Chicago Defined The Jazz Age
And . . . Put the Roar in the Roaring 20s
3 Days | Spring | Summer | Fall
Starting At $Flexible Pricing
Chicago, the city that arguably defined the Jazz Age, Prohibition, gangster wars, flappers and boom times, thrived and survived the ’20s. And like the rest of America, it started the decade like a giddy adolescent, grew up in 1929 when gang wars built to a bloody crescendo and the stock market crashed.
We are happy to accommodate Groups who want to add a night or two, or further customize their trip.
StarrGroups Flexible Pricing:
- Customizable Comps
- Commissionable or Net Rates
- Luxury or First Class Hotels & Meals
- Motorcoach Transportation & Professional Tours Managers are available
Whatever you want, StarrGroups will be happy to structure tour prices to match your needs. Just let us know!
Day 1 – Chicago – Jazz Club Dinner or Chicago Magic Lounge
Arriving today in Chicago, IL, check into your hotel for a two-night stay. Tonight, enjoy an included dinner at a local restaurant. Group can choose from a Jazz Club Dinner or dinner and evening at the Chicago Magic Lounge.
Jazz reached Chicago in the Roaring Twenties. Chicago’s prosperous manufacturing, railroad and meatpacking industries attracted and influenced this relocation. This transfer became the turning point for jazz music in Chicago. It expanded various popular music styles and introduced jazz to the Chicago city and the rest of the nation.
OR Following an included dinner at a local restaurant, groups enjoy an evening at the Chicago Magic Lounge. Part theater, part speakeasy, and now 100% Amazing!
Enter through the laundry, but beyond that room is an absolutely gorgeous venue serving as a destination for “Chicago-style magic shows.” Be transported out of the everyday and into a mysterious, magical experience. The Chicago Magic Lounge features performances by the best magicians working today, from talented House Magicians to guest entertainers, this magic show promises an evening you won’t soon forget. Cocktails are available for purchase and a generous dose of magic and surprises to provide you with a memorable and marvelous encounter every time you visit. (D)
Day 2 – Gangster Tour – Free Time at Magnificent Mile – Chicago Architecture Cruise – Dinner at Harry Caray’s – Nitti’s Supper Club
This morning, meet a local “Gangster” for an Untouchables Gangster Tour of Chicago. Have a bang-up time on this romp back to the Roaring Twenties. Hear an accurate account of the activities that were going on in Chicago during the 1920’s and ’30’s (Prohibition). You will hear the exploits of Capone, Moran, Dillinger and the rest of the boys! Some sites included are the St. Valentine’s Day Massacre, the Biograph Theatre, and the Holy Name Cathedral.
Next, enjoy some free time for lunch on your own and shopping at Magnificent Mile. This is one of the most iconic shopping areas in the world. This cosmopolitan, history-packed strip on downtown Michigan Avenue leads you from department stores to luxury boutiques to brand name retail chains — all within a scenic stroll of each other.
While on Magnificent Mile, be sure to notice the Art Deco Skyscrapers from the 1920s. Art Deco was a popular, modern style whose lavish materials and geometric ornament epitomized the prosperity and optimism of the Roaring 20s.
The afternoon also includes a Chicago Architecture Cruise. There’s nothing quite like seeing Chicago’s world-famous architecture from the Chicago River. From hidden treasures to the city’s most well-known sights, you’ll view over 40 Chicago landmarks on this river tour. Enjoy the spectacular views as you listen to your tour guides tell you how Chicago’s buildings, architecture, and engineering made the city famous.
After this full day of sightseeing, your group will have dinner 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. (B,D)
Day 3 – Depart for Home
After breakfast depart for home. (B)