how to make the most out of a short trip + chicago recap

Chicago has been on my travel bucket list for quite a while. Not only have I heard it’s a beautiful city filled with lots of fun things to do, but my grandfather grew up there! Lucky for me, a few BMA friends and I decided to attend a marketing conference held in downtown Chicago earlier this month – we were only there for a few days, so I had to make the most out of a short trip.

how to make the most out of a short trip

From first hand experience, I can confirm that Chicago is indeed a BEAUTIFUL city filled with LOTS of fun things to do! While I was in the conference for the majority of my trip, I did my best to make the most of my time there.

don’t sleep in

This might sound silly, but when you’re taking a short trip somewhere, don’t sleep in! You’re not there to see the inside of your hotel room – you’re there to explore, see new things, and experience the city!

One of the best decisions I made while in Chicago was waking up for an early morning run! It allowed me to see parts of Chicago I wouldn’t have seen otherwise. We ran through downtown and around the lake. I hadn’t realized how close the lake is to downtown! It was a beautiful morning and I loved having the opportunity to go a little out of my comfort zone (…I’m not usually a fan of group runs!).

try new restaurants

We all have to eat, right!? 🙂

While trying to make the most out of a short trip, be picky with your food choices! Don’t settle for a chain restaurant – get out there and try something unique to the city you’re in! As most of you know, I am a HUGE fan of eating. With this being said, food is one of my favorite ways to experience a new place.

prioritize tourist stops

When you’re short on time, it’s not realistic to see everything. Prioritize the touristy things on your list. I always think of experiences that are unique to wherever I am. For example, in Chicago, I knew I wanted to see The Bean and the skydeck at Willis Tower. Since I had already been on the morning run and saw the lake, I was okay with skipping out on that during our tourist stops.


I can’t WAIT to go back to Chicago for a longer trip with Oakley. Until then, I truly feel like I got to experience the city during my short time there.

What tips do you have on making the most out of a short trip?

Lots of love – ked

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4 thoughts to “how to make the most out of a short trip + chicago recap”

    1. Courtney – LA!! How fun!!!!! Looking forward to hearing about your trip!

  1. Glad to hear you had a good time! I managed to cram most of that in the 9 hours I had in the city! I definitely agree with staying away from chain restaurants unless it a chain local to that area. A great app to find local restaurants is myfab5. I would also suggest taking a little time each night to plan out your next day. It’ll help you be more productive with the limited time you have. I also suggest leaving a little margin so that you can have time to enjoy the little things you may stumble upon. I would have run while there but it was about 20 degrees and snowing.

    1. Greg – I’ll definitely have to look at myfab5! Thanks for sharing!! And I agree with you – there’s no way I would have run in that kind of weather!!

      Ps – I hope your pup is doing well 🙂

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