7 spots to wow out-of-towners this holiday season

So, you’ve got visitors for the holidays who want to see all of the shiny, sparkly sights; where to start? Right here, in fact:

Holiday Lights Trolley


Chicago Trolley and Double Decker Co.’s ‘Holiday Lights Tour’

This marvelous company can check off so many stops on your jingle bell-bedecked tour–and fill you with plenty of holiday spirit to boot! These festively decorated trolleys are a terrific (and traffic-free) way to explore the best of downtown, taking off from the John Hancock Plaza Tree (875 N. Michigan Ave). Once aboard, all Holiday Lights Trolleys whisk folks to …

Sprinkle’s Cupcakes

… For a complimentary, handcrafted holiday cupcake! Any time the beloved cupcake confectioners (50 E. Walton St) offer you a treat like this, you don’t think twice. While there, check out their famed Cupcake ATM; it’s restocked day and night with their signature cupcakes so, if you have a post-trolley hankering, you know where to go.

Macy’s Holiday Windows

Hop back on the trolley to peep on the iconic Macy’s windows (111 N. State St). Take a moment to revel in the fact that it’s totally easy–and totally legal–to gawk at these beauties for as long as you want since you’re not actually driving a car right now. (Rinse and repeat for State Street lights, the rest of Mag Mile and hidden gems on some downright spectacular side streets.)


Whether you’re a fan of the mulled wine, the roasted pecans, the delicate ornaments or a combo of all three, this stop on the trolley’s tour (50 W. Washington St) is a Chicagoan’s quintessential December activity. Hopping back aboard after imbibing and indulging at the German Village easily ensures that the goodwill towards all extends long after the glühwein is gone.

Lincoln Park’s Zoo Lights

Kids (and their kids-at-heart counterparts) won’t believe their eyes, not to mention the sheer enormity of lights adorning Chicago’s impressive zoo (2001 N. Clark St). You know what’ll help to appreciate the millions of lights? 3D glasses, of course. Come for the striking displays, stay for the ice carvings and warm, warm beverages.

Signature Lounge at the 96th Floor

After the Holiday Lights Tour ends, what happens if you want to stay and play downtown? Simple (and impressive): Where the tour lets off is where you catch that (long, long) elevator up to the 96th floor of the John Hancock building (875 N. Michigan Ave). Not only is it an incredibly cool place to take in a holiday drink (Kentucky egg nog or prickly pear martini, anyone?) but the unparalleled view is so good that you might just spy a reindeer or two.

Holiday Tea at the Drake Hotel

If your guests are still feeling the Chicago love the following day, take their urban experience over the top with a simply stunning high tea at the Drake Hotel’s famed Palm Court (140 E. Walton Pl). They have a terrific “kids’ menu” in the form of a “Little Prince and Princess Tea,” too! Between the live harpist, glitzy decor and whatever magic they put in those petit fours, ending your whirlwind December tour at this stop might just convince your out-of-towners to take up a new residence.

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