Chicago is a great place to live. It’s so great, that old friends from across the country are always coming to visit.

The Windy City is a day’s drive or a reasonably-priced flight away for most of my friends. Next to Facebook, living in such a hub is a great way to stay in touch.

But Chicago’s popularity and awesomeness can be a burden for the hostess that doesn’t live in Gold Coast.

Lots of visitors wanting to share your city means lots of people want to hit up all that Chicago has to offer: Museums, food, theater, shopping, food, baseball games, music. Did I mention the food?

So when perhaps my oldest girlfriend – a classmate from kindergarten! – showed up for her first real visit to the city I was, I have to admit, a little relieved when she said she just wanted to hang out like anybody else who lives here.

On a sunny fall Sunday, the choice of how to spend the day was clear. I grabbed my whiffle ball bat, and we headed for Lincoln Park.

A warm day, we took our time walking down there, and my friend got to see the city from plenty of angles. We passed the local pubs, full of regulars arguing football, and crossed a bridge that looked across to the skyscrapers downtown.

We took a detour through the ultimate freebie: The Lincoln Park Zoo. Free every day of the year, we passed on the overpriced popcorn, but took in every slot in the big cat house. We watched the one-armed gibbon enjoy his monkey chow, but saved our spending splurge for later.

We went through the zoo, past the flamingos and into the park. We met up with some friends from the neighborhood and had a full whiffle ball game going for the afternoon.

After a few hours of playing and lounging in the park, we walked back for a nap. Deep dish pizza from the local joint goes a long way, so we had the leftovers for dinner as we made plans for that evening.

It can be hard to have a big night out in a big city when you’re living on small cash. But we were in luck. An off night promotion at Kingston Mines, a famous blues club in our neighborhood, and some not-too-old student IDs meant we could get in for $5.

Every night, Kingston Mines features blues and soul music on two stages. The stages play back to back to back until the early hours of the morning, so you don’t have to stop dancing. The cheap cover meant I had budget space left for exactly two drinks.

Two stages, two drinks, two friends. Who says three is the magic number? Lots of dancing and laughter later, we split a cab back to my place.

Monkeys, dancing, cold pizza, whiffle ball. I’ve given lots of unofficial tours of the city, but this might be my favorite.

Total charges for the day: $15.25.

We’re kicking off a new blog series here at the Debtress called “The Best Frugal Day Ever.” The goal is to share and show how you can have without spending loads of cash.

Anyone can live it up when you’re spending money like Trump, but it takes a special kind of person to live large while spending meagerly.

We’ll put up our inaugural post soon, but I wanted to give you a rundown first because I’m hoping some of you will put in your two cents and participate.

The Best Frugal Day Ever isn’t really a Blog Carnival, but it will be a series of post by myself and many of you out there that highlighting the best day you ever had while spending little cash.

For example, this post is called the Best $1.15 Day Ever because I’m excited to get this series started, it’s almost Friday and I’m eating chocolate chip cookies I baked from some pre-made dough that was on sale for $1.15.

That’s a pretty good day, right? But I think we can top it. To contribute, email your best day ever to thedebtress@totalattorneys.com and I’ll post it here on my blog. Or, tell me about your day on your blog and send me a link.

Here are the criteria:

• Your day must be really, really awesome.
• Outline your frugal expenditures, and put the title in the post. Tell us how you scrimped and saved your way to fun.
• There is no limit on how much you can spend or how much fun you can have. Hey, if you get the whole family into a water park for $30, that’s a good deal!

There’s no deadline for submissions. We’ll keep this going as long as we keep getting good stories.

In my magical fairyland of adventure, there is a pill you can take that will transfer unwanted body girth to your wallet or purse – just swallow the dose and voila! You look like Christie Brinkley and no Mercedes is good enough for your garage.

But hallucinations aside, there are some ways that debt management and health management (I don’t like the term weight loss) are linked.

Good Advice for All Goals

Turns out, the age-old advice you’ve heard spouted from magazines and the health segments on news shows could just as well be about eliminating debt. Watch this:

• Focus on permanent changes. Crash diets don’t work, and neither do crash savings plans. Sure, you can stop buying toilet paper, but only for so long. So rather than trying to find quick fixes, focus on long-term goals (e.g. buying store brands at the grocery store).
• Take it slowly. Significant, lasting change doesn’t happen overnight (unless you live the aforementioned fairy land). Don’t expect it to. Take time to assess your debt (or health), then make the necessary changes over time (e.g. save small amounts of money rather than buying lottery tickets).
• Retrain your gimme gene. Learn to resist the urge to buy extra stuff. When you’re at the checkout counter, the merchandise looks tempting because it’s designed to. If you must, shop with a buddy who you can count on to ask if you really need something.
• Tell some people. Okay, I know debt can be embarrassing. But telling a few close friends that you’re trying to improve your finances can be inspiring – your motivation to maintain becomes a (more immediate) matter of saving face as well as a (vaguer) matter of saving your finances.
• Reward yourself. As with building health, your finance rewards shouldn’t be splurges that cancel your progress. But remember to celebrate the small steps along the road to progress with little treats.

