Holidays In Chicago

Gift Guide: For The Explorers

Eat. Drink. Gift Merry.

Our online shop is a great place to take a piece of the CAA experience home, from Skate-Worthy Tube Socks to Winter’s Favorite Blanket. But when the holiday season rolled around this year we couldn’t get the idea of the gift of experiences out of our heads. Because after the last few years, being able to have a joyful night out with friends or a delicious cocktail feels like the biggest gift of all.

That’s why we’ve rolled up 12 of our favorite CAA experiences (Get it? 12 Days of CAA!) for the ultimate in turnkey meets experiential gifting. These experiential gift cards cover all the highlights of taking in our storied building, from roller skating the night away to a private tasting in our speakeasy-style Milk Room.

Today we’re exploring gift ideas for the explorers in your life. The friends and family members who can’t wait to uncover that new cocktail or dish, unearth hidden treasures in the city or just get out and about to take it all in.

You’ll notice a common trend with these gift ideas. Namely, that our playground of experiences under one roof is the perfect launching pad. Not only are we in a great locale to explore Chicago, you’ll discover many architectural gems, dining and drinking experiences and unique events during any CAA stay.


Weekends in Chicago
Who wouldn’t love to receive a weekend escape in the best city in the world? Give the gift of exploring Chicago with a two-night stay in an elegantly-appointed hotel room, along with a $150 cocktail and cuisine credit for use at any of our seven dining and drinking establishments.

Friends Getaway
Grab your crew and start planning that much-deserved adventure. Our Friends Getaway package includes a weekend stay for six in our Bi-Level suite, as well as a $1500 cocktail and cuisine credit that can applied towards a dinner at Cherry Circle Room or Cindy’s Rooftop.

Family Time
With so much to do under one roof, a family retreat is one of our specialities. Our Family Time getaway package includes a one-night stay for up to six in our Bi-Level suite, as well as private Stagg Court usage for family fun and an in-room Shake Shack movie night and dinner experience.


The explorer may be keen just to get out and see where the day takes you, but these annual favorites invite all sorts of exploration, excitement and discovery.

Until January 2, 2022

There’s so much to uncover at the Lincoln Park Zoo and taking in the ZooLights, a favorite annual tradition, invites you to chart your own path through the park finding a variety of displays and activities throughout the holiday season. There’s also some new features this year, including a light show on the South Lawn and a 18-foot holiday tree outside the newly-renovated Pepper Family Wildlife Center.

Until January 2, 2022

Venture just outside of the city and you can experience one of the most beautiful places in the Chicagoland area all lit up for the holidays – the Chicago Botanic Garden. Lightscape is a beloved, quick-to-sell-out holiday happening that invites you to explore a 1.25-mile path after-dark that includes a series of installations. A few favorites not to miss? A 110-foot tunnel made up of 100,000 lights and a group of trees festooned in bulbs that “sing” holiday songs.

CTA Holiday Train and Bus
Through December 23

The ultimate challenge for the ultimate explorer? Track down via the CTA Train Tracker or the CTA Bus Tracker the Chicago holiday-themed busses and trains and take a festive ride through the city. Passengers weren’t allowed on the Chicago Transit Authority’s annual Holiday Train and Bus last year, which makes this year feel even more special.

Decorated with shimmering lights and LED signs, expect Santa and his reindeer to be along for the ride. Just keep an eye out for the candy cane icon that signals the holiday bus or train’s arrival.

Interested in more CAA gift experiences? Eat, drink and gift merry with all 12 of our experiences here.