Fun Family Getaway: Chicago!

22 Reasons Why a Family Vacation in the Windy City will Blow You Away

“Chicago is America’s dream, writ large. And flamboyantly.”

– Studs Terkel[i]

Some guys will do anything for a buck. At least that’s what one romantic soul surmised after attending a freshman orientation dance in Chicago.

It seems that our anonymous inamorata and her girlfriends came to the dance at the University of Chicago and found themselves under the scrutiny of every eligible young man in attendance. Across the room, one brash paramour – let’s call him John – elbowed his buddy (we’ll name him Ray). Then he pointed to our anonymous lady and said, “See that girl there? That’s the woman I’m going to marry.”

Ever the skeptic, and something of an opportunist, Ray simply shrugged and said, “I’ll bet you a buck that you don’t.”

That was a bet John was willing to take. He walked across the room, introduced himself, and asked the pretty girl to dance. The next several months were spent in the romantic whispers of library study sessions, until finally John got the courage to ask our lady for a “real” date. She accepted and a budding romance was born.

The advent of World War II threatened to cost friend John the bet, but the two Chicagoans stayed true while the young soldier fought bravely for his country. When he returned from war, John and his freshman dance partner were, at last, married.

Some 60 years later, they are still together and report that they are “Happy in Lafayette, Calif.” As for Ray, well, he tried to avoid paying up on his wager. For years he hoarded his buck, but finally, the lady says, “We were expecting our third child when John received a letter from Ray with a dollar bill and a note. It said, ‘You win!’” And that was when she finally proclaimed, “Some guys will do anything for a buck.” Even, it seems, fall happily in love at a freshman dance in Chicago.[ii]

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Now, we can’t promise that you’ll find true love on your next visit to Chicago, Illinois – but we would be willing to bet you a buck that, by the time you leave, you and your family will be deeply infatuated with the famed White City. And why wouldn’t you? With all there is to do in this Midwestern playground on the shores of Lake Michigan, it’s no wonder that 60,000 Travel and Leisure magazine readers named it one of “America’s Favorite Cities” in 2007.[iii]

Within the 3,721 square miles that make up the greater Chicago metropolitan area are some of the best restaurants on the planet, art and architecture like no other, one-of-a-kind historical sites, world-famous museums and parks, thousands of entertainment options offered daily – and did we mention that whole “best restaurants on the planet” thing?[iv]

Also wrapped up in Chicagoland are the buoyant, bustling, historic neighborhoods that populate this place: The Loop, Lincoln Park, Gold Coast, Old Town, Streeterville, and more.

Of course, there’s no way we could fit every neighborhood and everything to see and do in Chicagoland into this article. But, for the next few pages at least, let’s figuratively “skip a stone” across a map of a few Chicago locales and see where it might land. Who knows? We might just fall in love…[v]

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Lovin’ The Loop

When people talk about downtown Chicago they’re talking about The Loop: the cultural center and beating heart of the Windy City.

It’s in this neighborhood that you’ll find historic skyscrapers, expansive parks, art, history, commerce, theater, and just about anything else that makes Chicago, well, Chicago. Here are a few things that keep us lovin’ The Loop…

1. Grant Park / Millennium Park

Smack in the middle of downtown sits the playground of the Windy City: Grant Park. This 220-acre recreational area spreads out from Michigan Avenue to Randolph Street in the north, and all the way to Lake Michigan in the east. It was originally designed by famed architect Daniel Burnham (who also designed the staging area for the 1893 World’s Fair) and was supposedly modeled after vistas of Versailles. Grant Park’s outdoor offerings include large gardens, baseball diamonds, miniature golf, tennis courts, bicycle and walking paths, outdoor concert pavilions, roller skating, ice skating (in winter), and the iconic Buckingham Fountain (featured in the opening credits of the sitcom, Married…with Children).

At the northwest corner of Grant Park is the recently opened Millennium Park, a wide-open place that features unrivaled landscaping, fascinating architecture, public entertainment venues (including an ice rink and theater), and outdoor concerts. The Frank Gehry-designed Pritzker Music Pavillion is always an attraction, as are impressive public art pieces like the Cloud Gate sculpture and the unique Crown Fountain, where giant video screens project faces of happy Chicagoans above the splashing waters.

With this kind of broad family appeal, Grant Park and Millennium Park shine like gems among Chicago’s finest crown jewels

2. The Field Museum

The Field Museum of Natural History opened in 1893 and gained its current name in 1905 from its primary benefactor, retailer Marshall Field. The museum was founded as a result of the 1893 Columbian Exposition (i.e. the Chicago World’s Fair) and designated as the place to house the biological and anthropological exhibitions from the fair. Today those collections have grown to include over 20 million specimens as well as more than 250,000 books that make up a world-class, one-of-a-kind natural history library.

