I’m from the Chicago area, so a lot of people ask me for travel tips when they’re headed to the Windy City for business or leisure travel. I’m always happy to oblige and travel vicariously to my favorite US city. Here’s my two cents’ worth!
Chicago was nicknamed the “Windy City” after its politicians, not its weather … although some days the weather disagrees. Poet Carl Sandburg referred to Chicago as the city with “big shoulders.” Frank Sinatra called it “my kind of town.” Home of the Cubs, Bulls, Bears, Blackhawks, White Sox, Lollapalooza, Capone, Daley and The Machine, the Obamas, great music, and amazing pizza … it’s a great city to visit!
Chicago is a true American melting pot with an amazing amount of ethnic diversity. With the largest Polish population of any city in the world outside Warsaw, as well as Americans of Irish, African, German, Asian, and Hispanic descent, Chicago retains its ethnic flavor.
Most of Chicago’s sights are contained inside the “Loop,” a roughly circular area bordered by one of Chicago’s infamous elevated, or “el,” train routes. Chicago doesn’t have a subway – its mass transit trains are elevated about one story above street level. Follow the tracks to find the next stop. “How often does the train go by? So often you won’t even notice.”
Here’s a walking tour to follow if you have a week or a weekend to spend in Chicago…
Taking the train into the city beats driving by a longshot. If you’re arriving by commuter train, you’ll probably arrive at the OTC Metra train station (formerly the Chicago & Northwestern station). Union Station, which serves both Metra and Amtrak trains, is a few blocks south.
Starting Your Tour
From there, walk east to Daley Plaza at the corners of N. Clark & E. Washington to see the big Picasso sculpture and the plate glass windows that Jake & Elwood drove through in “The Blues Brothers” (the Cook County Assessor’s office is across the street). The 1985 Bears did the Super Bowl Shuffle in the Plaza after Chicago’s only Super Bowl victory.
From Daley Plaza, walk a block north on Clark Street to the Thompson Center (formerly the State of Illinois Building) – big, modern, white, orange, & glass, on the northwest corner. Go inside and check it out. This is where the shootout at the end of the 1986 movie “Running Scared” (with Billy Crystal & Gregory Hines) was filmed. Controversial architecture at the time it was built … called “Thompson’s Folly” after then-governor and current building namesake Jim Thompson. Visitors used to be allowed to take the elevator up to the top floor (16), peer down, get vertigo, and sign the guest book near the elevator before descending. Ask security if they’ll let you do that. After they say no, ask why both sets of elevators don’t go all the way up to the top. Then it’s probably best to move on.
Walk east on Randolph Street to Michigan Avenue, Chicago’s Main Street. From here, you can see the Aon Building (formerly the Standard Oil, later Amoco Building) on the left. It’s tall, white, stunning at night, and my favorite skyscraper in Chicago. Behind it are the new and old Prudential Insurance buildings. The short one with the Prudential logo on top was, from 1955-1968, the tallest building in Chicago at 42 stories. Now the Aon, which dwarfs it, is only the 3rd highest in the city.
Parks & Museums
You can walk south on Michigan Avenue to lakefront Grant Park. President Obama delivered his election night victory speech here in 2008. Right next to it you’ll find Millennium Park with its high-tech interactive fountains and required photo-op mirrored sculpture known to locals as “The Bean.” Spend some time here enjoying Chicago and Chicagoans. Then head to the Art Institute, which was built for the 1893 Columbian Exposition. It’s a world-class art museum. Check out the lions out front on your way in – if da Bears are headed to the Super Bowl, these lions may be adorned with Bears helmets. Before you go in, make a quick detour down to Congress Parkway. From there you can walk toward Lake Michigan and see Buckingham Fountain (namesake of the 1960s band “The Buckinghams”) in the center of Grant Park (if you insisted on driving downtown and couldn’t find a parking spot, there is a massive parking garage below the park).
