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A Little Bit of Everything
A week-long introduction to The Windy City
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Steak, pizza, baseball, museums, comedy, tours, and Lake Michigan. What's not to like?
 Day Note
Day 1: Saturday, June 21st
Welcome to Chicago! A great way to get a quick overview of the city is to take a Gray Line Tour on one of their double decker buses. The tours can be a bit long (up to four hours), but will give you a preview of several sites that you will be visiting later in your trip.
After your Gray Line Tour, head to the old Marshall Field’s store (now Macy’s) on State Street to dine at the Walnut Room. This is a favorite spot for locals and tourists alike, and since Macy’s was nice enough to keep the Walnut Room (and Frango chocolates- make sure to buy some in the basement of the store), it’s like being back in Marshall Field’s.
Spend the afternoon wandering through the Art Institute’s wide and varied collections. The Art Institute has the largest collection of Impressionist Art outside of the Musee d’Orsay in Paris, and it is impressive (please pardon the pun). If you are traveling with children, there should be some children’s activities and docents during Saturday hours in the event they get tired of debating the realism of Nighthawks.
When you leave the Art Institute, head north on Michigan Avenue to Millennium Park. Cloud Gate is a great spot for photos, both of the sculpture itself and the skyline behind it. The Crown Fountain to the south of Cloud Gate, or The Bean as locals call it, and Pritzker Pavilion to the east, are the other main attractions in Millennium Park.
Dinner at Trattoria No. 10 should be a nice treat at the end of a pretty long introductory day to the Windy City. Chicago is known for its Italian food, and this establishment has both great food and great service.
After dinner, enjoy a show at the Oriental Theatre. (At the time of this writing, “Wicked” is still playing at this theater, and we assume it will still be there when you visit, since it’s been in an open run since 2005 and doesn’t look to end anytime soon). Even if you’re not much for Broadway shows, the theater itself is probably enough to keep you enthralled for a couple of hours. The interior is incredibly ornate, and the theater is supposedly haunted, which you should learn about on your supernatural/ghost tour later in your visit.
This tour provides an excellent overview of Chicago. Titled "Inside Chicago," the tour includes a four hour bus ride through the Loop, the South Side, the Lakefront, Hyde Park, the Magnificent Mile and Gold Coast areas. You can also take the "Sky Deck" tour, which features a double decker bus with open top seating and makes extra stops at the John Hancock and Sears Towers.
Inspired by a style called "Opium Dream," this theater has a quasi-Arabian theme, from the statues that peer down on the audience to the intricate wrought-iron work on the staircase. This was the premier place to see movies in the Loop, and it later housed such live acts as Fred Astaire and Jimmy Durante. However, it fell into grave disrepair in the 1970s and was shuttered for good in the early 1980s. In the mid-1990s, it was purchased by Canada's Livent Theater Group and painstakingly refurbished with money from the Ford Endowment for the Performing Arts, giving it an expanded name. Today it is one of Chicago's premier showcases for musicals such as Ragtime and Cats.
This is possibly the most-photographed spot in Chicago, but more for its picturesque view over the river than for its historic significance. Plaques embedded in the sidewalk mark the spot of the original Fort Dearborn, where Chicago's first settlers staked their claim off of Lake Michigan. The bas-relief sculptures on the bridge represent important events in early Chicago history. They are interesting and controversial because they depict Native Americans as the bad guys in the struggle over the "Chickaguo" territory.
This popular sculpture in Millennium Park has become a landmark of Chicago's cityscape. Ever since the public first glimpsed the then-unfinished structure in 2004, its unique appearance has drawn a great deal of both criticism and praise. Designed by British artist Anish Kapoor and forged from steel plates that have been polished to a mirror-like finish, Cloud Gate has been affectionately named "The Bean" by city residents because of its legume-like shape. At 66 feet long, 42 feet wide, and 33 feet high, this is one mighty bean, weighing in at 110 tons. The highly reflective surface and curved shape create an effect similar to that of a funhouse-mirror, distorting the shape of curious onlookers and making it a popular attraction for children of all ages. The sculpture often takes on a life of its own as its surface reflects Chicago's skyscrapers and the blue sky.
Classic Italian dishes with a contemporary flair have made Trattoria No.10 a Chicago favorite since 1989. Specialties on the daily menu include unique, homemade ravioli, rustic pastas, freshly prepared risotto, fresh fish selections and grilled filet of beef. The subdued elegance of the interior, with arched walkways, murals and original art provides an intimate atmosphere that is perfect for business lunches, pre-theater dining, romantic dinners or private parties.
