Welcome to the start of your great American road trip: Route 66! 

Go on - take your obligatory pic at the start sign of Route 66, but the real excitement begins once you leave the city and its urban sprawl. Along the way, you'll discover iconic Route 66 attractions like Muffler Men, restored gas stations, and a historic maple syrup shop dating back to 1824, as well as a giant covered wagon.

Chicago, the Windy City, throbbing with the heartbeat of America, is the launch pad for the iconic Route 66, a sort of asphalt umbilical cord connecting the nation's past to its present. The city teems with points of interest for those with extra time to explore its rich history and diverse attractions. From the vertiginous heights of the Sears Tower (now the Willis Tower, with tickets available here) to the stately exhibits of the Chicago History Museum, the Pullman Historic District, The Field Museum, Shedd Aquarium, and the Art Institute of Chicago, this metropolis offers a kaleidoscope of experiences for the curious traveler. Chicago is also a hotbed of world-class performing arts companies and home to formidable national professional sports teams like the Cubs and Bulls. Chicago offers a staggering variety of things to see and do, and we recommend acquiring a good Chicago guidebook if you have more than a day to spend in this cultural melting pot. Check our suggested excursions at the end of this article.

To commence your journey from the "official" starting point of Route 66, you can set out from either Jackson Boulevard at Michigan Avenue or Jackson Boulevard at Lake Shore Drive in Chicago. These beginning points are just a few blocks apart, and small brown Route 66 Begin and End signs are posted in Chicago, though not at the actual official beginning or ending points. The Route 66 Begin sign, last seen on E. Adams Street at Michigan Avenue (with the End sign just a block away at Jackson Boulevard and Michigan), is worth a visit for a photo opp.

As you traverse Ogden Avenue in Chicago, you'll encounter the Castle Car Wash, a former castle-like car wash hailing from 1925. Initially the John J. Murphy Filling Station, it later transitioned into a car wash. In Cicero, you'll find vintage Route 66 era motels and signs such as the neon sign at Henry's Drive-In. The castle-like Hoffmann Tower in Lyons, built in 1908 to attract visitors to a park, is another point of interest. History buffs might want to head to the Chicago Portage National Historical Site, often referred to as the "birthplace of Chicago." This site offers historical information as well as hiking and biking opportunities.

Joliet is a great town to explore as it is the "unofficial" starting point for what most people imagine Route 66 to be like. With Route 66 era businesses and signs, and the Route 66 Welcome Center & Gift Shop at the Joliet Museum, it's an ideal place to stop and actually feel that you are starting Route 66. Joliet also boasts the Rialto Square Theatre, a beautifully restored 1926 vaudeville theater that offers both performances and tours, the Jacob Henry Mansion (an impressive 1873 mansion built by a railroad magnate, with the interior not usually open to the public), and the Joliet Iron Works Historic Site (a land preserve with historical panels, perfect for a picnic or walk).

In Towanda, a Historic Route 66 self-guided walking trail stretches 1.6 miles, meandering past a sign denoting the infamous "Dead Man's Curve," a once treacherous bend in the road that claimed many lives in its time.

The town of Normal boasts a restored filling station, the 1931 Sprague Super Service Station, as well as the Normal Theater, an Art Deco-style gem from 1937 (still in operation). The Eyestone School Museum, a one-room schoolhouse built in 1899, sits on the Illinois State University campus, a tangible echo of a simpler time.

Bloomington's attractions invite exploration, such as the McLean County Museum of History, Miller Park Zoo, Prairie Aviation Museum, and the stately Victorian David Davis Mansion.

In Shirley, the Funk Prairie Home Museum, a family home built in 1864, houses a sizable mineral and gem collection. To tour this fascinating treasure trove, you'll need to reserve a spot in advance.

Funks Grove is home to the famous Funks Grove Maple Sirup, a family-run operation sweetening lives since 1824. Meanwhile, the restored Dixie Travel Plaza in McLean has been catering to travelers and truckers since 1928.

Atlanta boasts another Muffler Man, the Bunyan Giant, as well as the Atlanta Museum (near the octagonal library building) and the intriguing J.H. Hawes Grain Elevator Museum, featuring a functional giant grain elevator from 1904.

Lincoln, the first town named after the former U.S. president Abraham Lincoln, has several sites commemorating its namesake, including the Lincoln Heritage Museum, Postville Courthouse State Historic Site, and a giant Lincoln statue accompanied by a covered wagon.

Springfield, the state capital of Illinois, is steeped in Route 66-era buildings and businesses as well as numerous museums and attractions. Among the Route 66 attractions are the restored 1920's Mahan's Filling Station and another Muffler Man, the Lauterbach Giant. As the city where Abraham Lincoln spent much of his adult life, Springfield is replete with sites related to the 16th president, including the Lincoln Home, Lincoln Tomb, Old State Capitol Building, Lincoln Depot, and Abraham Lincoln Presidential Library & Museum. Other non-Lincoln attractions include the Illinois State Museum, the tourable Elijah Iles House, Illinois State Military Museum, and several Frank Lloyd Wright-designed buildings, such as the Dana-Thomas House and Lawrence Memorial Library.

If you are a keen enthusiast of Abraham Lincoln, consider taking a brief 30-minute journey from the city to explore the Lincoln’s New Salem State Historic Site. Keep in mind, however, if you plan to tour all of the significant Lincoln-associated locations in and surrounding Springfield, it would be wise to allocate an entire extra day in Springfield to your itinerary to ensure sufficient time for your visits.

