The best Chicago staycation ideas

These Chicago staycation ideas include modern rooms with amazing amenities and classic comforts near top attractions

Whether you have extra vacation days to burn or need some time away from your cramped studio apartment, a Chicago staycation is the solution. Without spending a fortune on flights, you'll be able to disconnect while enjoying the city's best restaurants and top attractions. We checked out Chicago's very best hotels and found something for every itch—spas, cocktail bars, free amenities and seriously amazing views. What are you waiting for? Pack a bag and check in at these staycation-worthy spots. 
RECOMMENDED: The best day trips from Chicago

Hotels
Geek out at Hotel EMC2
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You may have spent the night in a hotel with a theme before, but you probably haven’t been to one that takes its premise as seriously as Hotel EMC2. The Streeterville boutique bills itself as “the intersection of art and science,” incorporating laboratory gear, surrealist paintings and a room service robot named Cleo that can bring toiletries, chocolates and other small items directly to your door. You can even summon the mechanical attendant (and whatever items you need) by simply talking to your in-room Alexa. It’s not quite like R2-D2, but it’s pretty damn close.
The futuristic touches don’t stop there—in your room, you’ll find a smart television that can control the lights, a backlit mirror and a glass shower that sits between the bathroom and the bed (there’s a curtain if you want privacy). The decor is more steampunk than Star Wars, with copper piping and leather accents that will make you feel like you’re sleeping in H.G. Wells’s time machine. There’s even a small horn speaker in each room, allowing you to insert your phone and amplify tunes (an epic sci-fi movie soundtrack seems appropriate).
Though EMC2 is situated within walking distance of GreenRiver, Eataly and Shake Shack, you can have a memorable meal (and a drink) without leaving the building. In-house restaurant Albert crafts contemporary fare like charred Spanish octopus and roasted Rohan duck, served in a two-story space that features towering bookcases and murals. After dinner, head for the second-story Archive Lounge to relax with a cocktail or a local beer. You won’t find robots mixing Negronis, but who knows what the future holds? —Zach Long
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Hotels, B&Bs
Reach peak coziness at The Publishing House Bed and Breakfast
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In a landscape filled with mega-hotels and Airbnb rentals galore, there’s something extra special about a good old bed and breakfast—just don’t expect to find floral wallpaper and canopy beds at the Publishing House in the West Loop. The quaint but impressive space houses 11 unique rooms (from cozy to XL) that are outfitted in cowhide rugs, clawfoot tubs and funky vintage furniture. Each room is wildly different, giving guests an excuse to venture back again and again.
Of course, B&Bs are just as much about the common spaces as they are about the private ones, and the owners of The Publishing House spared no expense to make every corner stunningly homey. Curl up with a book in the downstairs office nook or head upstairs to the sprawling living and dining room. There you’ll find chairs and couches, a sleek grand piano and snacks leftover from earlier in the day (peanut butter cookies and berry muffins the night I visited). When evening rolls around, there are plenty of fantastic dining options in the neighborhood (Elske, The Loyalist and Honey’s are within walking distance), but you’ll want to start with a glass of vino and a few bites at the delightful downstairs wine bar The Press Room.
As much as you won’t want to leave your room in the morning, one whiff of breakfast—cooked by owners Shawn Uldridge and Kimberly Lowery—will surely draw you out of bed. Just-baked pastries, fresh juice and cereal await on the buffet, but the couple offers a few daily specials from the kitchen as well. It's the best way to recharge before heading back to the real world. —Morgan Olsen
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Hotels
Explore Fulton Market at Ace Hotel Chicago
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Nestled in the West Loop’s booming Fulton Market District—across from the Google building and steps from the Green Line—Chicago’s first Ace Hotel provides a unique, food-filled launching pad for locals and tourists alike. Like the lobby, the rooms here are decked out in minimalist-modern decor and retro accents like a turntable and small, curated record collection for your private listening pleasure. Homebodies will appreciate the stocked minibar with booze and gourmet treats galore.
When hunger strikes, there are plenty of stellar options at your fingertips. In-house restaurant City Mouse offers breakfast, lunch and dinner service from the minds of chef Jason Vincent, chef Ben Lustbader and Josh Perlman (the guys behind lauded Giant in Logan Square). If weather permits, grab a seat at the outdoor patio, which is dotted with fire pits for chilly nights. For nightcap needs, book it upstairs to rooftop bar Waydown, where you’ll find expertly crafted cocktails from beverage director Caitlin Laman, curated DJ sets and a stunning terrace with knockout views. If you’d rather get out and explore the ‘hood, consider critic-approved spots like Roister, La Sirena Clandestina, Bonci, the Publican or Cold Storage. (This is just a short list; there are quite literally too many good restaurants in the area.)
