I lived in Chicago for the better part of 4 years. I moved there for work as many people do. In the end it wasn't really for me. I live in Denver now and its the right size for me.
I wrote this to help educate someone thinking about moving to the Chicago, and help them make decisions on where to live, and what kind of lifestyle they want. I hope this is useful to someone.
Chicago is a big city that sometimes has a smaller feel. In other mid-size cities (I moved from Grand Rapids, MI) you might be used to traveling downtown to bars, the north side for a convention, the west side for the mall, etc. In Chicago people typically find the area they traverse doesn't really encompass the majority of the city. Most working professionals spend their time downtown during work hours and travel within in a 5 mile radius from downtown, primarily to the north and north-west for a Cubs game or to travel home.
Chicago is very segregated between north and south, it is considered one of the most segregated cities (by race and culture). As a general rule you'll spend all of your time north of Roosevelt.
I found the people in Chicago significantly more friendly and open to starting friendships. In common spaces people will openly comment about the weather, or make general observations and this isn't considered invasive. People are generally helpful and friendly.
I remember when I visited LA for the first time, at the airport I asked a man a question and he responded "Do I look like a map mate?"... I've never had an experience like this in Chicago, even the plumber I use is friendly.
If you are used to open spaces and low-congestion traffic most of the time it will take some getting used to. There is rush hour, and commuting by car is a waiting game during the morning and from 5-7pm.
Tourist season in the summer is fun, because of all the events and things to do, but it also means a lot of crowds, sometimes I avoid touristy spots just to not have to deal with hundreds of people standing around on the sidewalk.
Work Culture
The places I've worked in Chicago have been in the technology sector, but I find that companies aren't as motivated by a meritocracy as I have found in other places I've lived. There is very much a political culture within the work places - there is an invisible pecking order that is important to understand more so than in other places I've worked. Results aren't as important as doing things in the manner your employer wants them done. Views inline with Taylorism I find are more prevalent.
There is a business man culture in Chicago more than an inventors or engineers culture that you might find more prevalent on the West Coast.
Your Commute
One of the biggest values you can add to your life in the city in my opinion is a short commute. I lived near the UIC campus, and traffic was always fairly light and easy to navigate by bike, or by train it was a very quick ride to downtown. This made my life wonderful. Compared to living on the north side and having a congested 40 minute commute to go 4 miles at times I could breeze to work in 9 minutes on my bike. This gave me so much more time in the evenings for other things - and left me stress free. I really recommend spending your money on a short commute, I would say give up your car and spend the money on rent if it means a short commute - you are going to be spending the majority of your waking hours commuting, or at work anyway.
Public Transportation
I had never used public transportation regularly before moving to Chicago. The combination of Uber and public transit allows you to get pretty much anywhere. There are light rail lines that extend outwards in a pinwheel fashion from downtown. It's very easy to travel north and south, both by car and rail, but much harder to travel east and west, this is important for several reasons I'll discuss later.
If you are going to live north of downtown and rely on the Red Line, just realize this is the busiest line in Chicago and is absolutely packed in the morning and evening. It is also very old, and isn't always the smoothest or fastest especially compared to the newer lines. You can look at train schedules online at 8am to see what your morning commute might be like. Don't be surprised if going 2 miles takes 20 minutes in the morning even on the train.
Another way to commute is using Metra which uses regular train tracks and terminates at one of 4 stations within downtown Chicago. If you want to live a little further from downtown this is a great way to "cheat the system" as the Metra trains are faster, and more comfortable. A person wanting to live in Ravenswood and using the Metra to travel downtown can expect a 15 minute commute and will pay around $6 for a round trip. Many people are unaware of this "hack".
If you have a flexible job schedule and you can leave for work a little later (9am) you can also expect a much easier commute as the CTA congestion quickly dwindles in the morning.
Outdoor Activities / Nature
I consider myself a lover of open spaces and being outdoors, so I knew Chicago would be an adjustment. I didn't have all the information when I moved so here I will present what things to look out for if being outdoors/active is important for you. Chicago has a lakefront, and team sports and leagues of every type imaginable. In the winter you can cross country ski in a couple places within a 30-45 minute drive (at the edge of the city basically) or along the lake trail.
The reason I keep mentioning the lake trail is that the further you live from the Lake and downtown the cheaper your rent is likely to be. But keep in mind, traveling East/West in Chicago can be difficult there aren't really any avenues that will quickly take you east and west. I lived only 1 mile from the Lake when I first moved to Chicago and I visited it very rarely because it was just difficult to fit it into my schedule or commute. When you live in Chicago it's not really reasonable to "bring a car with you" when you visit the lake or the beach it will just get too darn expensive so your options become fitting your belongings in a taxi or whatever you can carry in your hands. This is important to keep in mind. Wanna go skiing? Live 2 miles from the lake front? I hope you can fit your skis on the bus or are comfortable making the walk with them. This inconvenience can sometimes prevent you from doing things you might have enjoyed previously. For me I stopped kayaking, skiing, and climbing regularly because the inconvenience was too great. If I had chosen where I lived more carefully and spent a little more money this wouldn't have been as much of an issue.
Another thing I'll point out quickly, escaping the city. If you want to visit the beautiful state parks of Michigan, or drive into Wisconsin it will take you some time to just leave the city. The commute from downtown to just get "out of" the congestion and suburbia is about an hour. The area is massive and has huge sprawl. Keep this in mind if you are planning on not owning a car but want to do outdoor activities. Finding a climbing/rock wall can also be difficult. Be prepared to spend a LOT of money to be a member of a gym with these types of amenities. Gyms are busy and the nicer ones can cost $70 - $120 a month for a membership. In the winter it can be worth it to have a place to get some exercise.
Owning a car
If you are going to own a car be prepared for some hidden expenses. If you can't afford a place with a parking spot, your bumpers are going to get scratched up and maybe worse. Parking on the street especially in the winter is the wild west and everything and anything happens to your car.
Parking is hard and almost impossible at times. If you commute and decide to stay at the office late, good luck trying to find a parking spot by 10pm, it's nearly impossible. The parking situation becomes much much worse the closer you get to the lake shore. If you aren't planning on getting a parking space really examine your choice to have a car and weigh the pros and cons. Worrying about a car is a pain. Ironically parking downtown in metered spots to run an errand can be fairly easy even on the weekends. If you live in or near a mid-rise or high-rise the parking situation on the street is going to be impossible. On the other hand if you live in a neighborhood with alleyways and most buildings have garages or parking spots behind them street parking is much easier (less competition for spaces). Living near a cemetery, or park, or railroad tracks (any land that isn't used for housing) makes parking easier. If a parking spot comes with your apartment, even for $100 extra a month DO IT! I cannot under-state the lessening of stress, worry, tickets, and time that comes from having your own spot.
Leaving the City
If you want to leave the city regularly I would suggest really considering your proximity to the train stations, Mega-Bus departure spot, and also the CTA rail lines that take you to the airports. If you are too far from infrastructure it may be very difficult to cut-out early on a Friday for a weekend skiing trip or to visit family. If I'm planning a visit out of the city on a Friday, I leave my car at a friends a couple hours away, I take the mega-bus to that city, then use my car for the weekend, I then have the option of leaving my car or driving back. Being able to relax/sleep in Friday rush hour traffic on a bus or train is amazing - and this is a great way to leave work on a Friday and get the most out of your weekend. I can not emphasize this enough, trains do not get in traffic jams.
Walking Distance
Make a list of the things important to you, and then think about how far you want to walk to them regularly, if you take the train to work are there amenities that you use regularly on the way home? If you are like me the gym needs to be either near work or one the way home to be used regularly in the Winter.
Fashion
People in Chicago are fairly fashion aware and you can expect to see quite a bit of a "keeping up with the Jones' culture". Be aware of your fashion, and plan to dress intentionally (notice I didn't say 'nice') there are many different styles, but dress intentionally if you want to "fit in" easily. I found I started taking my dress more seriously after I saw how everyone else was dressed - it made me feel more at-ease if I visited a upscale lounge after work with friends.
