Chicago
Route 66: Just the phrase creates a vision of America – of travel, adventure, experiences and even a few surprises. It’s become as American as mom, apple pie, the 4th of July and the road trip itself. Since its inception in 1926, generations of travelers have used it to explore a new horizon, whether seeking a new beginning or just experiencing a cross-section of this great land of ours.
From Chicago to Los Angeles, over 80 Best Western hotels - many right along the original Route 66 - are there to serve you. Many of these locations, each independently owned and operated, offer a suite of services including wi-fi, free continental breakfast, workout facilities, an indoor and/or outdoor pool, and a clean, comfortable night's stay after a fun-filled journey.
The Mother Road is calling; let’s answer it.
Where it all begins. Chicago (pop. 2.7 million) is the hub of the Midwest, the third largest city in the U.S. and according to Forbes magazine, the world’s 5th most economically powerful city.
Chicago’s rich history includes fire and rebirth, gangsters, colorful politics, a rich pattern of immigration, music, culture and deep dish pizza, just to name a few things. From its founding due to a portage between the Mississippi River and Great Lakes watersheds (we’ll discuss that in more detail shortly), Chicago has always been a major transportation hub. To aid in helping railroad schedules, the time zones for North America were first standardized in Chicago in 1883. Two years later, it became the birthplace of the skyscraper and for 24 years, the 110-story Sears Tower (now the Willis Tower) was the tallest building in the world (as of 2011, it’s still the tallest in the Western Hemisphere.) Chicago’s O’Hare Airport has perenially been the world’s busiest, and is always in the top three. The other major airfield, Midway Airport, was the world’s busiest before O’Hare opened in late 1950s.
Chicago has always been a key location for corporate headquarters, among them Sears, Roebuck & Company; McDonald’s; Kraft Foods; Walgreens; Allstate Insurance; Boeing; United Airlines; Baxter International; Abbott Labs and more. Even newer companies like CareerBuilder.com and Groupon began in Chicago. Major league sports teams are plentiful: the Cubs and White Sox for baseball, the Bears for football, the Bulls for men’s basketball and Sky for women’s, the Blackhawks for hockey and the Fire for soccer. There is also a complement of minor-league teams in a variety of sports from the city and suburbs.
Chicago has a dizzying array of restaurants, museums, parks, cultural facilities, events and other points if interest. If we got into all of them here, there wouldn’t be time to drive Route 66. Many are concentrated where the Mother Road begins, including the world-famous Art Institute, which sits along Michigan Avenue between Adams Street (the start of westbound 66) and Jackson Boulevard (the end of eastbound 66.)
Before you start, there are two great Best Western locations right in downtown Chicago: the Best Western River North Hotel and the Best Western Grant Park Hotel.
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Best Western PLUS River North Hotel 125 W. Ohio Street Chicago, IL 60654-7168 (312) 467-0800 |
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Best Western Grant Park Hotel 1100 S. Michigan Avenue Chicago, IL 60605-2301 (312) 922-2900 |
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Best Western PLUS Hawthorne Terrace 3434 N. Broadway Chicago, IL 60657-2516 (773) 244-3434 |
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Best Western Inn & Suites - Midway Airport 8220 S Cicero Ave. Burbank, Illinois 60459-1510 (708) 497-3000 |
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Best Western Des Plaines Inn 1231 Lee St Des Plaines Chicago Airport Area, IL 60018-1512 (847) 297-2100 Fax:(847) 297-7884 |
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Best Western Naperville Inn 1617 N Naperville Wheaton Rd Naperville Chicago Area, IL 60563-1524 (630) 505-0200 Fax:(630) 505-4291 |
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Best Western PLUS Oakbrook Inn 669 Pasquinelli Dr Westmont Chicago Area, IL 60559-1251 (630) 323-1515 Fax:(630) 323-1516 |
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Best Western at O'Hare 10300 W Higgins Rd Rosemont Chicago Airport Area, IL 60018-3818 (847) 296-4471 Fax:(847) 296-4958 |
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Best Western PLUS Chicago Hillside 4400 Frontage Rd Hillside Chicago Area, IL 60162-1734 (708) 544-9300 Fax: (708) 544-7600 |
Route 66 officially begins at the intersection of Adams Street and Michigan Avenue (eastbound ends one block south, at the corner of Jackson & Michigan.) Just standing at the corner provides some terrific views: the Art Institute to your east, with Lake Michigan’s Monroe Harbor and Lake Shore Drive just behind it; the wall of buildings lining the west side of Michigan Avenue contrasting with the parkland of Grant Park, Millenium Park and Buckingham and Crown Fountains to the east; the glistening stainless steel sculpture known as Cloud Gate; one block away, an “el” (short for “elevated”) train line running along the top of Wabash Avenue; further west, the Willis Tower – formerly the Sears Tower – the tallest building in the western hemisphere and, at 1,707 feet, the world’s tallest building period from 1974 to 1996.
