View Current Travel Advisories

Trailways Bus Tickets
from Lee, MA to Chicago, IL

Choose one way or round trip:
(*) indicates a required field
Type the date in date format 2 digit month slash 2 digit day slash 4 digit year or press tab to use the date picker pop up calendar

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 Lee, MA to Chicago, IL

Buses from Lee, MA to Chicago, IL travel the 746mi (1200.57km) journey, taking approximately 1d, 2h, 15m. Usually, there are 4 buses operating per day. While the average ticket price for this journey is around $161.93, you can find the cheapest bus tickets for as low as $161.93.

  • Distance
    746mi (1200.57km)
  • Average trip duration
  • Average bus ticket price
    $161.93
  • Trips per day
    4
  • Top Carriers
    Greyhound Lines

Bus Station Information for Chicago, IL

Chicago (95th & Dan Ryan)

Curbside Stop, use arrow keys or tab to explore more about this bus station

Chicago, IL 60628

Curbside Stop
Address
95th & Dan Ryan 
Chicago, IL 60628
Phone Number
(800) 858-8555
More Detailsabout Chicago (95th & Dan Ryan) Curbside Stop

Chicago (Cumberland Avenue)

Curbside Stop, use arrow keys or tab to explore more about this bus station

Chicago, IL 60631

Curbside Stop
Address
5800 N Cumberland Ave 
Chicago, IL 60631
Phone Number
(800) 858-8555
More Detailsabout Chicago (Cumberland Avenue) Curbside Stop

Chicago (Bus Station)

Bus Station, use arrow keys or tab to explore more about this bus station

Chicago, IL 60607

24 Hours
Bus Station
Address
630 West Harrison Street 
Chicago, IL 60607
Phone Number
(800) 858-8555
More Detailsabout Chicago (Bus Station) Bus Station

Chicago (Amtrak Union Station)

Curbside Stop, use arrow keys or tab to explore more about this bus station

Chicago, IL 60606

Curbside Stop
Address
225 S. Canal St. 
Chicago, IL 60606
Phone Number
(800) 858-8555
More Detailsabout Chicago (Amtrak Union Station) Curbside Stop

City InformationforLee, MA

Hop on a bus to Lee, MA and indulge in the charm of this picturesque New England town, nestled in the scenic Berkshires. Known for its small-town warmth and vibrant arts scene, Lee offers an inviting escape for your next adventure. Once you're there, don't miss the vibrant culture of the Berkshire Scenic Railway Museum—perfect for history buffs and train enthusiasts alike.

For a taste of the outdoors, head to October Mountain State Forest, where lush trails and sweeping vistas await your exploration. Lee's bustling Main Street offers cozy cafes and charming boutiques, making it a perfect spot to unwind and watch the world go by. Art lovers will find a treasure trove at nearby Norman Rockwell Museum, capturing the essence of American creativity and nostalgia.

From serene hikes to cultural delights, Lee is a hidden gem waiting to be explored. Revel in the town’s inviting ambiance and make it your own getaway destination. Grab your bus tickets to Lee and let the adventure unfold!

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.

Scenic photo of Chicago, ILScenic photo of Chicago, ILScenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL
Scenic photo of Chicago, IL

Frequently Asked Questions about the Bus Ride

Looking to catch a bus from Lee to Chicago? Book a trip to Chicago from Lee for as low as $161.93. We have 4 trips departing daily. Find your bus ticket to Chicago now.