The woody interior of this restaurant stirs many memories for locals, evoking a warmer, more amiable time in history. No wonder this is still a favorite for families and couples alike during the Christmas season. Be prepared to wait, however, as reservations are not accepted during the holidays and lines do get long. Ask for a seat near the gigantic Christmas tree. For the rest of the year, the Walnut Room offers a lunch escape for Loop professionals who are sick of the standard faux fast food places and want to eat off of real plates with real utensils for a change. The food is wonderful and reasonably priced, the crowds are manageable and service is smooth. Be sure to try classics, like the chicken pot pie and apple pie, as well as newer additions, such as the vegetarian burger.
Millennium Park is one of the newest additions to Chicago's many wide-open urban spaces, and is host to a range of indoor/outdoor activities for the entire family. You can listen to top musical events at the outdoor pavilion, or glide across the bustling ice skating rink come winter. The park is also home to some of the city's best public art, such as the interactive Crown Fountain, and the scene-stealing Cloud Gate, a mirrored sculpture situated in the middle of the plaza. For a scenic walk, take a stroll through the Lurie Garden, or wind your way along Frank Gehry's BP Bridge. For a bit of the park's history, be sure to take a peek at the Peristyle, a replica of the curving row of paired Greek columns that were on the corner of Grant Park near Michigan and Randolph from 1917 to 1953.
From popular Rembrandt masterpieces to recent works by lesser-known artists, this museum houses one of the finest art collections in the world. Spanning centuries of human creativity, exhibits include a distinguished collection of prints and drawings, an internationally acclaimed collection of Impressionist and Post-Impressionist paintings, sculptures, photographs, Asian, African and American arts, architectural drawings, textiles and more. Many pieces are on loan from the famed Terra Foundation for American Art. Educational programs and guided museum tours are available. Art books, reproductions, postcards and other items are available in the museum shop. Free public lectures are given during weekends.
The exquisite chandeliers high above the Rococo interior peer down on you with pomp and grandeur in the elegant lobby. Built in 1927, this hotel reflects an era that once defined opulence in America. The rooms are plush, too, but usually come with a price to match. However, weekend deals can be quite affordable. If you choose to stay elsewhere in the city, at least stop by the hotel's lobby to check out the architecture.
Millennium Park
Day Note
Day 2: Sunday, June 22nd
Today you’re going to explore the South Side, specifically Hyde Park. The best way to get to the Museum of Science and Industry, the first stop of the day, via public transit is the #10 bus, which runs express to the MSI from Roosevelt. You can catch the #10 at Balbo and Michigan starting at 10:49 am (according to www.transitchicago.com), running every 20 minutes thereafter.
The MSI usually has a pretty neat traveling exhibit (such as Body Worlds and Leonardo da Vinci’s inventions) and several great permanent exhibits, such as the U-505 submarine (the only German sub in the U.S.), an intricate doll house, and a scale model of downtown Chicago. The museum building is the only surviving structure from the 1893 World’s Columbian Exposition, which took place in the surrounding area of Jackson Park, to the museum’s south.
Stroll through Jackson Park and find a replica of Daniel Chester French’s The Republic, a large gold statue from the Columbian Exposition.
Lunch is at Harold’s Chicken Shack, a South Side favorite.
Begin your afternoon at the DuSable Museum of African American History. Named after Jean Baptiste Pointe du Sable, the founder of Chicago, this museum is the first and oldest dedicated to the study and preservation of African American history. When fished at the DuSable Museum, cross over into Washington Park, which is Chicago’s proposed site for the Olympics in its bid to host the 2016 Summer Games. Until the 1920s, sheep grazed in Washington Park as a means to keep vegetation under control.
Enjoy a leisurely dinner in Greektown at Greek Islands (or Santorini across the street if there is a wait). Be sure to get the sagnaki (flaming cheese), and remember to save room for baklava for dessert. Everything on the menu is great!
Cap off your day with a stroll through Grant Park to Buckingham Fountain for nightly light and music show. There are great views of Lake Michigan to the east, the skyline to the west, and the museum campus to the south from this spot, so take your camera for some night-time shots.
This place is a perfect place to spend a sunny afternoon or weekend. Bring a picnic and enjoy the children's playground areas, fishing pond, basketball courts, and baseball diamonds. A three-story water slide and figure-eight spray pool are favorites with kids in the summertime. A dozen fountains shoot water as high as seven feet in the air from the shallow end of the pool. The DuSable Museum of African American History is also located here.
One of the most boisterous and hopping of all the Greektown restaurants. Somehow it manages to maintain a sophisticated atmosphere even amidst loud noise and busy waiters. If you have three or more people, order one of the family style dinners, which include saganaki, taramosalata (salmon pate), lamb, meatballs, dolmades (stuffed grape leaves) and more. Part of the charm is that you can dress up and feel comfortable, or go in jeans and feel at home. Try the Greek beer or one of the exotic Greek wines.
