Holiday Eats and Drinks Near Our Downtown Chicago Tour

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December 4, 2017

If you’re planning a trip to Chicago for a holiday vacation, now is the best time to snag tickets to our Hop On, Hop Off Tour. In addition to the 14 amazing stops throughout the city, you’ll have the opportunity to indulge in some delicious holiday food and drinks specials. We’ve listed our favorite holiday-inspired cuisine, all conveniently located near one of our Hop On, Hop Off stops, so you can make the most out of your weekend in Chicago.  


Christkindlmarket – Daley Plaza

[Image Credit: Christkindlmarket Chicago]

When you’re on a holiday tour of Chicago, there’s no way you’re going to want to skip the famous Christkindlmarket in Daley Plaza. You’ll be transported to an old German village with quaint shops, offering handcrafted goods and delicious eats and drinks. On the menu you’ll find everything from savory bratwurst, to stuffed pretzels, to warm, sugary strudel pastries! To top it all off, hot spiced wine will be served throughout the market to keep you toasty as you shop. Don’t miss out on this Chicago tradition!


Sprinkles Cupcakes – Gold Coast

[Image Credit: Sprinkles Cupcakes]

Conveniently located near our Michigan Ave. Bridge stop, Sprinkles Cupcakes is a “must try” on your holiday tour of Chicago. Using only the finest ingredients, from sweet cream butter to bittersweet Belgian chocolate, topped with their famous trademark modern dots – you won’t be able to put these treats down! They’ll be sure to have festive decorative cupcakes on hand, including chocolate peppermint, gingerbread, and red velvet varieties. They also offer delicious hot cocoa to warm you up on those cold winter nights. Holiday gift boxes are available, perfect for gifting friends or relatives this holiday season.


Cindy’s Rooftop Restaurant – The Loop

[Image Credit: Cindy’s Rooftop]

Walking distance from The Art Institute of Chicago, or stop number 3 on our tour, is Cindy’s Rooftop Restaurant. Located on the top floor of the Chicago Athletic Association Hotel, this one-of-a-kind eatery offers spectacular views of Millennium Park, Lake Michigan, and beyond. What makes Cindy’s so special for the holidays is their famous trio of hot chocolates. They serve a classic Belgian topped with fluffy homemade marshmallow, an Ecuadorian hot chocolate featuring milk and dark chocolate with banana-infused milk, and a hot white chocolate with speculoos shortbread. Delish! If you’re feeling adventurous, add a splash of liquor to kick your cocoa up a notch.


Firecakes – River North

[Image Credit: Firecakes Donuts]

If you’re hopping off in River North, the restaurant choices can be overwhelming. We recommend making a stop at Firecakes Donuts to enjoy a specialty holiday donut. Sink your teeth into their signature eggnog donut, filled with whipped eggnog mousse and glazed with eggnog frosting. The sugar cookie donut is glazed with sugar cookie frosting and topped with red and green sprinkles. Just like mom used to make! And don’t forget the chocolate peppermint bark donut for the chocoholic in your family.


Eataly – River North

[Image Credit: Eataly]

What holiday visit would be complete without a visit to Eataly? Located in River North, this two-story, sprawling indoor marketplace features a wide range of Italian restaurants, deli counters, bakeries, and more. We recommend grabbing a loaf of panettone – a rich, fluffy cake hailing from Northern Italy. Traditionally served around the holidays, this seasonal treat is perfect paired with coffee, nutella, or wine.

If you’re looking to buy a gift for the food-lover in the family, Eataly also offers premium gift boxes, hand packaged with the highest quality food and drink directly from Italy. They’ll hand wrap each gift box and personalize it with a festive card – perfect for those who made the “nice list” this year!


Chicago is the perfect destination for a Christmas getaway, and the best way to experience the magic of the Windy City is with a Chicago Trolley & Double Decker Hop On, Hop Off Tour! Not only will you have access to the best shopping, light displays, and festivals – you’ll savor the best food and drink specials the city has to offer. With the list above, you’re well on your way to tasting the best of the holidays in Chicago. Book your tour today!