Before you check out, make it your mission to find the old-school photo booth on the first floor (it’s hidden on the north side of the building) to snap a souvenir-worthy pic for the road. —Jaclyn Rivas
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Hotels
Indulge your senses at Viceroy Chicago
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The Viceroy’s top-notch dining options are what set it apart from the barrage of Gold Coast hotels. With two outposts from Boka Restaurant Group (the folks behind Girl & the Goat, GT Fish & Oyster and Swift & Sons), the Viceroy aims to be a destination for Chicagoans and out-of-towners alike. Somerset, the lavish, all-American restaurant adjacent to the Viceroy lobby, serves breakfast, lunch and dinner with a side of country club vibes. Upstairs at rooftop bar Devereaux, guests can order shareable snacks and cocktails (we loved the fruity gin-based Salty Dog). Oh, and there’s a rooftop pool—talk about swanky.
That said, the hotel itself is absolutely lovely, and it’s clear that no design decision went overlooked. The spacious, elegant rooms offer unparalleled views of the Gold Coast and, if you’re staying on a top floor, sweeping views of Lake Michigan. With its modern amenities and stylish fixtures, it's an ideal spot for an occasion-worthy stay (like a bachelorette party). But with a friendly, accommodating staff, the Viceroy doesn’t feel stuffy whatsoever.
And where better to staycation than the Gold Coast? The Viceroy is nestled in the heart of the neighborhood, a stone’s throw from Michigan Avenue, making it perfect for all your shopping spree desires. Plus, the John Hancock Building, the MCA and Newberry Library are all right in the area, too. —Grace Perry
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Eat (and drink) well at The Robey
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Occupying the 1929 office building formerly known as Northwest Tower (and known to some neighborhood residents as “the Coyote Building”), the Robey—named for Damen Avenue’s former moniker—opened in late 2016 at the heart of Wicker Park. The new hotel has plenty to offer locals without booking a stay, but spending a night or two could give you a whole new perspective on your own neighborhood. The 12-story hotel offers just 69 rooms, and they’re dotted with mid-century modern design touches to complement the building’s vintage charm (think push-button light switches and frosted chicken-wire glass walls separating the bathroom from the main room) along with modern amenities like smart TVs that let you log in to your own Netflix account or play music from your phone via Bluetooth.
The Robey’s drinking and dining options are many. The building is the tallest for several blocks around, and the Robey puts that to its advantage with not one but two rooftop bars. Up & Up, on the 12th floor, offers stunning 360-degree views with its craft cocktails; if it gets too windy, you can retreat inside the cupola, which has been turned into a cozy lounge. The Cabana Club, on the sixth-floor rooftop of the Robey’s neighboring sister hotel Robey Hall, lets you sip fruity drinks around a tiny but functional swimming pool.
The second-floor Robey Lounge, with library-style tables and low-slung sofas, is a great place to send some emails over an Americano during the afternoon, then order an Old Fashioned once 5pm hits. Ground-floor restaurant Café Robey, with a recent menu overhaul by new head chef Kevin McAllister, serves up terrific New American fare at dinner and does brunch seven days a week. And if you still feel the need to leave the building with all that, well, you’re in the middle of one of the city’s hottest entertainment ’hoods. Tacos at Big Star? Drinks at the Violet Hour? A show at SubT? Wicker Park is your oyster. —Kris Vire
Hotels
Stay for a show at Marriott Marquis Chicago
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The South Loop has long been a destination for conventions and trade shows at McCormick Place, but the opening of Wintrust Arena (which will host DePaul’s basketball teams, the Chicago Sky and concerts) has the potential to turn the area into an entertainment destination. The towering Marriott Marquis is connected—via pedestrian bridges—to both of the aforementioned venues, making it the logical choice for an impromptu, post-event staycation.
The sleek furniture and towering art that fills the lobby signals the Marquis’ status as one of Marriott’s flagship properties—in case the 1,205 rooms didn’t tip you off. Inside each room, the aesthetic is clean, minimalistic and functional, with a chaise longue and plenty of conveniently-placed outlets for your various devices. You’ll want to throw back the curtains and admire the spectacular, unobstructed views of Lake Michigan, the Chicago skyline and the city’s South Side.
Once you start feeling peckish, you’ve got options: If you’re a Platinum and Gold Marriott Rewards member (or willing to pay for the upgrade), stop by the M Club Lounge on the fourth floor where you’ll find free breakfast, snacks and nightly cocktail service. In the lobby is the hotel’s restaurant, Woven & Bound, where regional ingredients garnish dishes like braised rabbit pappardelle pasta and a dry aged pork chop. Of course, you’re not far from breweries like Baderbräu, Motor Row and Vice District, where you can get a taste of the local flavor before following the red glow of the Marquis’ prominent LED lighting back to your room. —ZL
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Hotels, Boutique hotels
Relax and recharge at dana hotel and spa
