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Chicago to Alton

Family Fun

6 Days 286 Miles


Alton, Bloomington, Carlinville, Joliet, Lincoln, Normal, Pontiac, Springfield

Five times each day, trains roll out of Chicago’s Union Station destined for St. Louis, stopping off along the way in some of the most fascinating destinations Illinois has to offer.

Day 1: The city of Joliet is among the fastest growing cities in Illinois and a popular satellite town for Chicago thanks to its thriving arts and entertainment scene.


  • Car racing

Each train passes under Chicago’s towering skyline, dotted with such legendary structures as the Willis Tower, the John Hancock Center and the Wrigley Building. Before long, even those architectural giants will recede into the skies as you cross the Chicago River and continue on your journey. But don’t worry; there are plenty of stops to look forward to before the St. Louis Arch appears on the horizon, and Joliet is first on the line.

The Rialto Theatre, said to be a favorite haunt of Al Capone, is known to many as the “Jewel of Joliet” for its well-preserved art deco design. It is considered one of the “150 Great Places in Illinois” by the American Institute of Architects and is still open for public performances and private functions. Those looking for a high-octane thrill will want to stop at Chicagoland Speedway, host to a variety of events from NASCAR and the Indy Racing League. Don’t miss the upcoming Teenage Mutant Ninja Turtles 400, where famous female racecar driver and Illinois-native, Danica Patrick, will race for victory on September 18. Prefer not to place your bets on the race track? Take them to Harrah’s Casino and Hotel instead. After a night out on the town, you’d be loath to pass up the city’s famous Home Cut Donuts, which has been serving delicious homemade donuts for more than 50 years.

Day 2: You may think that Pontiac is a destination for car lovers – and you’d be right!


  • Route 66 Sign

Not only is the city named after a popular former car model, but it’s also home to the Pontiac-Oakland Automobile Museum, where enthusiasts can check out one of the world’s greatest collections of classic cars and automotive artifacts. Even more car memorabilia can be found at The Route 66 Association of Illinois Hall of Fame and Museum, which houses a teeming collection of Route 66 memorabilia.

Along with plenty of artifacts and Route 66 history, Pontiac is well known for its artistically funky and beautiful murals around the town—with more than 20 murals to see. Snap a photo with the World’s Largest Route 66 shield or view unique sidewalk art.

Day 3: Those who are keen on the green will need to make a stop in Bloomington-Normal, a town comprised of two adjacent municipalities that has been named by Golf Digest as one of the “Top Five Best Places to Play” the game in the U.S.

Bloomington Normal

  • Person playing golf

If you’ve ever wondered if Route 66 and Abraham Lincoln have any connections, you’re in luck. Visit the Cruisin’ with Lincoln on 66 Visitors Center, which combines two of McLean County’s most significant attractions: President Abraham Lincoln and Route 66. Visitors can compare the travels of Lincoln with those of tourists and automobilist during the golden era of Route 66. To learn more about area’s rich Lincoln history, take a walk around the McLean County Museum of History to see what life was like back in the day for those who encountered Abraham Lincoln.

If you’re hungry after exploring Bloomington-Normal’s history, grab a bite at Epiphany Farms, located right in downtown Bloomington. Epiphany prides itself on a “Farm to Fork” approach to cooking, and is definitely a local favorite. The restaurant uses locally sourced ingredients to create delicious seasonal dishes—it’s loved by all visitors who stop in for a tasty meal.

Day 4: The town of Lincoln received its name in 1853 and remains the only city named for Honest Abe prior to his election as president.


  • Wax dolls of Lincoln in his house with wife

Appropriately, one of the town’s premier destinations is the Lincoln Heritage Museum, which exhibits a rare and valuable collection of artifacts that tell Lincoln’s true life story and legacy. Standout artifacts include an 1860 campaign poster, Mary Lincoln’s jewelry and an actual lock of Lincoln’s hair. After exploring the area’s presidential history, make sure to visit the Lincoln Balloon Festival in late summer. This fun-filled weekend has activities like carnival rides, beer gardens, a balloon glow and live music.

Lincoln has some great drinks and eats, including Spirited Republic. They offer great brews on tap, wine, and local Illinois beers, and will start brewing beers as a microbrewery later this year! For amazing barbeque, check out the Up In Smoke on the Square festival that takes place in June every summer. Watch top Illinois cooks battle for the title of “Grand Champion” during the Steak Cook Off. You can also try amazing ribs at the Backyard BBQ Competition for amateur chefs and vote for your favorites!

