There are 9 ways to get from Orlando to Chicago, IL 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
5h 2m$89–437Bus
- Take the bus from Orlando RedCoach Station to Atlanta - Civic Center MARTA Stationbus Orlando
- Take the bus from Atlanta Bus Station to Chicago Bus Stationbus FlixBus 2512 / ...
22h 49m$117–361Train (Amtrak)
- Take the train from Orlando to Chicago Union Stationtrain Floridian
39h 4m$370–850Drive 1,110.2 mi
- Drive from Orlando to Chicago, ILcar 1,110.2 mi
19h 29m$203–293Fly Orlando to Chicago O'Hare International Airport
- Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
5h 20m$89–367Fly 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 25m$186–693Bus 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 19m$109–523Bus 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 39m$134–343Fly 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 21m$162–811
Orlando to Chicago, IL by bus and subway
Questions & Answers
The cheapest way to get from Orlando to Chicago, IL is to fly which costs $85 - $370 and takes 5h 20m.
The fastest way to get from Orlando to Chicago, IL is to fly which takes 5h 2m and costs $85 - $440.
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, IL is 1025 miles. The road distance is 1116.7 miles.
The best way to get from Orlando to Chicago, IL without a car is to bus which takes 22h 49m and costs $110 - $370.
It takes approximately 5h 2m to get from Orlando to Chicago, IL, including transfers.
Orlando to Chicago, IL train services, operated by Amtrak, depart from Orlando station.
The best way to get from Orlando to Chicago, IL is to fly which takes 5h 2m and costs $85 - $440. Alternatively, you can bus, which costs $110 - $370 and takes 22h 49m, you could also train, which costs $370 - $850 and takes 39h 4m.
Chicago, IL is 1h behind Orlando. It is currently 4:45 AM in Orlando and 3:45 AM in Chicago, IL.
Orlando to Chicago, IL train services, operated by Amtrak, arrive at Chicago Union Station.
What companies run services between Orlando, FL, USA and Chicago, IL, USA?
Frontier Airlines and Southwest Airlines fly from Orlando (MCO) to Chicago Midway International Airport (MDW) every 2 hours. Alternatively, you can take a bus from Orlando RedCoach Station to Chicago Bus Station via Atlanta - Civic Center MARTA Station, Civic Center Station, Garnett Station, and Atlanta Bus Station in around 22h 49m.
- Website
- southwest.com
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 2h 54m
- When
- Every day
- Estimated price
- $85–430
Flights from Orlando to Chicago Midway International Airport via Louisville
- Ave. Duration
- 4h 20m
- When
- Monday
- Estimated price
- $85–430
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Every day
- Estimated price
- $50–270
Flights from Tampa to Chicago Midway International Airport
- Ave. Duration
- 2h 48m
- When
- Every day
- Estimated price
- $95–490
Flights from Tampa to Chicago Midway International Airport via Indianapolis
- Ave. Duration
- 4h 35m
- When
- Monday
- Estimated price
- $95–490
Flights from Tampa to Chicago Midway International Airport via Nashville
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $95–490
Flights from Tampa to Chicago Midway International Airport via Columbus
- Ave. Duration
- 4h 45m
- When
- Monday, Thursday, and Friday
- Estimated price
- $100–550
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 7m
- When
- Every day
- Estimated price
- $60–310
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 3h
- When
- Every day
- Estimated price
- $140–750
Flights from Orlando to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 35m
- When
- Thursday and Friday
- Estimated price
- $150–750
Flights from Orlando to General Mitchell International Airport via Nashville
- Ave. Duration
- 4h 50m
- When
- Monday to Friday
- Estimated price
- $150–750
Flights from Orlando to General Mitchell International Airport via St. Louis
- Ave. Duration
- 4h 50m
- When
- Thursday and Friday
- Estimated price
- $160–800
- Website
- united.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 15m
- When
- Every day
- Estimated price
- $50–270
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 7m
- When
- Every day
- Estimated price
- $60–310
- Website
- aa.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $50–270
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $60–310
- Website
- flyfrontier.com
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 3h 2m
- When
- Monday, Thursday, Friday, Saturday, and Sunday
- Estimated price
- $85–430
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 22m
- When
- Every day
- Estimated price
- $50–270
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 12m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $60–310
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 3h 15m
- When
- Every day
- Estimated price
- $140–750
- Website
- allegiantair.com
Flights from Orlando Sanford to South Bend
- Ave. Duration
- 2h 34m
- When
- Every day
- Estimated price
- $110–600
- Website
- delta.com
Flights from Tampa to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 58m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $60–310
Flights from Orlando to General Mitchell International Airport via Atlanta
- Ave. Duration
- 4h 41m
- When
- Every day
- Estimated price
- $150–750
- Website
- spirit.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 10m
- When
- Every day
- Estimated price
- $85–360
Flights from Tampa to Chicago O'Hare International Airport
- Ave. Duration
- 3h 2m
- When
- Every day
- Estimated price
- $110–310
- Website
- suncountry.com
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 3h 3m
- When
- Thursday and Saturday
- Estimated price
- $140–750
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
- $370–850
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $18–45
- 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
- +1 877 733 0724
- Website
- redcoachusa.com
Bus from Orlando RedCoach Station to Atlanta - Civic Center MARTA Station
- Ave. Duration
- 7h 15m
- Frequency
- Twice daily
- Estimated price
- $28–140
- Website
- https://www.redcoachusa.com
- Web
- $28–140
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 14h 25m
- Frequency
- 3 times a day
- Estimated price
- $85–150
- Schedules at
- flixbus.com
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- Every 4 hours
- Estimated price
- $9–17
- 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 Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h
- Frequency
- 4 times a day
- Estimated price
- $120–220
- Website
- https://www.greyhound.com/
Bus from Orlando Bus Station to Tampa Bus Station
- Ave. Duration
- 2h 55m
- Frequency
- Once daily
- Estimated price
- $13–26
- 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 Orlando to Chicago, IL is 1117 miles. It takes approximately 19h 29m to drive from Orlando to Chicago, IL.
Book your Orlando to Chicago, IL train tickets online with Omio.
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