The Best Date Night Spots In Chicago

Mar 7, 2018

plaid topshop skirt

Turtleneck: Madewell – love this version and this pricier one is totally worth it! | Skirt: Topshop – love these paper bag waist skirts and think they will be so easy to transition to spring and summer | Boots: Stuart Weitzman also available here – love this more affordable version and this waterproof one! | Handbag: Chanel – similar affordable version! | Lips: NARS


Having my mom in town the last few weeks has been a real treat! Not only do I love watching her and Zain but Trevor and I have been able to get out for a few date nights too. I won’t lie, it’s been a while since we ventured out without Zain and it’s been really nice to get dressed up and try out new restaurants. 

Since we knew we had a few weeks I reached out to my girlfriends and did a little bit of my own research and compiled a list of the best date night restaurants we wanted to go back to or try for the first time and thought I would share. 

This outfit was one of my favorites for date night so thought today’s post was the perfect way to pair the two. I haven’t worn my boots as much as I would like for some reason this season but I absolutely love the way they look with skirts. This new line of skirts from Topshop that have the paper bag waist are perfect because they have an elastic band and it’s really easy to play with where you want them to sit on your waist. I paired it with a tissue turtleneck since it was still pretty chilly and thought it was comfortable, left room for eating but still so chic. I always recommend showing just a tiny bit of leg when you pair skirts with over the knee boots so it looks classy šŸ˜‰ 

I also receive a ton of questions about over the knee boots and how to choose so I shared a full breakdown previously. I also found these affordable dupes that I’ve actually tried on and think fit most like the Stuart Weitzman Lowland boot if you are still searching! 



Le Colonial 

A favorite of mine for date night or girl’s lunch really! I love almost everything on this Vietnamese menu (get the fried rice) and the ambiance is so romantic at night. 


Tango Sur

A date night recommendation from my friend Blair that didn’t disappoint! I believe they only take reservations by phone but we just went. It’s a sister restaurant that we have been to in Wicker Park called Folklore (true story: Trevor saved a woman’s life there by giving her the Heimlich) and the filet was to die for.  



A Peruvian recommendation from tons of friends downtown that we haven’t made it to yet but they do take reservations so it’s on the short list!


Piccolo Sogno 

Another spot I love for date night and girl’s night! I think it’s best during the summer when you can sit outside under the lights on the gorgeous patio. 



If you guys haven’t been, go! So romantic inside and the food is phenomenal. They have huge portions that are perfect for sharing and do yourself a favor and get the chocolate cake. 


Maude’s Liquor Bar

A cozy spot in the West Loop that has a similar vibe to Bavette’s. The food portions here are also huge to me and perfect for sharing. We love their cocktails too!


Ada St.

A spot in Lincoln Park we’ve been to several times and don’t mind because their menu is constantly changing. 



A newer spot in West Town that I first went to with my girlfriends! Loved the ambiance and decor as much as the food and am actually dying to go back for brunch. 



A South Loop favorite where we often just grab a seat at the bar and order the burgers. The tasting menu can get pricey but the food is always amazing. 


City Mouse & Giant

Sister restaurants that we are dying to try! Friends have recommended over and over again and just hoping one day soon I can plan far enough ahead to pick a date and book one! 


Boarding House

Finally just went this past weekend and we loved it! No matter what glass of wine you pick on the menu, you will love it! Some of our favorites were the burrata, shaved brussels sprout salad, scallops and short rib!


Do you guys have any date night spots you would add? 


topshop plaid skirt

chanel flap bag

chicago mom blogger

stuart weitzman lowland boots

easy winter outfit

chicago fashion blogger

plaid topshop skirt

affordable winter outfit

chic winter outfit



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  1. Ellen says:

    Thankful for this post! Nom noms always looking for suggestions ????

  2. Kat Barto says:

    You should try Cellar Door Provisions! They do dinners on Friday and Saturday nights, and have an amazing breakfast. Their quiche is otherworldly! I honestly believe they are making some of the best food in Chicago right now. You won’t regret it!

  3. Carolyn says:

    Love this post! Great suggestions. Iā€™m dying to know what some of your favorites were from Boarding House since it stops mid-sentence. šŸ˜›