The best thing I can recommend in good weather is river camping. A canoe will hold two people and a couple hundred pounds of camping equipment, musical instruments, etc. You can go down the Chicago river to the DesPlaines and the Illinois or you could start on the Illinois. The Mississippi, the Missouri, the Wisconsin, the Rock are all easy, smooth rivers. Go see it. It's free. Even the locks are free. All you need is a car at the other end, downstream, to pick you up. Try to camp on sandy beaches in the wind to avoid insects. Here's some tips I wrote on WIKI for river camping:
Simplify. Make one item do many tasks. Like Paper towels can serve to clean you, your cooking items, serve as toilet paper, then burn to leave no trace. Practice setting up your tent/shelter in your living room before you leave home. It is not difficult to get two hundred feet from a water source, that's only thirty yards into the woods-- a few mosquito bites on the butt will be worth the peace of mind. Unless the ground is very dry a stick will dig a hole as well as a shovel, but there are special "cat shovels", small, light plastic utensils available at camping stores. You would be safer to eat food from grocery stores in river towns than the fish in the river. There may be heavy metals, pesticides and herbicides and microbial contaminants in the water-- plus unless you're in a pristine environment teeming with fish, you might think twice about killing someone who lives there and eating him unless you really need to. Pork chops, eggs, steak and other perishables will keep overnight without refrigeration if merely kept cool and out of the sun. Just buy more tomorrow. Pasta will give you stamina to paddle all day tomorrow. Forget strike anywhere matches, the single best item you can bring is a few new bic lighters. Also bring a magnifying glass for splinters and fire. Bring a flint and steel and learn to use it. There will be plenty of free, dry firewood-- mostly old oak and other hardwoods, but those green willows on the banks burn just like dry hardwood. Bring a canoe repair kit. If fiberglass is punctured, duct tape is a temporary quick fix, but a fiberglass repair kit is a light, small kit that can get you home. Radio is non-optional. Weather reports can save your life and ball games, news and music are a delightful connection to the real world as well as a source of luxurious comfort. Get a tent you can stand up in. Getting dressed sitting down is a drag and if you need to stay in tent throughout a rain event, a roomy tent is a must. Tent must also keep water from soaking in through the floor. Digging a trench around tent or locating on high ground doesn't work so well in sand, which is what you'll find on many navigable rivers. Go to a canoe store to benefit from the wisdom, and experience of personnel. They'll help pick the right canoe and maybe show videos of what to avoid or how to deal with storms, wind, traversing large lakes and oceanic bays, etc. If you keep a level head, you can canoe the Great Lakes or the Inside Passage of southeast Alaska. The canoe is a very stable boat if you keep a low center of gravity and will float like a bubble on the water through the worst rainstorm and high winds. By the end of my first trip, I paddled standing up for variety. Avoid being on the water during lightning storms. Read the beginner's boy scout manual on canoeing. It will jump you way ahead on technique, strokes, and other stuff it would take days or weeks to figure out for yourself. Go in early spring. The symphony of birdsong will be a revelation, if you be quiet and listen. You will also hear deer and elk trumpet incredible harmonic sequences, and the occasional beaver will slap the water to startle you and try to get you out of his turf. At first, paddling will seem like hard work. That's why the boy scout manual. But after a few days it will be easy and seem like second nature to paddle from dawn to dusk. You will naturally learn to read the surface of the water for signs of wind and currents. Try to stop early, with several hours of daylight left. You will be able to see well enough to pick a good campsite, pitch a tent, make a fire, and cook before dark. After sunset, one cannot see well enough to avoid poison ivy, one can not see the very banks of the river. If on the water after dark light the boat so others can see you. Bring a six-volt lantern and a couple of LED flashlights. The lantern will be strong and penetrating and the LED's will last for hundreds of hours. Enjoy-- life is so short and seldom so sweet as floating downriver with the current.