by Hope
We are having a great time in Chicago with Gymnast. Once we landed Saturday morning, History Buff, Princess and I rode the train into the city and then walked to our hotel.
Gymnast’ dad met us (Princess, History Buff and I) with him at the hotel when we arrived Saturday morning. We had lunch together (their dad even paid for all of us – whoa!) and then he drove us minus History Buff down to see his mom. The little kid’s hadn’t seen their paternal grandparents in years.
Then he dropped us at the hotel and headed up. They live about an hour outside the city. And I was all set to enjoy 3 glorious days with 3 of my 4 kids in one of my favorite cities in the world.
As I mentioned when I planned the trip, the airfare and hotel were covered, so I just had to plan financially for food and entertainment. We didn’t spend ANY of our grocery budget for February so technically I have that $400. And I have been hoarding gift cards and extra income.
So I have splurged a little bit…
- I gave each of the kids $30 for spending money. This will allow them to have a little splurge themselves without asking me. (And yes, I gave the same amount to History Buff.) – total $90
- I bought the cheap seats to a Broadway show for the littles and I (History Buff was not interested in a musical) – total $102
- A client gifted me 4 tickets to an Improv show at Second City. (She used to work there.) – total FREE
- I made reservations at Texas de Brazil for our last night together – total $150ish? BUT Sea Cadet gifted me about 1/2 of that in gift cards he had left over from taking his girlfriend here. (He bought a gift card at Christmas time and then they gave him a $25 bonus card. So he gave me the money they had left over + the bonus card.)
Our breakfasts are free. We have snacks we brought from home. And we are eating one other meal a day…
Saturday night, we ate at Panera. So it’s not free but we are sticking to the cheaper side of things. (We had hot dogs for our first meal here.)
Yesterday we spent the day wondering around Navy Pier and the Magnificent Mile before heading to the the comedy show.
It has truly been one of the best trips I have had in a long time. AND I am squeezing in a few hours of work every day here and there.

Hope is a resourceful and solutions-driven business manager who has spent nearly two decades helping clients streamline their operations and grow their businesses through project management, digital marketing, and tech expertise. Recently transitioning from her role as a single mom of five foster/adoptive children to an empty nester, Hope is navigating the emotional and practical challenges of redefining her life while maintaining her determination to regain financial control and eliminate debt.
Living in a cozy small town in northeast Georgia with her three dogs, Hope cherishes the serenity of the mountains over the bustle of the beach. Though her kids are now finding their footing in the world—pursuing education, careers, and independence—she remains deeply committed to supporting them in this next chapter, even as she faces the bittersweet tug of letting go.
Since joining the Blogging Away Debt community in 2015, Hope has candidly shared her journey of financial ups and downs. Now, with a renewed focus and a clear path ahead, she’s ready to tackle her finances with the same passion and perseverance that she’s brought to her life and career. Through her writing, she continues to inspire others to confront their own financial challenges and strive for a brighter future.
I mean, done is done, but I’m not sure why you are splurging, here. I know it is relatively low cost, but I wish you would save these splurges for a reward for achieving something relating to your debt reduction. I don’t think you have to live like a monk, but you bleed lots of little bits of money that, IMO, could be better used on your now years long, and still meandering debt journey
She mentioned she wants them to do another big family trip when Princess or Gymnast wrap high school. I hope this shows her she can get a great trip on a smaller budget! Hope isn’t perfect but she deserves a break now and then even with her mistakes.
Another big trip is exactly the reason she shouldn’t be splurging one this one. And I’d hardly call $10,000, the number she mentioned for the next big trip, a smaller budget.
This is the problem: “We didn’t spend any of our grocery $ for February so I have an extra $400.” This is how a poor person thinks. A sensible person would say “wow, unexpected windfall” and throw that either towards an emergency fund (which she is sorely lacking) or the debt. And it’s not as though $30 for each kid is a grand amount of money – but plenty of people with a lot more money than she has travel places and don’t buy any souvenirs at all. Why can’t the memory be the souvenir?
It was a choice to not spend our grocery budget so I had that “eating out” money for this trip. This prevents me from dipping into other money and is always good to eat through the stuff that just sits for sit long in our freezer/pantry.
Aw, I am glad y’all are having fun. I am over 30, and my mom still gives me what she calls ice cream money – for trips! (last time she gave my sister, me, and my two nieces $40 haha) And how wonderful that Sea Cadet gave you those gift cards.
@Kim I would think this would be the exact sort of splurge to save up for. Hope only gets to see her son in Chicago a few times a year.
She saw him 6 weeks ago at Christmas. And did she save for it? What was her actual budget?
I love Chicago too!! Have fun and enjoy and don’t sweat the splurge! You work and save really hard plus your kids are growing up and out of the house – you won’t regret this trip!