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Orlando, FL, USA to Chicago, IL, USA from $44: 8 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Orlando, United States of America
to
Chicago, United States of America

How to Get from Orlando to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$44 - PlaneBest price
1596 kmDistance
4h 27m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Orlando to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Average Duration
4h  27m
Estimated price
$44-387
Recommended
route map
Distance: 1596 km
Duration: 4h 27m

See more options

Company
various
Bus
Plane
Average Duration
7h  34m
Estimated price
$47-381
Company
various
Plane
Average Duration
4h  58m
Estimated price
$49-287
Company
various
Bus
Plane
Average Duration
7h  6m
Estimated price
$62-391
Company
Greyhound
Bus
Average Duration
24h  25m
Estimated price
$91-440
Company
Palmland
Bus
Average Duration
32h  5m
Estimated price
$441-442
Company
Amtrak
Train
Average Duration
41h  59m
Estimated price
$443-444
Company
various
Drive
Average Duration
18h  59m
Estimated price
$445-446
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Traveling From Orlando to Chicago

The journey from Orlando to Chicago offers a striking contrast between Orlando's sunny theme parks and warm beaches, and Chicago's vibrant city life filled with architecture, deep-dish pizza, and diverse cultural scenes.

Best Neighborhoods in Chicago

Chicago's neighborhoods each offer unique flavors and experiences for visitors.

Lincoln Park
• Home to the Lincoln Park Zoo, free entry.
• Scenic parks and beaches along Lake Michigan.
Wicker Park
• Trendy boutiques and vibrant street art abound.
• Enjoy diverse dining options and live music.
Magnificent Mile
• Premier shopping destination with luxury brands.
• Iconic skyscrapers provide stunning city views.

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can elevate your experience.

The Art Institute of Chicago
Visit early in the morning on weekdays for fewer crowds and a more intimate experience with the art.
Millennium Park
Go during weekdays in the early afternoon to enjoy the park and group activities without overwhelming crowds.
Willis Tower Skydeck
Aim for late afternoon visits to catch stunning views during sunset and avoid peak tourist times.

Chicago Weather: What to Expect Year-Round

Chicago experiences a humid continental climate, bringing cold winters and warm summers that can impact your travel plans. The best times to visit are typically spring and fall, when the weather is milder and more enjoyable for exploring the city.

Dining Recommendation in Chicago

Try the iconic deep-dish pizza at Lou Malnati's, where the rich, buttery crust and savory layers of cheese and toppings create a hearty contrast to the lighter fare often found in Orlando. This dining experience in Chicago invites you to savor bold, local flavors in a cozy environment that celebrates the city’s culinary heritage.

Orlando - Chicago operators

Explore transport companies operating between Orlando and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights
Website
southwest.com

Plane from Orlando (MCO) to Chicago Midway (MDW)

Average Duration
2h 52m
Estimated price
$3875-3876

Plane from Orlando (MCO) to Chicago O'Hare (ORD)

Average Duration
3h 8m
Estimated price
$2872-2873
Website
flyfrontier.com

Plane from Orlando (MCO) to Chicago Midway (MDW)

Average Duration
3h 1m
Estimated price
$449-494

Plane from Orlando (MCO) to Chicago O'Hare (ORD)

Average Duration
3h 17m
Estimated price
$497-498
Website
delta.com

Plane from Orlando (MCO) to Chicago Midway (MDW)

Average Duration
4h 26m
Estimated price
$3878-440

Plane from Tampa (TPA) to Chicago O'Hare (ORD)

Average Duration
4h 47m
Estimated price
$2870-2871
Train Show train routes
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Orlando to Alexandria

Average Duration
17h 18m
Estimated price
$495-2875

Train from Alexandria to Chicago Union Station

Average Duration
23h 41m
Estimated price
$495-620
Bus Show bus routes
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Orlando Bus Station to Atlanta Bus Station

Average Duration
7h 15m
Estimated price
$447-3875

Bus from Atlanta Bus Station to Chicago Bus Station

Average Duration
16h 10m
Estimated price
$623-3879
Contact phone
+1 (855) 626-8585
Website
flixbus.com

Bus from Orlando Bus Station to Atlanta Bus Station

Average Duration
8h 15m
Estimated price
$495-2870

Bus from Orlando Bus Station to West Palm Beach Bus Station

Average Duration
3h
Estimated price
$622-2877
all-pages.other Show other routes
Website
palmlandlines.com

