Chicago in December

We are back from our week-long trip to Chicago and I must say that this was perhaps one of the most fun and productive vacations we have ever taken. It’s funny because this isn’t exactly what one expects when visiting Chicago in the winter.

But having lived there for many years before moving to NC, we knew that there was a very good chance that the holiday spirit of the city was well worth braving the cold. In fact, Chicago is a terrific time to visit in December when all the lights and the holiday decorations make the city feel like a fantasy land!

We flew on Southwest airlines from RDU to Midway, with the flight time right under two hours. This was Ajay’s first plane ride but like a pro he went with the flow as if he had done it a million times. Asha and Arjun are still at that age when the excitement of the trip starts as soon as we park our car and take the shuttle, because riding in buses is not something we do around here. From start to finish, Devang and I were a well oiled machine getting everything and everyone to the gate in record time.

Once in Chicago, we picked up our rental car and started to drive towards the city on what ended up being a very cold, rainy, and cloudy day. We had opted to stay at an Airbnb in our old neighborhood (steps away from our old condo actually). On the way there, we stopped at what used to be our favorite grocery store (Stanley’s) to get fruit, veg, cheese, and other munchies, and also picked up lunch from our favorite Thai take out (Thai Lagoon).

The Airbnb is in a new building that didn’t even exist when we lived across the street. Lucky for us the 2-bed-2-bath space was so big and so well furnished that it felt like a fancy hotel suit. Bonus of traveling to Chicago in winter is that we probably paid much less for what this place would have gone for in the summertime! The super best part however, was that it looked over the Western train stop. We were so close that I could have a staring match with people waiting on the platform, if only they knew that I was watching them (not creepy at all, right!). But the windows were surprisingly insulated and we weren’t bothered by the sound at all. The kids were glued to the floor-to-ceiling windows anytime we were inside, and yelled “trainnnnn” every 5 minutes. I think they were in transportation heaven. I thought it would get old after the first few minutes, but I was wrong!

After eating and catching our breath, we bundled up and went out walking to meet some old friends and neighbors!! It was so cold and windy that it took my breath away, BUT, we were too excited to care!! Dinner was from another old favorite (Irazu), eaten at home, while we hung out with cousins who were sweet enough to visit with their newborn even on a weekday.

Next morning, Stanley’s loot made for a good breakfast for the kids, and we got our favorite coconut latte at Ipsento. Well fueled, off we went to one of Devang’s favorite places – Garfield Park Conservatory. Once inside and surrounded by all the tropical foliage, we forgot that it was snowing outside. It felt like we were walking around in a rain forest somewhere. I still don’t know how this place is free!! By the time we finished, I felt like my lungs had gained five extra years of life after breathing in all that good air!

For lunch we met a friend at The French Market, another awesome place to hang out regardless of the weather; I definitely wished I had come here more often. The hubbub inside the market felt like being in a tiny European city during the holidays! Then with enough soup, bread, crepes and chocolates in out bellies, we bid our friend good-bye and headed home for some rest. Later for dinner, we met more friends and family at Reno in Logan Square. It was the perfect place to end the night.

On Friday morning we walked on the 606 trail to meet friends for brunch at Toast in Wicker Park. There was still enough snow around from the previous day to have a mini snowball fight. Even though it was sunny, it was freezing cold! But while trying to nail her brother with a snowball, Asha yelled “I love Chicago”, and needless to say, it melted my heart! In the afternoon, as Arjun napped, I took Asha to get a haircut at the same place where she had her first ever haircut! Seeing her so big, getting a shampoo, and chatting with the stylist, almost made me tear up. One downside of finishing a pending task while on vacation however, was paying city price for a kid’s cut, dear lord!

Later, Ajay and I took the train to my old office to see colleagues and reminisce about having a job, ha! After getting off at my “usual” stop, I realized it didn’t have an elevator. So I took off the carseat, collapsed the stroller, and carried it up the stairs. Once up, I realized the door to the building wasn’t wide enough and the side door was tricky and so heavy because of the wind tunnel effect. It took me just as much time to get up to my office as it did to get to the train stop in the first place!! So yeah, may be this was one time when I didn’t mind living in a place where you just drive up to places! It felt so surreal being in the lobby of the Chase building! It was pretty and festive just as I had remembered.

Later, dinner included deep dish pizza at Pequods (the only one to eat if you ask Devang), and then we had an open invite for friends to meet us at the bar (Remedy) attached to the building where we were staying. Luckily, my father-in-law was in town for work, which meant that after we showed off our kids, they went back with Grandpa and enjoyed the rest of their night running around and having fun. Ajay stayed behind with us where he switched between napping by the fireplace in his carseat, or being held and bounced by our friends. At first it didn’t feel weird having a baby in the bar because it was still early for the “party goers”. But somewhere around 10:00pm, we realized perhaps it wasn’t the best place to hang out with a baby. We called it a night and simply walked up the stairs and rolled into bed!

The next morning we decided to check out another neighborhood of ours where we rented an apartment before having kids. Gold Coast is one of the most magical places I have ever lived in. It was amazing to see our old high rise surrounded by a new one, even taller and shinier! Luckily a friend had recently moved in there and so we got to check out the view, which for a hot minute, made me want to move back!! You guys, it was so beautiful! Then, after a stroll down Old Town, Lakeshore Drive, and Michigan Avenue, we bid farewell to Chicago and headed to see our family and celebrate our nephew’s first birthday in Bourbonnais. While there, we even got to take our first ever family picture with Santa, thanks to a birthday party miracle! In a way, the credit for this amazing trip goes to the little guy without whom we wouldn’t have planned any of this anytime soon.

The weekend with family in the suburbs was exactly what we needed to relax before heading back to Raleigh. This was such a fabulous trip. I think Chicago in December might just end up being a new family tradition!

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Chika Gujarathi is a freelance writer and a mother of three from Raleigh, NC. She writes for national and local publications about lifestyle, travel, books, and of course, motherhood! Her most current project involves illustrating and publishing a children’s Hindi book. When not adventuring with her family in the minivan, you can find her riding the streets of Raleigh on her beloved bike Linus.

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