Chicago Loop
Romantic Activities for Couples

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Our most recommended Chicago Loop Romantic Activities for Couples

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

1. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

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: Private 3-Hour Al Capone Gangster Tour

3. Chicago: Private 3-Hour Al Capone Gangster Tour

Experience amazing stories of true crime coming to life on this three-hour private tour. Visit many of the old venues where gangsters used to operate, including old speakeasies and historic hotels. Your expert historian guide will accompany you and your private group in luxury accommodation to historically significant locations in the city. View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, and the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy guns. See the site of the infamous St. Valentine’s Day Massacre, and sit in Al Capone’s booth at the Green Mill. Finally, visit the location where Public Enemy #1 John Dillinger was assassinated by the FBI.

Frequently asked questions about Chicago Loop Romantic Activities for Couples

What are other things to do than Romantic Activities for Couples that are worth visiting in Chicago Loop?

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Which Chicago Loop Romantic Activities for Couples are taking additional COVID-19 precautions?

These Chicago Loop Romantic Activities for Couples are taking additional COVID-19 precautions:

Other Sightseeing Options in Chicago Loop

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What people are saying about Chicago Loop

Had a great time on our food tour! It’s a great way to learn about foods that were improved upon by this city, some of the history and see a few blocks of downtown.

Loved our food tour. Guide Julia was great. Very knowledgable and entertaining. What a nice way to learn and eat some of Chicago food. Would highly recommend it.

Our tour guide (Julia) was AMAZING!! Super friendly and energetic! We had a lot of fun, even on a cold and kind of gloomy day :)

Fun, informative, very tasty tour. Dylan, the guide, was knowledgeable and super fun.

Justin was phenomenal! So enthusiastic about the city. Made it so fun! Also, the food