Route 66 is one of the oldest highways in the country and arguably the most famous. It will be celebrating its 90th birthday this year, is more than 2,400 miles long and passes through some of the most famous landmarks, such as Chicago’s own Art Institute of Chicago, California’s Santa Monica Pier and the Gateway Arch in Saint Louis.
But while landmarks are an exciting find, everyone knows the true gem of road trips is the cuisine, which is exactly where Route 66 and our own journey starts, right here in Chicago on Adams Street between Michigan and Wabash Avenues. Though there is some discussion whether the official starting point of Route 66 is at Tesori’s—an Italian-inspired restaurant— or the nearby comfort food-style eatery Lou Mitchell’s, you really can’t go wrong wherever you begin the adventure. Both have tantalizing options and are available for private parties—Lou’s offering a full buyout and Tesori’s accommodating up to 400.
So buckle up and get ready as we take you on a guided tour down Route 66’s Illinois stretch—encompassing 90 different communities—on a foodie path filled with fried chicken, a sandwich topped with french fries and roast beef and a little entertainment in between, including where to dine, meet, and stay at each stop.
Of course, Chicago has its famous attractions— deep-dish pizza, the Bean, Lake Michigan—but our starting point also has a few hidden gems you should know about, too.
Population: 2.7 million
Dine: With its small-town feel, Lou Mitchell’s is the perfect place to begin. When women and children visit the restaurant, which has been open since 1923, they each receive a box of Milk Duds. The practice is in homage to the Greeks, who always offer something sweet to visitors. This is just one example of the diner’s outstanding customer service.
Must-try Dish: Deep dish, hot dogs and Italian beef are the obvious answers, but Nuts on Clark’s caramel/cheese popcorn and Bang Bang Pie & Biscuits are two of many options that shouldn’t be ignored.
Know: Over the course of the year, Chicago holds 15 citywide music festivals, nearly 50 smaller neighborhood music festivals and 35 community food festivals.
Meet: Host your event in the company of Dali, Picasso and Monet while at the Art Institute of Chicago, which has more than 10 event spaces and capacity for upwards of 4,000 guests.
Do: Jump out of your car and into one of Chicago’s First Lady Cruises, the best of which is the architecture tour. You’ll sail along the river and listen to a genuinely interesting presentation of more than 50 Chi-town buildings and how they came to be.
Stay: A restored 123-year-old Venetian Gothic building, the Chicago Athletic Association Hotel is the perfect place to stay away from chain brands. With 241 rooms, a number of restaurants and dining outlets (and a perfect location on Michigan Avenue), you won’t be disappointed.
Romeoville is said to be named after the famed star-crossed lover in Shakespeare’s Romeo and Juliet, with Joliet acting as its romantic twin city and rival.
Dine: White Fence Farm is a popular dining venue with crispy chicken and fresh corn fritters. It’s also one of the oldest—it dates back to the mid-1920s. Others of note: McMichael’s, Fat Ricky’s and At’s a Nice Pizza.
Must-try Dish: White Fence boasts the “world’s greatest chicken.” Fried to perfection, it’s hard for us to disagree.
Know: Romeoville is known for its limestone—historical records note that the area’s sedimentary rock was used to build the Illinois State Capitol Building.
Meet: The almost two-year-old Edward Hospital Athletic and Event Center features 76,000 square feet, community meeting rooms, multipurpose rooms and even basketball courts and an indoor soccer field.
Do: Unique to the area is the Isle a la Cache Museum, which gives visitors a history lesson on the French voyageurs who trekked along the area in the 1700s. It also can be rented out for events.
Stay: Romeoville doesn’t have any hotels along Route 66, but there a number of hotels just minutes away.
After leaving Romeoville, Joliet is a muststop city. And, of course, the must-stop city has a must-see landmark: the Joliet Area Historical Museum. Here you can find the perfect introduction at the Route 66 Welcome Center.
