- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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The cheapest and fastest trains from Winter Park, FL to Chicago, IL
Showing times and prices for Aug 06
Cheapest price
$456
Average price
$456
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 $456 if you buy it on the day, but the cheapest tickets can be found for only $456.
Fast trains
Of the 1 trains that leave Winter Park, FL for Chicago, IL on Thu, Aug 06, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Aug 06 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 Thu, Aug 06 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.
11:07 PM38h38Winter Park, FL1:45 PMChicago, IL$4561One-way0 transfers
- 11:07 PM38h38Winter Park, FL1:45 PMChicago, IL$4561One-way0 transfers
Journey information
Overview: Train from Winter Park, FL to Chicago, IL
USAUSA
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 $248 (€202) but you can travel from only $93 (€76) by flight.
There are 1 trains per day. The earliest train runs at 12:53, 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 $93 (€76)
Distance 981 miles (1580 km) |
Average train duration 37h 29m |
Cheapest ticket price $248 (€202) |
Trains per day 3 |
Direct trains 1 |
Fastest train 38h 38m |
First train 12:53 PM |
Last train 7:07 PM |
Cheapest Month May |
Cheapest Day Fri |
High Season Jan - Mar |
Low Season Oct - Dec |
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 $93 (€76)
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, Wednesday, August 5. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 11:07 PM Winter Park, FL | 38h38 | 1:45 PM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Train companies: Amtrak from Winter Park, FL to Chicago, IL trainsAmtrak trains will get you between Winter Park, FL and Chicago, IL from $93 (€76). 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
$248 (€202)
Amtrak frequency
3 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 $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
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.
Train ticket prices from Winter Park, FL to Chicago, IL can vary. The cheapest ticket starts at $248 (€202), while the average price is around $384 (€312).
The train from Winter Park, FL to Chicago, IL takes 38h 38m and runs 3 per day.
The distance by train from Winter Park, FL to Chicago, IL is 981 miles (1580 km).
The first train from Winter Park, FL to Chicago, IL leaves at 12:53 PM.
The last train from Winter Park, FL to Chicago, IL leaves at 7:07 PM.
There is no high speed train available 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.
Unfortunately, there is no night train available from Winter Park, FL to Chicago, IL.
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 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.
Yes, you can take the train from Winter Park, FL to Chicago, IL.
Popular day trips by train from Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular train stations
Popular train stations from Winter Park, FL to Chicago, IL
Most Winter Park, FL to Chicago, IL trains use the Winter Park Station to Union Station station pair. Use this guide to compare Winter Park, FL and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Departure train stations in Winter Park
Arrival train stations in Chicago
Which Winter Park, FL station do trains to Chicago, IL leave from?
Trains from Winter Park, FL to Chicago, IL leave from Winter Park Station. The station is 0 miles (1 km) from Winter Park, FL city centre at 150 West Morse Boulevard, Winter Park, FL 32789, USA.
Winter Park Station150 West Morse Boulevard, Winter Park, FL 32789, USA+1 800-872-7245
City-centre transport
Getting to Winter Park Station from Winter Park city centre
Winter Park Station is 1 km from Winter Park city centre. Public transport options include:
Bus43 · 4m · $2 · every ~2 min
Winter Park Station train station facilities and services
Winter Park Station has practical services for this route, including Lockers, Parking, Dining, Taxis, Accessibility, WC, Hotel, Ticket Office, Information Desk, and Luggage Carts.
Food and drink
Food options include: Bosphorous Turkish Cuisine, Prato
Tickets and information
Ticket office support is available at Winter Park Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Winter Park Station.
Parking, taxis and toilets
Available at Winter Park Station: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Winter Park Station.
Shops, hotels and contact
Nearby hotels include The Alfond Inn, Park Plaza Hotel.
Which Chicago, IL station do trains from Winter Park, FL arrive at?
Trains from Winter Park, FL to Chicago, IL arrive at Union Station. Union Station is 1 miles (3 km) from Chicago, IL city centre.
Union Station225 South Canal Street, Chicago, IL 60606, USA+1 800-872-7245
City-centre transport
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · $4 · every ~13 min
Union Station train station facilities and services
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food and drink
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Wi-Fi and ATMs
Free. ATMs are available in the train station.
Tickets and information
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Union Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Union Station: Parking, Taxis, WC.
Bike and car services
Available at Union Station: Bike Parking, Car Rental.
Accessibility
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Shops, hotels and contact
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Most popular train connections from Winter Park, FL
More options for your journey from Winter Park, FL to Chicago, IL
Here are some other resources that might have the information you need
Most popular trains to and from Chicago, IL and Winter Park, FL
Most popular train connections to Chicago, IL
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