How long does it take to get from Middletown to Chicago?

On average, it usually takes about 2 days 13 hours 20 minutes to get from Middletown to Chicago by bus. Weather and traffic patterns on the way to Chicago may cause unexpected delays. Plan ahead and book early to avoid a later-than-anticipated arrival.

How many buses are there from Middletown to Chicago?

There are currently 2 daily trips from Middletown to Chicago. You can plan on the trip taking about 2 days 13 hours 20 minutes. You can buy your ticket to Chicago on your website.

How early should I arrive at Middletown?

Arrive at the Middletown terminal half an hour before your departure to Chicago to guarantee fast, convenient boarding. About two hours before your bus leaves, there will be a special check-in link in your email. For smooth boarding, have your mobile pass ready to show your driver as you enter the bus to Chicago.

What is the average cost of the trip?

We have routes to Chicago costing as little as $560.56. Ticket prices from Middletown typical cost about $560.56. Compare different routes to find the time and fare that works for you.

What bus companies offer services?

This carrier offers our passengers additional options for bus tickets between Middletown and Chicago: Adirondack Trailways. With a low starting price of $560.56 to $560.56, tickets are affordable for any budget.

How long does it take?

Trailways averages about 2 days 13 hours 20 minutes to get from Middletown to Chicago. While we endeavor to arrive at the expected time, occasionally traffic increases travel time. Consider the possibility of unexpected delays when making your travel plans.

What if my question isn't listed?

Do you have additional questions about booking a trip from Middletown to Chicago? We offer customer support from 7 AM to 10 PM every day, including weekends. Or, if you prefer, go to our Customer Care page to send us a message.

View Current Travel Advisories

Trailways Bus Tickets
from Middletown, NY to Chicago, IL

Travel made simple with Trailways

Unbeatable Prices

One of the best inventories of bus tickets in one place - with exclusive fares you won't find elsewhere.

Proven Reliability

On-time travel services - trust our reputation for reliable bus transportation.

Comfort and Convenience

Numerous upgraded buses with large leather recliners, free wi-fi, and power outlets for each seat.

Overview

About buses from Middletown, NY to Chicago, IL

Buses from Middletown, NY to Chicago, IL travel the 1657mi (2666.68km) journey, taking approximately 2d, 13h, 20m. Usually, there are 2 buses operating per day. While the average ticket price for this journey is around $560.56, you can find the cheapest bus tickets for as low as $560.56.

Distance
1657mi (2666.68km)
Average trip duration
2 days 13 hours 20 minutes
Average bus ticket price
$560.56
Trips per day
2
Top Carriers
Adirondack Trailways

Bus Station Information for Chicago, IL

Chicago (95th & Dan Ryan)

Chicago, IL 60628

Curbside Stop

Address: 95th & Dan Ryan
Chicago, IL 60628

Phone Number

(800) 858-8555

More Details

Chicago (Cumberland Avenue)

Chicago, IL 60631

Curbside Stop

Address: 5800 N Cumberland Ave
Chicago, IL 60631

Phone Number

(800) 858-8555

More Details

Chicago (Bus Station)

Chicago, IL 60607

24 Hours

Bus Station

Address: 630 West Harrison Street
Chicago, IL 60607

Phone Number

(800) 858-8555

More Details

Chicago (Amtrak Union Station)

Chicago, IL 60606

Curbside Stop

Address: 225 S. Canal St.
Chicago, IL 60606

Phone Number

(800) 858-8555

More Details

City InformationforMiddletown, NY

Set your sights on Middletown, NY, where small-town charm meets an array of memorable experiences. A bus to Middletown will drop you into a world rich with history and unique local flavor. Begin your journey with a visit to the Galleria at Crystal Run, a shopping haven perfect for snagging that "just-because" gift. History enthusiasts won't want to miss Thrall Library, a beautiful building brimming with local stories and architectural interest.

Nature lovers, get ready to head outdoors. Fancher-Davidge Park is ideal for a peaceful hike or a lakeside picnic, while adrenaline junkies can opt for zip-lining at Tuxedo Ridge. Don’t leave without exploring the local arts scene; the Middletown Arts Center showcases engaging exhibitions that spotlight community talents and creativity.

Hungry? Local diners and eateries promise comfort food that hits the spot. The town’s down-to-earth vibe and friendly faces will make you feel right at home. Booking a bus to Middletown, NY, isn’t just the start of a trip; it’s the beginning of your next great adventure.

City InformationforChicago, IL

There’s so much to see in the Windy City, you’ll be booking your next bus to Chicago before your trip is over. No matter the season, there’s plenty to do, from lounging on lakeside beaches in the summer to ice skating in Millennium Park.

Chicago’s famous for its dogs and its deep dish, if you’re looking for eats. Museums dot the map, including The Art Institute of Chicago, Field Museum, and Griffin Museum of Science and Industry. Catch a game if your sport’s in season – Bulls or Bears, Cubs or White Sox.

If you ask a local – which we always do – an Architecture Tour is on the don’t miss list. And if you’re on a budget, just go for a stroll on the Riverwalk, Navy Pier, or by “the bean” - Millennium Park’s famed Cloud Gate sculpture.

Whatever mood strikes you, Chi-town's got something to keep you busy.

Frequently Asked Questions about the Bus Ride

Reach Chicago easily by bus from Middletown. We have 2 trips starting at $560.56 with an average travel time of 2 days 13 hours 20 minutes. Take a convenient and affordable bus trip to Chicago today!

How long does it take to get from Middletown to Chicago?
How many buses are there from Middletown to Chicago?
How early should I arrive at Middletown?
What is the average cost of the trip?
What bus companies offer services?
How long does it take?
What if my question isn't listed?

Trailways Bus Tickets
from Middletown, NY to Chicago, IL