Other Money-Health Links

And here are some steps you can take today to whittle your waist and fatten your savings account:

• Walk more. Drive less. Easy.
• Eat at home. Restaurant portions are big and expensive.
• Quit the gym. Do you ever even go? Besides, now that you’re walking all the time, who needs it?
• Buy whole foods. Pre-cut veggies and fruits may look yummy, but they’re much more expensive than the real thing. You’ll get more good food for your dollars.
• Turn down the heat. Dance for a while to warm up. Think you’ll look silly? I just confessed to believing in fairies!

Remember: Debt management is not easy, but it is doable if you’re committed, determined and willing to make some sacrifices!

Budgeting can be tough at the best of times, and during the holidays I often feel like I’m in some sort of financial obstacle course—every time I turn a corner, there’s another (usually pretty good) reason to drop some cash.

So, to help us all, I’ve compiled some successful techniques I’ve seen for maintaining the holiday spirit and your bank account.

Choosing Names

If you get together with a lot of family members for holidays, finding the time and money to get gifts for everyone can be a major source of stress – and, ultimately, unwanted “stuff” for everyone. Consider one of these options:

• Draw names “Secret Santa” style: Have every family member pick one person to give to. You can even set a price limit. That way, individual gifts are more meaningful.
• Make it a game: Have every family member bring a gift of a set price limit. Then draw numbers and let each number picked a wrapped present. Encourage exchanges or make up your own rules. That way, you’re focusing on the family interactions rather than the things.

Group Gifts & Donations

If your family or group of friends has a charity or cause that’s close to your hearts (e.g. the research organization for a particular disease or a child’s school), consider donating money as a group.

Like everyone else, charities are hurting this year, and if you’ve considered cutting back on your usual donations, you’re not alone. But if you can get a group together to give to a good cause, you’ll have a sense of satisfaction (and no new junk to lug home).

Experience Gifts

If you’d like to do something special for your loved ones but can’t think of any stuff they’d like, consider offering them a chance to have rewarding experiences. For example:

• Knowledge: Classes in cooking, a foreign language, ceramics or anything else that a loved one has expressed interest in could say more than a(nother) new tie.
• Time: We all know busy people. Consider offering to help ease someone’s load by giving a coupon for babysitting, a spa day, a “sisters night,” or even a few batches of laundry. Gifts like this are often great for kids to give, too, because they can be free!
• Memories: Putting together a scrapbook of a specific time (like a vacation) or of someone’s life can be a fun experience for everyone. And older recipients, especially, may appreciate a chance to have their favorite photos arranged in an easy-to-show-off format.

Remember: Focus on Them!

No matter how you celebrate the holidays, remember to focus on what will make your loved ones happy – not what you think should make them happy!

We all take steps to lower our own personal debt. But what steps are you taking (or willing to take for that matter) to lower America’s debt?

A recent article from CNN Money reports on a rarely mentioned law passed in 1961 that allows individual citizens to make contributions toward lowering the national debt.

Here’s how it works.

National Debt Vs. National Deficit

As the web site for the Public Debt (www.publicdebt.treas.gov) explains, there is a difference between national deficit and national debt.

• Deficit refers to the annual difference between money the government collects in taxes (i.e. government revenue) and the amount it spends. In other words, the deficit is contained in yearly chunks.
• Debt refers to the accumulated deficits plus any surplus spending not mentioned in a year’s budget but spent by the government. In other words, debt builds up as the years go by (assuming the government is running a deficit).

Thanks to heavy government spending to help get the nation out of the current recession, our national debt and current deficit are both considerable – in fact, our country’s current debt level is $12 trillion – and it will get bigger before it gets smaller.

Giving to Uncle Sam

So, it seems, concerned citizens can make tax-deductible payments in any amount to help ease the nation’s debt. Currently, Americans have two options:

• Send it with your tax return: You can send a check when you next mail your tax returns.
• Send it today: Or you can mail it to the address provided on the aforementioned web site.

Do Citizens Actually Lower America’s Debt?

You may be wondering whether this program actually yields the government any earnings. Sources indicate that, in fact, it does – but very little.

Donations to date this year, for example, have reportedly totaled a little more than $3 million – hardly a drop in the debt bucket, really.

In fact, the best feature of this law may be its potential for stopping the complaints of citizens. While few of us are thrilled about the prospect of covering the government’s expenses in years to come, even fewer of us enjoy listening to others gripe about this phenomenon.

So bring up this law next time. Tell whiners to send a check.

Additional Resources

2009 Tax Code (Check out p. 91)

Holiday travelers may have extra reason to celebrate this year—free WiFi connections for their laptops and smart-phones, thanks to Google.

Google is teaming up with Virgin American airlines and a number of wireless internet providers to give travelers free internet access in 47 airports across the country, and onboard Virgin American flights.

