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Date Ideas in Chicago

A couple holding hands.

At first, it seemed like 2020 was not a year for dating but many are now saying it merely changed people’s approach to it. Isolation restrictions meant people became far pickier about who they were going to spend their precious outdoor time with. The world surprised itself with the creative alternatives people came up with. The year when couples got into jigsaw puzzles, a man asked out his neighbor via drone and then subsequently went on their date in a bubble suit. Don’t let the bleak start to 2021 bring down your dating game, Chicago has plenty to offer to keep you entertained. Here’s our guide to the romantic date ideas Chicago has to offer.

First Dates

First dates can go either way, some people like to go all out and impress from day one, whereas others like to keep it low key and surprise their date with a quirky idea rather than flashing the cash.

If you’re looking to stand out from the get-go, why not treat your date to takeout from Chicago’s award-winning Boka restaurant. The eatery, located in Lincoln Park, has acquired 7 Michelin stars over its 15-year history. Their weekly changing menu is available for delivery or pick-up and is sure to impress your dining partner.

If you’re looking for something outside the box, consider a drive-in movie theater. ChiTown Movies in Pilsen and the Chicago Drive-In of Bridgeview are both good options adhering strictly to social distancing measures. Make the evening romantic by preparing a gourmet picnic. But don’t forget the blankets and a flask of something hot!

Dating in Your Bubble

For couples who have been in lockdown together, it’s hard to get out of the daily routine of working, cooking, eating, sleeping. We’ll try our best to tempt you with some irresistible date night activities.

Make the most of the weekends and get out into the fresh air. Wander hand-in-hand down the Lakefront Trail and gaze out over the frozen lake at sunset. Or get out on the ice yourself with a visit to the rink at The Forge in Lemont Quarries Adventure Park. Reservations are required, as are masks and social distancing. It’s an opportunity to enjoy the outdoors in safety.

If you haven’t already, now is the time to explore all those places in Chicago you’ve always meant to visit. Venture into Chicago Botanic Garden with your partner. The cafe and greenhouses are temporarily closed due to COVID restrictions, but there are plenty of other areas to explore. Walk through the Japanese Garden, check out the miniatures in the Dwarf Conifer Garden, and watch the sun go down between the Roman pillars in the Enabling Garden.

For the couples who connect over a dish of something delicious, shake up your normal cooking routine with a virtual cooking class with chefs from the aforementioned Boka restaurant. Learn to make some of their signature dishes like black truffle stuffed chicken and homemade pasta from scratch. Not only will you receive the guidance of an expert chef, but you’ll also be sent the top-notch ingredients to cook with. After cooking up a storm with your other half, light some candles and sit down to the gourmet meal you’ve cooked together.

Sniff and swirl your glasses in an online wine tasting session with your one and only. Check out the virtual tasting offered by City Winery, an urban winery in the heart of Downtown Chicago. The semi-private activity is as stress-free as it gets, simply choose the package you want for your romantic evening, select a date, and City Winery will send you the wines! All you need to do is tune in on the day and enjoy. The tasting will be led by the winemaker and supported by the virtual party host to ensure guests are entertained. If you want to make the evening particularly special, why not add on a cheese or charcuterie board? It’s a great option for those looking for date ideas in Chicago without having to mingle in big crowds.

Dating at a Distance

For those who are quarantining or separated from their other half, we‘ve got you covered too! There’s no need to think distance means dating is dead. If 2020 has taught us anything it’s that with a bit of imagination and innovation we can entertain ourselves pretty well.

For the culture vultures, curl up on the sofa with a glass of wine to watch the Joffrey Ballet perform or rehearse Bolero or Under the Trees’ Voices. You and your partner can watch from your separate homes while you Zoom to catch a glimpse of each others’ reactions and chat during the interval. If ballet isn’t your thing, enjoy a group virtual tour of the Notorious Rbg: The Life And Times Of Ruth Bader Ginsburg exhibition put on by the Illinois Holocaust Museum & Education Center.

Why not challenge your date to an online game of Settlers of Catan? The widely popular game is now available online, making it the perfect entertainment for a video call. Then, when you’re able to see each other again in person, you will have honed your skills enough to have a nail-biting game.

Valentine’s Day Chicago Style

This Valentine’s Day, we’re showcasing the romantic date ideas Chicago has to offer. Whether you’re deciding to spend it at home or hoping to get out of the house, there’s an option for everyone.

For those looking to add a little illusion to their evening, take a peek at the Magic Parlour’s At Home Show on the 14th. The Parlour has created this live show, especially for distanced audiences. Sit down to watch with your chosen refreshments and be transported into the world of magic for an evening.

If you and your date are looking for a change of scenery and some delicious cocktails, then curling on the rooftop of The Gwen Hotel might be what you’re looking for. Reserving the rink will give you 45 minutes of curling time as well as a complimentary cocktail. After your game, cozy up around a fire pit and gaze out over the Chicago skyline.

We hope there’s something to tempt you in our list of things to do in Chicago with your date. Remember our 2021 season reopens in May, so come spring, you can surprise your significant other with a cruise down the Chicago River. Get in touch with any questions!

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