfers.
Orlando to Chicago bus services, operated by Flixbus USA, depart from Orlando Bus Station.
Orlando to Chicago train services, operated by Amtrak, depart from Orlando station.
The best way to get from Orlando to Chicago is to fly which takes 4h 46m and costs $190 - $500. Alternatively, you can bus, which costs $160 - $300 and takes 24h 15m, you could also train, which costs $900 - $1,500 and takes 38h 55m.
What companies run services between Orlando, FL, USA and Chicago, IL, USA?
Frontier Airlines, 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 Chicago Bus Station via Atlanta Bus Station in around 24h 15m.
- Website
- southwest.com
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 Columbus
- Ave. Duration
- 4h 25m
- When
- Monday, Thursday, and Friday
- Estimated price
- $85–440
Flights from Tampa to Chicago Midway International Airport
- Ave. Duration
- 2h 42m
- When
- Every day
- Estimated price
- $85–430
Flights from Tampa to Chicago Midway International Airport via Indianapolis
- Ave. Duration
- 4h 15m
- When
- Sunday
- Estimated price
- $85–430
Flights from Tampa to Chicago Midway International Airport via Louisville
- Ave. Duration
- 4h 25m
- When
- Sunday
- Estimated price
- $85–430
Flights from Tampa to Chicago Midway International Airport via Columbus
- Ave. Duration
- 4h 25m
- When
- Sunday
- Estimated price
- $90–450
Flights from Tampa to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 35m
- When
- Tuesday, Wednesday, and Sunday
- Estimated price
- $85–430
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $120–650
Flights from Orlando to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 32m
- When
- Saturday and Sunday
- Estimated price
- $120–650
Flights from Orlando to General Mitchell International Airport via Nashville
- Ave. Duration
- 4h 40m
- When
- Monday to Saturday
- Estimated price
- $130–650
Flights from Orlando to General Mitchell International Airport via St. Louis
- Ave. Duration
- 4h 42m
- When
- Monday to Friday
- Estimated price
- $130–700
- Website
- delta.com
Flights from Orlando to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $65–340
Flights from Tampa to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 5h 3m
- When
- Every day
- Estimated price
- $65–340
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 46m
- When
- Saturday
- Estimated price
- $120–650
Flights from Orlando to General Mitchell International Airport via Atlanta
- Ave. Duration
- 4h 38m
- When
- Every day
- Estimated price
- $120–650
- Website
- united.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $65–340
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 5m
- When
- Every day
- Estimated price
- $65–340
- Website
- aa.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 18m
- When
- Every day
- Estimated price
- $65–340
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 6m
- When
- Every day
- Estimated price
- $65–340
- Website
- allegiantair.com
Flights from Orlando to Chicago Midway International Airport via Knoxville
- Ave. Duration
- 4h 5m
- When
- Monday and Friday
- Estimated price
- $80–420
Flights from Orlando Sanford to South Bend
- Ave. Duration
- 2h 26m
- When
- Friday, Monday, Saturday, and Wednesday
- Estimated price
- $120–650
- Website
- flyfrontier.com
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 3h 1m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $190–490
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $70–350
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 4m
- When
- Every day
- Estimated price
- $140–190
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 3h 14m
- When
- Tuesday, Thursday, and Sunday
- Estimated price
- $170–550
- Website
- suncountry.com
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 3h 2m
- When
- Thursday
- Estimated price
- $120–650
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
- $900–1,500
- Website
- Amtrak
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $45–75
- Website
- Amtrak
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Hourly
- Estimated price
- $14–17
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $14–17
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 4 hours
- Estimated price
- $4–16
- Schedules at
- Northern Indiana Commuter Transportation District
- 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
- Every 4 hours
- Estimated price
- $12–19
- Schedules at
- Flixbus USA
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- Every 4 hours
- Estimated price
- $12–19
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Orlando Bus Station to Atlanta Bus Station
- Ave. Duration
- 10h 10m
- Frequency
- Once daily
- Estimated price
- $70–110
- Website
- Greyhound
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h
- Frequency
- 4 times a day
- Estimated price
- $110–190
- Website
- Greyhound
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 3h 5m
- Frequency
- Once daily
- Estimated price
- $13–22
- Website
- Greyhound
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 3h 5m
- Frequency
- Once daily
- Estimated price
- $13–22
- Website
- Greyhound
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Orlando to Chicago bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago is 1h behind Orlando. It is currently 02:05 in Orlando and 01:05 in Chicago.
Orlando to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Orlando to Chicago is 1112 miles. It takes approximately 19h 37m to drive from Orlando to Chicago.
Book your Orlando to Chicago train tickets online with Omio.
Book your Orlando to Chicago bus tickets online with Omio and FlixBus.
There are 1309+ hotels available in Chicago.