Dine: Head straight back to the ‘50s at the Joliet Route 66 Diner. The mom-and-pop restaurant embraces its roots with woodpaneled walls, neon lighting along the ceiling and a long counter at which to eat the heartiest of comfort foods.
Must-try Dish: While Joliet isn’t known for any specific food, it does have a number of restaurants right along the route, including a bevy of breakfast joints like Home Cut Donuts, Silver Dollar Restaurant and Old Fashioned Pancake House.
Know: The very first Dairy Queen—that renowned server of ice cream treats— opened its doors in 1940 in Joliet.
Meet: The vaudeville Rialto Square Theatre is the perfect place for those looking to inject a little culture into their event with room for up to 300 guests.
Do: Only a tad more exciting than Route 66 itself, the Route 66 Raceway is a drag racing stadium that, along with hosting pro shows, lets you hop in the driver’s seat and take a spin.
Stay: Harrah’s Joliet Casino & Hotel has 200 rooms, more than 6,000 square feet of meeting space for up to 325 guests and a world-class casino. So, there’s really no gamble when staying here.
Back in the 1800s, Braidwood was a booming town for miners. The town recently commemorated its rich history with a time vault buried in a nearby park.
Dine: Visitors must pull up to the Polka Dot Drive-In. Opened in 1956, the interior seems to not have aged a day, transporting patrons to the glory of the ‘50s. Statues, including Elvis and Marilyn Monroe, line the outside of the restaurant.
Must-try Dish: It’s a tie between the roast beef sandwich at the Polka Dot Drive-In and the fried chicken at the family-style Golden Mine.
Know: While Braidwood is relatively small, visitors from all over the world—including Australia, Germany and Japan—flock to the area for a taste of that small-town feel and natural beauty.
Meet: While the town doesn’t have much meeting space, there is room for 200 at the local Immaculate Conception Church.
Do: Housed in a restored train depot, The Braidwood Historical Society Museum has memorabilia from all the way back to the 19th century.
Stay: There isn’t a hotel yet, but, according to Mayor James Vehrs, talks are in progress about breaking ground on a Drury Inn in the near future.
While Pontiac may be small in size, it is a gold mine when it comes to Route 66 history and landmarks. “Pontiac is one of the crown jewels anywhere on Route 66,” says Bill Kelly, executive director of the Illinois Route 66 Scenic Byway—a nonprofit dedicated to preserving the special road. “[The city] made a major commitment to Route 66, and it has paid off handsomely.”
Dine: Edinger’s Filling Station will more than fit your fancy. Designed to look like an old-school gas station, complete with a garage door, the restaurant dishes up some of the best small-town comfort food, perfect for every road trip.
Must-try Dish: Pontiac doesn’t have a traditional dish to its name, but the town can boast that, aside from fast food restaurants, all of its dining spots are locally owned and operated. “It is a necessity for our restaurants to service delicious food, or they won’t last long,” says Ellie Alexander, tourism director for Pontiac.
Know: The town has been a part of the road since its inception in 1926. Meet: Recently renovated, the Eagle Performing Arts and Conference Center is perfect for groups. It can seat 250 auditorium- style and 186 with round tables.
Do: No trip to Pontiac (and Route 66 itself) would be complete without a visit to the Route 66 Association Hall of Fame and Museum. Among other memorabilia, it includes a Volkswagen van owned by a traveling artist from the area that inspired a character in the movie Cars.
Stay: There are a number of chain hotels within the town, but if you’re looking for a historic, no-frills hotel, the Fiesta Motel is a must.
With homegrown restaurants and historic landmarks, “Bloomington-Normal is a great place for food and travel on 66,” says Samantha Morehead, tourism marketing manager of the Bloomington-Normal Area Convention & Visitors Bureau.
Dine: Beningo’s is one of the area’s “hidden gems,” located mere blocks from Route 66. You cannot go wrong with any of the mouthwatering Italian options at the 45-year-old, family-owned restaurant. “[Beningo’s] is authentic and has the best food ever,” says Morehead. “I have had everything on the menu, and it’s all homemade.” Making the restaurant feel even more homey is owner Janet Whitworth, who leaves the kitchen nightly to chat with patrons.
