Have a Mini-Holiday in Chicago


If you have only a few days to spare and are not keen on another “stay-cation,” consider a long weekend in Chicago. Rich in landmarks, art and history, the Windy City offers visual and cultural opportunities for every age and budget.

Plan to arrive on a Friday afternoon and head over to one of the more than 50 hotels conveniently located on North Michigan Avenue (be sure to reserve before you leave home), otherwise known as Chicago’s Magnificent Mile. Once you’ve checked your bags, head out for a cheeseburger at the original, legendary Billy Goat Tavern on North Michigan Avenue, made ultra-famous in the 1970s by the late John Belushi and other cast members from Saturday Night Live (“Cheezborger! Cheezborger! No fries, cheeps! No Pepsi, Coke!”).

Chicago Ferris Wheel

From there, take a walk to Navy Pier, one of Chicago’s most spectacular landmarks since 1916 and home to a number of attractions including a 150-foot high Ferris Wheel modeled after the original erected for the 1893 World Columbian Exposition. For those people who aren’t height phobic, the Ferris Wheel is the crown jewel offering expansive views of the city as well as the interior of the Pier.

Chicago Carousel

A recreation Mecca with both indoor and outdoor shops, restaurants and entertainment, Navy Pier also includes a musical carousel with hand-painted animals, an IMAX Theatre, Children’s Museum, an 18-hole miniature golf course, an ice rink in winter (converted to a 1500-seat theatre in summer), the Crystal Gardens (an indoor atrium filled with palm trees) and a seven-story Shakespeare Theatre.

Chicago coastline

If you plan to travel with children, you might consider booking a room in one of the hotels on Lakeshore Drive such as the W Hotel or the Affinia, both with stunning views of Lake Michigan and just across the road from Navy Pier. You could easily spend an entire day exploring Navy Pier with the kids and, if you’re lucky enough to visit during certain months of the year, stick around for the fireworks and music on the Pier at night. Check the website for dates and times.

American Gothic Statue

On Saturday morning, take a stroll down the Magnificent Mile starting at the American Gothic Statue (also known as God Bless America) by J. Seward Johnson, the American sculptor famous for his large-scale painted bronze statues. At 25-feet high, the statue depicts the couple from the famous 1930 Grant Wood painting in striking trompe l’oeil detail.

Chicago Georgia O'Keefe

Conveniently, just down Michigan Avenue about a half-mile south is The Art Institute of Chicago, home to the original Grant Wood painting and thousands of other treasures including some very famous Van Gogh, Monet and a particularly notable showing of Georgia O’Keefe paintings. The museum offers several areas specially designed to delight children (as well as adults) including a gallery of exceptionally detailed scale miniature rooms, vintage toys and play areas.

Chicago Crystal Ball

Just outside of The Art Institute is Millennium Park where you can experience the interactive Crown Fountain designed by Jaume Plensa, and Cloud Gate, a giant mercurial mirror ball, designed by Anish Kapoor.


As you meander through the park, you’ll come to the hard-to-miss Jay Pritzker Concert Pavilion designed by Canadian/American architect, Frank Gehry, well known for his groundbreaking architectural designs including the famous Guggenheim Museum in Bilbao, Spain. This band shell is home to The Grant Park Music Festival, held each year from mid-June to mid-August. The venue is utilized, also, for movie screenings and a variety of other local events. But, even when the stage is quiet, be prepared to marvel at the grandeur and artistic execution of ribboned steel and lattices. Adjacent to the Jay Pritzker Pavilion is the Gehry-designed BP Pedestrian Bridge spanning Columbus Drive on the opposite side of the Park. This stainless steel footbridge is the only bridge designed by Frank Gehry and should not be missed along with the public exhibitions of contemporary and modern art by living artists displayed across the outdoor Boeing Galleries.

Chicago Boat

Once you leave Millennium Park, take a short walk to the Chicago Riverwalk at Michigan Avenue and Wacker Drive for a 90-minute tour of the teal-hued Chicago River on Chicago’s First Lady featuring an historic commentary of over 53 landmarks, bridges and significant sights. When you disembark, linger at the Riverwalk for dinner at one of several eateries ranging from the Chicago River Dog CafĂ© for quick bites to Cajun, Sushi, Pub-style or Wine Bar establishments. If you have kids in tow, you’ll probably need a break so head back to your hotel and get some rest. Or, sans kids, now would be the perfect opportunity to experience one of Chicago’s famous Blues clubs. Check www.CenterStageChicago.com for a list of venues and up-to-date performance schedules.

Chicago Tall Buildings

A trip to Chicago without a visit to a tall building would be a heartbreaking misstep. Spend your Sunday morning either at the Hancock Observatory or Willis Tower (the Tower formerly known as Sears). Both provide views across Illinois to Indiana, Michigan and Wisconsin but the wait at the Willis Tower Skydeck can often reach three hours or more. If Sunday is your last day in town, use it to meander about, take in the street life and step into a few shops. From downtown Chicago, it’s impossible to miss the site of corncob-like Marina City Apartments on North State Street, once the tallest residential buildings in the world with 65 identical floors apiece and reportedly, the most photographed buildings in Chicago. Continuing on North State Street, you’ll come to the historic Chicago Theatre built in the early 1920s mainly as a venue for live entertainment and silent film screenings. Built primarily in the French style, the theatre was modeled after the Royal Chapel at Versailles. Today it’s used as a concert and live entertainment hall with Marquee Tours available on certain days of the week.

As you depart, you’ll realize one weekend in Chicago simply isn’t enough time to see and appreciate all the city has to offer. You’ll certainly wish to return but you will feel as if you’ve had a substantial vacation in just a few days without the substantial investment of time.


Hard Rock Hotel
230 North Michigan Avenue, Chicago

166 East Superior Street, Chicago

W Chicago Lakeshore
644 North Lakeshore Drive, Chicago


Billy Goat Tavern Original
Near Tribune Towers and Wrigley Building
430 North Michigan Avenue at Lower Level

Chicago Riverwalk Restaurants, Tours and Attractions
North Michigan Avenue and Wacker Drive, Chicago


Navy Pier
North Lakeshore Drive, Chicago

Art Institute of Chicago
North Michigan Avenue, Chicago

Millennium Park
North Michigan Avenue, Chicago

Chicago’s First Lady
Wacker and Michigan Avenues, Chicago

John Hancock Observatory
875 North Michigan Avenue, Chicago

Willis Tower Skydeck (formerly Sears Tower)
233 South Wacker Drive, Chicago

Marina City Apartments
300 North State Street, Chicago

The Chicago Theatre
175 North State Street, Chicago

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