How to Have the Ultimate Date Night in Chicagoland

Ok, mom. Sit down and listen to me. YOU NEED A DATE NIGHT. And I’m not taking no for an answer. Why? Because it is an excuse to get out of your yoga pants, actually take a shower, and focus on YOU (and maybe even give some attention to your partner or spouse instead of the kiddos) for a change. And c’mon, doesn’t the thought of enjoying a meal without having to cut up someone else’s food sound simply AMAZING? Yep, I thought so.

For those of you reading this thinking of a million other things you should be doing instead of going out on a date…ditch the guilt. Because it will get you absolutely NOWHERE. Believe me, I lived it and learned it. Haven’t you ever heard the phrase, “You can’t pour from an empty cup?” I’m pretty sure that was directed towards overtired moms who have been forced to exist solely on Goldfish and Disney Junior for WAY too long.

Has it been so long since you dusted off your heels and ate at a restaurant that doesn’t have high chairs? Don’t worry, I’ve got you covered. Here are my tips on how to have the Ultimate Date Night in Chicagoland, from babysitters to romantic restaurants and where to find the cutest outfit for your big night out.

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First things first…there is no date night without child care, plain and simple. And when you can’t rely on family members to watch your kids, it can be a bit nerve wracking to have a stranger come and stay with your kids. Thankfully there is K Grace Childcare, a mom owned business that provides fully vetted and trained babysitters that are matched to your family. Another option is drop off care such as Take a Break Play Care if you are open to dropping off your child at the playroom into the late evening hours. Some businesses are even starting to cater to families and include child care in their entertainment package, such as I Do Dance Studio.


One of my favorite things about having a date night on our calendar is that I can then take some time to prep for it and try to hide all of the gray hairs that my kids have given me (and what mom isn’t thankful that ombre color hair is STILL in style to help hide her roots?!?!) and take care of myself. There is nothing better than getting a blow out at Blowtique or JOOJ Blow Dry, and my nails always benefit from some extra love at Noktivo or Egea. And while we are talking about treating ourselves, don’t forget that a date night ALWAYS gives you an opportunity to get a cute new outfit or accessory. There is nothing I love better than a new piece of jewelry, clutch or jacket…and I just tell my husband that it is an old outfit and he totally believes me.


I have already written some articles about my favorite romantic restaurants and spots for delish food and drink, but here’s the thing…I prefer my date nights to be more of an experience. You too? Then check out the Underground Supper Club hosted by All Natural Chicago, or simply open up a bottle of wine and order in food while relaxing at the members only Birch Road Cellar.

We always like to scope out what is offered over on Groupon Coupons and have gotten some great deals on last minute concerts and comedy shows, too! Another favorite is to learn a new skill through activities such as the hands on cooking classes offered at the Chicago Botanic Gardens. And don’t forget to listen to what YOU like to do. Are you more at home attending bingo at your local VFW hall with a pitcher of beer? Go for it! Would you rather sip cocktails at an underground bar like the Watershed? Enjoy! Your date night isn’t for your Instagram or Facebook feed…it is for YOU.

Have fun, mama!
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  1. Alli Smith says

    Our kids are all grown and we’re enjoying our empty nest. We still go on date nights because it’s fun to get out of the house and enjoy fine dining experiences.

    • Amanda says

      Any of your favorite date spots make the list? If not, tell me about your top spots so I can selfishly try them out!

  2. Jeanette says

    You have some very interesting ideas here! I definitely want to go on a date night with my husband, I like a lot of your ideas and although I don’t live in Chicago I can definitely carry over these ideas to where I live.

  3. Pam says

    Great tips and spots to check out for anyone planning a date night in Chicago! I love that you gave childcare suggestions.

  4. Destany says

    We don’t have as many date nights as we should. But we’re more homebodies anyway, and love hanging out with each other at home. These are great ideas, tho! We’re not too far from Chicago – so this is a great list to check out!

  5. Annemarie LeBlanc says

    My hubby and I travel a lot, but usually for business. However, the best times we’ve spent is at home, relaxed, doing movie marathons and stuffing ourselves with snacks. Maybe sometime we can visit Chicago for a romantic getaway. Hmmm… maybe on our wedding anniversary! Yay! Thanks for this date night list. Now we know what to do and where to go if we are ever in the area.

  6. Dee says

    These are some awesome ideas to have when you are trying to figure out what to do for your date night. I would have to share these with hubby so we can start looking to see what else is around our area.

  7. R U S S says

    I like date nights and I think that couples should do them regularly. Both can be creative and there’s something to look forward to. I agree that date nights make one of the perfect ‘reasons’ to treat yourself. Of course, we ladies, still need to look good despite years of being together. I think that matters.

  8. adriana says

    Date nights are so important, especially when you have kids and don’t get out much! I love your ideas! Thanks for sharing!

  9. Natalie says

    My sister in law lives in chicago. I will have to keep these in mind for our next trip. Sadly we rarely get nights out unless we are by family.

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