- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
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The cheapest and fastest trains from Winter Park, FL to Chicago, IL
Showing times and prices for Jun 21
Cheapest price
$525
Average price
$525
Fastest journey
1 d 13 h 38 m
Average duration
1 d 13 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 $525 if you buy it on the day, but the cheapest tickets can be found for only $525.
Fast trains
Of the 1 trains that leave Winter Park, FL for Chicago, IL on Sun, Jun 21, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sun, Jun 21 the direct trains cover the 1580 km distance in an average of 1 d 13 h 38 m but if you time it right, some trains will get you there in just 1 d 13 h 38 m .
On Sun, Jun 21 the slowest trains will take 1 d 13 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.
7:07 PM37h38Winter Park, FL8:45 AMChicago, IL$5251One-way0 transfers
- 7:07 PM37h38Winter Park, FL8:45 AMChicago, IL$5251One-way0 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 $93. For those with little time consider booking a flight which can get you there in 5h 15m. The ticket price range depends on the travel mode: a flight costs an average of $93, and a train costs an average of $247.
Distance: 981 miles (1580 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$382 Average price | $127 Average price Cheapest | $186 Average price | $226 Average price (fuel + tolls) |
37h 59m Average total duration 37h 29m Onboard + 30m Additional time* | 8h 15m Average total duration Fastest 5h 15m Onboard + 3h 0m Additional time* | 27h 21m Average total duration 26h 51m Onboard + 30m Additional time* | 16h 59m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Winter Park, FL to Chicago, IL is a flight with an average price of $127 (€104).
This is compared to other travel options from Winter Park, FL to Chicago, IL:
A flight is $58 (€48) less than a bus for this route with tickets for a bus from Winter Park, FL to Chicago, IL costing on average $186 (€152).
A flight is $254 (€208) less than a train for this route with tickets for a train from Winter Park, FL to Chicago, IL costing on average $382 (€312).
The fastest way to travel from Winter Park, FL to Chicago, IL is by flight with an average journey time of 5h 15m.
Other travel options to Chicago, IL take longer:
Bus takes on average 26h 51m.
Train takes on average 37h 29m.
It's helpful to compare your options as there are 3 ways to travel between Winter Park, FL and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Winter Park, FL to Chicago, IL among Omio's users.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.
Tickets start at around $382 (€312) compared to roughly $226 (€185) in fuel and tolls — a saving of about $-155.92 (€-127.61). The journey takes 37h 29m versus 16h 59m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
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 tomorrow, Sunday, June 21. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 7:07 PM Winter Park, FL | 37h38 | 8:45 AM Chicago, IL | 0 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.
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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 $247 (€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 $247 (€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)
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
$247 (€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
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
- Must visit
Millennium Park
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
- Must visit
The Magnificent Mile
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
- Must visit
Chicago Riverwalk
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 20-40 per person at a mid-range restaurant.
- Fine dining
- USD 75+ per person before drinks and tax.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
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 $247 (€202), while the average price is around $382 (€312).
The train from Winter Park, FL to Chicago, IL takes 38h 38m and runs 3 per day.
The first train from Winter Park, FL to Chicago, IL leaves at 12:53 PM.
The distance by train from Winter Park, FL to Chicago, IL is 981 miles (1580 km).
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 cheapest way to get from Winter Park, FL to Chicago, IL is by flight, with a cost of around $93 (€76).
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.
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.
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.
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.
Yes, you can take the train from Winter Park, FL to Chicago, IL.
Since neither Winter Park, FL nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
Popular day trips by train from Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
We recommend using the train as it is the most popular way to get from Winter Park, FL to Chicago, IL among Omio's users.
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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