Planning a Trip to Chicago

Planning a Trip to Chicago

Warning: I may be posting (too many) Instagram pictures from the Windy City soon.

Recently, I got a mini-trip to Chicago all planned and booked! I’m looking forward to taking a few days off and exploring. I’ve been to Chicago many times before, but it has been a while since I’ve actually been downtown.

I’m planning on enjoying some of the classic tourist spots, like Shedd Aquarium and Navy Pier. Also, you can’t forget Millennium Park and the world’s largest Starbucks. Of course, I’m looking forward to some iconic Chicago deep-dish pizza too. If you have any recommendations, let me know!

I’m planning on exploring some new-to-me areas of Chicago as well. For example, my stay is booked at the Moxy downtown. I was sold as soon as I saw that the hotel had a taco bar in the lobby. I was even more excited when I saw some of the spots to check out around the Moxy. For example, there’s a radio-themed bar/restaurant just a couple of blocks down. Understandably, this may just be cool to me since I work in the industry. But, if the food/drinks are good, I’m sure I can convince my travel partner that it’s a good place to be.

Once I’m back from the trip, I plan on recapping it on the blog like I did with my Nashville getaway! Then, I can share some of my thoughts and recommendations for what to do in Chicago.

In the meantime, I do have a few tips for you if you’re planning a trip to Chicago:

Purchase your parking ahead of time. If you’re driving to your destination, plan where you are parking! Also, beware that not all hotels have parking. For my stay, I pre-paid a 3-day parking pass at a nearby ramp.

Purchase your passes ahead of time. This will also save you a headache and some money. If there is something that you want to see or do, don’t wait until the last minute to buy tickets. Often, tourist stops have higher prices at the door than online.

Stay loyal to a hotel chain. Many hotel chains or groups have loyalty programs that are free to join. I’m part of Marriott‘s rewards program, so I typically try to book with Marriott. Then, I get better rates and can rack up points!

Download OpenTable. A lot of restaurants use OpenTable to manage reservations. With the app, you can easily make dinner plans on the go and avoid waiting for a table.

Make a list of what you want to do. Prioritize the items that you 100% want to experience, and keep some bonus items in your back pocket. This ensures that you will get the most out of your trip!

Have fun! I know this is an obvious point, but it’s the most important. Sometimes staring at a computer screen and booking hotels isn’t the most exciting process, but it’s part of the bigger picture: your vacation! Enjoy the process of customizing your trip and curating an experience for yourself.

Have you ever explored Chicago? What are some of your recommendations? I would love to hear your thoughts in the comments or on Instagram. Let’s chat!

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