Day 5: The state’s capital is, of course, known for its many Lincoln historic sites.


  • Abraham Lincoln in front of the Old State Capitol

These sites include the Lincoln Home National Historic Site, Abraham Lincoln Presidential Library & Museum, Old State Capitol State Historic Site, Lincoln-Herndon Law Offices State Historic Site(temporarily closed for remodeling) and the Lincoln Tomb. Daily guided tours to these locations and more give an in-depth look at the life and times of Lincoln.

But the legendary president isn’t the only attraction in town. Many of the city’s young people gather often at Obed & Isaacs Microbrewery and Eatery, serving the freshest and best locally-made beer paired with a menu of American classics. The social spot includes an outdoor patio and bocce ball court. The morning after some late night fun at Obed & Isaacs, you’ll enjoy a steaming cup of Joe from Custom Cup Coffee. The roast-to-order coffee shop service specializes in small batch and hand-picked beans sourced from across the globe. If you’re still craving their custom java after returning home, you’re in luck since Custom Cup ships their product nationwide. Another local favorite, Maldaner's, is a great farm-to-table restaurant that uses solar panels, a rooftop garden and bee hives to run their business. They are as sustainable as possible and use only fresh fruits and vegetables from local farmers. You can taste the incredible freshness in every bite!

Day 6: After passing Springfield, the trail rolls into Southern Illinois.


  • Historic Building

The downtown Historic District includes beautiful architecture like the Macoupin County Jail, Million Dollar Courthouse and the largest collection of Sears & Roebuck mail-order homes in the U.S. There are other cute 19th century homes in surrounding neighborhoods to explore. Close by, the Anderson Mansion serves as the museum of the Macoupin County Historical Society and has an extensive collection of memorabilia from the area. The museum includes an authentic schoolhouse, blacksmith shop and print shop so you can imagine what life was like during the 19th century.

This scenic region of the state has also recently been gaining national acclaim for its stellar vineyards and wineries. In Carlinville, take a moment to sit back, sip and relax at the Plainview Vineyard & Winery. The winery’s secluded location creates a quiet and serene atmosphere for visiting imbibers. Every bottle from Plainview Vineyard is handcrafted from the 17 varieties of grapes they grow on site. If you love the outdoors, the Carlinville Campground and Lake is a great place to fish, boat and enjoy the nature in the area.

Day 7: The final stop along this Illinois route, Alton, has been named a “Top Girlfriend Getaway Destination” by Country Living, and also has great activities for all.


  • Couple Looking At View

It’s located at the confluence of the Illinois, Mississippi and Missouri Rivers and you’ll be hard pressed to turn any direction without observing some incredible views of the waters and bridges extending above them. In the winter, it is one of the top places in the country to spot American Bald Eagles, pausing on their migratory journey south to hunt and fish in the rivers.

Like many places around the state, Alton has its share of incredible Lincoln history. The seventh and final Lincoln-Douglas Debate was held in 1858 in what is now called the Lincoln-Douglas square. You can imagine what the fiery, three hour debate sounded like when you see the life-sized bronze statues of the two politicians. After learning about Lincoln heritage, you can order dessert before dinner at a local favorite, My Just Desserts. They serve fresh-baked favorites like the Tollhouse brownies and Mrs. Ledbetter’s chocolate pie. Every morning, nine to 13 pie varieties are baked, so go early in the day because these delicious desserts sell out fast!

If you want to grab a drink, there is no better spot than The Old Bakery Beer Company. The brewery and restaurant has been home to at least three bakeries in its 100-year history, and now serves high quality local beer and food downtown. Fast Eddie’s Bon Air is another incredible spot that serves 4,000 half barrels of beer and thousands of cases of cans, bottles and liquor yearly. The food bar also doesn’t disappoint with burgers, Big Elwood Steak and unforgettable bratwurst.

In addition to great eats and beer, downtown Alton has amazing antique shopping where you can find hidden gems. From restored antique fridges to classic glasses and architecture details, the Alton Antique District has been a favorite of antique dealers and collectors for over 30 years. Want a new souvenir made by one of Alton’s very own artisans? Be sure to stop at Mississippi Mud Pottery, where every piece of functional art created is derived from a passion formed along the banks of the mighty Mississippi River. Their pottery pieces will make great additions to any home.

Amtrak provides convenient access to some of Illinois top travel destinations, without having to deal with highway traffic. So next time you’re planning a trip to see the Cubs play the Cardinals in St. Louis, or are heading even further south, consider stopping over in one of these iconic towns. You’re bound to experience something amazing and new.

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