South of there along the lake: the Field Museum of Natural History (great dinosaur bones, and a great museum), Shedd Aquarium (with a great exhibit on the Pacific Northwest!), Adler Planetarium, renovated Soldier Field (home of da Bears), and the enormous McCormick Place convention center. Those are a bit of a walk, but if it’s a nice day, a walk through Grant Park is worth it.
Further south along Lake Shore Drive (and too far to walk) at 57th is the Museum of Science & Industry, much larger than Portland’s OMSI. It’s a HUGE museum, and the building was one of many constructed for the 1893 Columbian Exposition. Most others are long gone. (Erik Larson’s amazing book Devil in the White City delves deep into the Exposition.)
Chicago’s Main Street
Heading back north on Michigan Avenue from Randolph Street is Chicago’s “Magnificent Mile.” Technically, it begins on the north side of the river, but prices at stores like Nordstrom, Saks, and Tiffany’s seem magnificent to me. Hang onto your pocketbook as you pass.
Look for the staircases going down below Michigan Avenue’s street level. Walk downstairs. Chicago doesn’t have many subways – this is what used to be street level on Michigan Avenue. Now everything (including the street) has been moved up to what was once the second story! Remember the Chicago floods in the early 1990s? The tunnel system that flooded (described in great detail at a Museum of Science & Industry exhibit) is even further below this subterranean level.
The Hard Rock Hotel, on the SW corner of Michigan & Wacker Place, may be worth a look.
Just before you cross the Chicago River at Wacker Drive, look down at the sidewalk. Brass markers are embedded in the concrete on both sides of the intersection indicating the site of long gone Fort Dearborn, reminders of the days when Chicago was on America’s western frontier.
Sightseeing & Food
As you cross the Chicago River, look up at the white Wrigley Building (as in Wrigley chewing gum and Wrigley Field) on the left and the neogothic Tribune Tower (as in Chicago Tribune and Tribune Broadcasting) on the right. Keep right after you cross the bridge and take a peek in the windows of the Tribune building. WGN-AM radio broadcasts from here … check out the weather, traffic, and other monitors. Don’t forget to look at the building itself. Dozens of chunks of other famous buildings are embedded (and labeled) in the facade of the Tribune Tower. Look to the west, across the street, and up: check out the suspended hallway connecting two halves of the Wrigley Building!
Need some fresh air? Cross the street to the Wrigley Building side and walk down the stairs on the northwest side of the bridge. From here, you can take a Wendella lake cruise (best taken at night … the illuminated skyline is great!). There’s a lock between Lake Michigan and the Chicago River which you’ll pass through on the cruise. The river’s flow was reversed years ago, and now the lake flows into the river instead of vice versa. The Chicago River flows into the Illinois, which eventually flows into the Mississippi near St. Louis.
If you’re not in the mood for a cruise, or if you have a few minutes before it departs, walk back up a few stairs from the Wendella boat dock and into the doorway which seems to lead to an underground parking lot. This is “lower” Michigan Avenue (remember “Lower Wacker Drive” from “The Blues Brothers”? It’s back across the river from here). Follow the subterranean sidewalk north one block, cross at the light, and on the northwest corner is the Billy Goat Tavern — the hamburger joint which John Belushi, Dan Aykroyd, and Bill Murray made famous on Saturday Night Live (“cheezborger, cheezborger!”). It’s worth a look and a Coke (“no Pepsi! Coke!”), but if you’re hungry, wait a few more minutes for Gino’s pizza!
Due east of the Tribune Tower (following Illinois Avenue) at the lakefront is the refurbished 3300′ long Navy Pier with restaurants, an interactive fountain, museums, a theater, snack & trinket carts, an IMAX theater, and a great Ferris wheel that for $6 gives you one slow loop with a great view of the skyline (best at dusk – and cheaper than the boat tour). The world’s first Ferris wheel was built just south of here for the 1893 expo. In the 1980s, before the refurbishment, Chicagofest was held here, complete with music, beer, and food … much like Milwaukee’s Summerfest. Chicagofest gave way to the new & improved Navy Pier, but Summerfest is still going strong. The world’s largest music festival, it’s well worth the 90 minute drive north if you’re lucky enough to be around during its annual two-week summer run.
