Skip to main content
Shedd Aquarium
Museum

Chicago to Quincy

Arts, Culture & History

4 Days 157 Miles

Highlights

Galesburg, Naperville, Princeton, Quincy

Heading west in search of adventure is as quintessentially American as apple pie, and Amtrak’s westward lines are among the most convenient ways to get you from Chicago to Quincy, and beyond.

Day 1: Naperville, the fifth largest city in Illinois, is the first stop on the train’s westward journey.

Naperville

  • An old cabin house

Imagine relaxing with a good book and beverage of choice as you roll past scene after bucolic scene of quaint farming towns, colorful fields and lush greenery, or dozing off as the setting sun splashes a breathtaking array of color over tranquil countryside vistas.

The westbound lines leave Union Station twice a day, stopping in three Illinois towns before hitting Quincy. Each station served offers an adventure of its own, with plenty to see, taste and explore before re-boarding for the return journey to Chicago.

Located just over an hour from Chicago, Naperville is known for both its family-friendly atmosphere and exciting nightlife. It is an ideal day-trip destination for city-dwellers, offering a variety of activities for those needing a time out from city life.

Stepping outside the Naperville Amtrak station, the first thing you will notice are the trees and greenery of Burlington Square Park. Got the kids in tow? Consider a stop at the DuPage Children’s Museum, located right next to the train station, and experience interactive learning exhibits on art, math and science. Just taking a day trip with friends? A 10-minute walk puts you in the heart of downtown Naperville, where you can belly up to the bar at Hugo’s Frog Bar & Fish House, voted Naperville’s best bar in 2016 by Naperville Magazine.

A stroll along the Naperville Riverwalk provides the perfect way to walk off a full meal. The more than 1.75 miles of brick paths meander past peaceful neighborhoods, parks and fountains and alongside the beautiful DuPage River. The walk will also take you past Quarry Lake, a man-made body of water where visitors can rent paddleboats and kayaks for a fun day on the water from mid-May through mid-October.

Just steps from the Riverwalk is yet another fun, family-friendly stop: the Naper Settlement. The 19th-century “living history” museum includes more than 20 historic buildings, which guests can explore as live costumed performers educate them about settlement life.

Day 2: Go one stop further and you’ll hit Princeton, Illinois. And once you step off the train and witness the well-preserved Main Street lined with historic buildings, you’ll understand its unique charm.

Princeton

  • A red barn bridge

Due to its accessibility via Amtrak and location near Interstate 80, the town has become a popular destination for both Chicago and the Quad Cities.

During the warm summer months, many visitors enjoy biking the scenic routes along the northwest Illinois back roads, which provide stunning views of the Bureau Valley countryside. Before setting out, be sure to pack a picnic stocked with goods from the Farmers Market at Darius Miller Park, where local vendors sell fresh, locally-grown fruits, vegetables, jams and fresh baked breads.

The highlight of each summer in Princeton is the annual Homestead Festival, which takes place the second weekend in September – so the summer celebrations can always last just a little longer in Princeton!  Every year the weekend always includes plenty of food with the annual BBQ rib cook-off, pie baking contest, pulled pork BBQ dinner and ice cream social. On Saturday, the annual Homestead Festival parade rolls down Main Street with local marching bands and festive floats. Other weekend festivities include a 5K race, horse-drawn wagon rides around town, a window display contest, museum tours, helicopter rides and performances by the Bureau County Chorus and Princeton Community Band.

Day 3: Next, you will reach the picturesque town of Galesburg, a place that saw exceptional growth after the birth of rail travel and remains a commercial and industrial center in Western Illinois with exceptional rail facilities.

Galesburg

  • Steam train

In fact, every fourth weekend in June, the town celebrates Galesburg Railroad Days, a celebration of the railroad’s contribution to Galesburg. Enjoy street fairs, railcar and tractor displays and special exhibits at the Galesburg Railroad Museum.

