My Holiday Tour of Chicago as a Local Tourist with Choose Chicago

Thank you Choose Chicago (aka Chicago Convention and Tourism Bureau) for for sponsoring this blog post. All photos and opinions expressed herein are my own.

Two weeks ago, I participated in Choose Chicago’s Influencer Holiday Tour! I was ecstatic and honored that Chicago’s tourism board invited me on this tour as its local influencer. As you know, I love sharing what Chicago has to offer. I thought I knew a lot about what to do in Chicago but this holiday tour opened my eyes to so much more, especially things you can do in Chicago during the start of the holiday season. Not only did I get to experience all the fun stuff in Chicago (including my first helicopter ride!) but I also took away a sense of pride living in this beautiful city. I now have a longer list of things to do in Chicago when friends, followers and readers ask me for suggestions.

The Influencer Tour kicked off on Thursday night and ended on Sunday night with a packed schedule of things to do and see in the 3.5 days. I was one of many influencers from around the country who were invited to participate on this tour. Through the course of the days and events of the tour, I was able to meet so many cool and interesting content creators. To say that I had a great time was an understatement.

Instead of sharing the whole itinerary of the trip, I decided to share the highlights that I enjoyed the most and what I would recommend to friends and strangers visiting the Second City.

My Top Picks –

What To Do in Chicago during the Holiday Season

Besides summer, the weeks leading up to Christmas are also my favorite because the city is decked out in holiday decorations and lighting, which helps me get into the holiday spirit. I always tell people that one of the problems of living in Chicago is choosing what to do. And the holiday season is no different.

Chicago’s holiday season officially kicks off the weekend before Thanksgiving with the city’s Christmas Tree Lighting Ceremony and Magnificent Mile Festival of Lights. All the activities during this tour were done during the weekend before Thanksgiving.

Christmas Tree Lighting Ceremony at Millennium Park

Millennium Park Christmas tree

To kick off the holiday season, the city hosts a tree lighting ceremony at Millennium Park (near Washington & Michigan Ave) on Friday evening (6 pm). The Christmas tree lighting ceremony included live music, on-stage dancing, and even an appearance by Santa and Mrs. Claus! The surprise of the event were the fireworks from a rooftop nearby after the tree was lit!

This is Chicago’s 106th Christmas tree! This year’s tree is 55 feet and comes from Elgin, IL. The tree has about 54,000 LED lights around it, making it a perfect place to take family photos!

I was lucky to include my family in this event as part of the tour. It’s definitely something we’ll be back to see for years to come.

Magnificent Mile Lights Festival

We have always been spectators of the Magnificent Mile Lights Festival Parade but this year, Luke and I were in the parade as part of the Choose Chicago float! I’m not sure if I can ever top that for Luke or the twins.

The Magnificent Mile Lights Festival parade is normally on the Saturday before Thanksgiving, starting at 5 pm. The parade begins on N. Michigan Avenue at Oak St. There’s always a great line up of floats with Mickey and Minnie Mouse as Grand Marshals lighting one million lights on Michigan Avenue along the way.

The Ledge at Skydeck Chicago

Jumping at the Skydeck Chicago

I often tell people…”If you didn’t go to the Skydeck when you’re in Chicago, were you even in Chicago?” The Wills Tower (formerly the Sears Tower) is an icon in the city. It’s the tallest building in the Western Hemisphere! The Skydeck Chicago, has glass boxes extending 4.3 feet up 1,353 feet or 103 floors. I am scared of heights but knowing that I’m in an enclosed space helps ease my fear. The pictures from the Skydeck are spectacular – you can see our Luke’s photo with Santa last year.

A River Cruise with the Chicago Architecture Foundation – Chicago’s First Lady Cruises

I always suggest a river cruise for anyone visiting Chicago, especially Chicago’s First lady Cruises with the Chicago Architecture Foundation. It’s such a unique way to experience Chicago. But I had no idea that you could take a river cruise during the holiday months (I guess weather permitting?). You learn so much about the architecture along the river with a live tour guide. It’s one of my favorite things to do as a local! Now I know we can go during colder weather. You don’t have to sit outside for this cruise. The boat has a lower cabin that is heated with a bar!

