I prefer towering mountains to towering skyscrapers. It's no secret. So it's safe to say, I didn't know what adventures to expect when I headed north for a Chicago weekend celebrating a bachelorette party and the 4th of July.

Well- like every other time I've visited Chicago, I was reminded of the vibrant life that fills the city from the lakeshore to the districts within.  After four-and-a-half days of walking, eating, laughing, and exploring, I'm happy to share the 8 Do's and Don'ts I learned from this trip that will help you have the best possible Chicago weekend.

1) Do: Spend your money wisely.

Did you know that it only costs $8 to tour the main floor of the Shedd Aquarium? Couple that with a $3 student discount, and that means I only spent $5 for an hour of quality amazement (Shout out to the Shedd ticket-man who gave me the discount without my ID).

Basically, there's enough to do in the city during the day that you don't have to drop a ton of money in order to have a great time. One of my favorite things about Chicago is that it borders Lake Michigan, and along the lake there are a ton of parks. One go-to spot that you shouldn't miss - the Buckingham Fountain in Grant Park. Yes, it's as fancy and wonderful as it sounds.

2) Don't: Be afraid to splurge a little.

We save money for a reason - to later spend it. So since you kept your cash in your pocket during the day, there are plenty of good ways to spend it at night. If it's near the 4th of July (which has already passed, I know, but remember this next year!) I'd recommend taking a boat out to watch Navy Pier's firework show. That's what I did with the rest of the bachelorette crew, and we avoided the craziness of the 100,000 people that flocked to the pier this year.

Another personal favorite is seeing the Blue Man Group or going to one of the many musical productions that are put on in Chicago. Since it's such a large city, there's a show, event, concert, dance party, or you name it going on in Chicago that fits your taste. Don't be afraid to lay down the money for it; I 10/10 recommend splurging on an experience rather than on a dress you can buy in the Nordstrom next to your hotel.

3) Do: Embrace the local food.

...and that local food is pizza (fact: this is only according to me because of my latest trip). During my Chicago weekend, I ate pizza two nights in a row. For anyone that knows me, that's a big deal (wait one second for the why).

If you're in Chicago looking to grab some deep-dish, I'd recommend Lou Malnati's. According to a Chicago native, this is the best place for pizza in the city. I normally don't eat pizza because of a dairy allergy (there's the why!), but 1. the smell and 2. the unveiling of four of these beautiful, cheesy pizzas in the bachelorette suite made me throw any care out the window (shoutout to my Lactaid pills for constantly having my back. You're the real MVP).

4) Don't: Try to count the calories.

In one day in Chicago, I walked eight miles. That made me hungry, so I ate pizza for a second night in a row. That made me feel uncomfortable so I decided not to eat pizza again. With the number of good places to try in and around Chicago (Hub 51, Nookies, too, and Smoke Daddy BBQ to name a few), it's not worth beating yourself up over going in for the second slice. Enjoy the company and enjoy your food - just don't make yourself so sick you can't enjoy the next day.

5) Do: Step outside your comfort zone.

The next sentence is not going to be one that anyone who knows me well will expect. As part of the bachelorette weekend, I went to a beginner pole dance exercise class. Now, to be clear, I've done dance exercise classes while in college, but it was nothing that featured a pole  I was expected to literally spin around by my ankle. Safe to say, I was a full two steps outside of my comfort zone headed into the ordeal. But, I loved it. Seriously.

The bachelorette girls and I were cracking up at the fact we were all trying the best we could, and what a sight it was. After the class was over, some people at the bachelorette party actually called me graceful (!!!!!!) and the instructor told me I "got it".

The lesson? If you see an experience that looks fun (but is safe and doesn't make you compromise yourself!), go for it.

6) Don't: forget to enjoy your classics.

When I think of a weekend in Chicago, I picture walking over a bridge on the Chicago river and down along the Riverwalk with my parents. I do this nearly every trip, and this time was no different. It just feels good to do the things that are 'classics' to you.

If you've never been to Chicago before, create your own 'classic' that you can do in other cities. Maybe you'd like to get ice cream from a local spot in every big city you visit (what a cool tradition that would be!) or rent a bike and see how far you can explore in one day. Another one for me - getting to walk my boyfriend's family dog around a local park instantly made me feel connected to the city.

7) Do: Dress for the weather.

This is just a friendly suggestion. Pack for your Chicago weekend in layers. When we were out on the boat, I was glad that I ruined my cute little black dress with a warm sweater. Definitely check the weather forecast, and make sure you understand that while it can be hot in the day, the nights get a little chilly. A raincoat and comfortable walking shoes are also musts to toss into your suitcase.

8) Don't: Dress to impress anyone else.

Quick story: I was about to go out and explore and didn't know if the threads on my ripped shorts were too long. I was considering cutting them, so I asked my boyfriend's sister, Abbie, if I should. After assuring me they were okay, Abbie gave me some insightful advice. She said, "Everything's acceptable in Chicago."

When we left to go walk along the lake and downtown, I realized she was right. Maybe it's every big city, but during that walk I noticed that people of all styles of clothing and styles of life were confidently moving throughout the city. So dress for yourself, dress to feel good, and enjoy the Chicago weekend.


take-by-kate-logo.pngKate's take: even a place you've visited ten times before will still bring you new memories and adventures if you have the right mindset.


I've been to Chicago more than a few times in my life, and even though I prefer mountains to skyscrapers, I really appreciated the city's beauty and liveliness this past trip. Maybe I could do the big city life after all.

Enjoy your next adventure!

With love,


Published by Kate Workman