The service starts today, November 10, and runs through January 15, 2010. The airports are mainly smaller airports and don’t include many of the “hubs” that travelers spend hours in during layovers (think Chicago, Denver or Phoenix).

However, it includes a number of vacation hotspots, like Orlando, San Diego, and Las Vegas. If you’re traveling over the next two months, there’s a good chance you’ll find yourself in a participating airport. (See the full list and more info online here: http://www.freeholidaywifi.com/.)

Win Prizes

Google is also holding a photo contest: take a photo of yourself using free WiFi in any participating airport on Virgin American flight to win (currently undisclosed) prizes.

Give Back

And because the holidays are all about giving, Google is encouraging donations to participating non-profit organizations. You can give online via Google Checkout, and Google will match up to $250,000. (More info on the Give Back program here: http://www.freeholidaywifi.com/give-back/.)

A fascinating article from Details magazine profiles Daniel Suelo, a Utah man who lives without money – literally.

He resides in a cave, bathes in a lake without soap, picks food from the mountainside and gleans the nearby town’s leftovers from garbage and recycling bins. While this lifestyle takes frugality to an extreme even I find excessive, his habits offer some important reminders about how much we waste – and could be saving.

• Heating & Cooling: Living outdoors is only pleasant a small fraction of the year – most of the time, the temperature will be either too hot or too cold for most of us. But Suelo serves as a reminder that we won’t die if we lower the heat or shut off the AC for a while (even in the desert).
  • Save Money: Layer blankets and clothes in the winter; sip icy drinks when it’s hot. Being a little tougher can save you serious money in electric and gas bills.
• Tossing Food: Be realistic with yourself. Don’t buy more than you can eat and learn to love leftovers (and Tupperware). While it may feel good to stock up on fresh fruits and veggies (look how healthy I am!), remember that these foods spoil fast, which can translate to wasted dollars.
  • Save Money: Learn recipes to salvage produce that’s near spoiling (banana bread, soups, stir-fry dishes, etc.) and, when buying, get stuff that still has a little shelf life left.
• Working too Much: In the article, Suelo mentions that, when working in healthcare, he felt guilty for getting paid when all he wanted to do was help people. This may sound a bit radical, but he makes a significant point: if your job is rewarding, you’ll want less money to do it.
  • Save Money: This is a tough idea to act on, but at least think about it: would you still do your job if you didn’t get paid? Few of us can answer “yes” to that, but remember that if you can, you likely won’t feel compelled to buy much “stuff.”

Easy Concepts, Tough Decisions

Suelo’s lifestyle is – as he admits – hard. It made my own life seem much easier in perspective – after all, I have a mouse-free bed to sleep in every night and I know I’ll have breakfast every morning.

And, while I don’t plan on renouncing cash or credit any time soon, I do appreciate his reminder that committing to frugal (or at least financially responsible) living has many rewards.

I took my car into the shop this week for what I thought was a minor problem and walked away with more than $1,200 in repairs. Luckily, I had emergency money to cover them, but the experience got me thinking: do other people have plans in place for when unexpected expenses arise?

If you don’t, here are some tips to help you develop one.

Step One: Imagine the Worst Case Scenario

I don’t mean that in a sinister, masochistic way – imagining the worst that could go wrong in the various areas of your life will allow you to prepare for such occurrences. It also helps to think of worst-case scenarios when you don’t actually have to deal with them, because you can reason more clearly.

Here’s the list I came up with, and initial steps to take if they happen:

• Major car repairs: Consult at least two mechanics. Consider ordering parts myself. Run everything by my dad (or an auto expert you know and trust).
• Job loss: Network (start doing this now). Sign up with career websites. Keep résumé up to date. Maintain positive relationship with boss (for recommendation letters).
• Serious illness or injury: Maintain medical insurance. Understand employer’s policies for paid and unpaid leave.
• House damage (from a storm, flood, fire, etc.): Update and understand insurance policies. Make sure I’m covered for disasters likely in my area.
• Car accident: Wear seatbelt. Maintain car’s safety with regular checkups. Review insurance policy.
• Serious theft: Install alarm system. Keep all credit card and bank numbers on file (along with phone numbers for issuers) to cancel them if necessary.
• Family member’s request for financial help: Be prepared to say no.

The Elephant (Not) on the List: Money

Naturally, every one of these emergencies would require at least a little financial investment. So that’s step two of the Emergency Plan: save money. If you aren’t much of a saver, read this page on why saving money important it is.

And, once you’ve been converted, take some time to estimate the costs each of your worst case scenarios. If you have a choice about how much you spend (could you live without a car? How much can you afford to give to a relative?), set a limit while you’re levelheaded. That way, if you’re ever forced to make a tough decision, you’ll have some numbers to look back on.

You may even want to open a separate savings account for emergencies, so that you’re never tempted by that money.

Additional Resources

Emergency Funds: Getting Started (PDF)

Savings Fitness (Personal Financial Planning Guide) (PDF)