Family Coming into Town? What to Do!

The holiday season is a time for family, friends, gratitude, and the joy of giving. Chicago embraces this festive spirit like no other city, celebrating in true style. From dazzling light displays and lively parades and charming holiday markets, the city is alive with seasonal cheer. Experience the magic of holiday pop-ups, scenic boat rides, and so much more. There’s no shortage of excitement to discover in the Windy City this time of year!

Shoreline’s North Pole

Celebrate the holidays with friends and family on Shoreline Sightseeing’s first holiday pop-up. Join us at Shoreline’s North Pole, hosted on Cap Streeter! The limited time pop-up just opened up to the public this past Friday.

Shoreline’s North Pole is located at 401 N. Michigan Avenue next to our running Chicago Architecture River Tours. This experience will remain dockside to ensure everyone the time aboard with Santa and the photogenic opportunities. Warm up with a hot drink… or an adult beverage, by our cozy fireplace on the lower deck surrounded by trees! You can find Santa upstairs taking pictures with each guest in front of a scenic backdrop for each to take home with them as a keepsake. 

For now, Santa at Shoreline’s North Pole will be greeting guests Fridays through Sundays and will begin to operate daily starting Friday, December 13th. He will then say goodbye and take his last photos on Monday, December 23rd. Santa wants to make sure all the gifts are ready for delivery on the night before Christmas!

Come see this special experience with great views, beautiful moments, holiday music, and a fun holiday atmosphere!

Light Up the Lake at Navy Pier

During the Winter season, Navy Pier is bringing back Light Up the Lake. Between November 29th and January 5th experience the sparkling lights along the pier. Take part in testing your axe throwing skills, slide down their new ice slide, take a trip to the sky on the Centennial Wheel. Or head over to the Beer Garden on the East end of the pier to warm up by the fire pits while soaking in the postcard view of Chicago’s skyline! 

The pier also has craft workshops and holiday artisan markets that are local for you to browse and pick something out that you or a friend might like. Almost like Summer, guests can catch Navy Pier’s Fireworks display on Saturdays and new holiday-themed drone shows! Head to Navy Piers website for more information on these activities and to purchase tickets in advance. 

Holiday Express Water Taxi Service

Making its return, one of our water taxis will be of service to you on weekends, Saturday and Sunday, to take you to and from all of our stops. The Holiday Express Water Taxi will take you from 200 South Wacker Drive, Michigan Avenue, and Navy Pier. At each of our stops, there’s a festive activity!

Find the iconic yearly Chriskindlmarket at 200 S Wacker Drive near the Willis Tower. Or head to Michigan Avenue for a stroll down the strip known for shopping. If shopping isn’t your scene, you can find Santa at Shoreline’s North Pole greeting visitors aboard a ship full of winter decorations and festive drinks right off of the Michigan Avenue Bridge! Navy Pier is full of activities and holidays as mentioned, Light Up the Lake.

Pioneer Court Marche de Noel

Head to the largest privately owned plaza in Chicago located at 401 N. Michigan Avenue where they are hosting a European-style holiday marketplace pop-up, Marche de Noel, a Bensidoun Market.

From Tuesdays through Saturday, open from 11am to 5pm when they will shut down till next time! Enter through Pioneer Court to find Retail Suite 110 where the charming stalls will be waiting for you in the warmth! Enjoy your visit filled with one of a kind finds, gourmet food, and overall a festive spirit that the community has.