Winter in Chicago: Top 5 Things To Do This Holiday Season

Hey there, winter wanderers! Wondering what Chicago has to offer this time of year? We promise, there is something here for everyone!

This holiday season, we have a list of 5 things to do in the Windy City. These activities will make your winter unforgettable. So, let’s get started!

1. Holiday Express Water Taxi

image of the Shoreline Sightseeing Holiday Express Water Taxi named Blue Dog

Kick off your holiday adventure with a scenic ride on the Shoreline Sightseeing Holiday Express Water Taxi.

Without-a-doubt the coolest way to zip between the Mag Mile (on Michigan Avenue) and Navy Pier.

The water taxis are a great way to relax, while exploring the city, running every 30 minutes. And the best part? A round-trip will only set you back $8 until the end of the year. Check out Shoreline’s Water Taxi page for the daily schedule.

2. Navy Pier’s Light Up the Lake

Next stop, Navy Pier for Light Up the Lake, the biggest holiday bash in Chicago. From November 24th to December 31st, the pier transforms into a winter wonderland.

You can come and see beautiful lights by the lake. You can also skate outside with a great view of Lake Michigan. Additionally, you can get cozy by the fire pits.

And guess what? On weekends, you can also check out an artisan market, live music, and even try your hand at axe throwing!

3. Shoreline Sightseeing’s Chicago Architecture Tour

Once you’ve had your fill of Navy Pier, we recommend hopping on our Chicago Architecture River Cruise. This 1-hour river cruise shows you the main and south branches of the Chicago River. You’ll see the city’s famous skyscrapers and landmarks.

You’ll learn about the city’s history from our expert tour guides, all while sipping on hot drinks available for purchase on the boat. Just remember to bundle up!

image of Shoreline Sightseeing's Chicago Architecture Tour boat named Skyview on the Chicago River
image of Shoreline boat at Navy Pier with ferris wheel

4. Hot Chocolate Cruise

This year, we’ve got a new and unique holiday experience for you! Don’t miss the Hot Chocolate Boat Tour. Without a doubt, this boat ride is one of the best views in the city. There is no better way to enjoy the skyline this time of year, than sipping on a free hot chocolate while admiring the buildings lit up at night from Lake Michigan.

And if you’re feeling a bit more festive, you can purchase additional hot chocolates, adult beverage add-ins, beer, and wine onboard.

5. Holiday Fireworks on Navy Pier

Cap off your day with a bang! As part of Light Up The Lake, Navy Pier is hosting a spectacular fireworks display every Saturday night through the end of the year.

You can see beautiful fireworks from the Pier. However, if you are looking for something a little more special, Shoreline offers cruises with Holiday Fireworks during the season. Check our schedule page for departure times and to see if tours are happening during unpredictable Chicago winters.

So, there you have it! 5 awesome ways to enjoy the holiday season in Chicago. Just remember to bundle up and have a blast!