Welcome to Adventures with Maddy + 10 Things To-Do in Chi-Town

A lot of things have changed for me in the last year. At the beginning of 2016, I had a New Year’s resolution to get back into blogging because it was something that I loved and missed, but, at the end of January, life threw me for a loop. I haven’t quite decided what level of detail I’ll be sharing publicly but long story short, I got divorced and it was not something I saw coming.

My previous blog’s name was Forever Maddy B, the B standing for my married name. When the site went live, people joked about the complications that could arise with the title being tied to my marital status. I was put off by this because of course I saw myself as forever Maddy B. I mean that’s what I promised in my vows and the commitment I made to my life partner. I didn’t think anything of it. Silly me.

After the divorce dust settled last year, I just couldn’t get back into blogging. I had this site that I poured hours of time and passion into, representing me and my life that all of a sudden felt like a lie. I didn’t have the capacity to figure out how to transition all that when I had to figure out how to transition myself and my life first.

So, it’s been about a year and a half since D-day and I’ve done a lot of soul searching, focusing on myself and who I am outside of an 8 year relationship that started when I was 17. Needless to say, I’ve learned a lot. Ha, could I be more cliche?! But it’s true, I have. Deal with it.

So what is Adventures with Maddy?

While Forever Maddy B was a fashion-focused blog, Adventures with Maddy will be centered around travel and adventure. There is simply SO much I want to do and this blog will be a diary of sorts in making that happen. Where am I going? What did I love to do there? What sucked? How did I get there? What did I learned? Etc, etc, etc.

To start things off I’ll be recounting some of my travels in recent year, beginning with a trip I took to Chicago last year…

It was a family reunion based trip as my dad’s Irish & Italian family is from the Chicago suburbs. And while it was amazing see family for the first time in over 10 years is was also so much fun to explore Chicago as an adult. I remember as a kid all I cared about was going to the American Girl Doll Store to get more stuff for my Samantha doll. Needless to say, I had some other interests as a 26 year old.

Below are my top 10 things to do on your next trip to Chi-Town:

  1. Renting bikes & The Lakefront Trail


    I was honestly surprised that I did not see more people using … since it significantly cut to cut down on walking and saved us money from Ubering my siblings. Maybe it’s just not well advertised? The siblings and i rented bikes for a few hours to bike from our L stop to the beach. We lucked out of weather as it was absolutely gorgeous out so biking was a great way to get around.

  2. The beach


    Yeah, as an inland city Chicago has a beach and it’s pretty cool to go from skyscrapers to a sandy beach in like 5 minutes. We didn’t bring bathing suits so the sister and I stopped at a beach bar for some mojitos. The only complication was that we didn’t have locks for our bike rentals so we had to keep a close eye on where we docked our bikes. At one point I had to run out of the beach bar to stop someone from trying to steal them! The security guard at the bar said told me afterwards that he had my back thank goodness.

  3. The Bean


    Completely a touristy thing to do and because of that I thought I would be underwhelmed by the Bean but it’s actually a pretty cool piece of art. My favorite part was seeing the Chicago skyline reflected in the surface.

  4. Shedd Aquarium


    There was a much cooler day so we decided to head to the aquarium on the recommendation of our dad. Now, I’m a little spoiled by the amazing-ness that is the Baltimore Aquarium but Chicago had a cool setup and a dolphin show which was super cute. This siblings and I had some fun goofing off in the gift shop.

  5. Murals & Architecture


    Two of my favorite things to experience in a new city as pleasant surprises and Chicago did not disappoint. I find murals to be a beautiful contrast to the hard lines of dark colors that are abundant in most cities. Architecture is a look into the past, a way to experience a time that you’ll never be able to visit and that fact amazes me.

  6. FOOD!

    Lou Malnati’s Pizzeria
    It’s sacrilege to visit Chicago and not get some deep dish pizza and there is no better place than Lou Malnati’s. Not to mention that pizza is my favorite food so I was quite happy with this meal choice.

    The Girl & the Goat
    The Girl and the Goat was a random find. Totally hipster with delicious food including some of the best oysters I’ve ever had.

    Burger Bar: Chicago South Loop
    Burger Bar was another random find and the perfect way to end our Chicago trip as we left here to go straight to the airport. They had a vegetarian burger but I really just wanted some beer and fried pickles and they did not disappoint. If I wasn’t vegetarian I would have ordered the Firehouse burger which is what my sister got and it smelled divine.

  7. Visit Millennium Park

    Millennium Park is a public park and actually houses the Bean. So, yes, it’s a bit of a duplicate item but there are a bunch of events, often times free, that you can attend. You can check out the monthly schedule here.

  8. Sears Towers sky deck


    Such a cool experience though a bit out of the way from the rest of the fun things to do in Chicago. Horizons fascinate me and the views from … aka Sears Towers did not disappoint. It did cost $ but I thought it was well worth it.

  9. Riding the L

    Not the most exciting thing to do in Chicago but I love trying out the public transportation in different cities. I found the L to be a bit more complicated to figure out than the metro in DC and it doesn’t go everywhere you need to but it was very helpful in getting from out Air BnB on the outskirts of the city to downtown. The coolest thing about the L is that it is an elevated transportation system, as in it’s rails are built lifted above the ground so you’re able to see a lot as you ride.

  10. Art Institute of Chicago

Located in Chicago’s Grant Park, the Art Institute of Chicago is one of the oldest and largest art museums in the United States. I know that a lot of people find museums boring but I truly enjoy seeing different exhibits. I should say that I know nothing about art but that’s doesn’t stop me from enjoying it.







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