Birthday Celebration Itinerary for Kids in Downtown Chicago!

Celebrating Addy’s 5th Birthday in Chicago

This past weekend, we booked a trip to Chicago to celebrate Addy’s 5th birthday, and it turned out to be one of those trips we’ll talk about for years! Addy’s 5th birthday was a special day for all of us, celebrating how far we have come from when we were struggling to conceive, health issues, a move, and finally settling and finding our groove as a family. I wanted to create a special weekend that everyone enjoyed and made Addy feel like the princess she is.

In this blog, I am sharing a full itinerary of where to stay, what to do, and an honest review on it all! (Spoiler alert, it was the best weekend ever so if you’re looking for a great time with kids in Chicago, this blog is for you).

Trump Tower and Hotel Chicago Review

Where to Stay: Trump Tower and Hotel Chicago

Address: 401 N Wabash Ave, Chicago, IL 60611

Our stay at Trump Tower and Hotel Chicago was nothing short of amazing. Right from the get-go, Curtis from the concierge team made sure Addy’s birthday was extra special by delivering balloons and cookies to our room. Thanks to the Trump Kids program, the hotel provided a fairy set and castle, making Addy’s stay as luxurious as ours. The rooms were just as impressive, combining comfort with luxury, ensuring our stay was relaxing and memorable. If you’re planning a trip to Chicago, this hotel’s top-notch service and amenities make it a must-stay. You can read my full Trump Tower and Hotel Chicago review here.

Book here

Downtown Chicago with Kids

Our weekend was packed with activities designed to spoil Addy, all conveniently located downtown and most are walking distance from our Hotel!

Thursday Night: We started with a walk from our hotel to the Museum of Ice Cream. It’s not your typical museum; it features interactive rooms and unlimited unique flavors of ice cream. Yes, we even tried hot dog flavored ice cream with real mustard and relish!

Next, we stopped by Build-A-Bear where we took advantage of their Birthday Program and Addy made a birthday bear for just $5  (tip: ask which bears are eligible for the birthday deal).

We ended the night with dinner at Volare Ristorante Italiano, the best Italian restaurant downtown. We’ve been reminiscing about our first visit here 8 years ago, and it was just as amazing this time around.

Friday: We kicked off the day with room service breakfast. Afterwards, we took the complimentary car service Trump Hotel offers, to the American Girl store. Addy enjoyed a day of pampering with hair and nail services for her and her doll, topped off with afternoon tea at the cafe. The personal shopping concierge, a complimentary service, added a touch of luxury to our visit!

After spending 5 hours at American Girl (it went by fast and she had the best day ever)  we returned to our hotel for an afternoon nap. The blackout curtains and comfortable beds made it incredibly relaxing and it is so close to everything downtown it’s easy to fit into your day.

For dinner, we dined at Terrace 16, located on the 16th floor of Trump Tower. The restaurant offers breathtaking views of the Chicago River and an experience that is truly unmatched. The staff were attentive, making our meal memorable.

Saturday Night Highlight: The weekend’s highlight was our ride with M&M Limo. We spent two hours driving around downtown Chicago, singing Elsa songs and enjoying the city lights. It was a blast! For more details on our limo experience, check out my post here.

Sunday: We wrapped up our magical weekend with another delicious room service breakfast before heading home, filled with happy memories.

It was the best two days ever, packed with fun, luxury, and lots of love. If you’re looking for a memorable way to celebrate in Chicago, especially with kids, I can’t recommend these activities enough!

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