Sweet Home Chicago

Get lost in the high-flying architecture, from the stratospheric, glass-floored Willis Tower, to Frank Gehry's swooping silver Pritzker Pavilion, & Frank Lloyd Wright's stained-glass Robie House. Art can be found on almost every corner. Explore world cultures as you experience Chinatown, Little Italy, Pilson, and Greek Town. Wrap up your visit with a Chicago Original Gangster Tour. Find a little something for everyone on this tour, Take A Fun Trip to Home Sweet Chicago!

4 Days /3 Nights

Group size

Tour Inclusions: 3 nights’ accommodation; 3 breakfasts; 3 dinners; admissions, entrance, and guide fees as stated in the itinerary, including taxes, and gratuity, except gratuity for guide fees is not included on adult tours unless otherwise requested. Based on 35 paying passengers and one (1) comp in double occupancy.
  • Magnificent Mile
  • Tommy Gun’s Garage
  • The Field Museum
  • The Shedd Aquarium
  • Willis Tower
  • Frank Lloyd Wright’s Home, Studio, & Unity Temple
  • Ernest Hemingway’s Birthplace
  • Gangster Tour
  • Navy Pier

Sample Itinerary:
Day 1 - Chicago City Tour & Tommy Gun’s Garage
  • Arrive in Chicago, IL. Enjoy lunch on own & free time to explore along the Magnificent Mile, the northern part of Michigan Avenue between the Chicago River and Lake Shore Drive.
  • Later, depart with your GUIDE and enjoy a tour of the city, including Chicago’s Amazing Architecture, Spectacular Views of the skyline, Michigan Avenue, and Lake Shore Drive.
  • Explore Chinatown.  Enjoy this colorful and vibrant neighborhood and learn about the history and immigration of the Chinese to the area.
  • Visit Little Italy and tour the Taylor Street area, home to generations of Italian families and businesses.
  • See Pilson and learn about the local murals that adorn the streets, and celebrate both Mexican and Mexican American culture and heritage.
  • And finally, enjoy a visit to Greek Town.
  • Stop at Buckingham Fountain. Buckingham Fountain is a Chicago landmark in the center of Grant Park. Dedicated in 1927, it is one of the largest fountains in the world.
  • Arrive to Tommy Gun’s Garage for dinner included & show. Enter Tommy Gun’s Garage through da rear entrance under da “EL” tracks. Psst…if you know da password to get in, you will be transported back to da 1920’s, da Boss’s 1928 Ford Model A car, a replica of da St. Valentine’s Day Wall and pictures of da Gangsters are da Coppers from da times. You’ll also be served great food and great hooch by da Gangsters and da Flappers. Let the show begin.
  • Enjoy an audience interactive “Speakeasy” which offers a Roaring 20’s musical comedy revue with da Gangsters, da Flappers, and YOU! Join “Vito”, “Gloves”, da “Mugs” and da “Molls” for non-stop comedy and dangerous fun. (Meals: D)
Day 2 - Field Museum & Shedd Aquarium
  • Enjoy breakfast included at the hotel this morning prior to a visit to the Field Museum. The Field Museum was incorporated in the State of Illinois on September 16, 1893 as the Columbian Museum of Chicago with its purpose the "accumulation and dissemination of knowledge, and the preservation and exhibition of objects illustrating art, archaeology, science and history."
  • After lunch on own, visit the Shedd Aquarium, the World's Aquarium, opened in 1929, it is one of the oldest public aquariums in the world.
  • This evening, dinner is included at a restaurant serving authentic Chicago deep dish pizza.
  • Depart for the Willis Tower (formerly Sears Tower) Skydeck. The Willis Tower is a triumph of ingenuity and innovation reflecting Chicago’s and America’s strength, vision and tradition of architectural excellence. The view is amazing! Imagine seeing Michigan, Illinois, Indiana, and Wisconsin just by walking around the Skydeck. (Meals: B, D)
Day 3 - Frank Lloyd & Ernest Hemmingway Exploring
  • Enjoy breakfast included at the hotel this morning prior to a visit to Frank Lloyd Wright’s Home and Studio. This extraordinary building in Oak Park, Illinois was the Wright family residence from 1889 to 1909.  Frank, his wife Catherine, and their six children - lived here while he developed his architectural practice, creating what became the "Prairie Style" of architecture. The studio annex was completed in 1898, and is one of the most marvelous workspaces to be imagined!
  • See Frank Lloyd Wright’s Unity Temple. Upon its completion in 1908, Frank Lloyd Wright said that “Unity Temple makes an entirely new architecture…and is the first expression of it. That is my contribution to modern architecture. And that, to me, is modern architecture.” Much of the architectural community quickly agreed with Wright’s own assessment of his design.
  • Enjoy a Walking Tour of the Frank Lloyd Wright Historic District. Oak Park is home to the world's largest collection of Wright-designed buildings. Discover the development of Wright's style between 1889 and 1909, and trace the evolution of American residential architecture as trained interpreters guide you through the Historic District surrounding the Home and Studio.
  • Lunch is on own today while visiting Oak Park.
  • Drive by Ernest Hemingway’s birthplace home. The Ernest Hemingway Birthplace Home is a large Victorian home built by his maternal grandparents that has been meticulously restored to its Turn-of-The-Century grandeur. One of the greatest writers of the 20th Century, Ernest Hemingway was born on July 21, 1899, and spent the first six years of his life in this grand house surrounded by his family.
  • Board the Spirit of Chicago this evening and enjoy a buffet dinner cruise. Prepare to have the time of your life while dining, dancing and seeing amazing Chicago views. (Meals: B, D)
Day 4 - Gangster Tour & Navy Pier
  • Breakfast is included at the hotel this morning prior to checking out and departing for Chicago’s Original Gangster Tour. These guys are gonna take you places. The Prohibition Era comes alive as costumed gangers guides take you on a ride back to the days when Al Capone ruled the South side of Chicago.  Hear the true stores – as only the charming guides can tell ‘em – of gangster legends like Dion O’Bannion, Bugs Moran, Johnny Torio, Machine Gun Jack McGurn, and John Dillinger.
  • Enjoy lunch on own and free time at the Navy Pier. Located on Lake Michigan, just East of Chicago’s Downtown, Navy Pier has been a Chicago landmark since it first opened in 1916. Originally designed as both a shipping and recreational facility, the Pier also served as a military training site during two world wars, a venue for concerts and exhibitions, and the temporary home for a once-fledgling University of Illinois’ Chicago campus.
  • See the beautiful Chicago Skyline on the Navy Pier Ferris Wheel. Depart for home. (Meals: B)

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