Guide to all the Best Chicago Neighborhood Spots

Throughout the years we have been to the windy city many times. In this guide to all the best Chicago neighborhood spots we will highlight all the must see places to eat, drink and explore.

We have been to Chicago for Christmas time, St Patrick’s day, 4th of July, and have even hiked a trail outside of the city. Another favorite Illinois town is Galena especially if small towns are more your style. Galena is a place many people from Chicago flock to in the summer months.

Guide to all the Best Chicago Neighborhood Spots: Logan Square

Logan Square is known for its many Greystone buildings, vintage Logan theatre with cute cocktail bar and the famous Chicago mural.

Navigator Taproom

Pour your own beer at Navigator Taproom’s beer tap wall. This place only charges by the ounce. Therefore, you can sample them all if you choose.

Pilot Project Brewing

  • Modern and cozy
  • Serve coffee and kombucha drinks
  • Always busy

Guide to all the Best Chicago Neighborhood Spots: Wicker Park

Wicker Park is known for its nightlife, art an food scene. This hipster neighborhood is ever changing and home to many affluent Chicagoans.

Emporium Arcade

Arcade and bar in one stop at Emporium Arcade in Wicker Park. Play skee ball while drinking a craft cocktail. It’s a modern day adult arcade.

Guide to all the Best Chicago Neighborhood Spots: Paradise Park

Paradise park is full of glitz, shiny d├ęcor, loud music, delicious pizza, and fun drinks. On a nice day check out their rooftop patio.

Eli’s Ark

  • Ice-cream toppings shaped like animals
  • Dairy free options

Whiskey Business

  • Craft cocktails with fun names
  • Rooftop patio with turf floor
  • Fun atmosphere

Guide to all the Best Chicago Neighborhood Spots: La Grange

La Grange is a suburb outside of Chicago. Its a cute village with great walkability from shops, restaurants, and quaint coffee shops.

Wheelys Coffee

Wheelys has delicious bakery items and an assortment of different coffee flavors.

Blackberry Market

Great lunch spot with fresh food. First, check out all the market items and order food with the cashier. Second, take the number to an open table of your choice. Lastly, devour every last thing you ordered.

Owl and Lark

  • Earthy with many plants placed throughout the space
  • Something to drink for anyone with coffee, smoothies and juice
  • Great people watching table by the window

Guide to all the Best Chicago Neighborhood Spots: Lynfred Winery

Lynfred Winery is outside the city. However, worth every second of the drive. The grandiose house can seat many people inside and outside. We were lucky to arrive on a nice day to sit on the patio out front in the sun.

Guide to all the Best Chicago Neighborhood Spots: River North

River North is located directly in downtown Chicago. This is where they dye the river green each year Saturday prior to St. Patrick’s day.

Northman Cider

There is food, cider, river views, occasional live music and great people watching at Northman Cider in the Summer.

Jojo’s ShakeBAR

Are you in the mood for a shake, booze and boozy shakes? Also, I was pleasantly surprised by how scrumptious the food was at Jojo’s.

Heaps Giant Pumpkin Farm

Make the drive to Heaps Giant Pumpkin Farm in Minooka September through October. Each year, Heaps allows people to purchase bucket to fill with as many flowers that fit inside it. They have the largest zinnia field and sunflowers galore.

Brookfield: Owl Social Pub

  • Games
  • Tacos
  • Large selection on beverages
  • Cozy industrial atmosphere


Andy’s Frozen Custard has over 100 locations across 15 states. Watch the custard being made and create your own treat with as many toppings as your heart desires.

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