- Must visit
The Art Institute Of Chicago
One of the premier art museums in the United States, known for its Impressionist masterpieces, modern works, and iconic collections in a landmark downtown building.
Cheapest price
$64
Average price
$64
Fastest journey
5 h 40 m
Average duration
5 h 40 m
Buses per day
1
Distance
440 km
The best way to find a cheap bus ticket from Douglass Hills, KY 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 Douglass Hills, KY to Chicago, IL will cost around $64 if you buy it on the day, but the cheapest tickets can be found for only $64.
Of the 1 buses that leave Douglass Hills, KY for Chicago, IL on Wed, May 27, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 27 the direct buses cover the 440 km distance in an average of 5 h 40 m but if you time it right, some buses will get you there in just 5 h 40 m .
On Wed, May 27 the slowest buses will take 5 h 40 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.


Omio recommends booking the flight as it is the most popular option from Douglass Hills, KY to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $64. For those with little time consider booking a flight which can get you there in 1h 44m. The ticket price range depends on the travel mode: a bus costs an average of $64, and a flight costs an average of $380.
Distance: 273 miles (440 km)
| Bus | Most popular Flight | Driving |
|---|---|---|
$64 Average price Cheapest | $380 Average price | $12 Average price (fuel + tolls) |
6h 10m Average total duration 5h 40m Onboard + 30m Additional time* | 4h 44m Average total duration Fastest 1h 44m Onboard + 3h 0m Additional time* | 4h 40m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Douglass Hills, KY to Chicago, IL:
A bus is $316 (€255) less than a flight for this route with tickets for a flight from Douglass Hills, KY to Chicago, IL costing on average $380 (€307).
Other travel options to Chicago, IL take longer:
Bus takes on average 5h 40m.
You'll arrive about {timeSavings} sooner ({durationInMinutes} by bus vs {drivingDurationInMinutes} by car) and save roughly {savingsAmount} compared to fuel and tolls ({cheapestPrice} vs {drivingPriceInCents}). You also skip the drive itself — no traffic stress, no parking, and you can use the time to work, nap, or catch up on a series with the onboard Wi-Fi.
Direct coaches are operated by {directProviders}.
Driving is still worth considering if you're travelling with bulky luggage, need flexibility on departure times, or plan to stop along the way.
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Transit Authority of River City | Departure Time 07:04PM | Arrival Time 08:00AM | Duration 12h56 | Departure days Sun | Cheapest price $64 |
Operator Transit Authority of River City | Departure Time 10:44PM | Arrival Time 08:00AM | Duration 9h16 | Departure days Mon, Tue, Thu, Sat | Cheapest price $64 |
Operator FlixBus | Departure Time 11:30PM | Arrival Time 05:10AM | Duration 5h40 | Departure days Wed | Cheapest price $64 |
The table below shows live departures for Douglass Hills, KY to Chicago, IL buses for today, Tuesday, May 26. You can also manually refresh the results below to see updated bus journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 10:44 PM Douglass Hills, KY | 9h16 | 8:00 AM Chicago, IL | 3 transfers | |
This is the last bus of the day. | |||||
Find all the dates and times for this journey
Compare 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.
Buses from Douglass Hills, KY to Chicago, IL run on average 8 times per day, taking around 5h 40m. Cheap bus tickets for this journey start at $64 (€52) if you book in advance.
There are 8 buses per day. The earliest bus runs at 23:30, the last at 23:30. The fastest bus covers the 273 miles (440 km) distance in 5h 40m.
Distance 273 miles (440 km) |
Average bus duration 5h 40m |
Cheapest ticket price $64 (€52) |
Buses per day 8 |
Direct buses 8 |
Fastest bus 5h 40m |
First bus 11:30 PM |
Last bus 11:30 PM |
Cheapest Month May |
Cheapest Day Tue |
High Season Jan - Mar |
Low Season Apr - Jun |
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 United States, known for its Impressionist masterpieces, modern works, and iconic collections in a landmark downtown building.
A world-class natural history museum famous for its dinosaur fossils, ancient cultures, and major scientific collections, including the celebrated T. rex specimen SUE.
A large interactive science museum in Hyde Park with hands-on exhibits, transportation displays, and family-friendly experiences in a grand historic building.
Chicago’s signature downtown park combines major public art, gardens, and event spaces, making it one of the city’s essential first stops for visitors.
The city’s best-known stretch of Michigan Avenue is lined with landmark buildings, shops, and hotels, and serves as a central walking route for first-time visitors.
A highly popular waterfront promenade with excellent architecture views, bridges, and easy access to boat tours. It is one of the city’s most scenic urban walks.
Chicago’s iconic thick, buttery-crust pizza baked in a deep pan with layers of cheese, toppings, and chunky tomato sauce.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, relish, tomato, pickle spear, sport peppers, and celery salt.
Thin-sliced seasoned roast beef served on a long roll, often dipped in jus and topped with sweet peppers or giardiniera.
A celebrated West Loop restaurant with bold small plates, creative flavors, and a vibrant, modern atmosphere.
Chicago’s internationally renowned fine-dining destination known for highly creative tasting menus and theatrical presentation.
A classic Chicago pizzeria famous for buttery-crust deep-dish pizza and a relaxed, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is reasonable, but hotels, parking, and fine dining add up fast.
Tip 18-20% at restaurants; 20%+ for great service. Bars: USD 1-2 per drink. Taxis/rideshares: 10-15%. Hotels: USD 2-5 for housekeeping; USD 1-2 per bag.
Find answers to the most common questions about traveling from Douglass Hills, KY to Chicago, IL by bus. 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 bus, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

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