My Favorite Date Night Restaurants: Chicago (and Those to Avoid!)

My husband and I keep our eating out relegated to the weekend. This is huge considering that, for the first three years of our relationship, my husband ate out three meals a day, six days a week! We challenged ourselves to change our behavior when we decided seriously that we needed to save money for buying a home. If we find somewhere that we really like, we will visit and re-visit it, as we have had far too many mediocre or altogether unpleasant meals.

Here are some of the Chicago date night restaurants we love to visit ,and even some that I think are best to avoid!

Favorite Date Night Restaurants Chicago: Heritage Caviar Bar

This restaurant is so delightfully unique in a city full of sameness. If neon catchphrase wall art, $12 avocado toast, and burrata appetizers are your must-haves, keep walking. If you appreciate menus with food you’ve never tried before, e.g. chicharron and different styles of caviar, stick with me. While mores may dictate that caviar is devilishly pricey, Heritage offers a range of caviar, making it more approachable than what you would expect.

What else: The servers and bartenders at Heritage know that you probably won’t be very familiar with caviar. They’ll help guide you with what is best suited for you, and then pair it with a great beverage.

Favorite Chicago Date Night Restaurants: Le Bouchon

According to The Perry Group, 70% of restaurants that survive one year in business will fail between the third and fifth year of incorporation. Le Bouchon has been a staple in Wicker Park since 1993. They are doing something right, and that something is French food. Mon Dieu. It’s not just that the food is exceptional. Le Bouchon authentically captures the feeling of a tiny French bistro. It’s a bit tight, but too small to be crowded. The tables are right on top of each other, but it’s wonderfully Francais. I don’t say that often about buzzy restaurants, but this one is a gem.

Ramen San: Not A Good Date Night Restaurant in Chicago

Lettuce Entertain You knows good food. They also know how to create a trendy, in-demand restaurant. It’s not bad for a girls night out, but my goodness, these places are loud, crowded, and terrible for dates. You can’t hear a thing, and good luck actually being sat on time. The food is great, but stick to take out.

Nic’s Organic Fast Food: A Fun Date Night Restaurant

Who doesn’t love a good burger joint? As the nation’s first fully certified organic fast casual restaurant, Nic’s Organic Fast Food has something for everyone. With vegan, organic, and gluten free nuggets and burgers, there’s plenty to eat. Not only that, there is kombucha on tap, artisanal sodas, and seasonal shakes and sundaes. In the winter, my husband and I love a weekend skate date followed by these burgers and shakes.

Favorite Date Night Restaurants Chicago: Bar Biscay

After visiting the Basque Region of Spain and France, I couldn’t get enough of pintxos and wine. How lucky it was that my sisters-in-law told me about a restaurant in West Town that specialized in Basque cuisine. It’s trendy, but the booths are incredibly cozy and private. If you are going on a date, see if you can request a booth. Other seating is available at tables and the bar, but my preference is for the booths. The booths let you get lost in your date and provides ample room to try all the dishes!

Chicago Date Night Restaurants to Avoid: Point and Feather

While the food and drink options should always be the star of date night, ambiance is obviously quite important. Some things can be corrected, like switching tables instead of sitting under an air conditioning, and often that is done as the result of an attentive waitstaff. When I visited Point and Feather for dinner one evening, it was so loud that I couldn’t hear my husband sitting across from me. It was 8:30 PM on a Friday night, so I didn’t think it would be an issue to ask if our server could have the music turned down a bit, or move us to a different table. She said she couldn’t, and then her manager came over and told us that we were at a bar, so we had to “deal with it.” We finished our meal with hoarse voices from shouting to one another, and urge you to avoid it if you don’t want to go on vocal rest the following day.

A Favorite Date Night Restaurant in Chicago: The Bar at Acadia

Acadia is a Two Michelin Star restaurant that is simply out of our price range for a frequent date night spot. The bar isn’t though! With the same kitchen and many dressed down options from the dining room, the bar at Acadia is delicious. Consisting of a couple high top tables, four low top tables, outdoor seating, and of course barside stools, it really is spacious and inviting for diners. The drinks are superb, the ambiance is fancy but not uninviting, and you can manage a great meal for two under $100.

Fogo de Chão: A “Something for Everyone” Chicago Date Night Restaurant

My husband loves red meat, but I pretty much avoid it except for in burgers. One place that satisfies his desires for all the red meat he can stand, and also all the seafood towers and salad bar I could ever desire, is Fogo de Chão. This Brazilian steakhouse allows for full churrasco meats of every style for my husband, and a more affordable “salad bar only” selection for me. The small tables along the rope wall are particularly romantic and intimate, and make for a great date night in Chicago.