Chicago Date Night Black Dress

Chicago Date Night Ideas

With demanding careers and two little ones at home, Jon and I try to make it priority to schedule a date night twice a month. Yes, schedule. Gone are the days when we could sporadically grab dinner after work or see a last minute movie on a Sunday evening. We are parents. Life is different. Here are some fun suggestions to help you get out of that rut!


  • Great way to converse, connect, chat about non-kid or logistical stuff. Get out of the house, put on a pair of heels and dangly earrings (dangly? Really? Who am I? My mother? #loveyoumom).
  • Some of our fave restaurants (we are not sceney people at all):
    • Greek Islands, Oyster Bah, Blind Barber (super fun speakeasy type place, I feel like we are late to the party here), Tied House (tip, full menu available at the bar!), The Warbler, Somerset
  • Spots we’ve been wanting to try:
    • Gibson’s Italia, RPM Steak, Twain


  • Pop-Up Events Like the Happy Place; still going on! See my pics HERE.
  • Movies
  • Bowling – Love the vintage 60’s vibe of King’s Bowling at New City
  • Concerts
    • Green Mill is a fave for a slower evening, great jazz music, delish martinis. Go early to get a seat!
    • Ravinia is a MUST! Bring your little table, blanket, gourmet spread and let the love & romance fill the air. We are seeing OAR Labor Day weekend with friends and are psyched!
    • City Winery has great musicians and yummy wine.
    • The Promontory in Hyde Park has the coolest vibe and gets the best talent.

Let’s Get Physical

  • Bike Ride along the Lake – picnic and watch the fireworks. A great way to use our annual Divvy membership!
  • Compete against one another at FlyWheel or OrangeTheory – both utilize scoreboard techniques to push you!
  • Diversey Driving Range

What are some of your fave date night activities? Or new restaurants to try?



Chicago Date Night Ideas White Brick

Dress, Ted Baker // Shoes, Sam Edelman– on sale!!// Purse, Saint Laurent // Earrings, Baublebar // Sunglasses, Chanel (old)

Chicago Date Night Ideas Blue Door


Chicago Date Night Outfit


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