DAY 3 PLAN: Chicago Visit



VISIT DAY: Chicago, IL

  • Breakfast, Explore the Area
  • 12PM – THE CHICAGO GANGSTER TOUR (2 hour live action tour)

NITE: Hotel (2-star) / Travelodge Downtown Hotel, Chicago, IL




Chicago Gangster Tour – Untouchable Tours – Chicago’s original gangster tour.
Phone: 773-881-1195

  • The Chicago Gangster Tour is a 2 hour live action tour: EXPERIENCE Chicago as it was during the 1920s and 30s! SEE the old gangster hot spots and hit spots! HEAR…historically accurate accounts of the exploits of Capone, Moran, Dillinger and the rest a da boys! FEEL the excitement of jazz-age Chicago during the era of Prohibition! ENJOY a journey into the past as we cruise the city in search of the old hoodlum haunts, brothels, gambling dens and sites of gangland shootouts!
  • Departure: from the 600 block of N. Clark Street (Clark St. and Ohio Ave.) on Clark St. in front of the Rock n Roll McDonalds
  • Schedule: daily at 10 am, Thurs-Sunday 12noon, Fri + Sat 2pm, Fri 730pm, Sat 4pm.
  • FEE: $28/person. Call To Reserve: 773-881-1195

Tommy Gun’s GarageChicago gangster show – interactive dinner theatre, in a 1920s speakeasy, with gangster themed show and jazz music
2114 S. Wabash, Chicago, IL 60616. Phone: 773-RAT-A-TAT / 312-225-0273 / 800-461-0178

  • Tommy Gun’s Garage and Chicago’s Roaring Twenties Dinner & Show: Tommy Gun’s Garage is an Audience Interactive “Speakeasy” that offers a musical comedy review wit da gangsters, da flappers and YOU!!!!!(uh, dat’s audience participation). After a delicious sit-down dinner, join “Vito”, “Gloves”, and da “gangsters” and da “flappers” for non-stop comedy and dangerous fun. You will be transported back to da 1920’s complete wit da boss’s 1928 Model “A” Ford, Roaring Twenties music and memorabilia from da Twenties. Da mugs and da molls dance and sing da Charleston and udder musical selections from Cole Porter to George Gershwin, Fats Waller, Duke Ellington and more…. All played by Chicago’s Sinfully Orchestra. Be ready to hide your hooch (alcohol) cause we could get raided by da coppers at anytime. Be careful, you could get pulled up on stage at any time to perform a sobriety test given by Officer Murphy.
  • Schedule: Wed – Sun: Wed, Thurs, Sat, doors open 6pm, show starts 715pm /
    Fri, doors open 7pm, show starts 815pm / Sunday, doors open 530pm, show starts 645pm
  • Price: $60/person (wed, Thurs, Sunday), $65/person (Friday), $70/person (Saturday)
    (includes dinner and show, coffee, tea or soda, tax and tip – no alcohol)

LODGING: Travelodge Downtown Hotel
65 E Harrison St, Chicago, IL 60605 at the intersection of Wabash & Harrison streets
(see hotel website)
Phone: 312-427-8000 / Fax: 312-427-8261 / E-Mail:

RATE: $103/nite plus tax and service charge and additional $28-$33/day for parking

Built in 1928 as the Harrison Hotel, the Travelodge Hotel Downtown has been a mainstay for generations in the area of Chicago now known as the South Loop.

Featuring the charm and ambiance of Chicago along with comfortable affordable accommodations, Travelodge Hotel Downtown Chicago is just the place to make your stay an unforgettable experience. Strategically located, Travelodge Hotel Downtown Chicago enjoys easy access to Chicago’s loop area shopping, theatres, museums, restaurants and most of the famous tourist attractions such as McCormick Place, Sears Tower, Grant Park, Millennium Park, Navy Pier, Lake Michigan and others. The hotel offers well-equipped accommodations with conveniences that are sure to satisfy your needs. Enjoy our two on-site restaurants. For the discerning business traveler, there is a well-equipped business center. The lobby, with its comfortable sitting area, is the perfect place to relax and meet.
We offer fun amenities to accommodate our customers’ needs. In-room coffeemakers, voicemail, high-speed Internet access, in-room safes, cable television, and free HBO are among the amenities you will find. We offer access to secured indoor and outdoor parking, and airport shuttle services are available for a fee. Take a look at our amenities page for more details on what we offer and feel free to ask one of our friendly staff members for more details. Let us know how we can help accommodate your needs and make your stay more comfortable and relaxing!

  • Free High-Speed Wireless and Wired Internet Now Available
  • Bar/Lounge In On-Site Restaurant
  • In-Room Coffeemaker with Complimentary Coffee
  • In-Room Safe, Large Enough to Fit a Laptop
  • Modem/Data Port, Free Wired and Wireless Internet Connection Available
  • Parking Rates: $28 per Night, Cars and Small Vans $33 per Night, Large Vans and Pick-Ups
  • Coin-Operated Washers and Dryers
  • Public Transportation within Walking Distance: CTA Red Line and Blue Line, 1/2 Block from Bus Stop
  • Business Center (Free use of Computer/Internet Connection and Printer)
  • Fax and Copy Services
  • Two Restaurants On-Site: Chicago Carry-Out (Fast Food) and Thai Spoon (Classic Pan-Asian Cuisine and Sushi Bar) (Independently Managed Restaurants)

LOCATION: From I-90 heading West, take Exit 51H for I-290 west toward Eisenhower Expy/West suburbs. Keep right at the fork, and follow signs for Congress Pkwy/Chicago Loop and merge onto Congress Pkwy. Turn right at South Wabash Ave. (2 blocks after State Street intersection), and make the first left onto E. Harrison street. The hotel is on the Right at the intersection of Wabash & Harrison streets


2 JAN 2010: we decided it could be fun to do something gangster-related, in terms of activities, since Chicago is famous for the 1920s gangsters, and after some quick research on the web we found a couple of fun sounding activities. this will be our send-off before hitting the actual historical route 66, and our only urban stopover before California!.


  • AAA guide (about the city, plus things to do, etc.)
  • Lonely Planet guide to Chicago (about the city, things to do, hotels, restaurants etc.)
  • Rough Guide to Chicago (about the city, things to do, hotels, restaurants etc.)
  • Chicago gangster tour – 2 hour tour of historical “chicago gangster” locations, with guide who tells you the history etc. (group tour with set times)
  • Tommy Gun’s Garage – interactive dinner theatre, in a 1920s speakeasy, with gangster themed show and jazz music