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Your Guide to Chicago’s Historic Uptown Neighborhood

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For more than a century, Chicago’s Uptown neighborhood has housed entertainers and artists from all walks of life, ushering in first the Gilded and then the Jazz age as the American economy boomed. Explore this historic district and see how shopping and restaurants are helping it to reinvent itself again in the 21st century when you book a ride with Signature Transportation Group.

The History of Chicago’s Uptown Neighborhood

Located just off the historic Lakeshore Drive, the Uptown neighborhood was originally intended to be a haven for upper-class families looking to escape the overcrowding of the city’s urban center. These residents built large, gracious homes on big lots, some of which still stand today, converted to apartments or other business uses. As the landscape changed and wealthy families moved further out of the city to the suburbs, immigrants came, giving the Uptown neighborhood a unique flavor unlike any found anywhere else in the city. Today, the gentrification of the neighborhood has brought in new businesses and increased traffic, resulting in a retail and culinary boom that offers residents and visitors a wide range of shopping and dining experiences to choose from.

Neighborhood Attractions

If you’re considering browsing the offerings of Uptown’s diverse neighborhoods, we recommend these shops and restaurants for a combination of fine dining, unique finds, and exceptional service:

  • Sol’s on Sheridan: Korean barbecue at its finest with meat and vegetarian options, classic Korean specialties, and sweet treats to die for.
  • Hopleaf: Belgian-inspired food, beers, wine, and spirits galore, as well as special events such as meet and greets and fish frys make this a community pub worth checking out.
  • The Reservoir: Diners can choose from diverse menu items like the lamb burger, biscuits and gravy, calamari, and even roasted beets with drizzled honey for hearty American fare with a twist.
  • Wooly Mammoth Antiques, Oddities, and Resale: Once your belly is full, check out this unique shop and its incredibly diverse collection of weird and fascinating items.
  • Andersonville Galleria: Shop art, accessories, chocolates, and more in this charming shop that specializes in unique gifts for the whole family.
  • Brown Elephant: The Brown Elephant Resale Shop offers a wide variety of clothes, household goods, trinkets, and more, with proceeds benefiting Howard Brown Health Center.

Who Are We?

At Signature Transportation Group, we are dedicated to providing a unique, one-of-a-kind experience for you and your guests. Use our online tools to contact an associate who can book you a car for your small group, or select a bus for as many as 39 passengers to take advantage of the amenities you prefer without paying for extras you don’t need. Then, relax as one of our professional, liveried chauffeurs picks you up, manages the route, and delivers you to your destination rested and refreshed. From start to finish, we’ll make sure your trip is something you can feel good about.

Explore Uptown Chicago Shopping and Restaurants with Signature Transportation Group

The Uptown neighborhood of Chicago has plenty of shopping and restaurants to keep you busy, so relax and enjoy your top picks with us. Contact Signature Transportation Group at (844) 266-5784 or visit our offices at 2300 Hamilton Road in Arlington Heights to learn more and book your reservations today.