- 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.
Omio recommends booking the bus as it is the most popular option from Highland Park, MI to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $44. For those with little time consider booking a flight which can get you there in 1h 29m. The ticket price range depends on the travel mode: a bus costs an average of $44, and a flight costs an average of $421.
Distance: 236 miles (380 km)
| Train | Most popular Bus | Flight | Driving |
|---|---|---|---|
$50 Average price | $44 Average price Cheapest | $421 Average price | $19 Average price (fuel + tolls) |
5h 59m Average total duration 5h 29m Onboard + 30m Additional time* | 5h 57m Average total duration 5h 27m Onboard + 30m Additional time* | 4h 29m Average total duration Fastest 1h 29m Onboard + 3h 0m Additional time* | 4h 12m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Highland Park, MI to Chicago, IL:
A bus is $6 (€5) less than a train for this route with tickets for a train from Highland Park, MI to Chicago, IL costing on average $50 (€41).
A bus is $378 (€309) less than a flight for this route with tickets for a flight from Highland Park, MI to Chicago, IL costing on average $421 (€345).
Other travel options to Chicago, IL take longer:
Bus takes on average 5h 27m.
Train takes on average 5h 29m.
Tickets start at around $50 (€41) compared to roughly $19 (€15) in fuel and tolls — a saving of about $-30.72 (€-25.16). The journey takes 5h 29m versus 4h 12m 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.
Compare bus, train, 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.
Trains from Highland Park, MI to Chicago, IL run on average 4 times per day, taking around 5h 29m. Cheap train tickets for this journey start at $50 (€41) but you can travel from only $44 (€36) by bus.
There are 4 trains per day. The earliest train runs at 21:11, the last at 21:11. The fastest train covers the 236 miles (380 km) distance in 5h 29m.
Distance 236 miles (380 km) |
Average train duration 5h 29m |
Cheapest ticket price $50 (€41) |
Trains per day 4 |
Direct trains 4 |
Fastest train 5h 29m |
First train 9:11 PM |
Last train 9:11 PM |
Cheapest Month Jan |
Cheapest Day Sat |
High Season Jul - Sep |
Low Season Jan - Mar |
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
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.
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.
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.
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
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.
Find answers to the most common questions about traveling from Highland Park, MI 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.

Most Highland Park, MI to Chicago, IL trains use the Royal Oak Station to Union Station station pair. Use this guide to compare Highland Park, MI and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Union Station is 3 km from Chicago city centre. Public transport options include:
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 options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
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