10 Activities To Entertain Your Family This Holiday Season
UPDATE: This story was originally published on December 6.
We'll admit it: As fun as the holiday season is (Presents! Lights! Pie!), spending that much one-on-one time with your extended family can be seriously stressful, too. After all, how many times can we grin and bear it when Mom reminds us that we're still single? Instead of pulling your hair out, we suggest going with the flow (and maybe keeping a bottle of wine on hand). After all, for better or for worse, our relatives are an integral part of the season, so we may as well have some fun with them, right?
Well, to make that a little easier, we rounded up some of our favorite ways to entertain all your cousins-once-removed in the Windy City—no tourist traps included. Whether it's going high-end with tea at a fancy hotel, trying out the newest resto, or getting your laugh on at an irreverent play (maybe leave Grandma home for that one), our list has something for everyone. Even your angsty teenage cousin will have a blast, we swear.

Chicago French Market
Even though this indoor marketplace filled with local artisans and vendors is open year-round, it gets even more amazing during the colder months. Our favorite stop? Bello Tea, for sips of flavors like Peppermint Bark, Snowflakes, and Winter Wonderland. These brews make perfect presents, or you can just enjoy them with your loved ones.
Chicago French Market, 131 North Clinton Street (between Randolph and Washington streets); 312-575-0306.
Dinner at Brasserie54 by LM
No holiday weekend (or any weekend, ever) is complete without a good meal at a hot resto. Plus, it's the perfect cure-all for any familial squabbles — after all, you can't argue when you're eating, right? We especially love the vibe at Brasserie54: The space is casual-cool, the food is upscale enough for Mom, and the beer list is hearty enough for Dad. Bases, consider yourselves covered.
Brasserie54 by LM, 5420 North Clark Street (at Rascher Avenue); 773-334-9463.
Chocolate At The Pen
The Peninsula Hotel is a classic Chicago establishment, and the elegance of the place is undeniable. For a truly decadent experience, visit the lobby lounge and partake in the chocolate buffet. For $50, you can indulge your sweet tooth with truffles and a chocolate martini, accompanied by live jazz music (hey, it is the Peninsula, after all!).
The Peninsula, 108 East Superior Street (at North Michigan Avenue); 312-573-6685.
Haute Chocolate at Allium
The Four Seasons hotspot is rolling out a brand new menu of hot chocolates, making for a family activity for all ages (you can bring the little ones to this!). Toast the season alongside a roaring fire with flavors like Mexican hot chocolate and hot buttered rum. And, since you are on vacation, there are liqueur pairings for every variety.
Allium, 120 East Delaware Place (between Michigan Avenue and Rush Street); 312-799-4900.
Second City Nut-Cracking Holiday Revue
For a lighthearted, hilarious take on the holiday season, look no further. Consider the comedy troupe's satire your respite from all things sugar plum fairies and cartoon elves. Shows run every weekend, so grab your tickets now.
Second City, 1616 North Wells Street (at North Avenue); 312-337-3992.
Photos: Cindy Kurman, Courtesy of Brasserie54, Courtesy of The Peninsula, Courtesy of Allium
We'll admit it: As fun as the holiday season is (Presents! Lights! Pie!), spending that much one-on-one time with your extended family can be seriously stressful, too. After all, how many times can we grin and bear it when Mom reminds us that we're still single? Instead of pulling your hair out, we suggest going with the flow (and maybe keeping a bottle of wine on hand). After all, for better or for worse, our relatives are an integral part of the season, so we may as well have some fun with them, right?
Well, to make that a little easier, we rounded up some of our favorite ways to entertain all your cousins-once-removed in the Windy City—no tourist traps included. Whether it's going high-end with tea at a fancy hotel, trying out the newest resto, or getting your laugh on at an irreverent play (maybe leave Grandma home for that one), our list has something for everyone. Even your angsty teenage cousin will have a blast, we swear.

Chicago French Market
Even though this indoor marketplace filled with local artisans and vendors is open year-round, it gets even more amazing during the colder months. Our favorite stop? Bello Tea, for sips of flavors like Peppermint Bark, Snowflakes, and Winter Wonderland. These brews make perfect presents, or you can just enjoy them with your loved ones.
Chicago French Market, 131 North Clinton Street (between Randolph and Washington streets); 312-575-0306.
Dinner at Brasserie54 by LM
No holiday weekend (or any weekend, ever) is complete without a good meal at a hot resto. Plus, it's the perfect cure-all for any familial squabbles — after all, you can't argue when you're eating, right? We especially love the vibe at Brasserie54: The space is casual-cool, the food is upscale enough for Mom, and the beer list is hearty enough for Dad. Bases, consider yourselves covered.
Brasserie54 by LM, 5420 North Clark Street (at Rascher Avenue); 773-334-9463.
Chocolate At The Pen
The Peninsula Hotel is a classic Chicago establishment, and the elegance of the place is undeniable. For a truly decadent experience, visit the lobby lounge and partake in the chocolate buffet. For $50, you can indulge your sweet tooth with truffles and a chocolate martini, accompanied by live jazz music (hey, it is the Peninsula, after all!).
The Peninsula, 108 East Superior Street (at North Michigan Avenue); 312-573-6685.
Haute Chocolate at Allium
The Four Seasons hotspot is rolling out a brand new menu of hot chocolates, making for a family activity for all ages (you can bring the little ones to this!). Toast the season alongside a roaring fire with flavors like Mexican hot chocolate and hot buttered rum. And, since you are on vacation, there are liqueur pairings for every variety.
Allium, 120 East Delaware Place (between Michigan Avenue and Rush Street); 312-799-4900.
Second City Nut-Cracking Holiday Revue
For a lighthearted, hilarious take on the holiday season, look no further. Consider the comedy troupe's satire your respite from all things sugar plum fairies and cartoon elves. Shows run every weekend, so grab your tickets now.
Second City, 1616 North Wells Street (at North Avenue); 312-337-3992.
Photos: Cindy Kurman, Courtesy of Brasserie54, Courtesy of The Peninsula, Courtesy of Allium
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