Other from West Palm Beach FL to Chicago IL

Average Duration
27h 20m
Estimated price
$623-2874

Orlando to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Orlando and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Orlando to Chicago spanning 1159 miles, offering a diverse landscape experience from the sunny shores of Florida to the urban bustle of the Windy City. 💰 Prices for this adventure by car range from $210 to $310, providing budget-friendly flexibility to travelers seeking a cost-effective journey towards the iconic skyline of Chicago. 🌆 After an 18-hour drive, immerse yourself in the vibrant culture, renowned architecture, and deep-dish pizza delights that await in the lively city of Chicago, making this road trip an unforgettable experience.
Average price
$210 - $310
🛤️ The approximately 41-hour adventure will take you through 1,673 miles of stunning landscapes and vibrant cities. With Amtrak as your operator, sit back, relax, and experience the unique charm of train travel. 💰 Prices for the Orlando to Chicago train ticket range from $73 to $548, offering options for every budget.
Departure Point
Orlando station
Arrival Point
Chicago Union Station
Useful tips for train travellers
• On your train trip from Orlando to Chicago, consider Amtrak as your main operator. They offer a Café Car with a selection of meals and snacks available for purchase, including breakfast options in the morning and pre-packaged meals later in the day. Don't miss their seasonal menu items for a special treat!
• Amtrak's long-distance service provides several seating options: Coach Class, which is budget-friendly, typically has reclining seats with plenty of legroom; Business Class offers more spacious seating and complimentary non-alcoholic beverages; and First Class, which is available on some trains, features even wider seats with enhanced dining services. If you're looking for comfort, opt for Business or First Class for greater amenities.
• Upon arriving at Chicago Union Station, know that you can leave your luggage at the Amtrak Baggage Claim area for a small fee, allowing you to explore the city unencumbered. Restrooms are readily available, but note that showers are not provided. If you want to grab a quick bite or a coffee before heading out, the station has several food vendors inside.
🛫 Planning a trip from Orlando to Chicago? Take a direct flight from Orlando Airport to Chicago Midway Airport, which only takes 2 hours and 45 minutes with Frontier Airlines, Delta, or Southwest Airlines. 🌆 Once you arrive in Chicago, you can explore the city's famous attractions like Millennium Park, the Art Institute of Chicago, and Navy Pier. The flight from Orlando to Chicago typically takes around 4 hours and 27 minutes, offering plenty of time to relax and enjoy the journey.
Departure Point
Orlando Airport
Arrival Point
Chicago Midway Airport
🚌 The journey from Orlando to Chicago by bus involves a transfer at Atlanta Bus Station and takes approximately 24 hours and 25 minutes. Greyhound USA operates the bus services for this route. 🛣️ Route option 1 covers a distance of 1,145 miles with 2 transfers: Orlando to Atlanta, Atlanta to Nashville, and finally, Nashville to Chicago. The total journey time is about 1 day and 1 hour. 🗺️ Route option 2 spans 1,155 miles with 2 transfers: Orlando to Atlanta, Atlanta to Cleveland, and then Cleveland to Chicago Amtrak. The total travel time for this route is around 1 day and 4 hours.
Departure Point
Orlando Bus Station
Arrival Point
Chicago Bus Station
Useful tips for bus travellers
• Plan for potential delays during your journey as transfers at Atlanta Bus Station can be tight; check the Greyhound schedule regularly for any updates at greyhound.com
• If you're taking the second route via Cleveland, bring snacks and entertainment, as the lengthy 9-hour and 20-minute leg of the trip on the Atlanta to Cleveland bus can feel long; ensure you download your favorite movies or playlists in advance.
• Upon arriving at Chicago Bus Station, familiarize yourself with the layout by reviewing the station map on the Greyhound website, and consider using public transit options like the Chicago Transit Authority (CTA) for easy access to the downtown area: transitchicago.com

Frequently asked questions

Find out more about the route from Orlando to Chicago.

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The distance between Orlando and Chicago is approximately 992 miles. The typical travel times vary depending on the mode of transportation. By train, it takes about 41 hours and 59 minutes to travel from Orlando to Chicago. By bus and plane combination, it takes around 6 hours and 58 minutes, while by plane alone, it takes about 4 hours and 27 minutes. Finally, by car, it takes approximately 18 hours and 59 minutes, and by bus, it takes around 23 hours and 7 minutes to travel from Orlando to Chicago.
The most cost-effective and time-efficient option for traveling from Orlando to Chicago is to fly. Flying typically costs between $35 and $250 and takes approximately 4 hours and 57 minutes. However, if time is of the utmost importance, the quickest option is also to fly, which takes about 4 hours and 27 minutes but may cost between $40 and $390. Taking a flight allows for a direct journey and minimizes travel time compared to other modes of transportation.
The prices for a train ticket between Orlando and Chicago can range from $73 to $548, depending on factors such as the class of service and how far in advance you book. Similarly, the prices for a bus ticket between Chicago and Orlando can vary from $68 to $151. It is recommended to check different providers and websites to find the best deals and compare prices before making a reservation.
To get from Orlando to Chicago without using public transportation, you can drive the distance of approximately 1159 miles. The journey takes approximately 18 hours and 59 minutes by car. The cost for a one-way trip can vary from $210 to $310, depending on factors such as gas prices and tolls.
To travel from Orlando to Chicago without a car, the best option is to take a bus. The bus journey takes approximately 23 hours and 7 minutes and costs between $65 and $160. Alternatively, you can choose to fly which takes around 4 hours and 27 minutes with prices ranging from $40 to $390. Another possibility is to take a train, however, this option takes the longest at 41 hours and 59 minutes with costs varying from $70 to $550.
There is no direct train from Orlando to Chicago, but there are train services available with transfers that take approximately 41 hours and 59 minutes. The train route includes a transfer at Alexandria. Additionally, there is no direct bus connection between the two cities, but there are bus services that take approximately 25 hours and 50 minutes with transfers via Atlanta. The bus services are operated by Flixbus USA and arrive at Chicago Bus Station.
The flight between Orlando and Chicago typically takes around 2 hours and 40 minutes on a direct flight. However, it's important to note that flight durations can vary depending on factors such as weather conditions and air traffic. In terms of cost, the prices for flights between Chicago and Orlando can range from $44 to $387, depending on factors such as the time of year, airline, and how far in advance you book your ticket.
There are plenty of options for accommodations near Chicago, with over 1116 hotels available. The prices for these hotels start at $58 per night. Whether you're looking for a budget-friendly stay or a luxury experience, there are options to suit every traveler's preference in Chicago.

Trips from Orlando

Trips to Chicago