Midwest Trips

Living in the Midwest has its ups and downs, but I have learned to love it now that I am living here. Personally, I am more of a beach kind of girl, so I definitely love the west coast a lot more, but you gotta work with what you got, am I right haha?! Since, I have lived here for a couple of years now, I have had the pleasure of visiting a few places in the Midwest and have compiled a list of some of the areas I enjoyed visiting. (Please note that I live in Chicago, so most of these are around and closer to that area, meaning there is soooo much more to the Midwest than just these trips).


Milwaukee (Wisconsin) – it is the perfect weekend trip. It has that big town small feel. It is filled with lots of breweries and lots of cheese (yummmm). It is fun to go any season because they always have fests going on or things happening. Check out a brewers game in the summer and hit up October fest in the Fall.

St. Louis (Missouri) – this city is home to the iconic Gateway Arch. It is another great place to visit for a few days. Make sure you go up in the arch because it is a killer view. Check out the zoo as well, it is free and probably one of the best I have been to. I also recommend going out there for Mardi Gras, because it is one of the best ones in the United States.

Chicago (Illinois) – this is my hometown so I may be biased when I say this is the best city in the Midwest. But honestly, it is a world known city and there is an endless amount of things you can do here. Summer is the best time to visit because nothing compares to a Chicago Summer that is filled with the outdoor bars, festivals, and of course the beach.

Starved Rock State Park (Illinois) – this is for all my nature lovers. It is a stunning place to see filled with beautiful cliffs and waterfalls (depending on the time you go). I love going in the fall because it is beautiful with all the colors, but the waterfalls might be dried out by then. Make sure to wear comfortable shoes and plan to spend a few hours hiking through it.

Galena (Illinois) – probably one of the most charming towns in Illinois. It is perfect any time of year but especially during winter because you will feel like you fell into a Hallmark Christmas movie. With one street filled with lots of local shops and restaurants, you will have plenty to do for a weekend trip. Nearby, there is also a ski resort, making it the perfect winter weekend trip.

Lake Geneva (Wisconsin) – this place is always a good time especially in the summer. It has a beautiful lake and a beach you can hang out at. It has a cute downtown with lots of shops and restaurants. Also, if you come in the winter, there is a ski resort where you can have some winter fun as well.

Holy Hill (Wisconsin) – this is another one for nature lovers. This is definitely only a day trip type of place because there is not much to see here other than the Holy Hill. I put this on the list though because this place is just breathtaking. On top of a hill is this magnificent church that you can climb all the way up and get stunning views from. I recommend going in the fall because it is beautiful, but I have seen pictures of it in the winter and would love to see it covered in snow as well. So if you are brave enough to bear the Midwest cold, then check it out in the winter as well.

Wassau (Wisconsin) – This town has a really cute downtown area filled with shops and restaurants. But that is not the reason why it is on this list. The best part of this is Granite Peak, which is a great spot for some Midwest snow fun. Grab your snowboard or skis (if you’re like me) and go hit the slopes for the weekend. There are a lot of resorts around there and you can even do a ski and stay package which is 100% worth it.

Wisconsin Dells (Wisconsin) – This is the perfect family vacation and it is great any time of the year! With lots of resorts filled with water parks to a cute downtown area with many activities offered, this is the place that you have to experience at least once.

For more of my favorite ski and snowboard destinations in the Midwest, check out my post on Skiing in the Midwest.


Obviously, there are so many more places to check out in the Midwest, but these are a few of my favorites that I have been to so far.

Happy Travels – xoxo Dre ❤

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Just a girl living out her dreams of traveling the world.

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