Walking Food Tour with Chicago Food Planet

After I took a food tour with Chicago Food Planet, I asked myself – “Why didn’t you ever do this before?” This was a such an appetizing and pleasant surprise for me. We took the Chicago Food Planet’s brunch tour through Chicago’s Wrigleyville neighborhood, home of the Chicago Cubs and Wrigley Field. We met up with our guide Bill (who is a retired broadcaster, a huge Cubs fan and Chicago expert) at Hotel Zachary. The food tour included doughnuts from Do-Rite, pizza from Maddon’s Post, omelets from Hotel Zachary, and cracker jack beignets from Mordecai. I left stuffed and happy.

Chicago Food Planet also offers food tours in other Chicago neighborhoods. I plan to do a food tour of the West Loop neighborhood. Don’t worry, you won’t be walking outside the whole time. You will be indoors eating.

Christmas Pop Up Bars

I admit it, I love Christmas bars…you know the ones decked out in Christmas decorations. It was a pleasant surprise that we were able to check out the Christmas pop bar at Hush Money, next to Hotel Zachary. I will be back for a moms night out to enjoy a cocktail or two.


We often try to make to Christkindlmarket – inspired by the Christmas markets in Germany – every year. The mulled wine and food are why I go but you can also shop for some great merchandise. Chicago has two locations – Daley Plaza in the loop and Gallagher Way in Wrigleyville.

WNDR Museum

The wndr Museum is a great place for parents and kids! The museum is located in the West Loop neighborhood with immersive art activations with many small rooms that that inspire and delight through all your senses. My favorite room, which is also home to Chicago’s first ever Infinity Mirror Room by iconic Japanese artist Yayoi Kusama.

Helicopter Ride With Chicago Helicopter Experience

Night time view of Chicago Skyline

The helicopter ride with Chicago Helicopter Experience was the highlight of the holiday tour because I’ve been in a helicopter or even flown in one. We took the tour in the early evening to see the city all lit up. I almost cried as we flew over the Chicago skyline because the city is just so beautiful. I didn’t know whether to take pictures of what I saw or just sit back and take it all in. The helicopter ride is about 20 minutes long, departing from Chicago Helicopter’s south Halsted location. I plan to gift this experience to Charlie for Christmas because I loved it so much!

Stay at the Sofitel Chicago

I’m a huge Francophile and was so happy that the Sofitel Chicago hosted me and my family for a couple of nights during this tour. Chicago is one of five cities in the U.S. with a Sofitel Hotel. The hotel is located in a great location in the Gold Coast, just less than five minutes by foot to luxury shopping, restaurants and Lake Michigan.

Where We Ate On the Holiday Tour

Chicago is such a great food city and this holiday tour had no shortage of restaurants and food for us to enjoy. I want to thank all the great restaurants that hosted us on this tour. I’ve also added what I liked to eat at each of these restaurants.

  • Offshore – the nation’s largest rooftop venue located at Navy Pier (spicy tuna rolls).
  • The Gage – one of Chicago’s most booked restaurants – effortlessly blending European influence with American style (fries with curry gravy).
  • Trulucks – we met at the bar prior to the parade (lobster bisque).
  • CDA at Sofitel – located in the hotel lobby (paella).
  • Lou Mitchell’s – Chicago iconic diner at the start of Route 66 (doughnut holes).
  • Theater on the Lake – historic building with views of Lake Michigan and Chicago’s skyline (steak and the mashed potatoes are so good!)

Thank You Choose Chicago!

The group’s first night and first time meeting one another at Offshore in Chicago!

I wanted to thank Choose Chicago for including me on this influencer holiday tour. It was such a fun experience for this Chicagoan. I fell in love with the city even more. I have so much more to share with my readers and followers on all things Chicago now.

Choose Chicago did a great job of putting together a diverse group of social media influencers from different backgrounds. But we all had many things in common – our love for traveling, taking pictures, and eating good food with a side of comedic relief.

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