I think we adults had as much fun as the kids and fairly cheaply. We got to socialize and come up with ideas every Wednesday. Happy memory of pitting endless fruit for Cherries Jubilee with the girls.

Since you initiated the idea, and already purchased it, I would just let them know some non monetary things they can contribute to. It’s harder to quantify items and favors so there isn’t the pressure to come up with a “magic number”. I agree with everyone else…most decent friends will WANT to contribute in some way so I like the idea of giving them other ways to pay you back…and let them decide if that includes giving you money.

Personally I hate taking money from friends unless there is a clear and specific discussion prior as to who is paying how much. Maybe you value the idea of staying in a lakehouse more than they do and you might be willing to pay more than they are as after all it was your idea, even if they agreed it would be fun.

(A little late to the show) – My wife and I volunteer at all sorts of events. Sometimes we get the best view of the show or whatever is taking place, sometimes we get to meet the exhibitors. We meet a lot of like minded volunteers and we often see friends who are attending as patrons. We’re helping local organizations, getting out of the house, seeing friends and enjoying ourselves. All for some cleanup, setup or just answering questions.

Tell your friends, “I want you to come. I’ll cover lodging, you provide food and your company.” or whatever it is. As people who have been on the receiving end of that before it is a difficult gift to accept but we do deeply appreciate it.

-Preview nights for the performing arts. In my city, those tickets are half-off.
-See if there’s a city e-mail with events for the week, with offers. My city also offers this, and usually there will be limited numbers of free tickets to the events being advertised. (Could be a comedy show, musical performance at a museum, etc.)
-Going for a bike ride/hike.
-A variation on The Big Game. In college we would get together for a tv show everybody liked. Also works for Oscars/Grammies, and other award shows.
-Karaoke at home (either real karaoke, or with a video game like American Idol: Karaoke Revolution).

Real friends will be understanding and find cheap things to do with you. My best friend and her husband are big spenders but when they hang out with us we make dinner and have drinks at home. Sure, they make fun of our frugality sometimes but they’re not offended. If a friendship is important to you then it shouldn’t matter.

I also agree that certain kinds of friends love to spend their money…and yours. Some people just can’t go out and have fun without dropping a ton of cash. I’ve thinned out the pack as far as friends go so luckily I don’t have many of them anymore.

This place is crawling with happy hour restaurants (1/2 off sushi, $2 tacos, $3 salads, etc) so I keep a log of different places in my phone so when I’m out and want to be spontaneous, I have my list of places I could choose from.

I know its been said here many times but Groupon, Living Social, Google Offers, Get My Perks, etc has been a Godsend for me. I just purchased a coupon for half off for “OMSI After Dark” next week – something I’ve always wanted to do, but didn’t want to pay $18 for. I have a Google Offers coupon for wine tasting at a local wine store that I’m going to take a friend too.

Of course there are so many free/low cost activities as well…

There are well-to-do folks who will only drink, say, the store brand of pop because that’s what they like (and actually, I think Warren Buffett does this, too). And then there are foodies who will buy cheap clothing and cut the cable bill so they can afford the truffle oil and expensive cheese – because that’s what they like.

http://www.chipublib.org/forteens/teenhowto/freechgo.php

It is under the “teen” section but adults can check them out.

Depending on how many sites you plan to visit, it may be beneficial to get the city pass.

http://www.citypass.com/chicago

I hope this helps! Chicago is really fun in the summer and there are many free things to do. Lincoln Park Zoo, Grant Park, Millennium Park, the beaches are great, and I enjoy walking around the museum campus just for the scenery.

And it’s definitely not a clearcut situation, but I think the house became your charge when you rented it on your own.

Now they will probably feel the obligation to pay no matter the cost to them– as I mentioned before, people have their pride, and most humans would rather go into debt or sell a kidney than lose face or come up short.

However, since you rented this on your own, and they had no part on the decision, you probably should do your best to let them off the hook.

Chances are they will insist they want to pay, but I would say best course it to refuse it politely and ask them to bring food and drinks instead– you want to foster a feeling of equality in the relationship, and a sense that everyone belongs and contributes something of value to the experience without having to summon an army of bean counters.

If they keep asking to pay their share you could say “look, I signed this contract without checking with you, so let me take care of i– how about you’re in charge of food for the week?” or something along those lines. Maybe they are terrible cooks and would rather hire magicians, I don’t know, but my point is that they need a way to not pay that lets them be equal partners.

Eh, I’m not the greatest diplomat either, so maybe someone can suggest something else, but that’s how I analyze that situation.