And, remember, that’s without even moving yet.
Heading east down Adams Street, you cross under the el tracks at Wabash and past a slew of retail store and office towers, all part of the bustling mix that makes Chicago one of the world’s most vibrant cities. To your left will be one of the city’s classic restaurants, The Berghoff (17 W. Adams Street, 312-427-3170). In fact, it’s the oldest continuously operating restaurant in Chicago and offers up a wide variety of German food and other fare. Berghoff began as a brewery in Fort Wayne, Indiana in 1887, but the lure of exposing millions to his beer lured them to Chicago in time for the 1893 World Columbian Exposition. The brewhouse landed on Adams Street, where it prospered until Prohibition, when they were forced to diversify to make up for a lack of (legal) alcohol sales – so The Berghoff became a full-service restaurant. Obviously, it turned out to be a great move.
Through this part of Chicago, which includes about a mile of the city’s famous Loop district, tall buildings line the street in a canyon-like configuration you’ll see nowhere else on all of Route 66. The biggest standout is, of course, the Willis Tower, which was the tallest building in the world when it was completed as the Sears Tower in 1974. Though the Petronas Towers in Malaysia surpassed it in 1998 and several others like the Burj Khalifa in Dubai have also reached up higher, the 1,729 foot structure is still the tallest in the Western Hemisphere and (as of 2011) the sixth tallest freestanding structure in the world. Bounded by eastbound Route 66 (Adams Street), westbound Route 66 (Jackson Blvd.), Wacker Drive and Franklin Street, the Willis Tower Skydeck open for tours seven days a week and offers unparalleled views of Chicago, portions of Wisconsin, Indiana, outstate Illinois and lower Michigan on a clear day… when you can also see the entire lower end of Lake Michigan, one of the largest freshwater lakes in the world. As you might guess, pretty much everything is a superlative in Chicago.
Ambling over the Chicago River, you reach Union Station, a beautiful, classic, and busy train station that opened in 1925, replacing an earlier station on site that dated back to 1881. When you factor in the approaches and storage tracks, Union Station is almost ten city blocks in size, although much of it lies underground and beneath skyscrapers that tower above. A total of 24 tracks run into the station. It’s where in the 1976 film Silver Streak, a train crashed full-speed into the endpoint of a railroad line and sent debris everywhere.While its heyday was during World War II when over 100,000 passengers used the station every day, today about 60,000 commuters and passengers still use the station daily. Route 66 hugs the station on the north and south, as Adams and Jackson westbound and eastbound.
Beyond Union Station, Route 66 spans the incredibly busy Kennedy Expressway (I-90/94) and begins its trek into city neighborhoods west of what’s known as “The Loop”. Westbound, you’re still on Adams and eastbound runs one block south via Jackson Boulevard.
The dense neighborhoods just west of Chicago’s Loop don’t last too long on Adams Street, as Route 66 turns at Ogden Avenue to begin heading southwest – the true direction for most of Route 66’s length across the nation. Ogden is a broader boulevard, ducking under railroad tracks, passing large medical complexes and factories and traversing a grittier part of the city than Adams does. When you reach Douglas Park, however, shortly after the intersection with Roosevelt Road, expect some beautiful parkland flanking the Mother Road.
Shortly after crossing Cermak Road, Route 66 leaves its city of origin and enters the suburb of Cicero, the first of hundreds of cities and towns you’ll encounter on your way to Los Angeles.








