The Perfect Chicago Valentine's Getaway for Every Budget and Timetable

From staycations to Wisconsin weekenders to the Caribbean

By Claire Young

The Perfect Chicago Valentine's Getaway for Every Budget and Timetable
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24 January 2019

Sure, Valentine’s Day is an extravagant marketing ploy, but they picked the right month: these Chicago winters demand cuddling up.

This year, don’t fight the romantic in your life. Lean in with something special — like, say, a surprise getaway for two, five of which we've compiled here today.

Setting aside time for romance? A little pampering? A night away from the chores and demands of home? Everybody wins.

Not every getaway requires you to break the bank or play hooky from work (though a couple really, really do), with options ranging from Chicago staycations to Wisconsin weekenders to, well, a penthouse overlooking the Caribbean’s most famous beach.

Good luck matching that one next year.


Image from Hotel Monaco

In the City: Kimpton Hotel Monaco Chicago

The Hotel Monaco puts you in the thick of it. Check out a show, do some ice skating at Maggie Daley park, or just order some room service and utilize the Do Not Disturb sign — this is your big night out downtown. Just be sure to hit up the hotel’s complimentary evening wine hour from 5 p.m. to 6 p.m. every night.

For a-one-of-a-kind experience, purchase the Curious Cupid package. Female guests will enjoy an in-room lingerie fitting with the 1920s-inspired Department of Curiosities. Let her surprise you with her purchases, or stick around to enjoy the view, plus Champagne and truffles. Rates start at $199.

Not your vibe? In Hotel Monaco’s other V-Day package, Made With Love, send the hotel a few details about you and your sweetheart and two bespoke cocktails will greet your arrival. Rates start at $139.

Both offers end February 28.


Image from Deer Path Inn

In the Suburbs: Deer Path Inn Lake Forest

Ditch the car and spend the weekend on a European vacation by way of Lake Forest. A five-minute walk from the Lake Forest Metra stop will have your sweetheart sure you’ve landed in England.

Fireplaces will be roaring at the 57-room English inn (built in 1929 and renovated in 2016). On Saturday, feast on scones, tarts and savory snacks during traditional afternoon tea. Just note that the British theme requires politeness, so call ahead to reserve your spot. In the evening, head to the relaxed White Hart Pub or formal English Room for dinner. On Sunday, dazzle your darling with a winter walkabout in the Chicago Botanic Garden. You’ll get creativity points for the unique view of the gardens under snow.

Rates start at $319. Don’t forget to pack your favorite wingtips and treat yourself to a complimentary shoe shine.


Image from Sundara Inn and Spa

In the Midwest: Sundara Inn & Spa Wisconsin Dells

Forget what you think you know about the Wisconsin Dells. Kiddos are not welcome to this tranquil, 38-room romantic retreat. Sundara is the award-winning, adults-only, destination spa you’ve never heard of.

Common areas are electronics free. Each suite has a gas fireplace. Guests have access to the indoor bathhouse and a Purifying Bath Ritual (read about it, you’ll want it), outdoor heated infinity pool (swimming next to snow will never not be awesome), meditation trail and fitness studio (yoga and guided meditation are on the menu). And be sure to pay a visit to the Woodland Reflection Room, where guests can snag two rocking chairs, hold hands and stare out the floor-to-ceiling windows until it’s no longer novel to see white-tailed deer.

Rates start at $422 for the XOXO Valentine Package (available February 10-14), which includes a chef-prepared dinner for two. Or if you need more flexibility on dates, try the Woodland Retreat Special, starting at $499. Enjoy a salt treatment in Sundara’s new salt therapy room, then return to your suite’s private outdoor hot tub.


Image from Terranea Resort

In the Country: Terranea Resort in Los Angeles

With 102 acres, 582 guestrooms, four swimming pools and eight “dining experiences”, Terranea is a massive Southern California oceanfront resort. Here, big is good, since all that space lends you the privacy of blending into the background.

Trade February in the Midwest for the sounds of the ocean waves rolling in and out beneath your balcony. Perched on the cliffs of Palos Verdes, guests can stare down at the Pacific Ocean from plush seats set about the property's numerous fire pits.

While Terranea is something of a hidden gem, it’s standard California: sun soaked, eco-friendly and high-end. As with most resorts, if you need to bring the family, they’ll find plenty to keep themselves occupied, leaving you and your special someone to your own devices. Throw on decadent robes and book an in-room spa treatment — it’s romance-a-clock. Rates start at $340.


Image from Ritz Carlton

Out of the Park: The Ritz Carlton on Grand Cayman

Just to put it all in perspective, there’s also the Valentine’s Day package from The Ritz Carlton on Grand Cayman.

Starting at $25,750 per night — yup — the package puts you in the Penthouse Suite with a squadron of help (private airport driver, private chef and personal assistant) and a surfeit of services (private beach cabana, rose petal turndown, chocolate strawberries, champagne, caviar spa treatment). The penthouse is what you’d expect: three bedrooms set on more than 8,000 square feet, private movie theater and a wraparound terrace looking onto the famed Seven Mile Beach.

This is obviously a package designed for a very specific couple, but don’t cross off Cayman. First of all, Cayman Airways flies nonstop from O’Hare. They have a turtle (dressed as a pirate) on their planes. Need I say more? The small island gets pretty booked up from December through April, so end Valentine’s Day 2019 by sliding an itinerary for next year’s stay at a condo on Seven Mile Beach, complete with lunch at the Cracked Conch and a day of holding baby turtles at the Cayman Turtle Centre.

You win at Valentine’s Day.

Main image from Terranea

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