Find out the best tours & events going on during the winter in Chicago

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What to Do in Winter in Chicago

Let’s face it.  It can get awfully cold in Chicago, Illinois during the winter.  But don’t let that stop you from having fun in Chicago.  There are a lot of fun winter activities going on all around Chicago.

Jack Frost Winter Village

Jack Frost Winter Village is a great event at Goose Island in downtown Chicago.  It has a lot of fun winter experiences, like ice skating and ice carving competitions.  It also has three full-service bars serving wintry cocktails, hot chocolate, and mulled wine.  So going there can be a lot of fun when you warm up with their drinks!

And you can get a great coupon for admission by clicking here.

Winter Pizza & Beer Tour

You get to eat some delicious pizza and drink some great beer during the Winter Pizza & Beer Tour.  It takes place in the River North neighborhood of Chicago.  You start at a popular Chicago pizza place, where you get an award-winning flight of 4 house-brewed beers.  You get two more beers of your choice at the next place.  And it finally ends at the landmark location of Pizzaria Uno, which was the birthplace of Chicago’s deep-dish pizza!

This takes place on Saturdays and Sundays through February 1, 2020.  You can get a coupon for this tour by clicking here.

Winter Wine Walk

The Winter Walk also takes place in the River North neighborhood of Chicago.  You’ll stop at three different places along the way.  And you’ll be doing a lot more drinking than walking!

You’ll get to taste white, red and sparkling wine at the places you’ll stop.  You’ll also get to enjoy great food that will pair with the wine.  This could include artisanal cheeses, fresh-baked bread, pickled vegetables, and house-cured meats.

The Winter Wine Walk takes place on Sundays this winter at 2:00 PM.  You need to reserve a ticket ahead of time, and you can get a discount ticket here.

Winter Cocktail Crawl

The Winter Cocktail Crawl is another great way to spend a Sunday afternoon this winter.  You’ll get to sample the best new seasonal, artisanal cocktails.  The crawl will rotate between different Chicago neighborhoods: River North, Lincoln Park, Lakeview, Gold Coast, and Andersonville.  Your tour guide will also tell you interesting facts and tidbits along the way.  The Winter Cocktail Crawl is similar to a crawl you might take during another season, but it is altered to keep the weather in mind.  In other words, you will be kept warm and indoors much more!

You can save at least 50% on this by clicking here.

Winter Beer, Wine & Swine Tour in River North

Here’s another great winter tour in the River North neighborhood of Chicago.  You get to enjoy some of the best craft beer of Chicago and wine.  And you get to enjoy them paired with bacon and pork treats!  You get to enjoy Chicago’s deep-dish pizza with bacon.  And Chicago’s best barbecue paired with red and white wine.

You can take this tour any date on Wednesday through Sunday through February 1, 2020 as long as you book in advance.  You can do so at a discounted rate by clicking here.

Winter Chicago Underground Pedway Tour With Small Bites & Wine

This is a tour through Chicago’s pedway, a tunnel system in downtown Chicago.  The pedway connects many of Chicago’s most famous landmarks, like Macy’s (Marshall Field’s), Millennium Park, The Thompson Center, The Daley Center, Block 37, City Hall, etc.  You’ll get to sample food at unique restaurants and cafes.  You’ll enjoy a stop at Macy’s Candy Kitchen.  This tour even stops by an unexpected underground American Victorian stained glass art exhibit.  This tour ends in the Chicago Cultural Center, which is home to the world’s largest Tiffany dome glass ceiling.  This tour was made with the fact it was winter in mind to keep you as warm as possible.

You can take this tour on a Thursday or Friday this winter at 50% off by clicking here.

Winter Chocolate, Cupcakes and Ice Cream Tour

If you’re like me and you love sweets, then you will love this tour!  It takes place in the Magnificent Mile area.  You stop at about five boutiques and bakeries.  And the tour has been designed to keep you indoors and warm as much as possible.

It takes place on Saturdays and Sundays through February 1, 2020.  You can click here to save 50% on your admission.

Winter Chicago Navy Pier Food Tour

This tour is great because you’ll get to sample delicious food at Chicago’s Navy Pier.  You’ll learn the great history of the Chicago Navy Pier while you take in the beautiful Chicago skyline.  But what’s really great about this winter tour is that takes place almost entirely indoors!

You can get a coupon for half off this tour by clicking here.