Chicago Trip Recap and Blog Updates

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Howdy all! As I shared a few weeks back, the family and I went on a short vacation last week to Chicago. We were gone for five days total and returned back this past Monday evening. The drive from Omaha is just shy of seven hours, so it’s not too bad though in our “comfy” Altima it felt a little longer than that at times. 🙂

I lived in Chicago for five years while growing up and most of my side of our family is originally from there so it feels like a second home to me. But, that said, it’s a great place to visit though don’t know that I’d necessarily want to live there. At any rate, we had a blast on our trip and are glad to be back home and back into the normal swing of things.

Few things in Chicago are cheap; heck, the amount we spent in parking and tolls alone made me want to scream. However, we had our hotel covered thanks to some Starwood Preferred Guest points so that cut down on the overall cost quite a bit.

We stayed at the Sheraton Suites in Elk Grove and really only slept there as we spent much of our time in downtown Chicago. The hotel also provided a nice breakfast so that helped us cut down costs quite a bit as we could snag some fruit and have that as a snack in the afternoon and only have to worry about buying dinner. That helped us stay within our travel budget, which is nice since our trip to San Diego to visit my in-laws this summer was a little over budget so it all balanced out in the end.

Chicago Highlights


If you’ve not been to Chicago, I highly recommend it. There’s a ton to do there, regardless of what you’re interests are. While it’s not cheap, per se, there are things you can do that can help cut costs quite a bit. They have a great public transportation system in the city and for a few dollars a day you can get to wherever you want. We chose against it this time with having the little ones with us, but it can definitely be done. The other thing to consider is to stay in the suburbs as opposed to downtown as that’ll cut your lodging costs in half.

We had four full days in the city and we spent two of them at The Shedd Aquarium, and The Field Museum. Neither are terribly cheap, which is sort of sad as you can go to many museums in New York or Washington for free or give a donation, but it is what it is. Despite the cost, I would highly recommend either if you happen to be in Chicago and are looking to kill a day.

The other two days we spent walking Michigan Avenue, visiting some old family haunts and seeing things like a few Frank Lloyd Wright homes. The picture below is actually of me in front of the John Hancock Building, which is one of the tallest buildings in the city and one that my grandfather helped construct back in the 60’s.


As you’ll see below, the other highlight of the trip was enjoying some Chicago style pizza. We actually ate at a different pizza place each night. I fully admit it doesn’t fit with our new healthy eating habitsbut I had busted my tail prior to the trip so I could enjoy it while there.


Now it’s back to the grindstone though. 🙂 Overall, it was a fun little trip though glad to be home.

Blog Updates


I love to travel, though with us being gone roughly five out of the past eight weeks it got a bit old. I think part of it was the traveling with kids factor, but the other part of it is not being around and not being able to work on things we want to be working on.

Thank you for your patience as I’ve not been around much the past few months and thanks to all the great contributions we’ve had from other bloggers in my absence. With that out of the way, I wanted to give some blogging updates on some things that have been happening and some upcoming things.

Hosting issues: Over the past few weeks the site has gone through some significant hosting and outage issues. The first of those was a botnet attack which took the site down for the better part of a day. The second was issues by my hosting company not being able to keep the site up. On a number of days this amounted to several hours at a time and just got to be a bit much, especially as readers were starting to reach out to me wondering why the site was down. In light of that, I’ve moved our sites to a new hosting company which should hopefully rectify the issue altogether. I apologize if you were not able to get on the site as a result. As an aside, if you’re a blogger, I highly recommend my good friend Grayson as he was a lifesaver. If you’re looking for someone to help with the technical side of running a blog he can be a huge help.

New series: I’ve hinted about it previously, but I’m going to be starting a new series starting in the new year. It’ll be running every Friday and will be posts on simple life hacks that can help you save money and live a little more frugally. I plan on covering a wide range of topics, but if you have something you’d like to see in the series let me know in the comments section and I’ll get it added. I talk a good bit about different ways to make extra money over at Sprout Wealth but think it’s the combination of earning extra money and living frugally that you can really start to see some significant headway on growing your wealth.

New Blog Coaching Service: I’ve also decided to begin offering blog coaching services for new bloggers or for those who have been blogging for awhile and are now looking to take their blog to the next level. I’ll share what I’ve learned about earning income from my blog, including affiliate marketing strategies. through building Frugal Rules as well as my other sites.