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If you’re looking for the kind of staycation that involves very little movement, check in at the dana hotel and spa, where everything you could possibly want is at your fingertips. The rooms here are modern and sleek with floor-to-ceiling windows, in-room tech and a fridge stocked with wines available for purchase (bonus: most are very reasonably priced).
Before your stay, though, you’ll want to check out the luxe spa offerings. Book an energizing ginseng facial, an aromatherapy massage or a citrus detox wrap—there’s not a bad choice on the menu. The spa itself, which is connected to a small hotel gym, is a soothing oasis with quiet music, a dimly lit waiting area and steam showers for a post-massage rinse.
Though you could spend hours in the spa, break for dinner at Portsmith, the new first-floor restaurant that specializes in pristine seafood and indulgent ingredients (uni-drenched cacio e pepe, anyone?). Before diving headfirst into the cloud-like beds upstairs to sleep off your food coma, you’ve got one last decision to make: Wildly weird (and very Instagrammable) cocktails at rooftop bar Apogee or sippable stunners at Leviathan, the lobby bar inspired by a sea monster? Don't worry, there's no wrong answer. —MO
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Hotels, Boutique hotels
Rediscover The Talbott Hotel
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This comfortable Gold Coast hotel just received a four-month interior makeover spearheaded by Chicago designer Karen Mann, who transformed the space from an old-school hideaway to a bright, modern city escape. Situated in the heart of the Gold Coast, it’s an ideal launching pad for a staycation—guests are just around the corner from Michigan Avenue shopping, Oak Street Beach and the MCA.
The Talbott was initially built as an apartment building and has retained that intimate structure through its cosmetic renovations. Its in-house restaurant, 20East, offers solid French-American fare in a cozy space; it almost feels like a living room. Though 20East isn’t a dining destination in itself, the building is a stone’s throw from buzzy spots like Maple & Ash, the Little Beet Table and Margeaux Brasserie.
Once back inside your room, you'll find plush bedding, handsome furniture and clean, sophisticaed design touches. Fitness buffs beware: The “state of the art” fitness facility is a windowless room tucked away in the basement with a handful of treadmills. All in all, the Talbott is a solid option if you’re looking for downtown accommodations with a lighter price tag. —GP
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FieldHouse Jones
Photograph: Courtesy FieldHouse Jones/Ryan Beshel
Hotels, Boutique hotels
Play hard at FieldHouse Jones
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This hotel/hostel hybrid, opened in early 2017, takes its conceptual cue from Chicago Park District fieldhouses—the winter-proof buildings that serve as recreation and community centers. The Instagram-baiting decor makes heavy use of repurposed athletic equipment like old scoreboards and gymnasium bleachers; an installation hanging over the lobby is made up of 400 wooden tennis rackets. Think of the aesthetic as the Chicago Athletic Association’s kid brother.
The room selection might not make FieldHouse Jones your first pick for a staycation: Apart from a couple of queen and full rooms, most of the private rooms contain bunk beds. We stayed in “The Ultrastar,” a long, narrow room with full-size bunks and a mini-kitchen with a sink, microwave, refrigerator and dishes in the cabinets for use. The flatscreen TV mounted on the wall opposite the beds feels a little incongruous; this is a room made for sleeping, not lounging. But loft-style apartments and two-bedroom suites, which sleep up to eight people, could make a fun homebase for when you have a big group of out-of-towners visiting for Lollapalooza or a college reunion.
FieldHouse Jones goes a step further in the hostel direction with its shared “dorm rooms,” each outfitted with four bunks, lockers and an en suite bathroom—the latter a step up from traditional hostels, at least. (In a nod to the building’s history as a Borden Dairy Depot, the hotel refers to these as “Borden Beds;” women’s accommodations are called “Elsie Jones” and men’s rooms “Elmer Jones,” after Borden’s bovine mascots.)
Dropshot Coffee Bar in the lobby serves espresso and matcha drinks and snacks including 5411 Empanadas; a bar, the Janitor’s Closet Speakeasy, is still forthcoming. There’s also a huge demo kitchen and laundry in the basement for guest use, as well as a rec room with giant-size slot-car courses, Ping-Pong, air hockey and foosball. Want to play some games of (slightly) more recent vintage? Head a block south to Headquarters Beercade. —KV
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Longman & Eagle
Photograph: Clayton Hauck
Spend a cozy night in Logan Square at Longman & Eagle
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Longman & Eagle is well-known in Chicago for its Michelin-starred restaurant and OSB (Off Site Bar), but its small hotel overhead is a seriously amazing hidden gem. Across from the Logan Square Blue Line, this cozy little getaway—it has just six rooms—is super convenient and feels like home (only way cooler). The rooms have a modern-rustic vibe with exposed brick, wood accents and unique art in each space. Aside from the standard hotel accommodations (plus plush upgrades like a classic, stand-alone tub and an oversized shower), Longman has quirky throwbacks like a cassette player and a collection of mixtapes for listening in your room.