Must-try Dish: Italian seems to be a staple in the area. The A La Baldini pizza at Lucca Grill is a standout topped with sausage, pepperoni and ham with a sprinkle of veggies for good measure. For those with a sweet tooth, the Avalanche at Gene’s Ice Cream is a must.
Know: Driving down the route through this area, you’ll encounter the “Dead Man’s Curve,” a dangerous bend on the original Route 66 that was famous for many accidents caused by daring drivers.
Meet: Formerly known as the Scottish Rite Temple, the historic Bloomington Center for the Performing Arts has an auditorium that seats 1,200, a ballroom that seats up to 1,400 and four breakout spaces with seating for 360 people.
Do: The Quinn Shell Station is a must-see. In use for 70-plus years, the now-closed gas station was inducted into the Illinois Route 66 Hall of Fame in 2012.
Stay: The Parke Regency, a boutique hotel just a short drive from Route 66, boasts 70 guest rooms and 11,500 square feet of meeting and event space.
As the state’s capital, Springfield is a nobrainer stop along Route 66. Says Alicia Erickson, marketing specialist for the city’s CVB, “We’re lucky to have both Route 66 and Abraham Lincoln to make visiting Springfield a unique experience.”
Dine: No visit would be complete without a visit to the Cozy Dog Drive-In for the famous treat on a stick, aka corn dogs, dipped in a secret recipe batter.
Must-try Dish: The horseshoe sandwich is famous throughout the state and can be found at a number of restaurants. An opened-face sandwich typically topped with a hamburger, french fries and some sort of cheese sauce, the horseshoe is a monstrosity with more calories than we care to think about.
Know: Each September, Springfield hosts the International Route 66 Mother Road Festival, where more than 80,000 spectators from 20 states come to ogle 1,000- plus cars.
Meet: With 65,000 square feet, the recently renovated Prairie Capital Convention Center’s main hall can hold up to 9,000 guests for a reception and 3,000 seated at round tables. Bonus: It’s located in the heart of the historic district, near a number of attractions.
Do: Of course, Springfield is best known for producing one of the most famous U.S. presidents of all time—Abraham Lincoln. To honor him, a visit to the Abraham Lincoln Presidential Library and Museum should be on the agenda. For visitors who want to experience Lincoln further, the Lincoln Home National Historic Site, the Old State Capitol and The Lincoln Tomb are must-sees.
Stay: Centrally located, the State House Inn can host events for up to 300 and has 125 rooms and suites.
Hailed by Kelly for its food, this town is a major player along Route 66 with the Ariston Café—the oldest continually operated restaurant along the route.
Dine: The aforementioned Ariston Café is known for its home-style cooking and historic roots—it was inducted into the Route 66 Hall of Fame in 1992. A back room is available for events.
Must-try Dish: Fried chicken and roast beef from Ariston and any type of baked good from Jubelt’s Bakery (you can’t go wrong with any of the tantalizing sweet treats).
Know: Aside from its delectable food offerings, convenience is a perk of the town. “Everything in Litchfield is located within half a mile and all within half a mile of Route 66,” says Sarah Waggoner, tourism coordinator for the city. “People are always surprised by that.”
Meet: The 1,066-square-foot conference center at the Holiday Inn Express/Suites Litchfield West has space for 75 reception-style and 50 banquet-style. The hotel has a real Route 66 vibe, with local artwork flanking the walls.
Do: Originally, the masterminds behind the Litchfield Museum and Route 66 Welcome Center met to compile a postcard book of the history’s past. The idea soon snowballed into something much larger, and a brick-and-mortar relic of the past stands now provides visitors with information from its incorporation in 1856.
Stay: If you don’t rent a room at the Holiday Inn Express & Suites, the Hampton Inn Litchfield with 64 guest rooms also is a safe bet. Or try Baymont Inn & Suites, Quality Inn, Super 8 Hotel or Americas Best Value Inn in Litchfield.