Illinois - The Prairie State: Chicago Skyline, Route 66 and Lincoln Country

Episode 27 • September 30, 2026 • 00:08:14
Illinois - The Prairie State: Chicago Skyline, Route 66 and Lincoln Country
Exploring America State by State
Illinois - The Prairie State: Chicago Skyline, Route 66 and Lincoln Country

Sep 30 2026 | 00:08:14

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Show Notes

Illinois stretches from Chicago's soaring skyline all the way down through prairie farmland and historic river towns along the Mississippi. In this episode of Exploring America State by State, we explore the Prairie State — birthplace of Route 66, adopted home of Abraham Lincoln, and home to deep dish pizza and world-class architecture.

We drive the Great River Road along the Mississippi, the historic opening stretch of Route 66 right from its Chicago marker, the Illinois River Road, and the surprising Shawnee Hills wine country. Along the way: the dramatic sandstone formations at Garden of the Gods, canyons and waterfalls at Starved Rock State Park, the ancient cypress swamp of the Cache River wetlands, Chicago's architecture river cruise, the Willis Tower Skydeck, Springfield's Lincoln Presidential Library, and Millennium Park's Cloud Gate.

We also flag the tourist traps around the Magnificent Mile and Navy Pier's add-on pricing, cover RV travel logistics on Illinois' flat downstate interstates versus Chicago's tighter city driving, the best free and paid RV camping at Starved Rock, Illinois Beach State Park, and the Shawnee National Forest, where to stay from downtown Chicago to historic Galena, getting around by Amtrak's Union Station hub and the CTA's iconic L train, and the food that defines the state — Chicago deep dish pizza, the no-ketchup Chicago hot dog, Italian beef sandwiches, and Springfield's horseshoe sandwich.

Plus: peak Chicago lakefront summer season, honest budget expectations, and cell coverage advice for the rural Shawnee National Forest.

Next stop: Wisconsin, a state of dairy farms, deep forest lakes, and a genuine Midwestern charm running through every small town.

