The Chicago Theatre

There is a reason why locals love this theater so much, and if you take theatre tours, you’ll instantly see why. The theater is equally magnificent today, as it was back in 1921 year, when was opened. Its iconic marquee six stories high, a remnant of its past, and big block letters CHICAGO are hard to miss.

Some of the biggest names in entertainment do their performance in this theatre. Kelly Clarkson, Paul Simon, Neil Young, Gipsy Kings, Ellen DeGeneres, Jerry Seinfeld and many others have left their marks on the stage of ChicagoTheatres. So, pay close attention to the Chicago Theatre concert calendar if you want to catch your favorite acts.

The Garfield Park Conservatory

For many people, this is one of the top romantic things to do in Chicago. Designed by William LeBaron Jenney in 1908, the conservatory is often described as "landscape art under glass". It is open 365 days a year, and it is free, but there is a requested donation at the door. Beyond a routine visit, you can also find various workshops and events throughout the year, from seasonal flower shows to cooking and crafts classes.

Chicago Architecture Foundation Tours

For those who enjoy architecture or want to see and learn more, the Chicago Architecture Foundation runs a variety of tours to showcase these impressive works. Tours are available late April through mid-November and run about an hour and a half in length. Some of the most popular tours are the river cruise tours on the Chicago’s First Lady. Seeing Chicago's architectural beauty is something you must do.

The Alfred Caldwell Lily Pool

Also known as the Lincoln Park Lily Pool, this oasis, has become a popular place for small weddings since it was restored in 2002. The Alfred Caldwell Lily Pool was designed by Alfred Caldwell in 1936, and it presents an outstanding example of Prairie School landscape architecture. The curving walkways, winding stepping stone limestone pathways, and circular benches…,  you can feel that romantic vibe everywhere.

Ice skating at Millenium Park

Perhaps you will fall in love here, at Millennium Park's McCormick Tribune Ice Rink. And if you don't know how to skate, there are free skating lessons every Friday, Saturday and Sunday an hour before the rink open. After skating, you can go for hot chocolate, and you’ve just got your perfect date.

Escape story Chicago

The coolest way to spend your date night is playing an interactive game – escape room. While many couples go into a crowded restaurant or watch the movies for two hours, you can take your partner in something way more interesting - Escape story Chicago. This real-life adventure game in which players solve a puzzle and riddles using clues and strategy, in order to escape the room within 60 minutes, is something that will both give you a great memory and conversation, the adrenaline rush, a lot of fun and joy.

And after you have escaped the room, you can go on for a drink together and round off the perfect night.