Winter Park, FL to Chicago, IL train with Amtrak

Fri, Dec 19
+ Add return
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1,000+ travel companies
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The cheapest and fastest trains from Winter Park, FL to Chicago, IL

Showing times and prices for Dec 23

Cheapest price

$255

Average price

$255

Fastest journey

1 d 14 h 38 m

Average duration

1 d 14 h 38 m

Trains per day

1

Distance

1580 km

Cheap tickets

The best way to find a cheap train ticket from Winter Park, FL to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.

The average ticket from Winter Park, FL to Chicago, IL will cost around $255 if you buy it on the day, but the cheapest tickets can be found for only $255.

Fast trains

Of the 1 trains that leave Winter Park, FL for Chicago, IL on Tue, Dec 23, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.

On Tue, Dec 23 the direct trains cover the 1580 km distance in an average of 1 d 14 h 38 m but if you time it right, some trains will get you there in just 1 d 14 h 38 m .

On Tue, Dec 23 the slowest trains will take 1 d 14 h 38 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

Amtrak
11:07PM38h38
Winter Park, FL
01:45PMChicago, IL
$2551One-way
0 transfers

Travel Information

Compare train, bus, and flight for Winter Park, FL to Chicago, IL

Omio recommends booking the train as it is the most popular option from Winter Park, FL to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from €100. For those with little time consider booking a flight which can get you there in 11h 28m. The ticket price range depends on the travel mode: a flight costs an average of €100, and a train costs an average of €204.

Distance: 981 miles (1580 km)

Compare train with

Most popular
Train
Flight
Bus

€204

Average price

€100

Average price

Cheapest

€161

Average price

37h 59m

Average total duration

37h 29m

Onboard

+

30m

Additional time*

14h 28m

Average total duration

Fastest

11h 28m

Onboard

+

3h 0m

Additional time*

26h 0m

Average total duration

25h 30m

Onboard

+

30m

Additional time*

Direct Options

Direct Options

Direct Options

Live departures

Winter Park, FL to Chicago, IL train times

The table below shows live departures for Winter Park, FL to Chicago, IL trains for today, Monday, December 22. You can also manually refresh the results below to see updated train journeys.

Last updated at 1:59 AM
ProviderDepartsDurationArrivesTransfers
Tickets
amtrak7:07 PM Winter Park, FL
37h38
8:45 AM Chicago, IL0 transfersDirect

This is the last train of the day.

Find all the dates and times for this journey

Compare prices and tickets Winter Park, FL to Chicago, IL by train, bus, or flight

Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.

Tue
Dec 23
Wed
Dec 24
Thu
Dec 25
Fri
Dec 26
Sat
Dec 27
Sun
Dec 28
Mon
Dec 29

Why should you book Winter Park to Chicago trains with Omio?

Amtrak operates all train services from Winter Park to Chicago. Omio is the only official third party seller for Amtrak tickets.

Why book with Omio vs Amtrak?

  • Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
  • Compare all your options: Omio allows you to compare Amtrak with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Winter Park to Chicago.

Why book with Omio over Trainline and Rail Europe?

Multiple modes of transport
  • Official reseller: Amtrak tickets can only be bought on Omio or Amtrak's website as Omio is the only official third party seller for Amtrak tickets. Trainline, RailEurope, and Rail.Ninja do not sell Amtrak tickets as they are not official sellers.
  • Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Winter Park to Chicago.

Journey information

Overview: Train from Winter Park, FL to Chicago, IL

USAUSA
USAUSA
Icon of train

Trains from Winter Park, FL to Chicago, IL run on average 3 times per day, taking around 37h 29m. Cheap train tickets for this journey start at $255 (€204) but you can travel from only $125 (€100) by flight.

There are 1 trains per day. The earliest train runs at 13:53, the last at 19:07. The fastest train covers the 981 miles (1580 km) distance in 38h 38m.

Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $125 (€100)
Distance
981 miles (1580 km)
Average train duration
37h 29m
Cheapest ticket price
$255 (€204)
Trains per day
3
Direct trains
1
Fastest train
38h 38m
First train
13:53
Last train
19:07
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $125 (€100)

Train companies: Amtrak from Winter Park, FL to Chicago, IL trainsAmtrak trains will get you between Winter Park, FL and Chicago, IL from $125 (€100). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.

