At night, gazing out the window of our hotel room in downtown Chicago, we get a sneak peak into the high-rise condos nearby and imagine what it would be like to live in the city. Like Sinatra said, Chicago is my kind of town. Not too big and not too small, the city offers great food and shopping, great parks and architecture, a beautiful waterfront and friendly residents. It might be the next best thing to my city of Los Angeles, if it wasn’t for below-zero temperatures and gale-force winds. So our L.A. family loves to visit Chicago for a long weekend. The sightseeing, shopping, dining and sports action can’t be beat.
Friday
Location, style and service make The Sutton Place Hotel (www.suttonplace.com) a great home base. This boutique hotel has a low profile, near the intersection of busy Rush Street and a quiet residential street a block from Michigan Avenue. The hotel has sleek, contemporary rooms with city views, friendly bellmen and front desk service, plus a bar/restaurant, Whiskey Bar & Grill. Shop travel websites for discounted deals on rooms here. After checking in, head for the Lincoln Park Zoo (www.lpzoo.org) just west of the city off of Lakeshore Drive. What makes the zoo special is its city location. You’ll feel like you’ve stumbled upon these 35 acres under the skyscrapers. Admission is free. For dinner, a local landmark is just down the street from your hotel. Gibson’s Steakhouse (www.gibsonssteakhouse.com), one of the city’s best-known restaurants, will give the kids a taste of old-school Chicago style, with lots of dark wood, cozy booths and a dressed-up crowd. We sat in a lively enclosed patio area that fronted the action on Rush Street. Afterwards, walk off dinner along Rush and glimpse the energy of the bar and restaurant scene. Head back to your hotel room and fall asleep to the spectacular nighttime city views.
Saturday
Take a short walk across the street from The Sutton Place and get in line for breakfast at The Original Pancake House. (www.originalpancakehouse.com) This old-fashioned favorite has hearty breakfasts, unusual pancakes and waitresses with attitude. After breakfast, head toward Michigan Avenue and along the way enjoy the old brick townhomes, condos and beautiful high-rise architecture, keeping in mind that Chicago is home of the skyscraper and a pioneer in early modern architecture. Keep walking to Lake Michigan. The kids will enjoy the beachfront, which will be windswept and covered with sand or snow, depending on when you visit. After the kids left off some energy, catch a cab to The Willis Tower, (www.willistower.com) formerly known as The Sears Tower, the tallest building in the Western hemisphere and the third-tallest building in the world. Travel to the one hundred and eighth-floor Skydeck for scary-high but incredible views of the city, suburbs and Lake Michigan. Then, depending on the time of year, go to a Cubs, White Sox or Bears game in the afternoon or evening. If time doesn’t permit you to go to a game, be sure to look into tours of either Soldier Field or Wrigley Field, homes of the Chicago Bears football team and the Chicago Cubs baseball club, respectively. Try a Chicago-style bratwurst at a game. If you don’t eat at the stadium, make a trip to the Billy Goat Tavern (www.billygoattavern.com), made famous by the Saturday Night Live skit featuring John Belushi. Enjoy a “cheezeborger” and “Pepsi, no Coke” and learn about the Billy Goat’s role in the curse of the Chicago Cubs.
Sunday
No trip to Chicago is complete without a Wendella Boat tour along the Chicago River. (www.wendellaboats.com) Tours depart throughout the day and take in the architecture of the city from a unique river perspective. When you’re off the boat, think about another authentic Chicago experience: eating deep-dish pizza. Visit Pizzeria Uno (www.unos.com) for a very filling pie. Finish your day with some shopping along North Michigan Avenue and Oak Street in downtown’s Gold Coast neighborhood. You’ll find shops that appeal to everyone, including the Blackhawks Shop at 333. N. Michigan Avenue, offering everything a Chicago hockey fan could dream of. Michigan Ave. is home to every upscale retailer you can think of, including Saks, Bergdorf Goodman and some fancy malls. Oak Street offers sophisticated chains and boutiques including Barney’s and Agent Provocateur. Walk or take a cab back to the hotel, depending on whether you’ve just window-shopped or are weighted down with shopping bags.