My first course: Finally, I’ve shared this with a few of you, but I’m actually in the process of developing my first course on Frugal Rules. I’m a bit hesitant to share it yet, but I figure if I make it public then I have greater accountability. 😉 Anyway, I’m still working on the details of what’ll be offered in it, what/if I’ll charge for it, etc. It feels a bit overwhelming at the moment, but is something I’ve been wanting to do for some time now and after going to FinCon last month I’m feeling motivated to get started.

I think that’s it, thankfully. 🙂


What’s new going on in your world? How much is too much traveling in your opinion? Where is your favorite city to go visit if given the option?



Photo courtesy of: ©

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I'm the founder of Frugal Rules, a Dad, husband and veteran of the financial services industry. I'm passionate about helping people learn from my mistakes so that they can enjoy the freedom that comes from living frugally. I'm also a freelance writer, and regularly contribute to GoBankingRates, Investopedia, Lending Tree and more.


  • Nice trip, man. Did your kid enjoy Chicago? Are there many family-friendly activities aside from the one you mentioned?

  • Greg lived in Chicago when we started dating- love that place! Glad you had a good time.

  • Perfect timing- I’m going to Chicago next month on tour! I’ll have to check out Michigan ave (if it’s not too freezing)

  • Kim says:

    I interviewed at the optometry school in Chicago but ended up choosing Memphis instead. It’s probably a good thing because I would have probably frozen in the winter! My favorite city to visit is San Diego. I think I could travel lots more if it didn’t mean extra work when you get home. That’s maybe the worst part of taking a trip in my opinion.

  • LOVE Chicago!! When I was a young gal, my peeps and I went to Chicago every summer, just for fun. I’d love for us to bring the kids there some time. Super cool about your grandpa and the John Hancock building!! Great about all of the changes with the blog too, John. I think you’ll be awesome as a blogging coach!

  • I LOVE Chicago!! I always tell people it reminds me of NYC (my first fave city) with a beach next to it. It is really pricey, though, like most major cities so I don’t visit it as often as I would like. And I am with you on hiring Grayson, he totally saved my butt last week on a blog site issue. I can’t wait for all of your fun/new changes for Frugal Rules. I agree, attending FinCon was incredibly inspiring and motivating for me as well.

    • John Schmoll says:

      Ha ha, that is a good comparison. I wish it wasn’t so expensive there, but it is what it is. Thanks, I’m looking forward to it myself…aside from the work that is. 😉

  • Glad you enjoyed your stay, you were literally down the road (Arlington Heights Road that is) from us. We are about 8 or so miles north of where you stayed.

    Chicago is a great tourist town and you are right things are not cheap in many cases. On future trips you might consider the Museum of Science and Industry, Navy Pier, and the Art Institute. Millenium Park is also nice if the weather permits.

    • John Schmoll says:

      Wow, I didn’t realize we were that close to you Roger. If we didn’t have the kids with us we could’ve met up.

      Yep, I’ve been to all of those places a number of times. We almost decided on Science & Industry, but the kids voted for the Field Museum instead. I’d love to go for a few weeks and take them to a number of places, but that would get quite costly as you well know. 🙂

  • I enjoy traveling as well but it is always nice to just come home. Sounds like you have some big plans in the upcoming months too…looking forward to seeing the new series and hearing about the course!

    I also can attest to how awesome Grayson is. He has helped me out of a jamb numerous times.

    • John Schmoll says:

      Yea, I’ve been putting them off for some time and just need to get off my butt about it.

      Grayson has been a huge help to me as well. Probably more often than I’d care to admit. 😉

  • Michelle says:

    Wow definitely sounds like you have a lot going on! We have been traveling a lot, and I pretty much recently had to beg Wes for a traveling break. I love being at home, and I’m a big homebody so it makes sense. I think it drives Wes crazy though! 🙂

  • I LOVE Chicago and have made several mini trips there in my lifetime. The museums are my absolute favorite! Looking forward to hearing about some of your upcoming projects!

  • Liz says:

    I agree with you, Chicago is an expensive city to live in. It is not one one specific expense but all the little things that add up. That said, we enjoy going to Chicago, hanging out in our old neighborhood or eating at our favorite restaurants. Our favorite deep dish pizza places are “Pizzanos” and “Uno’s”.