The museum is a center of activity and a magnet for visitors all year long. It maintains a number of permanent exhibits that cover a wide variety of topics, from Animal Biology to Inside Ancient Egypt, to the Hall of Jades, the Malvina Hoffman Bronze Sculptures, and even more. Additionally, temporary exhibits capture the imagination with displays about Nature Unleashed, Mythic Creatures, and The Aztec World. In all, a day spent at the Field Museum is one that most families will never forget.

3. Sears Tower

At one time the tallest building in the world, the Sears Tower still stands as the highest skyscraper in North America and the third-tallest man-made structure on the planet. With 110 stories, it rises 1450 feet into the Chicago skyline at 233 South Wacker Drive. The lobby of the Sears Tower showcases a unique, moving mural called Universe created by the famous sculptor, Alexander Calder. At the 103^rd floor is the Skydeck – which offers city views that can stretch visibility up to 50 miles on a clear day – as well as multimedia exhibits on Chicago history and kid-friendly displays called Knee-High Chicago. One other thrill for kids: a whooshing elevator ride that goes from the ground floor to the 103^rd in a speedy 70 seconds! Because the Sears Tower is a popular tourist spot, plan to visit in late afternoon or early evening to avoid the crowds.

4. The Theatre District

Chicago may be nicknamed “The Second City,” but this place is second to none when it comes to stage shows! Although there are hundreds of options citywide, the nexus of performance venues lies in the old “Theatre District,” just north of Randolph Street, on State Street in The Loop. For instance, the Cadillac Palace Theatre – once a thriving vaudeville house during the roaring 20s – plays host to Broadway hits like The Producers, Mamma Mia, and Dirty Dancing. The Ford Center for the Performing Arts / Oriental Theatre opened in 1926 as a cinema with an eastern fantasy setting that included turbaned ushers and “hasheesh-dream décor.” Fully renovated in the late 1990s, it now delivers lavish stage shows like Fosse, Ragtime, and Wicked. Also showcasing unforgettable shows in the theatre district are the Auditorium Theatre (opened 1889), the Chicago Theatre (also originally a movie palace), and the Goodman Theatre (an art deco masterpiece that opened 1923). In all, Chicago’s theatre district is a grand spectacle that any visitor here should see.

5. John G. Shedd Aquarium

More than 2 million people walk through the doors each year at the Shedd Aquarium on South Lake Shore Drive (near the Field Museum). What keeps the masses coming back to this indoor water world? That would be the thousands and thousands of river, lake, and sea creatures housed in the unique and ecologically accurate habitats inside this impressive, marble building.

Exhibits here are large – and fascinating. The Caribbean Coral Reef is a massive, 90,000 gallon tank that is home to nurse sharks, barracudas, stingrays and other Caribbean species. During daily feedings (between 11:00 a.m. an 2:00 p.m.), a diver hand-feeds the fish and (courtesy of an underwater microphone) offers interesting insights about the denizens of this tank. Other attractions include the Oceanarium (where beluga whales, dolphins, and sea otters live), a 60,000 gallon Penguin Habitat, and the Amazon Rising exhibit.

The Shedd Aquarium can get crowded in the afternoons, so best bet to visit here is in the morning.

6. Art Institute of Chicago

Two stone lions flank the Michigan Avenue entrance to the Art Institute of Chicago. They took up their protective poses in 1893, a gift of Mrs. Henry Field to celebrate the opening of the Institute at this location. More than a century later, they remain symbols of the vast aesthetic wealth inside – an astonishing array of more than 5,000 years of artistic expression from all over the world.

Permanent collections in here showcase African and European paintings and sculptures, Contemporary Art, Textiles, Architecture, Photography, Arms and Armor, French Impressionist works, and more. Special exhibits, on display only temporarily, include fascinating subjects such as Benin Kings, A Mind at Play (illusionary photography), and art and photography of Paris. By far, the best way to experience the Art Institute of Chicago is simply to walk in and wander through, but if time is an issue on your trip, consider taking one of the museum’s free “Highlights of the Art Institute” tours which occur on Saturdays and Sundays at 2:00 p.m.

Eat Here in The Loop!

