There are 7 ways to get from Lake Mary to Chicago by plane, bus (Flixbus, Greyhound), train (Amtrak), car, 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
5h 49m$187–421Fly Orlando to Chicago O'Hare International Airport
cheapest- Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane MCO - ORD
6h 7m$77–411Bus
- 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
26h 26m$180–315Train (Amtrak)
- Take the train from Deland to Chicago Union Stationtrain Floridian
39h 23m$903–1,504Drive 1,102.3 mi
- Drive from Lake Mary to Chicagocar 1,102.3 mi
20h 5m$202–291Fly 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 17m$112–473Fly 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
8h 9m$462–1,195
Lake Mary to Chicago by train and bus
Comparing Your Travel Options
The cheapest way to get from Lake Mary to Chicago is to fly which costs $75 - $420 and takes 6h 7m.
The fastest way to get from Lake Mary to Chicago is to fly and train which takes 5h 17m and costs $110 - $480.
No, there is no direct bus from Lake Mary to Chicago station. However, there are services departing from N Garland Ave & W Amelia St and arriving at Chicago Bus Station via Orlando Bus Station and Atlanta Bus Station. The journey, including transfers, takes approximately 26h 26m.
No, there is no direct train from Lake Mary to Chicago station. However, there are services departing from Lake Mary and arriving at Chicago Union Station via Deland. The journey, including transfers, takes approximately 39h 23m.
The distance between Lake Mary and Chicago is 1049 miles. The road distance is 1108.7 miles.
The best way to get from Lake Mary to Chicago without a car is to bus which takes 26h 26m and costs $180 - $320.
It takes approximately 5h 49m to get from Lake Mary to Chicago, including transfers.
Lake Mary to Chicago bus services, operated by Flixbus USA, depart from Orlando Bus Station.
Lake Mary to Chicago train services, operated by Amtrak, depart from Deland station.
The best way to get from Lake Mary to Chicago is to fly which takes 5h 49m and costs $180 - $430. Alternatively, you can bus, which costs $180 - $320 and takes 26h 26m, you could also train, which costs $900 - $1,500 and takes 39h 23m.
What companies run services between Lake Mary, FL, USA and Chicago, IL, USA?
Frontier Airlines, Southwest Airlines, and Allegiant Air fly from Orlando (MCO) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a train from Lake Mary to Chicago Bus Station via LYNX Central, N Garland Ave & W Amelia St, N John Young Pkwy & Business Center Blvd, Orlando Bus Station, and Atlanta Bus Station in around 26h 26m.
- Website
- southwest.com
Flights from Orlando to Chicago Midway International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $85–420
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $130–650
Flights from Orlando to General Mitchell International Airport via Chicago Midway International Airport
- Ave. Duration
- 4h 35m
- When
- Saturday, Tuesday, Wednesday, and Sunday
- Estimated price
- $130–650
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 40m
- When
- Monday to Friday
- Estimated price
- $140–700
- Website
- united.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 9m
- When
- Every day
- Estimated price
- $65–330
- Website
- allegiantair.com
Flights from Orlando to Chicago Midway International Airport via Knoxville
- Ave. Duration
- 4h 5m
- When
- Monday and Friday
- Estimated price
- $85–420
Flights from Orlando Sanford to South Bend
- Ave. Duration
- 2h 26m
- When
- Friday, Monday, Saturday, and Wednesday
- Estimated price
- $85–440
- Website
- aa.com
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 18m
- When
- Every day
- Estimated price
- $65–330
- Website
- delta.com
Flights from Orlando to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 55m
- When
- Every day
- Estimated price
- $65–330
Flights from Orlando to General Mitchell International Airport
- Ave. Duration
- 2h 46m
- When
- Saturday
- Estimated price
- $130–650
Flights from Orlando to General Mitchell International Airport via Atlanta
- Ave. Duration
- 4h 34m
- When
- Every day
- Estimated price
- $130–650
- 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
- $180–410
Flights from Orlando to Chicago O'Hare International Airport
- Ave. Duration
- 3h 13m
- When
- Every day
- Estimated price
- $70–350
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
- $130–650
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Deland to Chicago Union Station
- Ave. Duration
- 37h 56m
- 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
- $110–170
- Schedules at
- Flixbus USA
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- [email protected]
- Website
- Greyhound
Bus from Orlando Bus Station to Atlanta Bus Station
- Ave. Duration
- 10h 10m
- Frequency
- Once daily
- Estimated price
- $75–120
- Website
- Greyhound
Bus from Atlanta Bus Station to Chicago Bus Station
- Ave. Duration
- 16h
- Frequency
- 4 times a day
- Estimated price
- $120–190
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
Lake Mary to Chicago bus services, operated by Flixbus USA, arrive at Atlanta Bus Station.
Chicago is 1h behind Lake Mary. It is currently 6:40 PM in Lake Mary and 5:40 PM in Chicago.
Lake Mary to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Lake Mary to Chicago is 1109 miles. It takes approximately 20h 5m to drive from Lake Mary to Chicago.
There are 1130+ hotels available in Chicago.