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Episode Transcript

[00:00:00] Welcome back to Exploring America, state by state after the delta blues and riverboat history of Mississippi. Today, we're heading into Illinois, a state stretching from Chicago's soaring skyline all the way down through prairie farmland and historic river towns along the Mississippi. Illinois is known as the Prairie State, a nod to the vast grasslands that once covered most of its landscape before farmland took over. This is the birthplace of Route 66, the adopted home state of Abraham Lincoln, and a place where deep dish pizza and architectural boat tours share the same skyline. Illinois rewards travelers willing to experience both the big city energy of Chicago and the quiet, rolling farmland stretching south toward the Mississippi River. The Great River Road follows the Mississippi river along Illinois's western border, passing bluffs, small river towns, and wide open water views for miles at a time. [00:00:56] Historic Route 66 actually begins right in downtown Chicago, and driving its early Illinois stretch takes you past classic diners and roadside attractions that help define the entire American road trip. The Illinois River Road National Scenic Byway winds along the river through wetlands and small towns most travelers never expect to find this scenic and the Shawnee Hills Scenic Byway in southern Illinois curves through the state's surprising wine country with rolling hills that feel nothing like the flat prairie further north. The Garden of the Gods, tucked inside the Shawnee National Forest reveals dramatic sandstone rock formations most visitors never expect to find in Illinois at all. Starved Rock State park offers canyons and waterfalls carved into sandstone bluffs above the Illinois River, a genuinely popular hiking destination. Most out of state visitors overlook entirely the Cache River Wetlands Preserve, an ancient cypress swamp in the state's southern tip, complete with trees over a thousand years old rising from the water. And Metropolis, which proudly claims the title of Superman's hometown, offers a genuinely quirky roadside stop most travelers stumble onto by accident. [00:02:10] Chicago's Architecture River Cruise remains one of the best ways to see the city's skyline, gliding past skyscrapers designed by some of the most influential architects in American history. [00:02:21] The Willis Tower Skydeck offers a genuinely dizzying view from over a thousand feet up, including a glass ledge that extends right out over the street below. Springfield's Abraham Lincoln Presidential Library and Museum, along with his preserved home, trace the president's life right in the city where he built his early career. Historic Route 66 officially begins in downtown Chicago, marked by a sign most travelers photograph before setting out on their own version of the classic drive. And Millennium Park's Cloud Gate, better known as the Bean, remains one of the most photographed public art installations in the entire country. [00:03:00] A few things worth restaurants along Chicago's Magnificent Mile tend to charge tourist markup prices for food you can find better and cheaper just a few blocks off the main strip. Navy Pier's attractions can add up quickly, so picking one or two specific experiences rather than trying to do everything saves real money. [00:03:20] And souvenir shops along the early stretch of Route 66 sometimes charge more than similar stops further down the historic road, so a little patience pays off. [00:03:31] Illinois's major interstates, I55, I80, I90 and I94 offer wide, well maintained routes connecting Chicago to the rest of the state comfortably for larger rigs. Downstate Illinois is almost entirely flat prairie, but making it genuinely easy RV driving outside of the city itself. Chicago's downtown traffic and parking are considerably more challenging for larger vehicles, so plan to park outside the city core and use public transit for your Chicago days for paid camping. Starved Rock State park offers a well maintained campground close to the canyons and hiking trails that make the park so popular. Illinois Beach State park, right on Lake Michigan, provides a rare stretch of sandy shoreline. Camping this far inland for free or low cost camping the Shawnee National Forest in southern Illinois allows dispersed camping across large sections of public land, a genuinely generous free camping option, though specific rules vary by district. [00:04:35] Downtown Chicago offers everything from budget chains to grand historic hotels within walking distance of the skyline and lakefront. [00:04:43] Starved Rock Lodge, built right inside the state park, gives you rustic charm just steps from the canyons and waterfalls. And Galena, a beautifully preserved 19th century town in the northwest corner of the state, offers historic inns surrounded by rolling hills unlike anything else in Illinois. Chicago's Union Station serves as a major Amtrak hub connecting Illinois to destinations across the entire country by railroad. Metra's commuter rail network covers the greater Chicago region extensively, and the CTA's elevated L train remains one of the most iconic ways to move around the city itself. [00:05:21] Beyond the Chicago metro area, Illinois is largely a car dependent state, so plan on driving between most of your downstate stops. Illinois's food identity centers heavily on Chicago's contributions to American cuisine. [00:05:36] Deep dish pizza, with its thick buttery crust and layers of cheese and sauce, remains the city's most famous culinary export. [00:05:44] The Chicago style hot dog, topped with a specific combination of ingredients and famously never served with ketchup, carries genuine local pride behind its assembly. The Italian beef sandwich, thin sliced beef simmered in seasoned broth and piled onto a roll, is a beloved Chicago classic found at counter service spots across the city and down in Springfield. The horseshoe sandwich, an open faced creation topped with fries and cheese sauce, remains a uniquely local specialty. Take Chicago's Architecture river cruise for a genuinely unforgettable perspective on one of America's great skylines. Drive the opening stretch of historic Route 66, starting right from its official Chicago marker. [00:06:29] Spend an afternoon wine tasting through the Shawnee Hills, a genuinely surprising wine region most visitors never associate with Illinois, and walk through Springfield's Lincoln Historic Sites, tracing the path of a president whose early career unfolded right in that city. Summer brings Chicago's lakefront and parks to life, with festivals, outdoor concerts, and beach days running from June through August. Starved Rock sees its best hiking conditions in early summer before the more humid stretches later in the season and Route 66. Classic diners and roadside attractions are at their liveliest during peak summer road trip season, when travelers from across the country retrace the historic route. Chicago runs genuinely pricier for hotels and dining, especially downtown near the lakefront and major attractions. Downstate Illinois is dramatically more affordable, with camping often running $20, $35 a night and hearty meals well under $15. [00:07:26] Balancing a Chicago stretch with a downstate stretch keeps your overall Illinois trip very manageable. Cell coverage is strong throughout Chicago and along the major interstates, with reliable signal for navigation and streaming in most populated areas. Coverage drops noticeably in the more remote stretches of the Shawnee National Forest and rural downstate farmland, so download offline maps before heading into those quieter regions. That's Illinois, a state holding soaring skyline architecture, prairie farmland, and the birthplace of America's most famous highway, all inside one genuinely varied set of borders. Next time we're heading into Wisconsin, a state of dairy farms, deep forest lakes, and a genuine Midwestern charm running through every small town along the way. Pack the cooler and I'll see you there.

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