Highlights

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Itinerary

Day 1 – Chicago – Three Nights at NEW Sable at Navy Pier Hotel – Dinner at Harry Caray’s – Nitti’s Supper Club

Arriving in Chicago, IL, check into the city’s newest hotel, Sable at Navy Pier for a three night stay. There’s an exciting new reason why Navy Pier is Chicago’s ultimate destination: Sable. A hotel experience that’s elevated. Sophisticated. And like its extraordinary location, unforgettable. Sable is the destination for Chicago’s most elegant weddings and parties, as well as the hottest spot for drinks high above the waves—in this city or anywhere. It’s the new Chicago landmark on Chicago’s most iconic landmark.

Enjoy dinner this evening at Harry Caray’s.  This Legendary Chicago Steakhouse pays tribute to the beloved Chicago Cubs sportscaster for whom the restaurant is named.

Following dinner, head to the second floor of Harry Caray’s for Nitti’s Supper Club.  Long before 33 W. Kinzie was one of Chicago’s most famous steakhouses, it was home to the notorious enforcer of the Al Capone gang, Frank Nitti. Nitti ran the Chicago Mob after Capone went to jail. Relics from his life of crime, including a safe and a phone book with alderman’s phone numbers, were discovered in the walls of the building.

As an homage to the building’s storied past, a speakeasy was reconstructed on the second floor. Guests gain entry by pushing a hidden button on a bookcase and are immersed in vintage décor which transports them back to the 1920’s. Once in the Speakeasy, they will be served special prohibition-era cocktails through a secret opening hidden in the wall.

Here you enjoy a show filled with laughs, gangsters, audience interaction and toe-tapping musical productions.  Nitti’s Supper Club and Speakeasy incorporates real characters from Nitti’s life of crime who would have walked through the doors of 33 West Kinzie. Join them on a trip back in time to the raucous world of gangland Chicago. (D)

Day 2 – Guided Chicago Sightseeing Tour – Meet the Blues Brothers – Visit the Chicago Cultural Center – Tour the original Chess Records – Free Evening at Navy Pier

 This morning, enjoy a guided city tour of Chicago. Discover the history, architecture and incredible stories that make up Chicago. Driving and stops along the way. The LOOP is Chicago’s business and theater district. You’ll see some of the most architecturally significant buildings in the world and artwork by Picasso, Calder, Miro, and Chagall. Walk thru Millennium Park with its stunning outdoor art and philanthropic spirit, Harris Theater for Music & Dance, Pritzker Music pavilion, Crown Fountain with a reflecting pool book ended by town 50- foot high towers of glass brick, plus see Lake Shore Drive.

Also during your morning tour, the Blues Brothers will hijack your bus for 30 minutes, they’re “putting the band back together” and you’ll find yourself “on a Mission from God” with Jake & Elwood Blues. “They’ve got a full tank of gas, half a pack of cigarettes, its dark out and they’re wearing sunglasses.”

Tour the Chicago Cultural Center, one of the city’s most popular attractions and the cultural heart of the downtown Loop neighborhood. Taking up an entire city block, the stunning landmark building is home to the world’s largest Tiffany stained glass dome. The Cultural Center also features free art exhibits showcasing local and national artists. There are also an ongoing free music series that takes place in jaw-dropping spaces, creating wonderful acoustic experiences.

The afternoon also features a tour of the original Chess Records where so many Rock and Blues artists created their hits. Muddy Waters, Howlin’ Wolf, Etta James, Chuck Berry and the Rolling Stones all recorded here. You’ll see the original recording studios, the offices of Leonard & Phil Chess and plenty of memorabilia from the era. Coincidentally, Chess was sold in 1969, and Leonard dies two months after Woodstock.

Enjoy a free evening and dinner on own at Navy Pier. Known as the “People’s Pier,” this landmark showcases more than 50 acres of parks, restaurants, attractions, retail shops, sightseeing and dining cruise boats, and more. There is also the iconic Centennial Wheel, soaring to heights of nearly 200 feet, the Wheel offers unparalleled, 360-degree views of Chicago and Lake Michigan.

If you are here in the summer, there is a spectacular Fireworks show every Wednesday and Saturday night from Memorial Day weekend through Labor Day weekend. Find a spot anywhere on the pier to take in this dazzling free display. Soundtracks feature dramatic and popular music with some special occasion soundtracks. (B)

Day 3 – Chicago History Museum Tour – Lunch at the Hard Rock Café – Chicago Architecture Cruise – Magnificent Mile – Dinner & Music at Buddy Guy’s 

This morning tour the Chicago History Museum. Discover the city’s vast history in Chicago: Crossroads of America. Whether you want to explore the grandeur of the world fairs of 1893 and 1933, or Chicago innovations that changed the world like skyscrapers and modern retail, or the diverse neighborhoods and lively cultural scene, this exhibition is a must see!

Lunch is included today at the Hard Rock Cafe, a one-of-a-kind dining and entertainment experience. It is known worldwide for embracing funky styles and blending them with legendary food, beverages, live music and music history. Hard Rock International is the world’s largest curator of music memorabilia, and the cafe walls are lined with priceless pieces from musical legends like Billy Joel, Buddy Guy, Jimi Hendrix and Prince.

Then take a Chicago Architecture Cruise.  Expert guides will share an insider’s glimpse into the buildings, architecture, and engineering that made Chicago famous as the birthplace of the skyscraper and home of modern American architecture. Nothing is more impressive than this world-renowned architecture as seen from the Chicago River. Tour highlights include Tribune Tower, Wrigley Building, Trump Tower, Marina City; and more than 40 Chicago landmarks.

Today, you will have time for shopping on the Magnificent Mile. From major fashion houses to trendy retailers, Michigan Avenue offers three shopping centers towering over a district overflowing with luxury retailers, unique shops and popular stores.

This evening, dinner is included at Buddy Guys Legends, the world’s premier Blue Club owned and operated by Grammy Award Winning Blue’s Musician, Buddy Guy. He is a Rock and Roll Hall of Famer himself and has had a major influence on rock titans like Jimi Hendrix, Eric Clapton, and Stevie Ray Vaughan Tonight enjoy Louisiana-style cajun and soul food – served while a Blues band makes a little music. (B,D)

Day 4 – Depart for Home 

After breakfast, depart for home. (B)

Tour Map