Next departures for Orlando to Chicago on November 23
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
Next departures for Orlando to Chicago on November 24
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Next departures for Orlando to Chicago on November 25
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
537-517 W. Jackson Blvd
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
Next departures for Orlando to Chicago on November 26
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Orlando Bus Station
Downtown Greyhound Station
CheapestFastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Next departures for Orlando to Chicago on November 27
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
Next departures for Orlando to Chicago on November 28
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Orlando Bus Station
Downtown Greyhound Station
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
Next departures for Orlando to Chicago on November 29
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Orlando Bus Station
Downtown Greyhound Station
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
No tags
Next departures for Orlando to Chicago on November 30
Operated by
Vehicle type
Departure time
Departure location
Trip duration
Arrival time
Arrival location
Recommended
Price and booking link
Bus
Orlando Bus Station
Chicago 95Th & Dan Ryan
Cheapest
Bus
Orlando Bus Station
Downtown Greyhound Station
Fastest
FlixBus + Greyhound Lines, Inc.
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Bus
Orlando Bus Station
Downtown Greyhound Station
No tags
Last refresh of the prices: Yesterday at 6:56 AM EST.
Compare 2 ways to go from Orlando to Chicago
We recommend taking the bus
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 2 hours 50 minutes and with fares starting at just $103, it presents an excellent value for a comfortable ride.
Flixbus is a European bus operator that offers intercity and bus travel in over 38 countries. Known for their easy-to-spot lime green buses and for offering affordable transportation between cities in Europe and the Americas, Flixbus is a good option for those looking for an affordable, reliable bus company. In their buses, you'll find free WiFi, bathrooms, and power outlets. You can also pay extra to choose your seat and get extra legroom, or even buy a snack or drink onboard directly from the driver. You can reschedule your ticket for a small fee, which varies from $1 to $5, depending on how close you are to the departure date.
According to customer reviews, there are complaints about the service provided by the bus company. Customers mention unpleasant experiences with unfriendly staff, questionable individuals at bus stops, and a lack of food options. Additionally, some customers report that their buses were cancelled without any prior notification.
Greyhound Orlando Chicago recent customer reviews
They should clean the buses better. A roach crawled on me. I was uncomfortable the whole ride.
2 out of 5 stars
Kiwaun S.
horrible cranky workers sketchy people at bus stops no food options
Frequently asked questions about traveling from Orlando to Chicago by bus
How far is Orlando from Chicago?
Orlando and Chicago are 984 miles (1587 km) apart.
What are the departure and arrival stations when taking the bus from Orlando to Chicago?
Most of the buses traveling from Orlando to Chicago leave from Orlando Bus Station and arrive at Downtown Greyhound Station. These are the most popular departure and arrival locations on this route, there are other pick-up and drop-off locations that could make it easier for you to reach your destination.
What are the best sights and things to do in Chicago?
Once in Chicago, you can start exploring the city and discover its surroundings. The top sights and things to do are Brookfield Zoo, Architectural River Cruise, The Field Museum, Lincoln Park Conservatory and Museum of Science and Industry.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
Best price found
11/21
$209
11/22
$218
Today
$227
11/24
$190
11/25
$195
11/26
$157
11/27
$140
11/28
$170
The cheapest trip from Orlando to Chicago was searched and found on Nov 27, 2025 with a price of $140
To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Orlando to Chicago, as early as possible.
You can expect to pay from $140 to $351 for a bus ticket from Orlando to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $140 which is on 2025-11-27.
Usually Greyhound, FlixBus will charge you higher prices for tickets closer to the departure date. To find the best prices, you should be flexible on your date of travel.
What's the cheapest way to go from Orlando to Chicago?
The bus is the cheapest travel choice for this destination