Chicago, IL, USA - there are a bunch of Chicagoans on here, so I hope others chime in.
Average housing cost: It really, really depends. Housing prices have been going up for a while. In close in neighborhoods, a 2 br condo goes for $400-$600k. A SFH for $800k and up. Further out neighborhoods you can get a SFH for $300-500k, and depending on the neighborhood, you might even get a good neighborhood school. In the current market, rent/buy is probably break even. In my neighborhood, rents for a 2 br range from $1300 for a smaller, older unit to $2000 for a high end unit.
Indoor Hobbies: The museums in Chicago are top notch. All of them have free days throughout the year. The Art Institute, consistently rated #1 on Trip Advisor, is free every Thursday from 5-8 p.m. for Illinois residents. There are two indoor conservatories with tropical plants that are great for warming up in the winter. The Chicago Park District has a number of indoor activities, mostly for kids, but there are also some adult leagues and indoor tennis lessons. The library system is pretty amazing. I’m also a fan of the Meetup scene here, which has just about every interest you can imagine.
Outdoor Hobbies: Hiking (although people from places with real terrain will call it walking), canoeing and kayaking, boating, cycling. There are lots of outdoor options within and hour or two of the city for camping and hiking. There’s a forest preserve system for Cook County and the areas surrounding Chicago, and some are even accessible by train. The park district sponsors lots of performances in the summer, including Shakespeare in the Park. The botanical garden is pay for parking but free admission, which means if you bike there you get in free, or you can take a train/trolley combo. The Lincoln Park Zoo is also free. There are also lots of community gardens, although I have to say they’re not the most Mustachian option for grow your own produce.
Weather: Hot in the summer, cold in the winter, moderate amount of snow. People say Chicago weather is notoriously extreme, but I have not found it any more intense than New England or other Midwestern winters and summers.
Favorite things: Chicago has a big city lifestyle with a moderate cost of living. Salaries seem to do better than COL would dictate because employers are competing for talent with other more glamorous cities. I love how much there is to do here - if you’re bored, you’re doing it wrong. Chicago also has an AMAZING food scene, which you can experience even on a Mustachian budget if that’s your thing. Arguably we have the best Mexican food outside of Mexico and L.A., and there’s huge diversity in cheap eats.
Least favorite things: Taxes are pretty ridiculous. 10.25% sales tax in the city, 4.95% income tax on your Illinois taxable income, and property taxes are average nationwide, but high for Illinois. Navigating the Chicago Public School system is a mess. The city is very racially and economically segregated, although there are some notable exceptions. On a Mustachian note, depending on your social circle, you might go against the grain a bit, as lots of people are into the high-end restaurant scene (which is among the best in the world) and there are basically unlimited opportunities for conspicuous consumption.
'Must Try': Art Institute, Garfield Park Conservatory, Shedd Aquarium, biking the lakefront trail, a concert in Millennium Park in the summer, neighborhood walking tours (I love
this book), the Architecture Foundation’s walking tours (the boat tour is great too, but walking tours are way more interesting and detailed, they’re the only paid thing on this list)
Stupid ordinances/laws: Taxes, as mentioned. Bag tax is 7 cents per bag, but you’re using reusable bags anyway, right?
Words of wisdom/Advice: I would probably rent if you are new to the city. Chicago is a city of neighborhoods and it’s best to figure out where you fit before you make the plunge to buy. Don’t rule out Chicago Public Schools if you have children, but do educate yourself about how the system works and what your options are. Neighborhood Parent Network is a good resource.
Sustainability options: there is municipal recycling, but no municipal composting. As mentioned, there are lots of community gardens. Solar is an option, although we’re not prime solar latitude and you’ll probably have trouble in a multifamily. Bike share is ubiquitous.