Highland Park Family Guide! | Chicago North Shore Moms

Highland Park Family Guide!


Highland Park is one of the larger areas on the North Shore along Lake Michigan with two main business districts, Port Clinton Square and Ravinia District. One of things we love most about this area is the large Park District that offers SO many recreation options for every age like Hidden Creek Aquatic Park, or Yoga at Rosewood Beach.  

Port Clinton Square gives the feel of the Chicago Neighborhood Southport Corridor, with big name shops like Blue Mercury, Free People, Anthropologie, and Pottery Barn, mixed with local boutiques and restaurants.  It’s a one stop destination for just about everything you might need, for everyone in your family!  




That Little French Guy is Delish all around with filling breakfast/brunch options like challah bread french toast to variations of avocado toast. The interior is French inspired with even a french radio station playing in the background!

Bluegrass Restaurant is the place to go for really great fish and excellent cajun food.  It’s our go-to special restaurant, but they have a really nice kid’s menu, too!

Coffee Speaks is a hidden gem of a coffee shop.  We say that because it’s a little hidden, and it’s great!  Located inside Port Clinton Square, their coffee and tea both hit the spot, the breakfast treats are tops and it’s convenient when shopping the area!  

Love’s is a go-to ice cream and fro-yo place. I love that you can get both here. It’s actually hard to find frozen yogurt these days!  We also like Sweet Home Gelato in Port Clinton Square.  

Food Truck Thursdays is a huge draw in the Summer months with multiple rotating food trucks and live music each week.  It’s so much fun for families, and a must do at least once! Be sure to follow, City of Highland Park for weekly events! 




Anytime Ellie needs a gift for her daughter’s friends or a friend, Style Shack is where she lands.  They have unique options in any price range and everyone is helpful and welcoming.  They also have a great selection of pretty, unique hand wash that I love! 

We love a stop in Beanstalk Toys for kids gifts.  The staff is friendly and they have a unique selection, plus free gift wrapping to make things super easy!

A short walk from Beanstalk Toys is a favorite clothing boutique of mine, Central.  Think Mom-Uniform upgraded!  This is a shop that’s hard to walk out of empty handed.  They also have a mens shop and juniors!  

Ross Cosmetics is an ode to the general store and I love that we have this in Highland Park. I come here for my Elta Sunscreens, hair care, camp gear, birthday gifts, and novelty candy for my kids. These ladies are on it when it comes to customer service!

I’ve been visiting Lotus Nails for the last six or seven years, and many of the techs have been there much longer!  I love that it’s bright, clean and consistent. They do a great job each time.

Lori’s Shoes has been a staple since our early Chicago days in the city.  This shop is great not only for summer sandals, but for cute summer dresses that are budget friendly.


Rivinia District is a quaint little strip and as the name implies, right next to Ravinia Festival grounds.  If you haven’t been to Ravinia, this is a North Shore MUST over the summer!  From throwing down a blanket to elaborate picnic set ups, this is the best place to listen to live music in the burbs! 

Ravinia Brewing Company is just down the street and is great for family dining, and the Ravinia Farmers Market runs late Spring through Summer each week.



Welcome to Highwood!  Small in size, but big in character this is where the cool kids hang on on the North Shore!

28 Mile Vodka Distillery for great drinks, and live music in a super cool space.

Longetude351 is fantastic!  I absolutely love the food here and could probably drink the chimichurri sauce. Lol

Del Rio restuarant has great Italian, with a nice basement room for quieter dining when you’re not in the mood for a boisterous dining room.

Alex’s Washington Gardens is a super family spot owned and operated by two super North Shore families!  The kids order the pizza, the adults order the fish- both are good!

Highwood’s Evening Gourmet Market is a must stop at least once over the summer. Typically this occurs on Wednesday nights and is host to kid’s activities and delicious food tables by local restaurants.  It’s a favorite way to spend summer nights in the North Shore!  Highwood also goes all out seasonally with festivals and events.  Be sure to follow on Instagram to stay in the know!

The Neighborhood and Realtor Guide is sponsored by our featured agents.  We appreciate their support of local businesses and park districts!  In the spirit of providing stellar, tried and true content for our viewers, the businesses shared are by personal experience and our own opinions.  We love where we live and will continue to share as we continue to explore Chicago’s North Shore! Thank you for following along and your continued support!

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