If flowers and a box of chocolates have always been your go-to for Valentine’s Day, this year, you probably want to do something different. Something out of the box. Something special to spoil your loved one. If you have yourself scratching your head with no idea where to start looking or what you could possibly do, fear not. Folks, we’ve lined up some of the top activities, places, and locations for you in Chicago this Valentine’s Day to make it a completely unforgettable one. Let’s take a closer look.

Get out in nature

While Valentine’s Day falls in the middle of winter, it doesn’t mean you should stay indoors. There are plenty of outdoor things to do and see in our gorgeous city. Jackson Park is one such spot. Featuring the absolutely splendid Osaka Garden, you’ll literally feel as though you’re in a Japanese woodblock print. It was designed by one of the landscape artists who designed Central Park in New York. It’s like walking into a piece of art. It will be both mesmerizing and special.

And speaking of mesmerizing, the Chicago Botanic Garden will soon feature its Orchid Show with over 10,000 blooms from around the world. A perfect way to indulge your senses and immerse yourself in something out of this world.

Get a taste of some wine, spirits, or cocktails

After being out in nature for a bit, you’ll want to warm up. And the perfect way to do that is with some wine, spirits, or cocktails. Chicago offers you plenty of options to choose from with the first on our list being wine tastings at the Wild Blossom Meadery where you can not only learn how wine is made but take part in some wine stomping, too.

And now we turn to the spirits. The Koval Distillery has a new tasting room in Ravenswood. Here, you can enjoy both tours and tastings, as you go about learning more about your favorite spirits.

Of course, we won’t leave out the cocktails! Chicago offers plenty of choices. You can head to some of the all-season rooftops such as the I|O Godfrey, Whiskey Business ski chalet in Wicker Park, and ABA’s rooftop with incredible west-loop skyline views and a rooftop patio.

Grab a delicious dinner

Now that you’ve warmed up with cocktails, it’s time to consider your meal. Now is the time to heat up the romance. Special. Unique. WOW! And of course, delicious. Luckily, there’s plenty of choice in Chicago and we start off by suggesting truly romantic places like Geja’s Café, a romantic fondue restaurant with twinkling lights, classical guitars, and flamingo music, Maple and Ash on Rush with master mixologists, an extensive wine list, their famous roasted seafood tower and special risotto frutti de mare, Ada Street (a farm-to-table type of cozy layout), Le Colonial, Bavettes, Gibsons Italia with a sexy, romantic vibe, as well as Tango Sur and its sister restaurant Folklore (in Wicker Park) offer enormous portions and they are both budget-friendly.

Other options you might consider include Adelina one of the most romance spots in Chicago and a cool basement Rose Lounge. Then there is BLVD, total elegance with old Hollywood-style vibes. Gemini Bistro is in Lincoln Park, Duck Duck Goat where you can get amazingly good Chinese food, Osteria Langhe in Logan Square, Le Bouchon (Parisian style bistro), and of course, there is Heritage – with an Eastern European menu.

Enjoy an evening performance

You thought that after your meal your evening would be over? Think again! Because The Newport Theater in Lakeview is transforming into an intimate Valentine’s speakeasy. The Raks Inferno: A Valentine Speakeasy will feature circus-inspired cabaret performers from all over the world.

Having been described as “absolutely electric”, you will have a phenomenal and unique show in this underground theatre. Some of the highlights will include fire spinners, bellydancers, and circus artists who have performed for audiences around the world including Germany, Morocco, Costa Rica, and the Czech Republic.

Spoil your loved one at a hotel

And to top off the evening, spend a night in one of Chicago’s signature hotels. If budget is something you are conscious of, then these ideas may help you out. First up, we have The Publishing House Bed and Breakfast. It is situated in a historic 110-year-old building. As a boutique hotel, it offers 11 different rooms of varying sizes.

Other options you might consider include Peninsula Chicago, offering a five-star getaway. It comes with some spa offerings and an indoor pool on the 19th floor. Exquisite to say the least and one of the best romantic hotels to celebrate Valentine’s Day.

If these don’t really meet your needs, you can always check out Viceroy Chicago (Gold Coast neighborhood), Villa d’Citta (think Italian vibes), The Hoxton (West Loop), The Langham Hotel (featuring views of the Chicago River and Lake Michigan), Nobu Hotel (also in the West Loop), Lowes Chicago (Streeterville), and Waldorf Astoria Chicago (guest rooms average 890-square-feet).

Have a spa day or do something completely different

We already mentioned the Waldorf Astoria Chicago as a possible destination for a lovely evening. But it also offers a spa day option as does the Four Seasons. Both offer incredible experiences, especially if you are ready to splurge a bit more than usual.

And our final recommendation is the AIRE Ancient Baths. AIRE is a restored 1900s factory that has been turned into a spa. Here, you can get into a bath filled with red wine. And for an even more romantic experience, why not try the Wine Bath for Two? The antioxidants are good for you, and so is the wine itself!

Getting around from location to location

If these ideas for Valentine’s Day in and around Chicago sound good, your final step in the planning process is to ensure you can get around. It goes without saying that the last thing you want to do is drive yourself or take a cab from location to location. Instead, think of booking your transportation needs with us at Bus Connection. We offer a variety of different-sized modes of transportation, including a full-size luxury SUV. Leave the road, navigation, and parking issues to us while you enjoy a splendid evening with your loved one. Cheers to an incredible Valentine’s Day this 2023!