All of your selections are fine trees, but many of them will not offer great privacy or shade. The Redbud is very upright and medium in size, the serviceberries bloom tremendously in the spring but are a very light tree with respect to shade and privacy. The white dogwood will likely survive unless you have a lot of wind as this would increase the windchill danger on these plants. The riverbirch love damp ground. I have one near a low area in my field and the tree has grown 3 feet per year for the past three years. They are ususally in clump form and are much stronger that way versus an individual specimen. Great trees but will get very tall in a hurry when established.
I would put the flowering Dogwood in front as long as there is ample sunshine for it to bloom properly. It will be vase-shaped and flower for you every year.
In the rear, the riverbirch in the middle of twin serviceberries would look great and give you the plants and look that you want. The privacy protection form these plants will be okay, but nothing like a conifer or maple might give you.

Goodluck,

Thanks for the response. Would a Paper Birch or Yellow Birch be a better choice for Chicagoland (harder wood, more disease resistant, more shade/privay etc). Would an Amur Maple, Red Maple, Sugar Maple, or Norway Maple be a good choice (prefer something that turns red in fall). Or possibly an Oak? Thanks again!

I would get a nice clumpform paper birch. They are always more impressive as a clumpform and less apt to blow down in high wind. There are purple leaved varieties now as well, like Articfrost. These purple-leafed varieties are stunning when larger. The leaf color is similiar to a Crimson King maple but on a birch tree. Never plant a Norway maple. They are the most invasive plant of all hardwoods and they will dominate your lanscape after 10 years or so. Most nurseries will not sell them now because of this. The Amur maples are a smaller maple with an orange color in the Fall. Make sure not to buy the dwarf varieties as they stay rather small.I have two full size Amur maples and they are very hardy, and not too large. The true red or sugar maples are great trees and you could tap the sugar maple to make syrup after it is large enough. Most red and sugar maples are indeed, red in the fall but conditions and individual specimens can be lighter or darker.
Oaks are very slow growing and not as red as some of the maples.
Remember, clump-forms on the birches and they will offer you more shade and tree strength.
A mixture of Serviceberries, Red or Sugar Maples, and birches will be impressive.
If you plant in the early spring, keep an eye on The Weather Channel during the first season to watch for drought in the area.

Msmity

In Chicagoland, the river birch would be the best choice among birches. It handles heat better than the northerners paper and yellow birch, both of which are decidedly happier in cooler zones.

River birch can suffer from chlorosis if your soil pH is too high. Soil sulfur, which is simply granular sulfur, can be applied quite heavily, and then covered with mulch. Bacteria in the soil slowly convert this to sulfuric acid, thereby lowering the pH. This works well, but may need to be redone occasionally. The material is inexpensive, and IMO, a better choice than the commonly recommended aluminum sulfate.

+oM

If you have room for the serviceberry, it would be a great addition. They are more a shrub than a tree, but can very full and around 8' in diameter if you prune it selectively. It makes a good screen when it gets mature. But the real reward is the birds it attracts. The Cedar Waxwings love this shrub's fruit and will descend on it and remain until all the berries are gone.

The Saskatoon is a good variety, as it is the most prolific berry producer of all the serviceberry. The berry is very good tasting and you can throw them on your morning cereal or make jam from them---if the birds let you get any of them!