It’s summertime, Chicago lovers, which means that colorful sky doesn’t hit the horizon until about 9:00 pm. 

With dusk happening so late, you’ll have the perfect romantic backdrop when daytime turns into date time. There will be no hot dogs or lame dinners here -- only fun, exciting, date ideas to light up the night.

Fun in the sun? How old school. The real fun begins when the lights go down and you get to turn up with bae.


You'll Be Counting Stars

Night Kayak
Chicago Date

It’s time to change up your dating scene. So get your sea legs ready, because you’re leaving land for a bit. Take your bae off the shore and into the middle of the Chicago river, where you’ll experience the most relaxing, romantic, and tranquil date of your life.  

See the lit up city sparkle along the bank of the river, and then look up to view a sky splattered with stars.  Paddle along as stroke by stroke the mood is set and you become one more star in your bae’s eyes.   

Discovery Center

They See Me Rollin'

Chicago Date

Tired of the same old bars, dates, and drinks? Grab your boo and bring them along for what’s sure to be a new and unforgettable night. First off, ditch the early happy hour -- you can bond over booze later.

Instead, trade the brandy for a bike and get fit before things get lit. On a nighttime Chicago bike tour, you’ll cover major landmarks of the city and see them under the glow of the moonlight.  Between the beautiful setting, the wind in your hair, and those flowing endorphins, you’ll be wishing the night would never end.

And it doesn’t have to -- the real question is, where do you go next?

Bike and Roll Chicago

Making Your Way Downtown

Helicopter Tour
Chicago Date

Looking for a date idea that will establish your reputation as a straight up baller? With a nighttime helicopter tour over Downtown Chicago, you can do no wrong.  

Rise up above the city and view all of the glimmering buildings underneath the slowly darkening sky. Impress your date with your knowledge of the city, or just let the view from up above speak for itself. The views are bound to be unforgettable -- almost as unforgettable as you’ll be to your date after pulling the helicopter card.

AM Air Service

Dancin' In The Dark

Night Cruise

Who said Mondays have to be tough? Start your week off right by making the most of thrilling Chicago nightlife. Grab your bae and hop aboard an after-work-cruise, which will wipe away all those Monday blues.  

Watch the sunset above the stunning Chicago skyline as you woo your boo. After enjoying some, ahem *strong* beverages from the bar, it’s time to hit the dance floor and top of the night with some sick dance moves. The city will set the mood, leaving it up to you to do all that smooth talking you’re known for. Ball’s in your court. (Or in your boat in this case.)

After Work Cruises

Kicking it Old School

Interactive Dinner

Get out of your comfort zone with a twist on your average date night. See what the old-time Chicago night life was like at the only speakeasy dinner show in the city! The entertaining will be done for you as you watch singing, dancing, and non-stop entertainment.

Enjoy a lively dinner across from your guy or girl, but don’t get too comfortable, because this show is full of audience participation. It’s the better version of a dinner date! Think you can handle the spotlight? We hope so, because if you’re called to participate it’s all eyes on you -- and that date of yours will be watching closely.

Tommy Gun's Garage