Last-Minute Trip to Chicago: Share Your Best Insider Tips

When your daily routine starts to feel monotonous, mix it up and plan a quick getaway. That's what I did when I booked a last-minute trip to Chicago.

For me, I’ve always been a planner. I love details. I love research. I love fitting the pieces together to form a plan or find the best deal. I love to find solutions and planning a trip always presents some of my favorite questions to answer. Destination, transportation, accommodation, what to see, all important questions that must be answered for a successful trip.

But, wait, what if you throw out the playbook and all the planning and just go?

Embrace your spontaneous side and visit that destination you’ve had your eye on. Well, that’s exactly what I’m doing. I decided on a whim to book a flight to Chicago for a quick weekend getaway in less than two weeks. So I’m not completely throwing out the playbook, but having less than two weeks before jetting off on a weekend adventure is certainly not my norm (like I said, I’m a planner). I think everyone needs a little spontaneity in their life, it keeps you on your toes and stops you from getting too comfortable with a daily routine.

When your daily routine starts to feel monotonous, mix it up and plan a quick getaway. That's what I did when I booked a last-minute trip to Chicago.

I’ve really been pushing myself to make travel a bigger part of my life, as if that wasn’t already evident by my pledging to take on the take 12 trips travel challenge this year. Not only has putting travel at the forefront of my priorities helped me discover new cities and cherish new memories, but it also pushed me outside of my comfort zone. I think that’s probably what enticed me to hit the “purchase” button and turn a crazy idea into a last-minute trip to Chicago.

Having lived in the Midwest my whole life, I think it’s a little crazy that I’ve never made it to Chicago. Chicago is one of the most visited cities in the Midwest and I was determined to make this year the year I finally check it off my bucket list. Keeping on track with the take 12 trips challenge, I knew I needed to explore somewhere new in April and since I’m slightly obsessed with all things travel I’m always keeping an eye on flight deals. Lucky for me, flights from Kansas City to Chicago were pretty cheap in a couple weeks and that was all the convincing I needed.

When your daily routine starts to feel monotonous, mix it up and plan a quick getaway. That's what I did when I booked a last-minute trip to Chicago.

While this is going to be a super quick two-day getaway to the Windy City, I’m determined to make the most of it. I don’t know very much about Chicago; I know there’s a big bean sculpture and it’s windy, but that’s about it. When I’m visiting a new city, I always try to get off the beaten path so I can really discover what a city is like away from the tourist spots. To do that, I’ll need your help.

Share with me your best Chicago travel tips and favorite local spots to visit. What are some places I can’t miss on my last-minute trip to Chicago? Leave a comment below and help make my first trip to the Windy City a memorable one 🙂