New Year’s in Chicago

Every year, we usually host a party at our house for New Year’s Eve. I cook a massive pot of chicken and sausage gumbo and everyone shows up “as they are.” Some people stay for hours, some just show up to say hi and leave. It’s always fun and a great way to connect with neighbors, friends, and family as we go into the new year. This year, we decided to abandon our annual get together for a winter trip to Chicago.

Donovan had been to Chicago once or twice for work, and I had never been – as long as you don’t count flying through O’Hare on my way somewhere else. We thought it would be fun to go to another big city and see what there is to offer. Plus, Chicago deep dish pizza on New Year’s Day to cure a hangover….you can never go wrong!

On our flight from DFW to Chicago, we got lucky and were able to ride First Class in the new American Airlines Boeing 787-8 Dreamliner. Donovan was very excited about this. We had great seats, were able to stretch our legs, and had wonderful service.

Once we arrived, we picked up our rental car and made the trek to Milwaukee, Wisconsin for dinner at The Safe House. Donovan was really excited to eat here (and was the only reason we rented a car!). It’s a Spy Bar and Restaurant, so there is definitely a cool vibe to the place. We were entertained with some magic tricks while we waited on our table. I will say that for a Thursday night, it was extremely busy. Even though we made reservations, we had to wait about half an hour for a table, and then our waiter wasn’t very attentive. We chalked it up to COVID and perhaps less people working, but it was a bit disappointing.

Back in Chicago, we stayed at LondonHouse which is pretty centrally located and near the Chicago River and Magnificient Mile. We had the PERFECT view outside of our hotel window, and we truly felt spoiled! While Chicago sometimes gets bad wrap for crime, we felt extremely safe at LondonHouse, and would definitely stay here again.

On New Year’s Eve day, we slept in a bit and did some walking around town before heading back to the room to get ready for our NYE dinner. We wanted to hit up the Starbuck’s Reserve, but it was absolutely packed, so we thought we’d try that again later. I’m not going to lie, it was pretty cold walking around downtown, but because we were layered up pretty well, it didn’t bother us too much.

For NYE Dinner, we made reservations at RPM Steak, and I can proudly say that we were NOT disappointed AT ALL! Probably one of the best steak dinners we had in a very long time!

If you’re a reality TV fan like myself, you’ll know that RPM Steak is owned by Bill Rancic (who married to Giuliana Rancic from E News!). Bill, himself, was one of the winners of Celebrity Apprentice. I won’t tell you how much we spent on dinner, but let’s just say it could have been equal to a mortgage payment (you decide how big the house is HA!). We ordered several glasses of champagne and coctails, appetizers, main courses, and of course the famous Baked Alaska! Oh man, it was so good, I’m drooling just thinking about it. We ate SO much food, I could have used a crane to get home.

Since our reservations were so early (4pm), it wasn’t terribly late when we left the restaurant. I think we were there about 4 hours or so. That morning, we had booked a reservation at LH Rooftop bar so we would have prime spots for fireworks. This was also not cheap, but definitely worth it to have a good view.

(Also, yes, I did do an outfit change! Don’t judge! I couldn’t decide which sparkly outfit to wear, so I got to wear both!) The rooftop had an open bar, dj & dancing, photo booths, and much more. Since we were trying to avoid COVID, we ended up just staking a spot outside near where the fireworks were going to be shot so we’d have a prime spot.

While (still) very cold, it was a great spot! We’d definitely do New Year’s Eve in Chicago again!

The next morning we woke up early to head to Aire Ancient Baths – a New Year’s Day treat! I almost hesitate to share about this place so we can keep it to ourselves, but it is too good not to share! Aire is located in a restored factory from 1902 and has several “baths” (or hot tubs) accessible. It’s a pretty exclusive place, and we couldn’t bring our cameras/phones inside. You’ll just have to take my word that it was awesome.

I left Aire feeling ridiculously relaxed (and if you know me, you know that’s quite a difficult accomplishment!). I wish there was an Aire in Dallas so I can go again very soon, but alas, it’ll just be a special option when visiting NYC or Chicago.

After our spa appointments, we wanted to get some true Chicago deep dish pizza. Everyone we spoke to recommend Lou Malnati’s – so that is where we went! This was also within walking distance of the hotel, which made it easy to get to. Fortunately, the wait wasn’t too long. The cool thing was that we could order our pizza while we waited for our table. The deep dish pizzas take almost 45minutes+ to cook, so this helped speed up the waiting time.

After we killed a pizza, we decided we needed to walk it off. It had just started snowing (sleeting?), and we thought, what better way to walk off a pizza then during a snowstorm?! Ha!

We tried to walk down to the Navy Pier (keyword: tried), but it was WAY too cold and WAY too windy. It was so windy that we could barely walk straight down the street! They don’t call it the Windy City for nothing! Instead, we turned around and headed back towards Millenium Park to get our picture with the famous “bean.”

Fortunately, because it was snowing and pretty dreary, there weren’t a ton of people around which made it easy to access and walk around without the fear of someone coughing on us.

The next day we were able to hit the ground running again. Since it stopped snowing, we headed back towards the Navy Pier after a delicious breakfast at the Starbucks Reserve. If you haven’t been to a Reserve, you must find one! It is definitely a treat! The food and drink options are more gourmet, and it has a fancier vibe. Only downside is everyone wants to go, so there is always a line!

At the pier, we received a tip that there was a good vantage point of the skyline from the top of a parking garage. We thought the person was nuts, but wanted to give it a try. They were not wrong!

We got some great shots of downtown and enjoyed playing in a little bit of snow that had accumulated on the top of the garage. It was definitely fun!

And that’s it! We headed back to DFW that afternoon (after a comedy of errors with flight arrangements). While it’s a bit warmer in Dallas than Chicago, we still miss the fun city life, and can’t wait to get out again soon!