Into Harley-Davidson motorcycles? It’s worthwhile to take a trip up to Milwaukee and visit the Harley-Davidson Museum, located at 400 W Canal St, Milwaukee, WI 53201. The time needed to walk through the museum really depends on how much you are into the history of Harley-Davidson motorcycles. You could get through it in an hour if pressed for time, but you could easily spend 2, 3, or 4 hours, there are interactive elements and lots to see. There is also a restaurant and a big gift shop. Entrance fee: $14.00 - $20.00

Numerous dining establishments dot this segment of Route 66, many of which hail from the Route 66 epoch, feature a Route 66 or vintage motif, or are staunch advocates of Route 66. We've sampled the cuisine in quite a few of them. Virtually any town you stop in along this route offers an appealing eatery, so rest assured you won't be left feeling peckish today!

Here's a full and detailed list of great places to eat along the way. The blue “thumbs up” dots state our top recommendation(s):

PS: since we don’t know when you’re feeling peckish, we have included an “along the way list” - pick your poison…

You're going to be in need of a roof over your head in Chicago, either preceding or following your scenic road voyage. Well, lucky for you, you've got an assortment as wide as the Chicago River to choose from, fitting every fiscal plan and taste. However, do bear in mind that parking isn't exactly a stroll in the Lincoln Park, with the cost of an overnight spot generally running a tab of anywhere between $30 to $50 daily. Therefore, if you fancy exploring Chicago's sights for a few days, you might consider postponing the collection of your motorcycle until you're geared up to kick start your road journey. Never fear the expansive cityscape, though, because getting around Chicago is as simple as pie, thanks to the city's public transport, taxis, and our trusty friend UBER. Now, listed below are a few choice accommodations that we feel might tickle your fancy, all conveniently situated a stone's throw away from the illustrious starting point of Route 66.

Chicago, IL

Now, suppose you've got a hankering to bunk down in Chicago before or after your grand road expedition, well, the good news is that you've got a banquet of choices, enough to suit every pocket and preference. But a word to the wise, parking's not the easiest gig in the city, with an overnight stay likely to set you back a handsome $30 to $50 daily. So if you're thinking of holing up in the Windy City for a few days, you might want to consider collecting your motorbike when you're actually ready to hit the open road. Now don't worry, getting about in Chicago is a doddle, with the city's public transport, taxis, or the ever-dependable UBER. And now, for your convenience, here's a handy list of lodgings you might fancy, all snugly situated near the famed starting line of Route 66.

	Congress Plaza Hotel Sporting a respectable three stars, this revered establishment first flung open its doors way back in 1893. A fair few presidents and celebrities have bedded down within its historic walls. Cast your gaze from the hotel's windows and you'll be greeted by the sparkling expanse of Lake Michigan. And while you'll have to shell out a few clams, private parking is conveniently at your disposal on the premises. What's more, this place is perfectly positioned for the Route 66 explorer - being merely a couple of blocks away from both the kicking-off and winding-down points of this famous stretch of Americana.
	The Langham If you are looking to start your Route 66 off with a luxury stay before hitting the road, you have loads of choices in Chicago. One recommendation is the 5-star The Langham, which is less than a mile from the starting point. Private on-site parking is available for a fee. Great for those with a larger budget who want to celebrate the start or end of their road trip.
	The Palmer House In the heart of downtown Chicago, just a minute's walk to the ‘Begin of Route 66’ sign,  the tale of the Palmer House Hilton is a potent mix of romance, resilience, and a dash of razzle-dazzle. Born from an extravagant wedding gift by business tycoon Potter Palmer to his bride Bertha, this luxurious hotel was tragically engulfed by the Great Chicago Fire just 13 days post its grand debut. But like a phoenix from the ashes, the Palmer House resurrected itself on November 8, 1873, thanks to Potter's indomitable spirit and a cool $1.7 million loan, launching its uninterrupted tenure as the nation's longest-running hotel. Over the years, it became a c hub of Chicago's social scene, frequented by illustrious guests from presidents to literary giants, and even crooners like Sinatra. Despite a recent $170 million facelift to cater to the modern traveler, the Palmer House remains rooted in its storied past, continuing to be the Chicago hotel the world knows and loves best.
	Travelodge Chicago You're onto a pretty safe wager if you're after a stay that's reasonably priced and conveniently positioned near the launch pad of Route 66. While the establishment doesn't offer its own parking, don't fret - there's a pay-as-you-go public car park just a brisk stroll away.

Springfield is our suggested overnight stop on the Route 66 itinerary. Here are our recommendations:

	Route 66 Hotel & Conference Center Decked out in Route 66-themed decor, this hotel is quite the hot ticket for those embarking on or wrapping up their epic Route 66 journey. It's an ideal spot for trading road tales with fellow travelers. As for amenities, it ticks the boxes with an in-house restaurant, bar, and a swimming pool for a dip.
	President Abraham Lincoln Hotel Located in downtown Springfield, a short walk from the Bank of Springfield Center and Abraham Lincoln Presidential Museum and Library. Illinois State Museum, Knights Action Park, and Abraham Lincoln Capital Airport are less than 15 minutes drive away. They have a free local shuttle, a pool, and a 24-hour business center. Enjoy a warm DoubleTree cookie on arrival.
	Holiday Inn Express & Suites Simple, smart travel with everything you need to fuel up, stay connected and sleep easy. Hot, fresh breakfast. Free wi-fi. All the must-haves. Located at I-55 this hotel is a good choice if you quickly want to avoid Springfield city traffic and get back on Route 66.
	Motel 6 Springfield Not much to say here - clean and simple. Our pick for a budget motel in Springfield.

Congrats! You have successfully mastered Day 1 of Route 66

We can highly recommend the following excursions if you have some spare time and arrive a day or two before your actual tour start.