Way back when I was a young farm kid who frequented no town larger than Janesville on a regular basis, one of the highlights of my year was the Rock County 4-H Santa Train to Chicago. All us country kids and our families would bundle up during a cold day in December, carpool to Harvard, Illinois and hop on the commuter train to downtown Chi-town.

When I was real young there was a Santa on the train and possibly even some Christmas carol singing. I don’t remember the details or even how my county 4-H chapter pulled off something that noisy on public transportation, but I’d be willing to bet my mother had something to do with it.

Over the years the Santas and the carols faded away, but the annual December trip remained all throughout my high school years. It evolved into a day of Christmas shopping with two of my best friends and all of our mothers. We ventured through the streets of Chicago past the Macy’s windows and down Michigan Avenue. Christmas trees and decorations around every corner guided our way. Christmas in Chicago became a regular thing. It almost didn’t feel like the holiday season until I grabbed my warmest scarf and headed down to the Windy city.

This tradition took a lapse for several years. All us 4-H kids went away to college. The train to Chicago got increasingly expensive on the weekends. December got to be a busier and busier month with two families to juggle and increasing amounts of holiday activities seeping into every spare minute. Christmas in Chicago was an expensive excursion that fell to the wayside.

Then last December I threw out my back right before my Carrot and I were slated to leave on a meandering road trip to Maine. Completely depressed over our missed vacation and still armed with a week of vacation days, we headed to Chicago for a night. I showed my Carrot all the favorite places of my childhood. The Christkindlmarket, Millenium Park, State Street, Michigan Avenue. Everything was red and green and just as festive as I remembered (and somehow also much, much colder).

My love for Chicago at Christmastime reignited and I knew I had to go back. This year we decided to take my Carrot’s mother along. She’s as much a lover of history, culture and holiday cheer as myself, and I just knew she would love it. The 24-hour trip was a whirlwind full of incredible food, a hotel room with a view, a lot of shopping, even more coffee and holiday lights around every corner. Here are the highlights of our trip.

Big Star // I have been wanting to try this taco joint for some time now. This year’s trip had us mostly enjoying downtown Chicago so we stopped at this Wicker Park staple on our way into the city for a quick lunch. There was no line, tasty cocktails and the start of what would be the best service I’ve ever received on a getaway. Plus there was a Christmas tree lot right next door. Chicago holiday cheer: 3 points. Highly, highly recommend this spot and it’s Queso Fundido (stuffed full of roasted poblano peppers and chorizo, and served with a stack of homemade corn tortillas) and the Taco de Pescado (also known as my favorite bite of the entire trip).

Renaissance Blackstone Chicago // This hotel is baller. And I do not use that term lightly. (Or ever actually). My Carrot took me here on our first ever Valentine’s Day as a couple and after six years of annual Chicago visits at all different times of year staying at all different kinds of hotels, this has officially become our favorite spot. It’s a bit far from the hustle and bustle of downtown, but we like that. And it is packed with history. Seven presidents stayed here. Over a dozen films shot scenes here. In fact some pretty big moments in history happened here (Eisenhower accepted his nomination for president from the Suite of Presidents at this very hotel). It was a hub for the Republican party and organized crime for a time. You can actually feel its grandeur when you walk into the lobby and that my friends, is my kind of hotel. I don’t want some trendy new space. I love a place with history and weight. Added bonus: it’s actually affordable as far as Chicago hotels go and a Lakeview room not only has a lake view, it also overlooks Grant Park. We spent many hours people watching from these huge windows. A+++

Christkindlmarket // This has been a Chicago favorite since those childhood trips 15 years ago. It’s German holiday market in the heart of downtown Chicago. It’s like nothing else you will ever experience. There are vendors from all around the world and two stores of hand-crafted remarkably beautiful German Christmas ornaments in every conceivable shape and theme. There’s mulled wine, schnitzel, bratwurst, soft pretzels and candied nuts. This year there was a theater group belting out Christmas Carols. Chicago holiday cheer: 20 points. Pro tip: Get there well before 5 p.m. when folks start arriving after their workdays. It gets packed shoulder to shoulder very quickly on weekends and evenings.

Magnolia Bakery // Great stop for caffeine and a sit down when your feets get tired from all the shopping and walking. Adorable floor tile, abundant desserts, and apparently world-famous banana pudding (which we thought was a joke until 8 of the 10 people in line ahead of us ordered it).

Macy’s // Now this, this is quintessential Chicago Christmas. It may not be as outwardly festive as the Christkindlmarket, but every second of your experience at the Macy’s on State Street in downtown Chicago will have you beaming. From the playfully decorated windows that always share an enchanting story to the Walnut room, Christmas cheer is everywhere. We spent an excessive amount of time on the eighth floor where there is a view of the two-story Christmas tree and dozens of living room arrangements to relax on.

Mortar & Pestle // We headed out of town relatively early on day two of our journey because it’s a 2+ hour drive home and then another two hours for my Carrot mom, but not before finding a dynamite brunch spot on our way out of the city. This time our stop was in the Lakeview Neighborhood at a small, recently-opened spot with comfy booths and a cool but homey atmosphere. We sipped three or four cups of coffee and reflected on a day well-spent. We ordered the English breakfast (which was probably my favorite), king crab benedict, a short stack of pancakes with orange and thyme butter, and a salad with fennel and strawberries that blew my vegetable-loving mind.

Hope you are busy celebrating your own holiday traditions. Lots and lots of cheerful Christmas love to you all.
-Leek