Disclosure. I was given a review copy. As always, the opinions expressed are those of my own. The post may have affiliate links.

If you haven’t noticed, I can’t get enough of bucket lists. So when I heard about this new book, 100 Things to Do in Chicago Before you Die by Chicago local Molly Page, I couldn’t wait to get my hands on it.  Besides being a fun and easy read, I now have more ideas to add to my never-ending bucket list!

So read on and find out what I thought about the book, then learn more about the author Molly Page in the interview below.


If you are a fan of buckets lists and have a sweet spot for Chicago, then this book’s for you. It’s a book that both tourists and locals can appreciate. Sure it includes the iconic greats like the Sears Center…er Willis Tower, but Molly also includes things I’ve never heard of like a Secret Agent Supply Store or the Magic Parlour. I consider myself pretty well-versed with the city of Chicago,and it looks like I could only check off 27 things. What? Only 27! Well, it looks like I have a lot of catching up to do!

100 Things to Do in Chicago Before You Die - Bridge

Photo by Becca Waterloo


  • Easy to read. Organized into sections for easy reading: Food & Drink, Music and Entertainment, Sports and Recreation, Culture and History, Shopping and Fashion. Plus, she even includes Activities by Season.
  • Small and compact. If we wanted to bring it along on our Chicago adventures, I could easily pop it in my purse and reference it when needed.
  • Itineraries for anybody. For anyone that wants a little guidance, the suggested itineraries sound like fun. How about Ferris Bueller’s Day Off or even a Family Field Trip?
  • A historic touch. Since the author Molly used to be a tour guide, she infuses a bit of her historic knowledge in each item.
  • Fun! As I was reading the book, it seemed as if Molly and I were chatting over coffee. She injects her fun personality into each listing.
  • Quick tips. As I was skimming through the books, I was immediately drawn to the Tips

We Wish:

  • The pictures were in color! What can I say? I love my colored photos.
  • There were more tips.Bottom Line:

I’ll definitely be keeping this in my travel collection. I think I’ll be getting to know Chicago better and I do see a challenge coming up soon! If you want to get in on the action, post your photos and tag them #ChiToDo. Who’s with me?

Get to know the author: Molly Page

Q: Tell us a little bit about yourself. Your background and why you decided to write a book.

MOLLY: I​’m not a Chicagoan by birth; I’m a Chicagoan by choice and from day one this city has felt like home. ​Chicago’s history, culture​,​ and world-class architecture ​​quickly won my heart​.​

N​ot long after moving to Chicago I became a docent at the Chicago Architecture Foundation (CAF). My involvement there gives me plenty of opportunities to learn about the city and serve as a host to all the people who visit Chicago throughout the year.

Reedy Press, the book’s publisher, started the “​100 Things” series several years ago and it’s grown quickly. When they asked if I’d be interested in doing a Chicago edition I couldn’t say yes quickly enough. As a freelance writer, it isn’t every day that a publisher approaches you and offers you a book deal. It’s not an exaggeration to say that that was one of my favorite emails that I’ve ever received.

Q: How long did it take you to research items for the book?

​MOLLY: Truth be told, I’ve been researching this book from the day I moved to Chicago. The actual process of writing the book went pretty​ quickly, though. From the first day I spoke with folks at the publisher to the day it appeared on shelves was almost a year to the day!

​I was able to move through the process as quickly as I did because of the help and input I got from several friends. I had a handful of Chicagoans – some lifelong residents, others who are transplants like me, some folks who work in the travel and tourism industry, and others who like to explore – review the list of “things” before I started writing to make sure it was solid. Putting the list together was no easy task. Narrowing the list to only 100 things was tough.

​Once I’d settled on a list I was happy with, the research portion was time-consuming but awfully fun. I guess it’s fair to say that I was the first person to cross all 100 things off the Chicago bucket list!

Q: What was your favorite thing you discovered about Chicago? Okay, maybe top 2?

​MOLLY: [Thanks for giving me two.]
First, what I was most happy to discover is that Chicago, no matter how well you think you know it, will always surprise you! There are so many hidden gems around this city that a list of 100 barely scratches the surface. That being said, I’m pretty pleased with the list I’ve compiled. Of course, the things you’d expect (Cloud Gate, Deep Dish Pizza, an architecture tour) are on the list, but it was my goal to include things that would surprise even lifelong Chicagoans. The best compliment a reader can give me is to tell me they learned something new.

​The other thing I’ve loved discovering is that Chicagoans love this city. As I’ve been promoting the book that has been so clear. They love to talk about it. They love to learn about it. They love to celebrate it. It’s been fun meeting people, hearing about all the local gems they think should have made the list, and comparing stories about the city. It’s a treat to live in a place that despite its flaws is still beloved by its residents. I think that civic pride is one of the reasons visitors end up loving the city too – it’s a buzz that’s contagious.

Nitty Gritty:

100 Things to Do in Chicago Before You Die
Reedy Press
160 pages
Order it on Amazon: