If you are moving to Chicago, there are a million little details to take care of. The infinite number of things you will need to do before, during, and after the move make relocating one of the most stressful things you'll go through in your lifetime. Getting organized at the start will greatly reduce the stress factor, and will also cut down on the chances that you will forget something, or that that an emergency will pop up that you are not prepared for.
No matter where you are moving from, whether near or far away, one of the best tips for relocating to Chicago is to get started early. The further in advance you can put these tips into action, the smoother your move will go.
Sometimes you don't have a choice on when you make a move. School is starting, your new employer expects you to be on the job on a specific date, or a number of other reasons might dictate when you move to Chicago. However, if you do have the luxury of setting your own moving date, choosing what season you move in can make the whole thing easier. December through March are snowy months in Chicago, so you'll want to avoid winter if possible. However, since summer is a popular moving time, relocating to Chicago between June and September can be hectic, too, especially if you will be looking for an apartment as part of your move. That leaves April, May, October, and November as the best months to move and start living in Chicago.
Start going through your personal belongings and household items at least two months before you move. Go room by room, closet by closet, drawer by drawer, and get rid of things you no longer use or don't want to schlep to Chicago. There will always be items that you don't necessarily use a lot, but that you don't want to throw out or give away, and that's OK. That is what self-storage is for. Box those items up as you go, and find a storage facility in Chicago before you move. Having those things separated ahead of time and knowing that they can go directly to a storage unit instead of cluttering up your new home checks one headache off the list.
Another useful tip while sorting is to take pictures of the rooms in your existing home before you begin packing. You can also make a written inventory of each room if you have the time and inclination, but taking pictures is a quick and easy way of making a record of the contents of each room.
If you already know where you will be living in Chicago, take measurements of the rooms and doorways of your new home. That will give you an idea of whether or not you will have a hard time getting larger items of furniture into the place, as well as where everything will fit. Use graph paper to draw a layout of your new apartment or house and make a plan for where everything will go. A lot of furniture and decor items will be able to go in rooms that correspond with your existing home, but some things might need to go into storage, at least temporarily.
Here is where the "million little details" come into play, and where a lot of people lose control of the balls they have been juggling trying to get ready to move to a new city. If you have kids, their school records will need to be organized and arrangements made to transfer them to their new school. You will want to find a doctor in Chicago and have your family's medical records transferred, too. At the very least, you should get an extra supply of prescriptions filled so that you don't run out of vital medication before you find a new pharmacy in the nearby Chicago neighborhoods. Also, if you have pets, you should make the same arrangements, finding a new veterinarian before the move, getting an extra supply of medications, and having records organized and transferred.
You will need new checks with your new address on them if you already have a permanent or semi-permanent place to live in Chicago. A change of address should be filled out at your old post office so your mail can get forwarded immediately. Also, take the extra step to personally notify certain organizations such as your bank, credit card companies, brokerage firm, and utility and insurance companies.
Unless you are just moving to Chicago from a nearby suburb, you should tune up your car a couple of weeks before the move. You don't want something going wrong on a road trip to your new home, so the further away you are and the more miles you will be traveling to make the move, the more important this tip is. Also, if Chicago will be an entirely new climate for you and your car, ask your mechanic if any environment-specific services are necessary.
For at least the first few days in your new home, you probably won't be doing much cooking. Almost everything you own will be in boxes, and you will not have had a chance to get to the supermarket to stock up. Do some advance research on restaurants and take-out joints near your new home. Chicago neighborhoods are notorious for offering some of the best food in the country. Everything from ethnic to fast food to cafes and comfort food--you shouldn't have trouble finding places to eat your first few days in the city.
Pay close attention to the boxes and furniture as they come into your new place. Check everything off your inventory list as it goes in, but also do a second check, room-by-room, when everything has been unloaded. You will be expected to sign a bill of lading before the movers leave, so you should know that everything has arrived safe and sound before putting your signature on the movers' inventory list.