Question
I just bought a home in Chicago Illinois. I LOVE working in the garden, however, I am not very good at it. I want a nice garden (who dosen't) but I want "simple" too. I would like to plant flowering plants that come back every year, and that can survive Chicagos winters when not in bloom... Ideas? THANKS IN ADVANCE

Answer
Nina,
Congratulations on your new home. I also have recently moved into a new/old home and can't wait to get started on my "cottage garden".Just can't seem to find the time yet.
Anyway you are in Zone 5 on the plant hardiness map of the US.You can find out which perennials(plants that return every year) will actually thrive the BEST in your area by going to a local nursery. Chicago probably has hundreds of them as compared to where I live in a small town in Western Kentucky.We don't have a lot choice but to buy expensive perennials. If we want them,we have to pay the price. You should be able to find less expensive perennials in your area because there is more competition.If by chance you cannot find the ones you really want I will leave a resource list of online nurseries that you can order perennials from.
Also you live in a great area for spring blooming bulbs that should be planted now or in the next few weeks. I will give you my top ten best perennials and bulbs that I have come up with over many years of gardening in the order of all around best performers in my zone 6 that I believe will be also tolerant of your zone 5.Hint: STAY AWAY from the tropical plant greenhouses.Tropicals are basically houseplants because they are suited for warmer climates but will never survive a Chicago winter.

Here are my choices:
1.Asters aka Michaelmas Daisy)blooms in fall

2.Achillea(aka Yarrow)blooms in summer and sometimes again in fall

3. Daylilies-bloom in summer

4.Perennial Dianthus Barbatus(aka Sweet William)

5.Dianthus(aka Garden Pinks)

6.Tradescatia(aka Spiderwort)long bloom period from early summer to frost

7.Purple Coneflowers bloom in summer and may return in fall.

8.Clematis vine-bloom summer and return in fall

9.Sedum( all types are great drought resistant and carefree perennials)

10.Evening Primrose(pink with yellow throat) and Missouri Primrose(yellow)
*Forgot to add Creeping Phlox.It blooms early spring and stays green throughout the winter.You can plant it with bulbs and they bloom beautifully together.

Spring bulbs:
Daffodils,Grape Hyacinths,Scilla Siberica,Chinodoxa,Lily of the Valley

There are many more to name but these I believe are ranked high on my list as far as low maintenance,not much watering,consistent in returning every year,and longest bloom time.

Here are some resources on the internet:
Shady Oaks Nursery,Thompson & Morgan Seeds,White Flower Farm, Van Bourgondien Bulbs and Perennials,Jackson & Perkins,Bailey Nurseries,Imperial Nurseries,
Bluestone Perennials,Musser Forest,Spring Meadow Nursery,Willoway Nurseries,Greenleaf Nurseries

Hope all goes well and you will have a beautiful "simple" garden!