The Winter
Invest in layers, and good clothing. Get Smart Wool socks, and stylish but water proof shoes/boots. Get a good coat! Avoid bulky things that are annoying to stow/keep in a restaurant or public place.
If you can leave an extra layer at work that is also a great idea in case it gets warmer or cooler than you expected. In the winter the bar scene explodes, because most people don't have big houses or apartments that they can entertain 8 of their friends in, people meet in bars. In the winter this becomes even more the case.
Shopping
Shopping in Chicago can be vastly more expensive than a short hour trip to outlets to the south or north. There are outlet malls in both directions that have amazing name brands and lots of deals where you can find things half or a quarter of the price of what they would be at a boutique in Chicago. Because of more limited space the selection is extremely seasonal in Chicago and much more limited. With that said if you venture just slightly out of the closest downtown and River North spots to shop you can find good deals at Nordstroms Rack and several other clothing stores. I'm a taller person and I find in the city everything is "skinny" and it's hard to find things that fit me at times. With that said, I was out running once when I noticed my running shoe was in bad shape, I literally walked into an Asics store and bought new shoes.
For groceries just shop at Jewel-Osco (the Walmart of groceries), there is Marionos which is upscale, and also Whole Foods as well. There are specialty grocers that sell only produce and also smaller stores in Hispanic neighborhoods that you can get amazingly good deals on food. If you are frugal your food dollar can go a long way in the city. If you are used to bulk grocery shopping, I would really suggest you get more in the habit of buying 2-3 days of food, or sometimes picking up only what you need for a meal. If a grocery store is in walking distance this can be a very enjoyable thing about the city.
Expenses
If you don't eat out everywhere and you are careful about how much you spend at the bar (all bars are expensive in Chicago) and you don't take Uber/Taxi everywhere you go. You can live pretty economically. If you are willing to have a roommate you can live very affordably in Chicago.
Meeting People
If you enjoy being social, find a friend or a group of friends that goes to house parties or knows someone that is hosting one. Once you go to a couple parties and meet people this is like a domino effect and you can meet more people and tag along to more parties - which is the cheapest way to be social. It is very common in Chicago for people you work with to go out after work and to have friends at work. Another common thing is for your friends to work nearby (most people do work downtown) so meeting up immediately after work to catch a show or hangout is common.
If you aren't sure where to start or how to meet people I really recommend joining some sort of club. Get on Meetup.com and find some of your interests.
Things to do
Intramural sports leagues - One of the primary ways people meet new people is through co-ed sports leagues for volleyball, softball, kickball, soccer, tennis, etc. Chicago has an extremely active recreation scene throughout the spring/summer/fall and this is probably the #1 best way to get plugged in. Also some bars host special events where you can drink beer and play sports - you usually have to sign up for these events a month or more in advance with friends. About 80% of my friends at some point dated someone they met through public recreation events.
Boating - you can rent a "timeshare" on boats - or sometimes your work place will do this for you - boating in Chicago in the summer is amazing and I recommend this.
Kayaking- Kayaks can be rented downtown, on the South side of the Chicago river, right next to the lake Michigan inlet.
Various other boat cruises - with a date or friends there are boat cruises you can signup for that leave from Navy Pear some are open to the public in advance - this is a great way to meet people secluded on a boat after they've had a few drinks.
Cycling - Cycling the paths in the city is a great experience I very much recommend it. If you are experienced cycling on the roads is really enjoyable as well. Bicycles are a great way to see the city and get around.
Various rooftop lounges - There are several rooftop lounges of varying dress-code that are amazing to visit in the summer and have a drink.
Block Parties - In the summer there are block parties in various neighborhoods where they block of the street play music have food, etc.
Concerts - There are always concerts going on, and it's very easy to catch a bus or the train to and from the common venues.
Opera/Orchestra - Chicago has a great music and opera house and if you're into that sorta thing it's awesome.
