Chicago
Off the beaten track

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Our most recommended Chicago Off the beaten track

  • Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour

    1. 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: Photo Shoot with a Private Vacation Photographer

    2. 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 o...

  • Lonely Planet Experiences: Chicago History and Food Tour

    3. Lonely Planet Experiences: Chicago History and Food Tour

    Experience the best travel stories for yourself! Join a local expert and uncover hidden gems on this Lonely Planet Experience. 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. We 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 work day, this local take on a hot dog is a debate-worthy food in Chicago and is taken very seriously by locals. We 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, we’ll ...

    The tour is short and informative and geared towards out of towners as indicated. Food was okay, considering some of the original locations were no longer open due too Covid-19.

Other Sightseeing Options in Chicago

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What people are saying about Chicago

Overall rating

5.0 / 5

based on 2 reviews

Great way to get lunch, history and anecdotes about the River North area. Fun foods that will fill you up....we weren't hungry for dinner until about 10 pm! Kelly was a great guide providing her knowledge of the restaurant scene and Chicago lore as we walked between classic food destinations and tasted the classic Chicago food: the deep dish pizza, the Chicago hot dog and the Italian beef sandwich.

This tour was great! Kelly was my guide and she was super knowledgeable about the city and the food. The locations she took us to were amazing and all of the food was delicious. I was pretty full by the end, but not too full to eat the dessert she had planned!

Knowing a city trough it's food is a whole experience. Our guide Wallach, was able to show us the city while tasting its roots. It is a wonderful trip for lunch time tasting Chicago classics and iconic food. Love and recommend this experience to everyone!

This was a great way to hear some of the darker history of Chicago. Elizabeth was very knowledgeable and interesting. The walk was easy with lots of stopping.

Lara was fantastic. We had a bunch of fun and tons of food to try with great information.