You're in Logan Square, so there's no shortage of excellent dining and drinking just steps from your bed. Eat in-house for a contemporary American menu that boasts everything from house-made pate to seared strip steak, or head over to Lost Lake for an island escape with tiki drinks and American-Chinese cuisine from neighbor restaurant Thank You.

Activities are plentiful in the neighborhood, too. You can catch a film at Logan Theatre, get playful and competitive with friends at Emporium or take in some live music and maybe even some dancing at the Whistler. Want to do some shopping? Check out Bric-a-Brac Records for cool collectibles or TUSK for stellar local fashion.
—Jaclyn Rivas
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Photograph: Courtesy Soho House
Have it all at Soho House
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If you aren't familiar with Soho House, it has turned the stuffy, private boys' club into a social club for creative souls. In 2014, the Chicago location of the British brand opened right around the corner from Restaurant Row. At the old Allis Building, formerly a leather tannery, you'll be welcomed by gritty exposed concrete, vintage chandeliers and eclectic contemporary decor.
After checking in, head upstairs to your guest room, where you’ll find high ceilings and a canopy bed with fluffy white linens. If you opt to be a shut-in, you’ll find company in the stocked bar, tea and coffee set, super soft robes, Cowshed bath products, a beautiful tub and a charming Marshall Stanmore Bluetooth speaker.
It’s worth mentioning that hotel guests have access to everything that Soho House members do: the boxing-centric gym (plus the amazing steam room and laundry service), fifth-floor club and rooftop restaurant and pool. Additionally, a huge perk of the Chicago location is its public spaces. Anyone can (and should) enjoy piled-high avocado toast and mimosas at The Allis, grab a nightcap at Fox Bar, cure late-night fried chicken cravings at Chicken & Farm Shop and book indulgent treatments at the Cowshed Spa.
If you must venture out, enjoy bubbly and bites at RM Champagne Salon, eat pizza by the pound at Bonci or find barbecue bliss at Green Street Smoked Meats. After you've had your fill, you'll be just steps away from falling into your heavenly bed. Sara Freund
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Hotels, Boutique hotels
Play tourist at The Kimpton Gray Hotel
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Billed as an “elevated-experience hotel,” the Kimpton Gray provides the ultimate in tasteful luxury. Though rooms here are a bit pricey, the space is neither gaudy nor over the top; it’s just plain lovely. The hotel is located in the epicenter of the Loop in the former New York Life Insurance building, an iconic piece of Chicago architecture. Its sleek, contemporary decor fits this century-old building like a glove.
The Gray is just a short walk from all those touristy things most Chicagoans avoid like the plague, but we challenge you to think of this staycation as a way to take advantage of the cultural offerings locals never do. Go to the top of the Sears Tower, take a selfie at the Bean, spend an afternoon at the Art Institute, see a show—the list goes on. 
After a long day of sightseeing, kick back with a martini at the Gray’s intimate, library-like cocktail lounge Vol. 39. When hunger sets in, make your way up to Boleo on the 15th floor to enjoy Peruvian fare and pisco-infused cocktails. 
To elevate your already elevated experience, make a reservation at the Gray’s spa. Or if that’s not your thing, play a round of pool in the leather-covered game room. The Gray is the place to lean into luxury, take your mind off things and simply relax. —GP
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Virgin Hotel
Photograph: Anthony Tahlier
Enjoy variety at Virgin Hotels Chicago
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As you might have imagined, Virgin Hotels Chicago is pretty swanky. Opened in 2015, this hotel in the heart of the Loop is all done up in red and white, with ultra-modern decor throughout. You may never want to leave your sleek, spacious room—it has free Wi-Fi, heavenly soft robes, pour-over coffee, a rainforest shower head, and an app that controls the room’s temperature—but you should. There’s so much to explore throughout the hotel itself.

