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Frank Lloyd Wright House and Studio - Oak Park
View of the Chicago Riverwalk at Night

Visit Classic Chicago

Three days in the windy city.

3 Days 25 Miles



It’s easy to see why Chicago is a hit with everyone: with its soaring skyscrapers and spectacular views along the Lakefront footpath. From Navy Pier to Second City and everywhere in between, Chicago has what it takes to keep you enthralled day after day, and night after exciting night.

Day 1: Take a river cruise, explore the museums, and see a birds-eye view of the Windy City.

Sights and Skyscrapers

  • Odyssey Passing Under the Chicago River Bridge

Enjoy a quick overview tour of the city and hop-on and hop-off at most major attractions with trolley and open top double decker bus tours provided by Chicago Trolley & Double Decker. A multi-day pass may also be used as convenient transportation during your stay. For a one-stop shop in all things enlightening, take a stroll on the Museum Campus, which boasts your choice of three world-class culture meccas. The Adler Planetarium is the first museum of its kind in the Western Hemisphere and boasts a state-of-the-art theater that will take you on a gripping journey through space and time. The Shedd Aquarium holds more than 32,500 fish, sea mammals, snakes and amphibians from aquatic habitats around the world. Widely renowned as one of the country's finest aquariums, you will have an exciting journey under the sea with dolphins, eels and Beluga whales. See exhibits — including the largest, most complete Tyrannosaurus Rex skeleton currently known — at The Field Museum.

Hungry for lunch? You don’t have to be a baseball fan to enjoy the American and Italian cuisine at Harry Caray’s Restaurants. Locations downtown include a historic building in River North district and a great spot on Navy Pier. Menus are available in seven languages.

Built in 1916 but reimagined in recent years as a festival destination of shops, dining, cruises, and activities is Navy Pier. Notable lake excursions range from dining cruises aboard the Odyssey or Spirit of Chicago Cruise ships; a Tall Ship sailing experience with Tall Ship Windy; and a very exciting speedboat tour along the lakefront with SeaDog Chicago. Back on land you will find entertainment along the dock including music, miniature golf, and an amazing view back on the city from Navy Pier’s Ferris Wheel.

While that view is great you simply must try one of two Chicago observatories for a top of the world perspective. The John Hancock Observatory, on the 94th floor of Chicago's fourth tallest building, offers a bird's eye view of our breathtaking downtown and the lakefront with an audio tour included with admission. Across town, The Ledge at Skydeck Chicago is the thrilling attraction at Willis Tower, the tallest building in North America. Step out past the building walls and into a glass box 103 stories above the street.

Chicago has emerged as one of the great gastronomic cities in North America as noted and rated by the Michelin Guide with 19 star restaurants and a total of 433 guide recommended eateries. The range of flavor palette includes classic fine dining, steakhouses, eclectic trend setters, family casual, and many ethnic dining options. See your concierge for a recommendation which suits your taste.

Day 2: Explore Chicago's most vibrant cultural institutions, from free zoos to spectacular theatre.

Shopping and Shows

  • View down mag mile chicago

How about starting the day with a little exercise? The Lakefront Trail is an 18 mile (29 km) jogging and biking path along Lake Michigan with convenient access to downtown hotels. Wander north, whether jogging, biking or walking, and explore one of the last free zoos in the United States, Chicago’s Lincoln Park Zoo. Chicago is home to one of the great art galleries of the world. Don’t miss the Art Institute of Chicago. With a collection of more than 300,000 works, the museum features frequent special exhibits and the largest collection of impressionist art outside of the Louvre in Paris. Housed in two extraordinary examples of great Chicago architecture you will discover many famous works from Picasso, Rembrandt, Chagall, Seurat, and more.

The first Chicago-style deep dish pizza recipe was created here in the 1940’s. For lunch stop by Lou Malnati’s and savor the buttery, flaky crust, tangy tomato sauce, and gooey mozzarella which makes it so famous!

Chicago is home to one of the great avenues of the world, North Michigan Avenue. Known to travelers worldwide as The Magnificent Mile, more than 460 retail stores, 275 dining options, and almost 60 hotels fill the district with vibrant options for any taste. Luxury retailers on Michigan Avenue and Oak Street include Prada, Ferragamo, Escada, Burberry, Louis Vuitton, Marlowe, Jimmy Choo, and many more. You will also find very accessible American shopping favorites and brands from around the globe in places such as the world’s first vertical shopping mall, Water Tower Place, as well as, 900 North Michigan Shops and The Shops at North Bridge.

Along The Magnificent Mile you may enjoy an early dinner in the historic 1890's McCormick Mansion at Lawry’s, The Prime Rib. Famous roasted prime ribs of beef are carved tableside from a silver cart, with Lawry's "spinning bowl" salad, Yorkshire pudding, mashed potatoes, creamed spinach, creamed corn and buttered peas.

Then it’s off to the show! The city boasts multiple Tony award-winning regional theater companies. And with more than 200 theater companies delivering everything from blockbuster hits to edgy improv skits, your entertainment options are endless. Explore the offerings at Broadway in Chicago for the latest Broadway-style shows; The Steppenwolf, Goodman, or Lookingglass Theatres for the kind of inventive original productions that has made Chicago’s theatre scene famous. And don’t forget long-running shows like the Blue Man Group for high energy fun!

Day 3: Don't miss out on culinary and cultural institutions that only Chicago can call its own.

A Day of Chicago Favorites

  • Three people jumping up in the air in front of The Bean landmark in Chicago

Breakfast offerings have grown significantly in Chicago in recent years with many neighborhood options to choose from. Enjoy delicious, direct trade coffee in a cozy atmosphere at Intelligentsia, which provides padded sofas for your espresso sipping experience or go all out and join their local roasting tour! What a perfect way to kick start your day. Chicago may be most notable for great architecture. The term “second city” may be in reference to the incredible rebuilding of Chicago following the Great Fire of 1871. View the significant works of these great architects from the river with guided tours on any of Chicago’s boat tour companies.

Explore Chicago's lush Millennium Park that is home to the famous Cloud Gate or "Bean" sculpture, Jay Pritzker Pavilion, Lurie Garden, and the Crown Fountain that spouts water from its digital faces. Millennium Park is constructed on top of a railroad yard and expansive parking garages — making it one of the largest green roofs in the world.

Are you ready for a Chicago culinary classic? Sample a juicy Italian Beef sandwich or a famous Chicago-style hot dog at Portillo’s Hot Dogs in River North district.

One of the most unique experiences in Chicago is our Museum of Science & Industry. The largest science museum in the western hemisphere, this expansive building boasts hours and hours of exploration opportunity. Board and tour a real captured U505 German submarine from WWII, sink deep into a working coal mine exhibit, and marvel at a 40-foot tornado before your very eyes in the Science Storms exhibit. There is something for everyone in this fascinating museum.

Nightlife options abound in the city. Catch dinner in the neighborhood before the show at The Second City — a comedy institution that's bred stars such as Tina Fey and Bill Murray. The Second City hosts shows seven days a week in multiple theatres, from standup shows to classic revues.

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