Amtrak

About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Duration
38h 38m
Cheapest Price
$255 (€204)
Amtrak frequency
1 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone

FAQs: Trains from Winter Park, FL to Chicago, IL

Find answers to the most common questions about traveling from Winter Park, FL to Chicago, IL by train. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

FAQs
To fully experience Chicago, IL, plan for at least 3-4 days to visit key attractions such as Millennium Park, The Art Institute of Chicago, Navy Pier, and explore diverse neighborhoods.
A day trip from Winter Park, FL to Chicago, IL is not feasible as the journey takes 38h 38m and covers 981 miles (1580 km). Trains run 3 times per day.
The distance by train from Winter Park, FL to Chicago, IL is 981 miles (1580 km).
The train journey from Winter Park, FL to Chicago, IL offers a mix of scenic views, including lush Florida landscapes, charming small towns, and stretches of the Appalachian foothills, providing a diverse and visually interesting experience.
In Chicago, IL, you can explore the Museum of Science and Industry and its interactive exhibits, enjoy the vibrant neighborhoods like Wicker Park and Lincoln Park, take a river cruise to view iconic architecture, and attend a live performance at the historic Chicago Theatre. Visit Lincoln Park Zoo for a free and enjoyable day. For sights, don't miss Millennium Park with its modern art, the renowned Art Institute of Chicago, the entertainment hub of Navy Pier, panoramic views from Willis Tower Skydeck, and the fascinating exhibits at the Field Museum.
The train station in Winter Park, FL that goes to Chicago, IL is Winter Park Station, Winter Park, FL, which connects to Chicago Union Station, Chicago, IL.
The train from Winter Park, FL to Chicago, IL takes 38h 38m and runs 3 per day.
Train ticket prices from Winter Park, FL to Chicago, IL can vary. The cheapest ticket starts at $255 (€204), while the average price is around $255 (€204).
The last train from Winter Park, FL to Chicago, IL leaves at 7:07 PM.
The cheapest way to get from Winter Park, FL to Chicago, IL is by flight, with a cost of around $125 (€100).
There is no high speed train available from Winter Park, FL to Chicago, IL.
Unfortunately, there is no night train available from Winter Park, FL to Chicago, IL.
The first train from Winter Park, FL to Chicago, IL leaves at 1:53 PM.
Yes, you can take the train from Winter Park, FL to Chicago, IL.
Yes, there is a direct train from Winter Park, FL to Chicago, IL. This service operates 1 times per day, provided by Amtrak.

popular train stations

Popular train stations from Winter Park, FL to Chicago, IL

Winter Park
Chicago
The major train station for departures in Winter Park is Winter Park Station. Find all the information you need to know about services, amenities and connections at Winter Park Station for your trip from Winter Park to Chicago.
Winter Park StationLockersParkingDiningTaxisAccessibilityWCHotelTicket OfficeInformation DeskLuggage Carts
Amenities at train station
LockersLockers
ParkingParking
DiningDining
TaxisTaxis
AccessibilityAccessibility
WCWC
HotelHotel
Ticket OfficeTicket Office
Information DeskInformation Desk
Luggage CartsLuggage Carts
information
phone
Phone Number
ticketOfficeHours
Ticket Office Hours
  • 6:00 AM - 10:00 PM Monday - Sunday
ticketOfficeHours
Distance to city center
1 km
platformCount
Number of platforms
2
Parking
Parking
  • Parking is available at the station.
Dining
Dining
  • Bosphorous Turkish Cuisine
  • Prato
Taxis
Taxis
  • Outside the main entrance.
Hotel
Hotel
  • The Alfond Inn
  • Park Plaza Hotel
Information Desk
Information Desk
  • Located in the main hall
Luggage Carts
Luggage Carts
  • Free
Station Plan
  • The station has a main hall with ticketing and waiting areas.
Public transit options for Winter Park Station
  • SunRail
  • Lynx Bus connections available

More options for your journey from Winter Park, FL to Chicago, IL

Here are some other resources that might have the information you need

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