Looking to plan a romantic night out? Make an unbelievable first impression? Or finally go on that date night you’ve been talking about?

No matter what your relationship status or your date night preference, Chicago has something for everyone. So, skip the stress of planning and get inspired with this list of ideas sure to heat up your Valentine’s Day—or any day of the week!

Savor the love

When you’re in a city full of mouth-watering restaurants that can please any budget or palate, the classic dinner date is always a good go-to. Curl up in an intimate booth, snag a chef’s table for some action or get swept away sharing tapas and stories. You can never go wrong with the West Loop and their showstoppers like Elske (which means “love” after all), Momotaro or The Girl and The Goat.

You can also head to Pilsen to grab dinner at Dusek’s Board & Beer, get drinks at Punch House or Tack Room and even check out a show at Thalia Hall without ever stepping foot outside.

Still craving more? Find the favorites like Geja’s Café and Bavette’s Steakhouse in this list of the most romantic Chicago spots.

Sip & swoon

Nothing goes better with dinner then a swoon-worthy drink before or after. Cozy up fireside at Moody’s Pub. Get adventurous at a speakeasy like Booze Box or Violet Hour. Take your cocktails to the next level at The Aviary or on a rooftop bar like LH Rooftop. Or, pretend you’re on vacation this winter by going to Lost Lake, Chicago’s very own tropical tiki bar. Any of these are perfect for Valentine’s Day, anniversaries and especially first dates.

Catch a show

If food isn’t enough (or leaves too much room for first-date conversation) then a show is a perfect way to shake things up. You can laugh the night away at Chicago’s well-known improv theater, The Second City, show off your more sophisticated side at The Lyric Opera or spice things up with a burlesque show at Untitled. You can even plan a real star-studded date with a Marquee Tour at the iconic Chicago Theatre to go backstage and back in time. If you’re staying at a Hilton hotel, you can get 20% off your tour tickets too.

Stir things up

Put on a show in the kitchen instead with a cooking class. Not only does a class give you both something to do and enjoy, but it basically plans the night for you! There are classic spots like The Chopping Block or The Wooden Spoon and even cocktail making classes like at Chicago’s local distillery Koval.

Get in on the action

Looking to up the ante? Try ice curling at Kaiser Tiger, axe throwing at Bad Axe Throwing (really get that pulse going) or karaoke battles and arcade games at Punch Bowl Social. There’s even ice skating at the Millennium Park ice rink that’s right in the heart of downtown—surrounded by shopping, restaurants and more. Plus, you can get free skate rentals if you’re staying with Hilton! While maybe not a typical date night, these options are sure to be ones you’ll both remember.

Have a spa day

Skip date night and have a day date instead, dedicated to rest and relaxation. Treat yourself to a massage, mani and pedi, facial—whatever your heart desires. You can’t go wrong with the award-winning Waldorf Astoria Spa & Health Club or The Spa at Palmer House for an hour….or five. Another spot to escape to is Aire Ancient Baths. Just like the name suggests, this spa features an assortment of thermal baths and calming rituals to leave you glowing and refreshed.

Take a staycation

Why not go big this Valentine’s Day or for an anniversary? Book a night at a luxe hotel and be a visitor in your own city. Sometimes we forget to stop and take in all we have at our fingertips in Chicago, and staycations are a perfect way to not only reconnect as a couple but reconnect with this amazing city! Stay downtown at The Conrad or TheWit Hotel and explore the museums, shop along Michigan Avenue and snag a reservation at one of the spots we listed above. Or, you can splurge on a night at The Waldorf Astoria and give yourself the royal treatment. After all, you are celebrating so enjoy!


Header photo credit: Adam Alexander Photography


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