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Season 5 – Episode 2: 10 Things To Do In Chicago Around The Holidays And What To Wear While Do

Updated: Jan 18, 2021

Hello All and happy holidays!

I know its been a minute since I’ve gotten a post up, when I say its been the hardest thing juggling everything I really mean it. I’m slowly but surely getting everything back together and feeling like myself. I’ve got some good content coming to my YouTube and here at the blog!

Ok thanks for accepting my apology… yet again..

I wanted to do something slightly different for at least one holiday posts this year. In this post I will tell you some great things to do in Chicago this holiday and what I think you should to wear while doing it!

Christmas market – ChristkindlMarket

This is one of my favorite things to do in Chicago in the holidays. If you are not from Chicago the Christkindlmarket is a place where you can get gifts and suviners. It is german and European inspired with food and fun activities and shopping of course. Going to christkindle you should for sure be comfortable cute because you never know who you are going to meet.

I would suggest a turtle neck sweater dress, thigh high boots and a cute puffer coat, along with a bucket bag. To know more about ChristkindleMarket dates and times check it out here.

Walk down Michigan Ave

I would start on the walk from state and michigan keep going until the end. As well Michigan Ave is so beautiful around the holidays why not enjoy it while you can it only comes once a year after all.

Now this one is super simple for your walk down Michigan Ave wear a cute chunky boot, Skinny Jeans a V Neck Sweater and a long pea coat and a structured bag.

Ice Skating near the bean

AHHH one of the things that I haven’t been able to excel in… ice skating. Located near the bean in Millennium Park. For this you should for sure wear a pair of skinny jeans (all the falling you might do) turtle neck and a winter coat for warmth as well a hat, scarf and gloves set. This look is still cute but warm look. We also cant forget the winter boots we don’t want our feet to freeze.

Dinner at signature room

Can anyone say date night?? Well if you haven’t been to the signature room its located on the 95th floor of the John Hancock Building located on Michigan ave and Chestnut St right next to the water tower place. On this date night wear a sequin dress, with a pair of black pumps (preferably a pair of Christian Louboutin shoes to have the contrast of the shoes and dress) You should also wear a cute black clutch to tie the look in and red lipstick to add into the sex appeal. The long aline coat will be your best friend until you take of your coat and the world sees how you shine when you walk into a room.

To Book a reservation here

The Drake Hotel NYE party

The NYE Party at the drake hotel is one of the biggest parties of the year in Chicago and we for sure need to look our best. I’m not going this year but I might go next year though. The drake hotel breaths fun and mystery along with sexy ness around the holidays.

For this look we are going to wear a sequin pant suit, a sequin pair of pumps along with a fringe clutch. With this look the hair will be pinned up in a high pony tail with sparkle hair clips to tie in the glam factor.

Have fun and don’t do anything I wouldn’t do 😜

To get your tickets to one of the biggest bashes in Chicago click here.

Zoo lights Lincoln Park or Brookfield Zoo

Now this one is such a fun activity to do walk around with family and friends and just enjoying the zoo lights and the zoo. I would suggest wearing a think pair of leggings due to the weather and walking, my favorite are from target here. A thick sweater that goes over the behind, a jacket with fur and a pair of combat boots along with a crossbody mini bag. Also repeat the hat and scarf set from the last look to stay warm just Incase you go on a cold or chilly night.

Lincoln Park Zoo Lights here

Brookfield Zoo Lights here

Ballet The nutcracker

This will be a beautiful and wonderful night. I seen the nutcracker last year and it was absolutely beautiful. Going to this event I would suggest wearing a a pair of dark jeans a blazer as a top and a pair of thigh high boots and choker necklace’s doubled up for a sexy but edgy effect, and a structured bag that you can turn into a clutch at any moment.

To get tickets to the Nutcracker click here

Morton Arboretum Illumination: Tree Lights

For this excursion I would suggest wearing a pair of warm leggings, a graphic t shirt and puffer coat with a thick scarf. I would also suggest a cute pair of winter boot wedges. This look works because you will be walking around seeing how pretty every tree and the details of the lights are and you don’t have to worry about being uncomfortable and the wedge boots will help with that.

To get tickets click here

Drive through the suburbs to see their house lights

Ahhhh one of my favorite things to do in the holidays. I would start in the north suburbs the houses are not only beautiful but the people that live in burbs go ALL OUT when it comes to the holiday time. For this activity wear a dark pair of denim jeans, a brown pair of booties, a black long sleeve top and a fur vest with a thicker over coat and a backpack to hold your snacks and whatever else you might need.

Christmas helicopter tour

Now this should be the most fun out of everything you might do around the holidays. A helicopter ride over the city is not only fun but it could be a great date night option and it’s beautiful to see the city from a different perspective. For this repeat the hat and glove set, along with leggings and a pair of thigh high flat boots, a long tunic and a leather jacket. Since you will be in a helicopter with the doors either on or off you want to make sure everything you have is secured and nothing falls out. So make sure to zip your bag!

To schedule a tour click here

Wow that was a lot to take in I’m sure. I hope you guys got some great ideas on what to wear to some of your holiday festivities. Remember it doesn’t matter what you are doing just make sure you look good while doing it.

Until Next Time


Teri Michele

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