11 Best Date Night Ideas in Chicago

I find going on a date to be slightly stressful and almost a nuisance. Picking out your perfect date night look can be a drag, then if you have to choose an activity… I would be lying if I’ve never uttered the words “I’m hungry but I don’t know what I’m hungry for” The men I’ve dated I’m sure have gotten quite annoyed with my indecisive nature. But living in Chicago I’ve learned this city has some of the most incredible places for the perfect date night. Whether you’re on a first date after matching on Hinge, or you and your significant other are looking for something to change up your usual couch and Netflix date night, this list of activities are sure to keep things exciting.

Lost Lake

Now I live up on the north side of the city and find myself venturing down to Logan Square all the time for fitness classes, my nail salon, and the bar scene. So naturally, my first spot on this list has to be Lost Lake, the coolest Tiki Bar in the city. With the most unassuming exterior when you pull open the front door you are welcomed by a tropical oasis. Their drink menu has won awards all over the world and they even have a fantastic tapas menu. This is a fantastic summer or winter destination for any date night.

Green Mill

The Green Mill is the perfect spot for any music lover or someone you’re trying to impress with your Chicago history knowledge. Mike and I love to hit up the Green Mill when he’s in town, Sunday nights are our favorite but with jazz every night of the week this historic club will never disappoint. Walking into the Green Mill is like walking into history. An old Al Capone club this bar has been perfectly preserved in the best way.


If you’re looking for a unique experience head to Untitled Supper Club for dinner and a show. Every Thursday night is Unbridled their burlesque-style variety shows that is incredibly entertaining. Head down for a drink ahead of time if their gorgeous and moody bar space and stay for the show.

Art Museum

If you’re looking for an indoor activity for a rainy day or if you’re trying to escape the summer heat I always recommend the Chicago Art Institue. Wander the maze of rooms and explore creativity at it’s finest.


I’m a huge space nerd, I love learning more about the planets and stars and what’s the those galaxy’s far far away. So Adler Planetarium is another fantastic option for indoor activities. Spend your day together exploring space, and on select days enjoy the planetarium after hours with Adler After Dark.

Second City

If you’re dating a funny guy or need a good laugh, check out a comedy show or some improve at one of the amazing comedy clubs around the city. See a show at Second City and experience a show at the place where comedians like Bill Murray, Mike Myers, and Dan Aykroyd all got their start. I also love Zanies over in Old Town.

Lincoln Park Zoo/Conservatory

On these summer days, I love being outside, I will happily walk all over the city to explore and enjoy the beautiful weather so that’s why the Lincoln Park Zoo and Conservatory are the perfect excuse for being outside. Both spots have free admission so spend the day wandering through nature and then hit up a spot on Lincoln Square for a nice meal.

Music In the Park

Summers are probably my favorite part of living in Chicago, when the weather gets nicer there is always something going on in just about every neighborhood. But my favorite summer activity has to be the Summer Concert Series in Millenium Park. Seeing live music in the middle of the city with the skyline all around you is incredible. Bring a little picnic and bask in the beautiful summer weather.

Sleeping Village

I think Sleeping Village is a very underrated spot tucked away in Avondale. It has an extensive beer selection and in the back, there is a very intimate music venue. Catch a show or sit out in their hidden yard for a quiet evening date.

Thalia Hall

Chicago has an incredible music scene and is an attractive stop on so many artists’ tours. I think my favorite venue to go to, to catch a show is Thalia Hall down in Pilsen. The venue is beautiful and has great energy, they also have a quiet bar upstairs you can grab a drink at too.

Beatnik On the River

Finally, of course, a nice meal is always an easy date option and luckily Chicago has a killer restaurant scene. While Fulton Market has new restaurants popping up like weeds, I think a seat right over the river can’t be beaten. Beatnik On The River is an incredible restaurant with amazing decor and their outdoor seating has the best view in the city.

Chicago is the perfect city to shake up your typical date night. Explore a new neighborhood, check out a show or hit up a new restaurant. Date nights should never be boring.


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