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5 Things to Do in the Winter in Chicago

January 19, 2022

moca chicago lights

Travel Guides

destinations, Guest Author, Illinois, North America, Travel Guides, USA

Big cities can be a lot of fun. I don’t know about you, but sometimes when the weather turns cold, my brain only thinks beach vacation. Well, if you’re a lover of big cities, then this post is for you. Don’t let the cooler weather turn you off to a city adventure! Here are a few things you can do in Chicago even when it’s cold

5 Things to Do in the winter in chicago

old downtown chicago
courtyard chicago

1. Whiskey Tasting at Conrad Chicago

Instead of just finding a bar, switch it up a bit and find a place with a view to do a whiskey tasting. You can accomplish this at the Conrad Chicago. The bar and small plates restaurant sits floors above the street, which offers a great view while you sip a wee dram. I had fun with this during my visit, especially as I read the cards that provided interesting information about each whiskey I enjoyed.

whiskey tasting conrad

2. An Old Fashioned and Lunch at Ralph Lauren

Some places are simply iconic; like the Plaza Hotel in NYC or Fortnum and Mason in London. The Ralph Lauren Restaurant in Chicago is on that same level–a place you should definitely visit while you’re exploring the city. Sipping an Old Fashioned here was on the top of my list of activities in the city. Be aware that it is a popular place, so you’ll want to plan ahead; even better,  make a reservation.

3. Go to the Museum of Contemporary Art

If you’re looking to get out of the cold, but not sure how to pass some time without breaking the bank [or because you’re saving up for a delicious dinner] check out the city’s museums. Some of the museums allow you to roam at no cost [although they suggest any donations you can spare]. I love a good art museum and the Contemporary Art Museum did not disappoint.

moca chicago lights
moca stairs chicago

4. Shop Some Boutiques

When in doubt, shop. While the city has all the big named stores, like Nike, H & M [which seems to have floors upon floors], Restoration Hardware and Apple, to name a few. Lovely boutiques that you don’t find in every other city are also fun to discover and browse. And check out one of my favorite stores, Barbour.

5. Pastry and Coffee Hopping

Sure there’s always the good ol’ pub-crawl, but on a cold morning, I like to find the best coffee and pastries! Here’s a few gems to try: Stan’s donuts, Sienna Tavern and HenrickX Belgian Bread Crafter. A hint for brunch and coffee at Sienna Tavern: go with friends, order different things and share them all!

stan's donuts chicago
sienna tavern coffee

I hope that gives you a little inspiration to keep Chicago on your list for the winter!

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