  • Glad you guys had fun. I’d definitely like to go travel again…haven’t really gone anywhere no that we have a little one. But that shouldn’t be an excuse since many still do travel…it’s just a little more hassle. Pretty cool that you’re working on some new projects. I probably could use some blog coaching, but it won’t be worth it until I take blogging more seriously.

  • Kassandra says:

    Grayson saved my site from the WordPress white screen of death a few weeks ago. I also highly recommend him. Sounds like you have a lot of good stuff coming up John! Great move on becoming a blog coach 🙂

  • Gretchen says:

    One of my non-negotiable when traveling is free internet and breakfast at hotels. Luckily, I work for Hilton, so I can stay at Hampton Inn that offers both for $29 a night. Even if it were more, though, I would still need that breakfast and internet. That chicago pizza looks delicious!

  • My wife and I have been considering/planning a trip to Chicago for quite some time now. With her working full-time and being in school, though, we are limited on when we can go. It’s about 7 hours for us, too, so perhaps we’ll make it work sometime next year.

    Sorry to hear about your hosting issues. It’s the little things like that that make running a blog a headache.

    • John Schmoll says:

      I’d definitely recommend it, especially when you have the time.

      Yes, it definitely was a headache…especially when I have no clue what I’m doing with regards to the technical aspect.

  • Sarah says:

    Your trip to Chicago sounds awesome!! I have always wanted to go there! Great idea on a weekly post – I’m looking forward to reading what you have to say!

  • Grayson Bell says:

    Thanks for the shout out sir! Glad I was able to help you with the transition. I know how much a pain in the butt that was.

    I knew about some of these features, but the others took me by surprise. Nice work!

  • Sounds like a great trip, John. I’ve been Chicago to work, which doesn’t give me much of a chance to really explore a city. The girls have never there but I think they would really enjoy it. We’d have to wait until summer though … we’re too wimpy to enjoy it during the winter. We go skiing a couples times every winter and that’s enough cold and snow for us! 🙂 Sorry to hear about your hosting problems. That’s always a pain to deal with. Looks like you have some exciting things on the horizon and I can’t wait to hear more about it!

  • We love our Starwood hotel points too! It’s such a great rewards system. I lived in southern Illinois growing up and we’d go to Chicago periodically, which was a lovely treat. It’s a fun city!

    I’m looking forward to your new Friday series–sounds great!

  • I was only in Chicago once on business for a brief time (conference) in my 20’s and I remember being bummed that I had thought ahead to get tickets for Oprah, not realizing that it probably would have been impossible. Mind you she was a lot younger then so you never know.

  • I don’t know if the words “too much travel” is in my repertoire…. Though I wouldn’t mind trying to find that limit 🙂 For me I’ve spent a lot of my last vacations in Southeast Asia, once you’re there it’s pretty cheap and nice. Though I liked Cuba a lot too, it really felt like I was transported back a handful of decades.

    • John Schmoll says:

      Ha ha, I wouldn’t trying to either. But, with having our business plus adding the kids into the mix it makes it a bit nutty.

      I’d love to go to Cuba – they just need to lift the crazy ban or find another way to get there. 🙂

  • Jason B says:

    There is no such thing as too much traveling. Chicago is one of my favorite cities to visit. I love the atmosphere of the. Did you guys get to eat at Giordano’s Pizza. It is my favorite deep dish pizza spot. My favorite city to visit is Miami Beach.

  • Susan says:

    John, is your course going to be a book or an online real-time webinar or a recorded offering or given live at conferences? Can’t wait to learn more!

    • John Schmoll says:

      Great question Susan. It’ll either likely be some sort of webinar version or recorded offering. I have an ebook that I’m about ready to launch and I’ll be using that as the jumping off point for the course.

  • Nicola says:

    Chicago is definitely on our list of places to visit one day – it sounds like you had a good time! And, looking forward to see what happens next – I might interested in the blogging course depending on the cost… 🙂

    • John Schmoll says:

      I highly recommend it, there’s plenty to do there. The course isn’t actually going to be on blogging, it’s going to be money related. That’s separate from the blog coaching I’m offering now. 🙂

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