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Chicago

Off the beaten path

Our most recommended Chicago Off the beaten track

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

1. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

2. Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

Spend an evening visiting the Chicago speakeasies that have been open since the Prohibition Era in the 1920s, many preserved in their original conditions. With your own private group, enter by way of secret entrances and enjoy the same cocktails ordered by infamous Chicago gangsters and bank robbers at these venues nearly a century ago. Relive the glamor of the 1920s while listening to stories of the rampant racketeering and bootlegging of the era.   Alcohol is available for purchase at the three to four different speakeasy stops. Your private tour guide will make Prohibition Era drink recommendations and tell you the stories behind them. Travel around with your young, professional guide and be chauffeured in luxury transportation, ranging from a luxury SUV to a full-sized luxury motor coach.

Chicago: Windy City Ghosts Haunted Walking Tour

3. Chicago: Windy City Ghosts Haunted Walking Tour

Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

Chicago: Ultimate Food Walking Tour with Tastings

4. Chicago: Ultimate Food Walking Tour with Tastings

Your Chicago food tour will take you through the River North neighborhood — the original Chicago foodie destination — to sample some world-famous Chicago dishes, local favorites, and sweet treats. Choose between a shared group or private tour. Start with a very well-known Chicago dish: the Chicago-style hot dog. Perfect for summers at a baseball game (cheering on the Cubs or Sox of course), or for a quick lunch on a workday, this local take on a hot dog is a debate-worthy food in Chicago and is taken very seriously by locals. You will also sample the world-famous Chicago deep-dish pizza! An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s when workers and families needed filling dishes at low prices.  After you’ve filled up on pizza and hot dogs, continue your tasting journey with a classic Chicago sandwich: Italian beef. This hearty meal came about during the Depression, and it’s here to stay. Conclude your Chicago foodie experience here, with easy access to the ‘L’. Even if you say you’ll never be hungry again, don’t forget to note some great dinner recommendations from your guide.

Chicago: Photo Shoot with a Private Vacation Photographer

5. Chicago: Photo Shoot with a Private Vacation Photographer

The tour provider will organize the locations for your photo shoot based on your own unique requirements, whether it be a family getaway, a romantic trip or a livelier one with friends.  Once the details are organized, you will receive confirmation of all the information you need, leaving you to simply meet the photographer on location in Chicago on the day and let them work their magic, capturing your travels in a contemporary and candid style of photography. Your Chicago vacation photographers are handpicked and highly experienced in addition to being local experts and will share their knowledge of the city with you like an old friend. Once your photo tour has finished, you will receive a link to your own personal online gallery (password protected) within 5 working days, containing your professionally edited images, all free to download. This photo tour will allow you to look back over your travels with fond memories, when all too often you are left with rusty memories of your journeys. Make sure that the next time you travel, you will have mementoes that will last a lifetime and beyond.

Los Angeles: Make The Most of LA Private Tour

6. Los Angeles: Make The Most of LA Private Tour

This is an example of your private customizable highlights tour. Meet your guide and get comfortable in a new, climate controlled vehicle. You'll begin with a brief drive to the beautiful neighborhood of Venice Beach. Once a seaside resort town, this surfer’s paradise is crisscrossed with canals, just like its Italian namesake. Venice is the center of counterculture in LA and is home to some of its most eclectic and bohemian residents. Stroll down the vibrant Venice Boardwalk and enjoy its street vendors, artists and performers as you learn about the birth of skateboarding and surfing culture and make your way towards the iconic Santa Monica Pier. Along the way, you will see the "Baywatch" headquarters, Muscle Beach, pass by the local Freak Show and let the laid-back ambiance of Venice Beach wash over you. Next, head to Santa Monica to learn about its interesting history. On the iconic pier, you will be dazzled by the local flavor of live music, laughing children, happy travelers and carnival noises which will heighten your senses and you will quickly come to understand why this is such a beloved part of the city. Try your luck at one of the carnival games and feel instantly transported back in time. Finally, snap a photo beneath the landmark sign and say you made it to the end of the historic Route 66. After a leisurely lunch, now it's time to glitz it up in the center of cosmopolitan LA. Your group will cruise by La Cienega’s restaurant row and see some of the world's most famous restaurants. View legendary institutions like the Saban Theater, home to many famous plays, musical events and filmed television segments from shows such as "Glee." Along the way, you'll cruise the Miracle Mile and see some of LA County Museum of Art outdoor exhibits. Right next door, the group will behold the wonder that is the La Brea Tar Pits - a natural pit of tar that has trapped prehistoric animals and now displays their large, dinosaur like fossils throughout the park. As you make your way into Hollywood, you will pass notable locations including the iconic Hollywood sign. Count stars on the Walk of Fame. Fit your hands into the impressions of legendary actors at Sid Grauman's Chinese Theater. Don't forget to strike a pose at the Dolby Theater, where the Oscars are held. Now cruise down Sunset Blvd. See iconic venues of famous rock stars such as the Doors, Jimi Hendrix, the Ramones, Aerosmith and more. The day will wrap up scoping out the homes of the stars in glamorous Beverly Hills. Join your guide and walk the grounds of a billion dollar estate, Greystone Manor. Drive past impressive estates such as the Playboy Mansion, the homes of Frank Sinatra, Lucille Ball, Marilyn Monroe, Simon Cowell and more. The journey will end on a high note with a visit to the premier shopping spot in America: 90210's Rodeo Drive.

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Frequently asked questions about Chicago Off the beaten track

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What people are saying about Chicago

Overall rating

5.0 / 5

based on 2 reviews

Nice trip filled with histories of mistery and crime. Our guide Conor was super knowlegable and was able to host us in professional and attractive way. The guide was super passionate about telling is insights and interesting facts about Chicago of the earla 1900’s. Highly recommended if you want to get some knowledge and have some fun.

The tour was superb, Conor our guide was very knowledgable and friendly and made the tour exciting. Would 100% do it again.

This was a great tour to learn a bit more about Chicago’s history. Our guide, Andre, was incredible!

We had a great tour, Baylor was our guide and so informative and friendly!! Highly recommend 5star!

Our guide leader was very animated and seemed to love telling us about the history of the City.