A classic getaway: Revisiting Chicago childhood favorites with my parents

Dec 30, 2021

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My heart is always in Chicago.

I grew up right outside the city and attended DePaul University for four years, living in the nearby Logan Square neighborhood. My entire childhood and adolescence were influenced by the Windy City, and I have no doubt I’ll someday return full time. It truly is, to me, the greatest city in the world.

Of course, I still visit often despite now living in New York, and I always try to be in Chicago for the winter holidays.

This year, I went back a bit early to treat my parents to a quintessential holiday getaway in Chicago. I attempted to remake a classic family holiday excursion in the city, featuring some of the things my family did when I was a kid. Plus, I threw in a couple of curveballs, too.

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A night at the Palmer House

Palmer House Entrance
(Photo by Andrew Kunesh/The Points Guy)

The Palmer House has been a Chicago institution for far longer than I’ve been alive. The historic hotel, which originally opened on Sept. 26, 1871, has been a part of the Hilton portfolio for years now. Everything about the hotel, from the lobby decorations to the classic architecture, screams holidays to me.

I booked a night at the property and reserved a standard room with two queen beds and was upgraded in advance to a larger room with two bathrooms. This was much appreciated, as it made sharing a hotel room considerably easier. Overall, the hotel was fine for what it is.

The lobby was exactly what we needed to get into the holiday spirit. It was decked out with holiday decorations: Christmas trees, lights, wreaths, you name it.

Even during the rest of the year, the Palmer House’s lobby features an intricately painted ceiling, a classic bar that serves up an assortment of cocktails and retro furniture I’ve always adored.

Unfortunately, the rooms are starting to show their age. I noticed wallpaper coming off the wall in our room, and the design needs an update. I think a fresh coat of paint and new furniture could go a long way toward making this property worth the often $300 or more it charges per night during the holidays.

(Photo by Andrew Kunesh/The Points Guy)

Regardless, we enjoyed our time at the hotel, and it made for a good home base for the rest of the festivities.

Related: 8 festive hotels for people who really love the holidays

The Christkindl Market — just not this year

(Photo by Andrew Kunesh/The Points Guy)

Chicago’s Christkindl Market is one of my absolute favorite holiday attractions in Chicago. Each year, vendors from all around the U.S., Europe, South America and more come to open up a shop outside of Daley Plaza in the Loop (Chicago slang for downtown).

As a result, you can buy unique gifts and sample an assortment of great German food and drinks, from mulled wine to bratwursts.

(Photo by Andrew Kunesh/The Points Guy)

I’ve gone to the market every year for as long as I can remember, except for 2020 when it was closed. We’ve gone as a family many of those years, and I’ve gone with my partner, exes, friends and pretty much everyone notable in my life over the last decade.

So, I was really looking forward to visiting it with my parents this year and getting a head start on my Christmas shopping.

We went on opening night (Nov. 19) and to say it was packed would be an understatement. There was barely any room to move around the market. We walked through and attempted to buy a bratwurst but were met with crazy lines.

(Photo by Andrew Kunesh/The Points Guy)

After our walk-through, my parents and I figured it was best to move on to the next attraction and try stopping by the market again the next day. It was just too crowded for comfort — even if the coronavirus hadn’t been a concern.

(Photo by Andrew Kunesh/The Points Guy)

Unfortunately, we came back the next morning and saw a line that wrapped around the block.

Related: From Philly to Chicago, here are 6 of our favorite US Christmas markets

ZooLights never fails to impress

After a non-starter at the market, we jumped in an Uber and drove to the Lincoln Park neighborhood to see ZooLights.

(Photo by Andrew Kunesh/The Points Guy)

ZooLights is an annual holiday event at the Lincoln Park Zoo, Chicago’s free zoo on the North Side. It’s right around the corner from where I went to college, so I used to walk through the zoo frequently between classes.

ZooLights has always been something I’ve enjoyed, too. The zoo is lit up with Christmas lights, and you’re free to explore on your own with a snack and a beverage.

