A Perfect Date Night in Chicago

Spend no more time stressing and scrambling on where to take your date for your night out! Come down to Chicago for a beautiful night in the city where the options are endless. These ideas are close by and within walking distance of each other with our Michigan Avenue Dock being the middle man!

Regardless of the occasion and whomever you plan on going out with, these activities are perfect for different occasions! It’s hard not to enjoy a night out in the city! Whether your family is in town, they’ll love seeing Chicago in these unique ways at beautiful times. A significant other will enjoy the city sunset scene as an intimate date with you! You and friends can also enjoy these ideas by catching up with food, drinks, and things to do!

Kickstarting the Night

A good date night restaurant we’ll guide you with whether its the first date or the fifth date starts at Moe’s Cantina in River North. Here you can order authentic Mexican food and enjoy the modern ambience. Perfect for an upper scale casual night out. With a variety of taco plates, plates to share, traditional Mexican plates!

Moe’s hosts a Taco Thursday, order as many tacos as your stomach can handle at a price of $4 each. This is a perfect way to try a bit of everything! To pair with your tacos on Thursdays, drink a $4 Tecate and they also have $4 shots of Tequila! If you find yourself having a date on a weekday like a Friday after work, come for their happy hour menu.

Happy Hour is available from Wednesdays through Fridays from 4 to 6PM. Within this two hour time frame you can sip on their traditional lime margaritas and palomas for only $8. For those looking for non-alcoholic drinks, Moe’s has Heineken Zero, Horchata, and more options!

The happy hour menu offers two delicious food options that are perfect for sharing with others. Indulge in their nachos, loaded with toppings on a bed of their house made tortilla chips. Try their elote, mexican street corn right off the cob to avoid the mess and still enjoy the flavors!

A Scenic Sightseeing Activity

After dinner, go for a quick walk to 401 North Michigan Ave to find the dock for our Architecture Tours! Our boat tours are versatile for various occasions, and occurring frequently for the customers convenience. That way you don’t have to rush during dinner or your walk!

Our tours are great for a date. A docent is teaching you in a fun way about Chicago’s Architecture that you can listen to upstairs. Or head to the lower deck towards the bow (the front of the boat) for a more intimate area that has limited seating. Here you are more open to your own conversations while still enjoying the Chicago skyline up close.

While you can make your own schedule and follow your own pace, we suggest the tour between 6:30PM through 8PM to hop on. This way you can catch the perfect sunset view along the Chicago River. Continue your flow of drinks if you would like with our full bar on the lower deck with some small snacks for options! The length of the tour is 75 minutes, not too long and not too short.

One Last Stop for the Night

Once you disembark our 75 minute tour, you can discuss your favorite buildings and highlights of the tour while heading to the Merchandise Mart. This is about a 15 minute walk. Head down to the riverwalk after the tour for a more scenic stroll the last activity for the night! Along the riverwalk are a couple of options to grab a glass of wine or cocktail for the show!

Art on the Mart is a dazzling projection show presented on Chicago’s own Merchandise Mart. The building acts as a huge canvas for featured artists. The show can be visible from Wacker Drive along the river. They built a viewing platform to make it comfortable for viewers.

We are currently in the first block of showings throughout the year. They run from April 12th through June 5th from 8:30PM to 9PM, June 6th through September 11th 9PM to 10PM. Then, they finish the year from September 12th through December 30th from 7:30PM to 8:30PM.

Watch the show with a drink and your date by the river in Chicago. Enjoy the view of people and boats passing by, creating a beautiful and memorable Chicago night scene! This is a great casual but unique idea to end the night before you say goodbye.

Follow these ideas for a fun night into the town or let it be some inspiration! Come back and check out our blog for our future date night posts for more! Your guide to our date night ideas in Chicago to make it easy for you!