Looking for Unique Date Ideas in Chicago?

Then you have come to the right place! What could be more memorable than a night spent walking the city together and exploring the sweetest spots around? You will have time to talk and bond as you go from location to location. Our tour is a treasure that will impress your date. It’s outside the usual “dinner and a movie” that so many couples schedule without even considering their other options.

Our dessert tour of Chicago makes an excellent celebration for a special occasion. Is it your anniversary? Is one of you celebrating a birthday? Or are you thinking of popping the question? The romance of enjoying sweets and drinks across the city will turn your special date into something you will both think of fondly for years to come. Since it’s customizable to your preferences, we can even help you with arranging the logistics of a proposal, if needed.

We take pride in being one of the fun things to do in Chicago for couples. Other benefits of booking with us include:

• Tasty treats: It’s impossible to overemphasize just how amazing the cuisine is on our Chicago dessert tour. You may find yourself thinking about the candies or chocolate days later.
• Off-menu samples: On many of our tours, restaurants or bars will offer specials to our guests that they won’t find on the menu.
• Having fun: It’s worth repeating that our tour is just plain fun! You will have a good time, and so will your date as you interact with your guide and the people at each stop.

This tour is a customizable tasting adventure focused on desserts and drinks in the River North area. Exercise your sweet tooth with candy-infused cocktails, gourmet chocolates, delicate French macarons, wine, and more!

One of our enthusiast and fun-loving tour guides will serve as your ambassador for the afternoon, leading you from sweet to sweet, pointing out iconic landmarks and institutions along the way.

You’ll explore Chicago’s vibrant River North neighborhood, stopping in at some of its most iconic eateries and bars.

The tour will begin with a stroll down the Magnificent Mile, the upscale shopping and dining strip located on Michigan Avenue.

Your party will stop at the world-famous Dylan’s Candy Bar, located in the stunning Tribune Tower. Dylan’s is not only one of the largest candy stores in the city, but also sports an entire bar serving candy-flavored cocktails. You’ll get to sip on one of these sweet and unique creations while learning all about the history of the company and the beautiful building in which it resides.

The tour then heads west for some organic chocolate truffles, known for their rich and exotic flavors.

Your group will get to experience the beautiful architecture of the Tree Studios Building up close and personal on the next leg of the journey. You’ll stop for some delicate and decadent French macarons, which have become a global phenomenon in last decade.

After that, you’ll indulge in a wine tasting with authentic Italian dessert pairing at one of the city’s most beloved Italian restaurants.

The best thing about this signature Chicago dessert tour is our ability to cater it to your specific tastes and group needs. Additional stops can be added for champagne tastings, cheesecake, artisan donuts, or more craft cocktails. The possibilities are endless!

The tour generally runs for about two and a half hours, beginning and ending at locations best suited for your party.

Our team is excited to work with you to craft the perfect sweet adventure for your celebration! There is no better way to see and taste Chicago than with a Bobby’s Bike Hike tour.