Head back upstairs and keep going north on Michigan Avenue. You’ll pass more of the big department stores (Macy’s, Saks, Tiffany’s, etc.) and art galleries. If you’re still hungry, turn right (east) onto Superior Street and Gino’s East pizza will be on the left about 1/2 block down (162 E. Superior). Possibly a long line (pass the time by reading the graffiti) but worth the wait. Bring a Sharpie and be sure to write your initials on the wall or the ceiling. THIS is Chicago. It’s also the original Gino’s…now there are a few in the ‘burbs, and they’re making your wait much shorter than it used to be. You once had to spend your time in line with tons of suburbanites who couldn’t believe how long they had to wait for pizza … but did it anyway!
Farther up Michigan Avenue on the left is the old Chicago Water Tower, just about the only thing left standing after the Great Fire of 1871. It’s now an official city visitor center. There are usually some great street performers around here. On the right (at Pearson St.) is Water Tower Place, a great multi-level shopping mall. At least go in, ride the escalator up, and take the elevator to the top so you can look back down. There’s a McDonald’s here if the line was too long at Gino’s. It’s a great place to get out of the rain, too! (But you should’ve waited for Gino’s!)
Just north of Water Tower Place on Michigan Avenue is Chicago’s 4th tallest building, the John Hancock Center. Go inside and pay the few bucks to ride the elevator to the observation deck on the 97th floor. (There’s a fancy restaurant on the 96th if you’re in the mood … but watch out for a dress code.) If it’s dark out, you’ll have a great view of the lighted skyline (of which you’re at the top!!), and of the Willis (formerly Sears) Tower, the second-tallest building in the Americas and once the world’s tallest building (which is more expensive to go up in, out of the way, and not in your view of the skyline when you’re inside it). If it’s daytime, look east (across the lake) and see if you can spot the Michigan shoreline. If you want to be able to see west, you’d better go up in the morning. The afternoon glare can be a killer, but the flat expanse of the illuminated urban grid is spectacular at night. Look down and wonder: if you dropped a penny, would it really go through the roof of a car? Feel the building sway in the wind. Trace your steps on the streets below. Find Wrigley Field to the north, Soldier Field and US Cellular Field to the south. Try to spot a few rooftop swimming pools!
After visiting the Hancock Center, either head north along Michigan Avenue to the Oak Street Beach, one of several city beaches along Chicago’s lakefront, or head back south down Michigan Avenue toward Ontario Street. Turn right (west) onto Ontario Street to visit Chicago’s Hard Rock Cafe. It’s a few blocks down on the left and has been around much longer than the Hard Rock Hotel.
If you do visit the Hard Rock, be sure to cross the street and go to the big McDonald’s to check out its rock & roll memorabilia. This building replaced the (much cooler) original 1950’s-era structure in 2005, but is still worth the walk across the street.
Another Chicago nostalgia spot is Ed Debevic’s (“Eat at Ed’s“), nearby at 640 N. Wells. The servers here are renown for their rudeness, so don’t be surprised! Other nearby eateries include cool diners and even another Gino’s East. Several funky nightclubs abound for great people-watching.
Whether or not you took the Ontario Street detour, it’s time to walk back south on Michigan Avenue and catch all of the sights one more time. Take a look at the floodlights on the Wrigley Building as you walk back. Stop on the bridge over the Chicago River (which is dyed green every St. Patrick’s Day).
Check out the skyline as you walk along the lakeshore of the only major U.S. city which planned to keep all of its downtown waterfront property as park land. This is especially apparent along Michigan Avenue across from Millennium Park. Grant & Millennium Parks offer great picnic spots and, in summer, Taste of Chicago, Independence Day fireworks, outdoor movie nights, and live music ranging from the Chicago Symphony to Lollapalooza. Great conversations abound if you find a few fishermen along the banks of the lake. Make some new friends – you might luck out and get some fresh fried fish!
Chicago is our favorite US city to be tourists in … what’s yours? Leave a comment and let us know. Enjoy your week or your weekend!