You can fly into O'Hare, then take a cab to Chicago. I advise to call American Taxi when you arrive at the airport, they are much cheaper than the taxis at the curb; they arrive in minutes too!
Once downtown use a cab, using a rental car is not neccessary, and expensive to park from $10-$50 depending on where, when and how long you park.
On the weekends there is a great free city service called the Chicago Trolley. It runs 10-6pm Sat. and 12-6 Sun. It will take you all around the city from Navy Pier, to the museums, to the train station, to the shopping areas. It comes every 30 mins. or less, and you stand by the trolley signs. P.S. Do not confuse the free trolley for the pay sightseeing trolley. The stops and more info. are at this website: (www.cityofchicago.org/Transportation/trolleys/)
Fly or take the train here. Do not rent a car. Take the train from the airport and use public transportation, your feet, or taxis. Do not drive here. We walk everywhere in all weather here.
Take your feet, take public transportation, take a taxi, rent a bike, skip and dance around our city.
Where the El doesn't run, it's usually convenient to take a cab. I had the best cab ride of my life in suburban Chicago. The cabbie knew a great 'secret back way' to the United Center where I was going to see a concert, and he spoke English!
Taxis are the best way to get around this city. Parking and the traffic would be hell. YOur best bet is to leave it to the pros. They can be found almost anywhere with about 2000 on the streets per day.
For getting around the city taxi cabs are plentiful and the quickest/easiest - just make sure you know where you are going so you aren't 'taken for a ride'. When my husband and I first moved here I think we were taken on the scenic route once or twice.
In the city and to head north to Lincoln Park, Wrigley Field, etc. you can take the 'El' - the elevated train system. Right now it is $1.50 per ride, very convienient and easy to use. I usually feel safe because there are many other people riding at the same time. If you are uncomfortable, get in the first car with the train operator.
Driving in Chicago is fine although some people who are not use to traffic find it quite stressful. Parking dowtown is expensive. There is a lot near Michigan Ave. that I pay aprox $15 for three hours. This is another great reason to take the El or a cab.
The best way to get around Chicago depends on your budget. If you have the money, cabs are an excellent way to get around. This is a very cab-friendly city in that you rarely have to wait long to spot a vacant one. Also, you can grab one just about anywhere, they're not generally picky about where they will pull over and pick people up.
A low-budget option ($1.50 one leg or $1.80 with a transfer) is the public transit system, which is the preferred method of many locals. You do need to know where you're going, though, and it's not always pleasant for the faint of heart--it can be a little bit dirty and unreliable. Pick up a 1-day, 7-day, or 30-day unlimited bus/train pass if you plan to ride more than twice a day. You can find them online (www.transitchicago.com), at either airport el station, or Jewel and Dominick's supermarkets in the area. System maps can be found at all el stations and online. If you're traveling to or from the suburbs, the metra train is an excellent option as long as you have a ride in the suburbs (cabs and buses are pretty rare there). Check that out at www.metrarail.com.
I highly recommend using the el trains to and from the airport (both Midway and O'hare) no matter what your budget. Those lines are usually clean and reliable. It covers a long distance much more cheaply than a cab, and you don't have to worry about traffic which can get nasty. If you have heavy bags and don't want to lug them around, you can always just take a cab to an el station somewhere in town, then take that to the airport, so your time on foot will be fairly minimal.
We took cabs all over the place in Chicago. They were always easy to find.
Can't believe one cabby let us pack six people into one! I know that'd never happen in Boston....!