7. Everest. Perched on the 40^th floor above the Chicago Stock Exchange, the view is as impressive as the salmon soufflé, the poached tenderloin of beef, and the white wine selection. www.everestrestaurant.com

8. Opera. Sumptuous Chinese cuisine served in a setting of majestic, old-school glamour (complete with velvet curtains and a grand staircase. An attractive location for romantic couples, specialties here are Peking duck, filet mignon, and the Tao of Chocolate dessert. www.opera-chicago.com

Uniquely Lincoln Park

Lincoln Park sits in a tony northern section of Chicago, and with this location cometh privileges. Upscale housing, first-class restaurants, one-of-a-kind cultural attractions, stylish theaters, unique shopping experiences, and miles and parks of beautifully-kept scenery are the norm in this plentiful playground. Highlights here include…

9. Chicago History Museum

Founded in 1856, the Chicago History Museum (located at the corner of Clark Street and North Avenue) shows off literally millions of artifacts from Chicago and US history. It includes a gallery designed just for kids (complete with a “Smells of Chicago” display), as well as perhaps the world’s finest costume collection. The Civil War collection here could keep aficionados occupied for a day all by itself. Among its Abraham Lincoln artifacts is even the bed on which our 16^th president died.

The entire second floor of this museum is called Chicago: Crossroads of America, and it traces the city’s past from its origins as a trading post, to the Great Chicago Fire, through the resurgence of the Second City, all the way to the city’s recent history. An mp3 audio for this floor can be downloaded from the museum’s web site (www.chicagohistory.org) – but don’t let that substitute for the hands-on thrill of walking these hallowed halls yourself.

10. Lincoln Park Conservatory

You don’t have to be a horticulturalist to appreciate the sheer beauty that grows within the four greenhouses of the Lincoln Park Conservatory – all you have to be is human.

Originally built between 1890-1895, this historic conservatory was designed by prominent architect, Joseph Lyman Silsbee in collaboration with architect M.E. Bell. Hailed as a “paradise under glass” for more than 100 years, it serves as a free showcase for exotic foliage and also as the supplier for the thousands of plants needed to fill Chicago’s city parks. The Lincoln Park Conservatory features four main display houses: the Palm House, the Fern Room, the Orchid House and the Show House. It’s open to the public seven days a week, with free admission all year long.

11. Lincoln Park Zoo

Just east of the Lincoln Park Conservatory is the place they call the “wildest spot in Chicago” – and literally speaking, the Lincoln Park Zoo is just that! Although it is one of the premiere animal sanctuaries in the world, the most unique aspect of this zoo might be its cost of admission: Free.

According to zoo officials, “Lincoln Park Zoo is a world of wildlife in the shadow of skyscrapers…The zoo has been a natural, free oasis for generations of animal lovers, who come to hear a lion’s roar echo off nearby apartment buildings, see gorillas climb trees as the Sears Tower looms in the distance, or forget where they are as they immerse themselves in tropical rainforests, dry-thorn forests or spacious savannas.”

The Lincoln Park Zoo is open 365 days a year, and yes – it’s always free.

Eat Here in Lincoln Park!

12. RJ Grunts. This place is lauded as having best burger and shake in the whole USA. In addition to their home-style, half-pound hamburgers, RJ Grunts is also known for presenting one of the first – and best – salad bars in America. 773.929.5363

13. Bacinos. Not in the mood for a burger? Then go here for the best stuffed spinach and mushroom pizza on the planet! Yes, there is usually a line here on weekends, but it’s definitely worth the wait. www.bacinos.com

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Magnificent Mile Memory-Makers

The Magnificent Mile sits just north of the Loop, along the edge of Lake Michigan, and in specific, refers to the stretch of North Michigan Avenue that runs from the Chicago River to Oak Street. Although primarily known as a shopper’s paradise (it is, after all, home to Saks Fifth Avenue, Neiman Marcus, Bloomingdales, Virgin Megastore, the huge shopping complex at One Magnificent Mile, Oak Street boutique shops, and so on), there is more to the Magnificent Mile than just a place to lighten your wallet. Consider…

14. Navy Pier

Extending more than a half-mile over Lake Michigan is Navy Pier, one of the “must-see” locations on any visit to Chicago. Originally built in 1916, and then occupied by the US Navy during WWII, Navy Pier today is a combination carnival and shopping Mecca for tourists and locals alike. With over 40,000 square feet of retail stores and dining establishments, there are plenty of places to happily charge up your credit cards –the international Fashion Bazaar, Build-a-Bear Workshop, Bike Chicago (where you can rent skates by the hour), Navy Pier Kids Store, Magic Masters trick shop, Ryba Fudge Shop, the Popcorn Palace and Candy Emporium, a full food court, Bubba Gump’s restaurant, Joe’s Be-Bop Café and Jazz Emporium, and more.

Other attractions include a classic Ferris Wheel that reaches 150 feet high, the Crystal Gardens (a six-story tall botanical park) a Musical Carousel, the Smith Museum of Stained Glass Windows, kid-friendly carnival games and rides, and so on. In all, it’s a fun family outing – but remember to wear comfortable shoes and take along a light coat as wind from the lake can bring a chill.

