Live an HGTV Fantasy

Carriage House on KenmoreLincoln Park

Staying here feels less like booking a rental and more like borrowing a designer’s spare keys. The three-bedroom residence sits behind the home of interior designer Shea Soucie, who uses it as a creative playground. It’s a true carriage house — down to the preserved windows and original bones — but everything in it reflects Soucie’s world, including the hand-knotted cashmere and wool rugs she created in collaboration with local brand Oscar Isberian.

The kitchen is built for real cooking, with high-end appliances and generous prep spaces. Bedrooms are outfitted with handmade English mattresses by Vispring (the kind you Google and realize cost $10,000). Downstairs, a hidden wine cellar is rentable for private dinners (starting at $250), while outside, a tucked-away courtyard with a sculptural fountain becomes the spot for coffee and wine. This is an ideal place for a girls’ weekend where the plan is to cook something ambitious, open something expensive, and pretend this is your house.

$850 a night
carriagehouseonkenmore.com

Spend the Night in a Private Art Museum

The Woodsman’s GalleryRiver West

This Airbnb isn’t trying to be a hotel that has art on the walls; it’s an actual gallery you happen to sleep in. It is run by Matthew Kellen, founder of Open House Contemporary, a Chicago-based project that turns living spaces into exhibition venues. Artwork rotates in and out of the condo, from sculptures that double as tables to wall-spanning murals. Current installations include a collaboration — an image-driven dialogue, really — between local portrait photographer Elaine Suzanne Miller and New York–based fine art photographer Jason Robinette.

The space is curated down to its core. Exposed beams, gallery-grade lighting, and uninterrupted sightlines keep the focus on the artwork, and four balconies — each facing a different direction — pull in different slices of the city. It makes an ideal base camp for gallery-hopping. A block away, you will find the makings of a stellar Milwaukee Avenue crawl: Start with coffee at Gallery Cafe (at 734 N.), swing by Intuit Art Museum (756) for a look at the recreated studio of artist Henry Darger, then pop into VSG Contemporary (673) for emerging artists’ work ranging from graphic pencil drawings to neoclassical paintings.

$200 to $850 a night, timing-dependent
www.airbnb.com/rooms/2396340

Be a Kid Again While Getting Back to Nature

Enchanted Garden TreehouseSchaumburg

You might never have imagined you’d be debating sausage vs. pepperoni after climbing up into a tree — yet here you are. Yes, you can order in pizza to your very own Swiss Family Robinson situation. This Airbnb favorite (open, astonishingly, year-round) sits above a leafy backyard layered with a koi pond, stream, and waterfall, which explains why some guests stretch and call it Bali.

The treehouse itself is small (about 15 by 16 feet, porch included) but features heat, running water, and a compost toilet. When the wind picks up, the structure sways just enough to remind you you’re sleeping in a tree. Most of your stay happens down below, drifting from the fire pit to the hammock to the cedar hot tub, tucked behind privacy blinds. Be sure to pet Titan, the owners’ Lab-collie mix.

$291 (weekdays) to $337 (weekends) a night
airbnb.com/rooms/440817

Pretend to Own a Fancy Rural Estate

Prairie Grove RanchMcHenry

The first clue that this place is going to reset your pace comes before you even pull into the driveway: an honor-system egg stand across the street, stocked with farm-fresh cartons and zero instructions beyond trust. You’ve crossed into Illinois farmland and into a different rhythm altogether. 

Set on seven quiet acres an hour northwest of Chicago, just past Moraine Hills State Park, the house is massive — 7,000-plus square feet and seven bedrooms (and equipped with enough beds to sleep 22) — yet it settles into something surprisingly livable, with multiple places to gather, eat, and recreate (downstairs has Ping-Pong and pool tables). The kitchen is built for gourmands, whether you’re doing the cooking or letting the management team line up a private chef. (Also an option if you’re committed to a rest: an in-home massage.)

The lure here, though, isn’t the interior. It’s out back, where horses from the neighboring ranch wander up to the white fence (you can feed and pet them, and, if you plan ahead, book rides). But from the impressively large heated pool and year-round hot tub, you’d never know they were there — a reminder that this is the kind of place where time stretches and nobody minds.

$1,300 to $3,000 a night, timing-dependent; surcharge for large groups
vrbo.com/2535497

Soak in a Hot Tub While Soaking in a River View

Hotel Baker (penthouse)St. Charles

The defining feature of this nearly century-old Gatsby-esque hotel’s apex accommodation is hard to miss: a hot tub planted squarely on a private rooftop balcony seven floors above the Fox River. It’s not hidden behind glass or tucked into a bathroom. It’s right there, outdoors, with charming downtown St. Charles unfolding below you. The penthouse spans two levels, and exploring it is part of the fun. There’s a sitting area and king bed downstairs, and a spiral staircase leads to the rooftop terrace, where you’ll be spending most of your time.

Miss out on the penthouse and you still have options: Four spa suites come with their own balcony hot tubs. It’s safe to say Colonel Edward J. Baker didn’t foresee that when he built the hotel in 1928 as a Midwestern riff on St. Mark’s Square. Still, the place has leaned comfortably into its next chapter, playing host to milestones like Jenny McCarthy and Donnie Wahlberg’s wedding in 2014. That sense of occasion still hangs around, especially downstairs in Rox City Grill, a spot for martinis, jazz, and piano bar energy.

$579 a night for the penthouse; $319 to $549 for a spa suite
hotelbaker.com

Be On Your Best British Behavior

Deer Path InnLake Forest

Opened in 1929 inside what was once prominent businessman Colonel William Sage Johnston’s home, the 57-room inn leans into an English country fantasy — Tudor architecture, afternoon tea with proper finger sandwiches. Book the Buckingham or Cornwall suites, where freestanding tubs fill from the ceiling and rearrange your priorities. But in any room, you’ll see that the staff sweats the small stuff: Handwritten notes appear on the nightstand, offering a personal welcome, and nightly turndown is a given. It’s less about grand gestures than impeccable details, making you feel quietly looked after.

Downstairs, the Bar is where things loosen up with serious sushi, an old-fashioned that people keep trying (and failing) to recreate at home, and bartenders who are happy to go off menu if you ask nicely. When you’re ready to hunker down with a hearty meal, the White Hart Pub has whatever you need to pair with a proper pint, from bangers and mash to cider-battered fish and chips.

$500 to $600 a night for a standard room; $800 to $950 for Buckingham and Cornwall suites
deerpathinn.com