Chicago Winter Wonderland – Activities to Cure the Winter Blues

  • The Bean Sculpture in Chicago

  • a tropical drink in a coconut shell

  • Tropical Cocktail in a flaming pineapple

Chicago is known for its chilly weather during the winter (perhaps, that’s an understatement). Most visitors probably imagine that Chicagoans even hibernate in the winter but contrary to popular belief that isn’t the case. Here’s a short list of places to eat and play during winter in Chicago.

Curling at Kaiser Tiger
Kaiser Tiger is the sister restaurant of Paddy Long’s, a Lincoln Park establishment that is famous for its wide variety of bacon, craft beers, and whiskeys set in a cozy pub-like atmosphere. Kaiser Tiger is similar but set in a large industrial space and offers all of the same delicious offerings plus an expanded menu and Curling in their beer garden. This is a can’t miss experience.

Must Eat: The Bomb Sandwich – a beef and pork sausage rolled in weaved brown sugar bacon with a drizzle of BBQ sauce.

Fire Pits with a View at Cindy’s Roof Top
Cindy’s Rooftop is a popular attraction for those that want a great view of Lake Michigan. While most people would assume that it is closed for the winter, Cindy’s actually sets up fire pits and provides blankets for those that want to experience one of the best rooftops in Chicago.

Must Eat: Skuna Bay Salmon – a perfectly pan-seared salmon served with an amazing potato rosti.

Brunch at Park & Field
Park & Field, a newer addition to the Logan Square neighborhood, is a “Vintage Sports club” with Bocce Ball and Shuffleboard to name a few of the activities offered. Guests can take their Hot Toddy’s outside to the fire pit and curl up under a blanket or grab a S’mores kit for some delectable fireside treats. This is truly a place to spend a lazy Sunday at!

Must Eat: Opt for their Bottomless Brunch including farm-to-table food offerings and “limitless libations” including Bloody Mary’s, Mimosas and Sparkling Rosé.

Discover Something New in Chicago
Here are some other winter activities and places to check out in Chicago to cure the winter blues:

Bad Axe Throwing
Bring out your inner lumberjack and try your hand at Axe Throwing. Axe Throwing has gained popularity around the country and Chicago is no exception. Bad Axe is the first Axe Throwing venue in Chicago. They also offer food and drinks to help keep you fueled.

Maggie Daley Skating Ribbon
Built in memory of Mayor Richard Daley’s late wife, Maggie Daley Park is a popular destination especially for those who enjoy ice skating. Skate around Maggie Daley Park in the quarter-mile skating ribbon that includes inclines to make skating more interesting. If you forgot to pack ice skates do not fret, ice skate rentals are also available.

Lost Lake
One of Chicago’s most popular bars – dip into Lost Lake and pretend you are on a tropical island. This Tiki Bar packs a punch and has a cozy atmosphere that will make you forget the cold outside. The libations are sure to warm you up. Ask for their secret menu (if only to peruse – it’s pretty impressive).

While winters in Chicago can seem intimidating, Chicago offers plenty of activities to keep locals and visitors entertained (and full). Come visit Chicago for a warm welcome, delicious food and unique activities.

To access more information about local restaurants, unique attractions, and special offers in Chicago, visit our Destination Guide, or explore Hilton properties in Chicago below.

Know Before You Go

  • Chicago’s nickname is “The Windy City.”
  • Make sure to visit Millennium Park so that you can see the world-famous Bean!
  • Avoid visiting in the winter if you aren’t a fan of cold weather! The weather warms up around May.
Lala S

This post was written by Hilton Suggests Team Member, Lala S. Are you interested in traveling to Chicago? Let us know if we can help you with any other recommendations. Tweet us for more great local travel tips!

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