15. Chicago Children’s Museum

At 700 East Grand Avenue in Navy Pier is the Chicago Children’s Museum – a three-story, hands-on, play-and-learn place for kids from ages two to 12. The Artabounds Gallery displays collaborative works of museum patrons; in the BIG Backyard, kids play in an oversized urban garden complete with giant insects, huge toadstools, and human-sized flowers (which laugh out loud for good measure). In the Dinosaur Expedition, children (and their parents) can dig for prehistoric bones in an authentic excavation pit. At Kids on the Fly, youngsters can pilot a plane and practice air traffic control. There’s also Waterways (a wet-n-wild exploration of water; yes giant squirt machines are included), an Inventing Lab and so much more.

If you plan to enjoy the Chicago Children’s Museum next time you’re in town, expect to follow your kids around for around three to four hours – about the average amount of time most families spend in here.

16. John Hancock Center

Completed in 1970, the John Hancock Center (or “Big John” as locals call it) adds its impressive profile to a skyline already inhabited with superlative architecture. This 100-story marvel holds the requisite shopping and dining attractions for a tower like this, such as an Aveda store, The North Face, Accent Chicago, Paul Stuart, L’Appetito restaurant, The Cheesecake Factory, and the Signature Room. But the real attraction here (aside from the architectural design and flourishes) is the Skydeck Observatory that awaits one high-speed elevator ride away on the 94^th floor. Although about 300 feet shorter than the Sears Tower, this observatory at the John Hancock Center offers phenomenal, panoramic views of the Windy City from any direction – making it a great place to stop during a romantic night on the town.

17. Fourth Presbyterian Church

Located at 126 East Chestnut Street, this historic place of worship first came into use in 1914 when the congregation moved from an older building into this one. In the near-century since, the Gothic architecture and interior design has been carefully restored and preserved to make it a living work of art within the city’s boundaries. Fourth Presbyterian Church’s ivy-lined courtyard (called “the most romantic church courtyard in the city”) centers around the gurgling of a classic fountain. Inside the building are intricate ceiling murals designed by renowned artist Frederic Clay Barton.

The current congregation’s dedication to the arts as an expression of worship toward Christ means that creative performances occur frequently here, including free classical concerts every Friday at noon, periodic “Jazz Vespers” featuring accomplished saxophonist Andy Tecson, and Taizé gatherings that incorporate spiritual traditions from all over the world every fourth Friday of the month.

Visitors are welcome to tour Fourth Presbyterian Church at any time. If attending a concert or church service, arriving early is recommended as their popularity can occasionally make the church a standing-room-only venue.

Eat Here in The Magnificent Mile!

18. Signature Room. High atop the John Hancock Center – on the 95^th floor to be exact – this restaurant serves American cuisine along with the absolute best views of Chicago’s cityscape. www.signatureroom.com

19. TRU. Known as a feast for the imagination as well as the taste buds, TRU has earned its elegant dining reputation with its art gallery interior that features Andy Warhol paintings, caviar served on a miniature crystal staircase, 10-course dinners, and even meals served atop a fishbowl with live fighting fish inside. www.trurestaurant.com

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Last But Not Least…

20. The Second City (Old Town neighborhood)

If you’re looking for night of comedy, The Second City (1616 North Wells) is the place you want to go. Famous for launching careers of comedy legends like Bill Murray, Alan Arkin, Dan Aykroyd, and John Belushi, The Second City delivers nightly shows (Tuesday – Sunday) of improv, skits, audience participation, and whatever else their wacky minds can think up. Parents be aware, though, that shows are uncensored and may be inappropriate for children.

21. Authentic Chicago Pizza (Various Neighborhoods)

Chicago-style, deep-dish pizza is plentiful in Chicagoland – and not to be missed! Here are some of the pizzerias we’d recommend: Pizzeria Uno (gourmet deep dish, located at 29 East Ohio Street); Gino’s East (also gourmet deep dish, at 633 North Wells Street); Lou Malnati’s Pizzeria (deep dish and thin crust, also has a low-fat cheese option, at 439 North Wells Street); Raynalli and Ryan’s (deep dish and thin crust, and also a large selection of beers, at 1925 North Lincoln Avenue); and Chicago Pizza & Oven Grinder (home of the one-of-a-kind “pizza pot pie,” at 2121 North Clark Street).

22. Chicago Comics (Lakeview neighborhood)

If there’s a super-fan in your family, then Chicago Comics is a place you won’t want to miss when you’re in town. Located at 3244 North Clark Street, it’s generally regarded as one of the best comic book shops in the entire nation. They’ve got everything here, from a huge selection of super hero works (both current and collectible – toys included) to a broad collection of anime and even one-of-a-kind works from local artists.

One caution, though, because of occasional subject matter and art styles, Chicago Comics may not be appropriate for younger children.