chicago trip

Snowy Chicago Trip

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A couple months ago my cousin, Maddie, texted me and asked if I wanted to go on a surprise trip with her in March. Yes, please! The trip ended up being a trip to Chicago and it was so much fun! Maddie was just the sweetest and planned this whole trip and found so many great things to do!


chicago trip
She had a pillow and magazines all ready for me!

chicago trip

This trip was a couple of weeks ago and we went to Chicago on a Tuesday. We did your typical road trip things and jammed out to music and gabbed the whole way. As we got closer to Chicago it started to hardcore snow and Maddie did a great job driving through it all.

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It was still snowing after we checked into our hotel, but we decided not to let it get us down and we walked around Magnificent Mile anyways! It was cooollldddd, yes, but the sun came out soon after and that made us happy!

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Maddie surprised me with tickets to an Arianna Grande concert for that night! I was excited because I’ve never been to a real concert before, let alone someone that was super famous. It was fun to watch everyone freak out about her and to see the cool stage theatrics and costume changes. They definitely plan to entertain you and that part is fun.

However, Maddie and I were so tired because even though the concert starts at 7 pm, Arianna didn’t even come on till 9 pm and by 10-10:30 pm we were losing steam. I’m glad someone else likes to go to bed early like me haha!

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After finally grabbing a cab back to our hotel, we warmed up and quickly fell asleep.


The first activity on the day was breakfast and I took Maddie to one of my favorite cafes. Maddie and I have very similar tastes and we’re very obsessed with French things. I first found this French-inspired cafe when I went to Chicago for my birthday 2 years ago and she loved it just as much as I did! Even though it’s a bit pricey for what you get (in my opinion), it has really good breakfast food and drinks and a nice atmosphere.

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On the itinerary that day she had us exploring different thrift stores. I was on the hunt for a used Chanel handbag under $200. If you know anything about Chanel bags you know I was setting myself up for failure and needless to say, I did not find one haha. Maddie got some great finds though!

We went to a Luxury Garage Sale and though nothing was garage sale price, I got to look at and touch designer clothes that were thousands of dollars. For a fashion blogger, this was really fun! For a fashion blogger that is more about a budget and maximizing your wardrobe, this made me feel quickly out of place 😉 We didn’t stay long.

Shopping took up most of the day and after warming up at the hotel we were planning our night. We thought it would be fun to go to a karaoke or jazz bar. There weren’t many that allowed people under 21 (Maddie’s 21st is in April), but we found one online and it had great reviews so we decided to check it out. Our cab took us to a karaoke place that was right outside of Chinatown. When we went inside it was completely empty. Just us and the workers.

chicago trip
it’s poppin

We look at each other and decide to at least sit down and get an appetizer since we just got there. The guy handed us a menu, but then said we couldn’t order anything. We asked about the karaoke and he said there wasn’t any karaoke. Ugh. Well, we decided to cut our losses and walk to Chinatown.

It was a cold, long walk (especially in heels for me), but we made it to an open restaurant in Chinatown and it was actually really nice! I had super yummy egg drop soup and we warmed up with tea. The ambiance was really cool and it ended up being a good night after all.


For breakfast, we just decided to walk and go to the first breakfast place we saw. We grabbed coffee drinks and cream cheese danishes at what we figured out was a college breakfast place haha. The girl even gave us a discount because she thought we were college students. We said we were just not in Illinois 😉

chicago trip

You would think by now I would know better about packing for cities. Just like my snowy trip to New York where I ended up buying boots, I had to buy something to block me from the cold since we did a lot more walking this day.

I couldn’t find anything warm I wanted to buy in my style (I know, beggars can’t be choosers) and there was just a tiny section of winter gear. I bought a fashion baseball cap as my warmth haha. I can just see my husband rolling his eyes. But it stayed on my head and helped a bit. Thankfully Maddie found a scarf and gloves and we ended being a little warmer!

Next, we went to the Chicago Multicultural Center and man oh man is that place beautiful! I’m a sucker for marble and beautiful architecture and this place was a photographer’s dream! We also went on the same day when they had flamenco dancers for a school presentation and we enjoyed that immensely. They are incredibly talented and enjoyable to watch and I even learned more about the culture and history of some dances.

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Our strategy for food is to keep walking and hopefully come across something good. It’s worked thus far! For lunch, we found this really good, but really cheap barbecue place. I got ribs and yum yum!

It was time to start the trek back to Iowa and sadly the trip had to come to an end. It was so much fun and I love having trips to look forward to. I would travel a lot with my cousin and her family as a kid and now it just gets even better because we’re older and can do a lot more things and go more places!

We went to Paris together with my sister, Chicago a couple of times, and we’re already planning our next trip hopefully in July! We’re thinking someplace warm this time 😉

chicago trip


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.