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Prairie Avenue Historic District

The Prairie Avenue Historic District is a Chicago South Side historic district that was once one of the city’s most prestigious neighborhoods. From 1872 – 1904, following the Great Chicago Fire of 1871, the area became known as “Millionaire’s Row”, with mansions owned by the likes of Philip Armour, Marshall Field, and George Pullman.

Prairie Avenue Historic District first became known as the site of the Battle of Fort Dearborn in 1812. It housed a cottonwood tree that stood on the site as a memorial marker, later replaced with a bronze statue, and was recognized as Chicago’s first landmark.

In the 1900’s, due to the growth of downtown and the spread of noise and pollution in the Near South Side, the district fell out of favor. By 1915, residences began to be replaced by industry. And, by 1944, only 11 residences remained.

The Prairie Avenue Historic District was added to the National Register of Historic Places in 1972 and was designated a Chicago Landmark in 1979.

Today, the district is once again a residential neighborhood, and includes 11 residences that survived the glory days. These include the John J. Glessner House and the Clarke House Museum, which are open for tours.

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Medieval Times Chicago

Experience entertainment fit for a king at Medieval Times in Chicago. The huge stone towers of the Schaumberg Castle house a rousing dinner and action-packed show that attracts travelers to the Windy City for a ringside seat at the tournament. Guests enjoy a full medieval-style feast (vegetarian options available) — no utensils allowed! While devouring the four-course meal, visitors can cheer and leer for their favorite armored knights throughout the show and its jousting tournament, horsemanship and falconry. Adult beverages are available for purchase from the full bar before, during or after the show, and travelers can also pop by the castle for a night of chivalry, sustenance and libations.

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Chicago Temple

There are plenty of stunning churches, glorious cathedrals and ornate temples throughout the world, but few offer up service with a view quite like the one located inside the Chicago Temple Building. This 23-floor building was built in 1924 and is, without a doubt, the tallest church in the world.

Travelers can visit this iconic destination, which is home to the Methodist Church, and see the 1,000-seat sanctuary located on the first floor, or head to the Sky Chapel. With seating for just 30 people, this tiny but beautiful sanctuary—complete with 16 stained glass windows—is the highest indoor worship space of record.

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Driehaus Museum

The grand opulence of Chicago from 1880 to 1920 is on display at the Richard H. Driehaus Museum. Its building, an ornate mansion built by prominent banker Samuel Mayo Nickerson in 1883 during the height of the city’s Gilded Age, is still in the thick of modern downtown Chicago, two blocks from the city’s dining and retail hub along the ‘Magnificent Mile.’

Unlike other restored mansions-turned-museums, the intent is not to showcase personal histories or artifacts of former owners. Instead, the building’s art nouveau architecture and interior design elements serve as an elaborate display case for a permanent collection of European and American fine furniture and artworks that typify the period. Visitors to the three-story building can look forward period immersion with moody chandeliers, Victorian paintings, carved ebonized Cherrywood paneling and an extensive collection of Louis Comfort Tiffany glass lamps, chalices and vases.

Self or docent-guided tours (for an extra fee) explore several rooms including the domed stained-glass ceiling and show-stopping fireplace in the Gallery on the west side first floor, intricately carved lamps and desk legs, and Romanesque sculptures in the Library and an Islamic-inspired smoking room with blue Moorish tiles off the Main Hall. Occasionally, themed exhibitions are incorporated into the space, such as the recent showcase of period costuming from the Masterpiece Theater television production Downton Abbey, and a collection of designer jewelry – including brooches, rings, pendants and hair ornaments – from the Victorian Era to the first World War.

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Hyde Park

A prominent Chicago neighborhood and public space, Hyde Park is an area full of historic sites and museums. It is also the home of the University of Chicago, and has seen more attention recently as the former residence of President Barack Obama.

When the neighborhood was established in 1853, it was the first suburb of the rapidly growing city. It remains known for its architecture, culture, and open-air spaces. Of particular note is the Museum of Science and Industry (great for families,) and the historic Robie House designed by Frank Lloyd Wright. The museum is the largest science museum in the Western Hemisphere.

Two scenic parks include Promotory Point, with great views of the Chicago skyline, and Jackson Park, a natural space with a small Japanese Garden. Hyde Park has also become known as one of the best dining and shopping spots in the city, with independent bookstores, street fairs, and farmers markets.

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Tommy Gun's Garage

Step back in time to the Roaring Twenties and the Prohibition era in Chicago at Tommy Gun’s Garage, an interactive dinner show in a speakeasy setting. Enjoy a sit-down meal and an evening of singing and dancing, comedy, and plenty of audience participation.

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Lookingglass Theatre Company
6 Tours and Activities

Founded in 1988 by graduates of Northwestern University, the award-winning Lookingglass Theatre Company is known for putting on cutting-edge works that sometimes incorporate circus acts. Located in the historic Water Tower Water Works, the company has staged more than 65 world premieres.

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Second City

If John Belushi, Bill Murray, Gilda Radner, Shelley Long, Mike Myers, Chris Farley, Steve Carell or Tina Fey have ever made you laugh, do yourself a favor and catch the next big comedian at The Second City, where dozens of legendary comedians and actors have gotten their start over the years.

Producing talented alumni since 1959, the comedy troupe originated at this Chicago location and specializes in sketch comedy and improv. There are shows every night of the week, and you can make it a date with a dinner-and-show package that features a meal from a local eatery within walking distance of the theater.

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House of Blues
5 Tours and Activities

Chicago is known as the home of the blues, so it is fitting that one of the most popular venues for live music in the city is the House of Blues. However, this local outpost of the national chain isn’t just a venue for blue musicians (and in fact, if the best blues acts are what you want to see, there are better venues in the city), but rather a showcase for international musical acts of every genre. Opened in 1996, the concert house, which was modeled after an opera house in Prague, has hosted some of the world’s most renowned musicians, including the Who, Pearl Jam and Al Green.

On nights when there are no ticketed acts, the Back Porch Stage offers shows with a $10 cover, which is waived if you dine in the restaurant before the show. The restaurant also serves lunch Monday through Saturday, and every Sunday, the House of Blues hosts its World Famous Gospel Brunch at 10:00 a.m. and 12:30 p.m. The brunch is a great opportunity to be inspired by a rousing gospel music performance while enjoying a hearty buffet complete with seafood, waffle, omelet and carving stations.

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Lake Michigan

Lake Michigan is one of the United States’ five Great Lakes, together with Lake Huron, Lake Superior, Lake Ontario, and Lake Erie. The lake stretches north-south and borders the states of Wisconsin, Illinois, Indiana, and, as its name suggests, Michigan. Chicago is the biggest city on Lake Michigan, which is the largest lake in the world that sits within one country. In fact, the lake is so vast that its waves are surfable—even in icy winters.

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