Trains aren’t the only celebrated vehicles in Galesburg. Every year in July, the town hosts the Great Balloon Race, where more than 30 hot air balloons sail into the air above beautiful Lake Storey Park. This creates a majestic, colorful sight in the sky for the whole town to enjoy. Another great festival includes the Carl Sandburg Music Festival in early June that celebrates the Pulitzer Prize-winning writer from Galesburg.  In September, Galesburg invites biplane pilots from across the country to the National Stearman Fly-In celebration. Aviation enthusiasts won’t want to miss this annual air show paired with plenty of soaring entertainment and food.

Speaking of food, Galesburg is home to a variety of tasty and truly unique food destinations. Start at Landmark Café & Creperie for casual American Bistro bites with a French flair. Landmark is housed in the first commercial building in Galesburg to be designated a historic landmark, due to its authentic turn-of-the-century architectural style. Another early 20th-century building-turned-restaurant is The Packinghouse, housed in a former meat packing plant with many of its original features still remaining. The Packinghouse is famous for its prime rib, steaks, seafood and baked fresh cinnamon rolls for dessert. After a great dinner and dessert, you must go to the local Galesburg favorite, Iron Spike Brewery. This craft brewery prides itself on its homebrewed beer, made-from-scratch food and live entertainment from local bands.

If you’re interested in the arts, head to the famous Orpheum Theater, described as a “house of enchantment.” Opened in 1916, the Orpheum is a restored vaudeville theater in the downtown area that has provided more than 100 years of entertainment for the town! 

Day 4: Your final Illinois destination on this westbound line will be Quincy, a town once ranked by Forbes Magazine as one of the top “10 Best Small Cities” to raise a family – and for good reason.

Quincy

Despite being a small town, Quincy has rich history, cultural institutions, amazing architecture and a thriving culinary scene to explore. Start the day by exploring Quincy’s Lincoln history. The town’s Washington Park hosted the sixth Lincoln-Douglas Debate in 1858 where approximately 12,000 people watched in awe! Continue on to the Villa Kathrine. Apart from being a gorgeous example of Mediterranean architecture, Villa Kathrine houses Quincy’s tourist information center, where you can gather all the information you need to plan the day ahead and even rent a bike to tour the town on two wheels!

Pedal down Quincy’s tree-lined Main Street and pause to explore The Quincy Museum, located in the mansion of a millionaire from the 1800s. Private Home Tours of some of Quincy’s legendary mansions can also be reserved. You won’t want to miss the Quincy History Museum, housed in the town’s original public library and home to Quincy area artifacts and a stunning stained glass gallery.

Did you know that Quincy has some of the most impressive architecture in the state with over 3,600 buildings on the National Historic Register? Many structures built as early as the 1830s can be found in the downtown area, and there are plenty of Federal to Greek Revival-style homes to see. The town’s self-guided Architectural Driving Tour has become a visitor favorite. It takes you through 15 key architecture areas of the city to experience diverse styles, or if you’d prefer, you can continue peddling your way through the town. Twice during October and May, Quincy Preserves offers Behind Closed Doors Home Tours where you can see six to eight homes with fantastic architecture!

Once you’ve worked up an appetite, stop at Maid Rite for its famous loose meat sandwich, crinkle fries and a creamy delicious milk shake. At Underbrink’s, an authentic 1929 German Bakery, you’ll find plenty of fragrant nut rolls and heavenly angel food cupcakes to take with you on the return journey to Chicago.

With easy access to these unique destinations from Chicago, Amtrak’s westbound routes make it easy to step outside of your routine and explore different cultures, festivals and cuisines, and return to the city with a trove of new stories to share with friends.

Back to Road Trip Itineraries

More recommendations

Where to next?

Subscribe to Our Newsletter

Get inspired by top travel stories, gain access to exclusive promotions and contests, and discover even more reasons to #EnjoyIllinois.