View Current Travel Advisories

Trailways Bus Tickets
from Stamford, CT 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.

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 InformationforStamford, CT

Set your sights on Stamford, CT, where urban energy meets coastal charm. Catch a bus to Stamford and discover this vibrant town's delights. Begin your adventure downtown, where impressive art installments like the Stamford Downtown Sculpture Walk paint the streets with creativity. For those who lean into the arts, the Stamford Center for the Arts hosts everything from plays to concerts, and the Avon Theatre Film Center features indie films in a classic setting.

Outdoor enthusiasts will relish exploring the Stamford Museum & Nature Center, where exhibits and wooded trails offer a perfect mix of learning and leisure. For a day at the beach, Cove Island Park beckons with its inviting sands and walking paths.

Food lovers, you’re in for a treat: Stamford’s dynamic dining scene ranges from trendy bistros to quaint cafes serving up everything from savory seafood to artisanal pastries.

With its stunning shoreline and lively atmosphere, Stamford has the right blend of adventure and relaxation to keep you coming back for more. Hop on that bus and let Stamford, CT show you what it’s got!

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