The University of Chicago has done it all, from the birth of the atomic bomb to the first living-donor living transplant to the birth of sociological study. On a lighter note, Chicago's famous Second City comedy group was conceived at the UOC, and the nation's first Heisman Trophy winner, Jay Berwanger, ran the pigskin here. Former home of Enrico Fermi, Albert Einstein, Milton Friedman and Saul Bellow, the UOC is rightfully proud that more Nobel laureates have studied or taught here than at any other university. The school was founded by the lakefront in 1891 and houses a richly detailed, gothic style campus. Take in one of many concert programs or events on campus, or take a stroll through scenic Hyde Park, the beautiful old neighborhood that engulfs the university.
This museum makes science fun with interactive, educational exhibits that stretch the imagination. Spend time in a 16-foot heart as you learn about how yours works. Find out how technology has influenced history by stepping back in time on 'Yesterday's Main Street'. Watch action-packed films in the museum's giant-screen Omnimax Theatre or take a ride down a coal mine. And don't leave without picking up some great souvenirs at The Big Idea museum shop. Omnimax requires additional fee. Parking available in underground garage for a small fee.
Salute the contributions African-Americans have made to world history, and learn about their culturally rich heritage. Galleries showcase extensive collections of award-winning photography, paintings, sculptures and other works by African and African-American artists. Original slave documents and civil rights memorabilia are also displayed. The museum hosts numerous public programs throughout the year including lectures, special exhibits and workshops. Admission is free on Sundays.
Don't judge Harold's by its dingy, slightly scary interior. Harold's sells what may be the best Fried Chicken north of the Mason Dixon line. Smothered in your choice of mild or hot sauces, served with fries over white bread, this is the stuff homesick South Side Chicagoans dream of when they are out of town. Working stiffs and University of Chicago professors alike can attest to the appeal of this greasy ambrosia. Numerous locations can be found around the city.
Starting behind the Museum of Science and Industry, Jackson Park contains acres and acres of re-created forest and lush greens. Be sure to stroll through the wooded island and stop at the Japanese pavilion, a re-creation of the one that stood at that very spot during the 1893 Columbian exposition. Along with the museum, the Wooded Island is one of the last remaining vestiges of that fabled fair. Well worth a visit after a trip to the museum, but be careful, the neighborhoods nearby can be shady after dark.
Shout "Opah!" (not Oprah) as you explore one of Chicago's ethnic neighborhoods. In the late 1800s, Greeks began immigrating to this part of the city. Today, much of the ethnicity of the neighborhood is gone, but a number of high quality restaurants are strewn over Halsted, and a trip here can be a culinary delight. There are also lots of friendly taverns open late, making this area of Chicago especially popular for those who want to grab a drink before heading back to their Loop hotels or apartments.
Graceful sea horses spray jets of water into the lagoon that surrounds what is perhaps Chicago's most beloved public piece of art. Philanthropist Kate Buckingham commissioned the fountain in 1927 in honor of her brother Clarence. Its design parallels one of the fountains at Versailles Palace in France. You may, however, recognize it from the intro to "Married with Children." Recently renovated, the fountain has been returned to its former splendor. At night, it becomes gorgeously illuminated, drawing crowds from May 1 (or earlier if warm) until mid-October.
Buckingham Fountain
Day Note
Day 3: Monday, June 23rd
Your first stop of the day is the Frank Lloyd Wright Home and Studio in Oak Park. You should take the Green Line to Harlem (the last stop on the line) and walk about ¾ of a mile north to the studio. Wright was one of several notable architects in the Chicago area at the turn of the cenury and went on to create the Prairie School of architecture and become “the greatest American architect of all time” according to the American Institute of Architects. Wright built this home in 1889 with a $5,000 loan from his employer, Louis Sullivan, another pre-eminent architect.
Lunch back in the city at RL Restaurant (short for Ralph Lauren, located next to the Ralph Lauren/Polo store on North Michigan Avenue). You may rub elbows with notable Chicagoans, as Maggie Daley, the Mayor’s wife, is known to dine there.
The rest of your afternoon can be spent leisurely strolling North Michigan Avenue, stopping at the Visitors Center, ascending the Hancock Center, and dipping your toe in Lake Michigan on Oak Street Beach (accessible via pedestrian underpass at Oak Street/East Lake Shore Drive).
A great pre-show dinner can be had at Adobo Grill in Old Town, next door to Second City. The entrees are all worth trying, but DO NOT SKIP THE GUACAMOLE. It is prepared tableside, and you can instruct the person making it on how spicy, garlicky, and tomatoey you’d like your guac. You will not be disappointed. Menu items are seasonal and tasty. It is easy to overeat at Adobo, but try not to go crazy, because you won’t want to miss a laugh at Second City afterward. Recent revue titles have been “Iraqtile Dysfunction” and “Between Barack and a Hard Place.” If you are unable to see a show on the main stage, where the revues are performed, shows on the e.t.c stage and Donny’s Skybox are quality alternatives.
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