The New Eastside of Chicago is bordered on the south by the Chicago River and is encompassed by the Loop neighborhood. This is a diverse area with buildings devoted to government and finance as well as theaters and shopping areas. Residential buildings are also a part of this neighborhood, mixed among other types of buildings in this mixed-use city area.
Most of this area has been developed from what was once water and the result is lovely views of water throughout much of the neighborhood. A triple level street system keeps trucks and other heavy traffic on the lower levels, allowing traffic to be at a minimum on the top street level. This means that while you certainly feel that you are walking through a city while you are on the New Eastside, you are not as disturbed by traffic as in some other areas of the city. Lots of green space also contributes to this being a pleasant neighborhood to walk through.
This flat city neighborhood offers lots of pleasant paths and parks that will make walking through this neighborhood feel very diverse and interesting for both you and your dog, though there are no real challenging areas. There are areas where you will need to keep your dog on a close leash and encourage discipline and a good heel, but frequent parks and grassy areas allow you to let your dog run on a looser leash so that she does not become frustrated with training.
Most natural areas in the city neighborhood are grass, but you can find more extensive and interesting shrubbery in Millennium Park and Lurie Garden. There isn't much access to the natural waterway in this neighborhood, but if you cross the Chicago River where it empties out into Lake Michigan, you can find your way to the Ohio Street Beach and many beaches further down for an opportunity for your dog to experience swimming and sand.
The New Eastside offers access to a huge variety of natural terrain for you and your dog to explore. While this is a city full of skyscrapers, so many natural spaces have been provided that you may forget where you are.
Your dog will love being able to run on a loose leash or flexi-leash without concern of traffic and plenty of room to get out of the way of pedestrians. This is also a great place to be on wheels with your dog, but make sure you have good control as there are a lot of other people in this area. South of East Side you will find a vast array of parks including Millennium Park, Butler Field, Grant Park, and many more. You can follow the water and, if you are so inclined, can continue all the way down the coast. If you go north, you will find your way to miles of gorgeous beach to explore.