(Photo by Andrew Kunesh/The Points Guy)

Nov. 19 was opening night for zoo members, so I signed up for a membership and reserved tickets a few weeks prior. Those who aren’t members buy tickets for $5 per person, and the money helps a great nonprofit zoo. Plus, admission is free for everyone on Mondays and Tuesdays.

ZooLights was much less crowded than the market, which was a huge relief. We first went to the concession stand where my mom got a hot chocolate and my dad and I bought Belgian beers (classic). There’s also a variety of snacks on sale, like pretzels and popcorn. Frankly, Delirium Tremens Belgian Christmas Ale is one of my favorite beers, so I couldn’t pass it up.

There’s plenty to see around the zoo. It’s completely decked out in lights, with everything from the zoo entrance to the lion cages being lit up with intricate (and mildly psychedelic) light displays. Plus, there are mazes and other fun activities around the park, great for those going with kids. Personally, I just enjoyed walking around the zoo with my parents, enjoying one of the last not-so-frigid nights of the year.

There was also an ice sculpture carving event going on that night, which was a nice touch and really fun to watch. It also reminded me of how much sooner winter arrives in Chicago compared to New York, which made me oddly nostalgic despite my years of endless complaints about the Chicago cold.

ZooLights will be available on select dates through Jan. 2, 2022, for travelers who want to stretch out the holiday spirit.

Related: From Branson, Missouri, to Newport Beach, California, here’s our guide to 13 of the best holiday light shows in the US

The Walnut Room is always a treat

Now, this one is a throwback: the Walnut Room at Marshall Field’s … I mean, Macy’s.

Back when I was a kid, there was no Macy’s in Chicago. Instead, we had our own department store: Marshall Field’s. Overall, it was the same general concept as a Macy’s with designer brands on display.

But the flagship store on Chicago’s State Street has always been something special around the holidays.

(Photo by Andrew Kunesh/The Points Guy)

When Macy’s took over Marshall Field’s in the early 2000s, it kept much of the store unchanged. We’ve gone to this Macy’s during many holidays over the years to buy gifts, see the decorated windows and have dinner by the Christmas tree at the Walnut Room, the restaurant inside of the State Street store.

We got a late lunch at the Walnut Room the following day. While the food is nothing special per se — it’s a limited holiday menu — the atmosphere is nostalgic. There’s a huge Christmas tree in the center of the room, one I’d seen a number of times as a kid but not in many years. The restaurant was filled with families enjoying their first taste of the holiday spirit.

The food was actually better than I remember it being, too. I had their chicken pot pie for the main course, which is one of the Walnut Room’s famous classics. For dessert, I ordered a Frango mint cheesecake. For some background on Frango: It was a Marshall Field’s chocolate brand that specialized in mint chocolates. After Macy’s took over the space, it remained a staple at the location.

If you want to swing by the Walnut Room this holiday season, make a reservation on OpenTable in advance. It’s a Chicago classic for many families, and reservations almost always fill up quickly.

(Photo by Andrew Kunesh/The Points Guy)

Related: Your complete guide to maximizing holiday purchases

Bottom line

Chicago may not be the first city on your list for a winter vacation — and I get it. The weather is often cold and depressing from the end of November through the middle of March.

But if you can overlook the weather, there are a lot of excellent seasonal activities for kids and adults alike, making it an ideal spot for a holiday getaway, whether you’re looking for world-class shopping on Michigan Avenue and State Street or a walk through the winter wonderland that is ZooLights.

This year, it was nice to spend time with my parents and revisit some old Chicago holiday staples. The whole trip was great despite our experience at the overcrowded Christkindl Market.

Beyond the sights themselves, though, it was nice to have some quality time with my parents before the craziness of the holiday season. That time is more valuable than ever these days and, as I get older, I’m learning to appreciate the time we have together more and more.

Happy holidays from the Windy City, folks.

Feature photo by Andrew Kunesh/The Points Guy

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