Chicago & Dempster


Situated between Downtown Evanston and Main Street sits the business district of Chicago & Dempster.  This little outpost of commerce provides local residents with a nice selection of restaurants, shops and one of Chicagoland’s best places to see a concert.  It also is a leisurely walk through one of Evanston’s historic neighborhoods to reach the waterfront.

For Saturday morning enthusiasts, Chicago & Dempster real estate has it all: good coffee, sunlit streets and a quiet outlet to enjoy your surroundings unencumbered.  A short walk west on Dempster, and you are at Hewn – one of Evanston’s best bakeries with a great mix of seasonal offerings and a socially conscious attitude.  For the chain shopper, you can head south on Chicago Avenue to Trader Joe’s and Whole Foods. Either way, 20 minutes at this intersection and suddenly you have the makings of a great day!

If the evenings are more your speed, a great night can be spent at Union Pizza/Space.  The bar is great, the pizzas are great, and – if you feel like seeing live music, the attached Space provides a venue that has hosted an eclectic mixture of up-and-coming acts, round-the-bend performers, and you-gotta-see-it-to-believe-it shows.  Depending on the night, you can walk up and get a ticket or else wait around the corner for the doors to open on a sold out show.  Either way: the shows have never been a disappointment.

In addition, you’ll find a mix of other restaurants and sites to explore in the area – see the ‘plan a visit’ tab to the right for more suggestions.

Accessible by both CTA and Metra, this neighborhood has much to offer for a variety of tastes!





  • Try the Monkey Bread at Hewn
  • Catch a show at Space


North – Wilmette
South – Chicago
West – Skokie
East – Lake Michigan

Zip Code(s):


Public Transportation:

  • Metra: UP North (Davis Street, Main Street)
  • CTA: Purple Line (Dempster Street)

Main Roadways:

  • I-90/94
  • Sheridan Road/Lake Shore Drive
  • Chicago Avenue


Chicago & Dempster Real Estate Listings


Natalie Smith

Natalie Smith

@properties Real Estate Agent

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