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My Favorite 25 Things To Do In Chicago Like A Local

I grew up in Chicago and still visit frequently and after traveling the world, it still remains my favorite city. Here is a list of my 25 top things to do in a Chicago.

Frank Sinatra said it best when he sang “My Kind of town Chicago is”. In the “Windy City”, there is a wide range of sights and things to do in Chicago for all interests. Here is my list of the top 25 Chicago attractions in my favorite city.

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The Best Chicago Street Art – Finding Murals, Sculptures and Other Public Art in the Windy City

The best Chicago street art comes in many forms – and it is free.

Growing up in Chicago I used to spend my teenage summers hanging out along the lakeshore, biking, swimming and sunning. Sometimes I would spend my day at one of the many sandy beaches, but more often than not, I would just bike the length of the rocks along the lakefront.

Those large limestone blocks were put in place in the early part of the 20th century to prevent erosion, but they eventually became a canvas for local want-to-be artists who covered them with cans of spray paint and multi colored paint brushes. This was the Chicago street art of my youth.

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Chicago in Winter – A Budget Friendly Weekend Break in My Favorite City

Chicago is a popular tourist destination. I often visit Chicago in winter for a budget friendly weekend break with cheaper flights, hotels and restaurant deals.

Chicago winters get a bad rap. Yes, Chicago is called the “Windy City” for a reason, and winters there do still get snowy and cold. But like everywhere else in the world, global warming has had its impact here as well, and Chicago winters are nowhere near as frigid as they were when I grew up there in the 70’s and 80’s.

If you are looking to visit Chicago on a budget, then consider a winter weekend break in my favorite city as your best option.

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Reflections from 2025

Another eventful year of travel is coming to a close.  I had a little less travel time than in past years, but then it is all relative. I still managed to explore various parts of the world for 152 days in 2025. Boats, planes, trains, and automobiles were all part of the adventure.

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Chasing the Aurora Around the World – My Tips to See the Northern Lights

After traveling the globe to personally experience the aurora borealis, these are my tips to see the northern lights.

Seeing the aurora as it undulates across the night sky is an unforgettable experience. I was fortunate to see it for the first time in Alaska. Since then, I’ve chased the northern and (soon) southern lights around the world and have been very fortunate to see them on many occasions.

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Yes, You Should Visit Fairbanks in Winter to See the Northern Lights!

Want to visit Fairbanks in winter? I am sharing my one week itinerary, personal experiences and tips on seeing the northern lights in Fairbanks, along with ideas for other things to do in Fairbanks and the surrounding area.

Alaska is a popular travel destination. With glaciers, an abundance of wildlife, and the tallest mountain in North America, the diversity of things to see and do is as big as the state.

For most people, an Alaska journey usually takes place in the summer months, but not for my husband and me. Always on the lookout for unique travel experiences, we chose to visit Fairbanks in winter because we hoped to see the northern lights.

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