Hit the “social hour” at The Commons Club any night from 5 to 6pm, for all the free, fanciful cocktails you can drink, or kick back at Two Zero Three Coffee and Wine Bar, the cozy coffee shop that looks out onto Wabash Avenue. Of course, there’s also Miss Ricky’s diner-style restaurant for brunch or lunch, and the super hip rooftop bar and nightclub, Cerise, for an evening of dancing. Then there’s The Trophy Room, a VIP area where you can call ahead to reserve a table by the windows to take in the night skyline or just hang out by the DJ’s table. The hotel also has a 24-hour fitness center.
But it wouldn’t be “vacation” if you didn’t play tourist a bit. The hotel is close to lots of activity, from the Chicago Riverwalk and Millennium Park to the theater district. Snag tickets to the Joffrey Ballet or stop by the Divvy station for a quick bicycle ride. Stock up on fine meats and cheeses at Pastoral, or have a cold beer at Billy Goat Tavern, just steps away.
—Laura Rote
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Chicago Athletic Association
Photograph: Courtesy CAA
Live the high life at Chicago Athletic Association
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Chicago Athletic Association is home to what is perhaps the best collection of cocktail bars in the city, which makes it easy to forget that the Michigan Avenue building is an incredibly extravagant hotel. You could spend the night in a room here and have a diverse, unforgettable experience without ever having to step outside.

After checking in to one of this historic building's fabulous rooms (which will make you feel a bit like Don Draper), you’re going to want to head up to Cindy’s on the 13th floor for a bite, a drink and one of the best views in town. If you’re feeling super bourgeois, you can reserve a spot at the Milk Room—an eight-seat bar that serves up an incredible menu of fine and aged liquors.

On the other side of the coin is Shake Shack on the first floor. It's a cheap way to pad your stomach from the copious amount of alcohol you’ll likely be drinking. There’s also the Game Room, a bar that features a medley of, well, games, including an indoor bocce ball court.

Upon waking up from your gauntlet of boozy deliciousness, head to the Cherry Circle Room for brunch, where you’ll almost certainly find something on the menu that tickles your fancy. There’s not a whole lot to do in the Loop at night, but there’s no shortage of fun to be had wandering the floors of CAA.
—Clayton Guse Book Online
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ACME Hotel Company
Photograph: Courtesy ACME
Explore impressive options at ACME
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Opened in 2013, the ACME cultivates a hipper, younger and more affordable vibe than the chain or high-end hotels in River North. The elevators are lined with album covers by the likes of Neko Case and Lady Gaga, and the rooms feature bold wall art and funky fixtures (including a glowing red "lipstick print" embedded in the bathroom mirrors). Amenities include the "Morning Joe" service, a complimentary thermos of freshly brewed coffee from the downstairs West Town Bakery dropped off outside your door at a time you request the night before. Room service is also "knock and drop"—no tipping or human interaction required. There's a small workout area and a spa area with hot tub and sauna in the basement level.

Food and drink options including Eataly, Shake Shack and Pops for Champagne are all within a block's radius, but be sure to check out ACME's own ground-floor bar and restaurant, the Berkshire Room, which has an impressive list of specialty and barrel-aged cocktails—or try a Dealer's Choice: choose a spirit, a flavor profile (such as smoky, fruity or spicy) and a style of glassware, and the bartenders will whip up an off-menu creation for you. After a few of those, you might need ACME's "Hair of the Dog" add-on, which for $25 provides two bottles of Gatorade, two packets of aspirin and a $25 gift certificate to MBurger.
—Kris Vire
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Hotel Lincoln
Photograph: Hotel Lincoln
Make Hotel Lincoln your home base in Old Town
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Situated in the heart of Old Town, the upscale and modern Hotel Lincoln makes for a staycation easily accessible to downtown, while tucked away in a neighborhood perfect for exploring. Traverse through the Lincoln Park Zoo and take advantage of the Green City Market during a summer stay, or get in a few laughs at Zanies, UP or Second City any time of year, with a plethora of bars nearby for a nightcap before making your way back to the hotel.

The greatest perk of Hotel Lincoln might be that, while the hotel is situated nicely on the outskirts of Lincoln Park, you could easily never leave the premises and have a great stay. Guests can enjoy fine dining at The Kennison, cocktails with a view any time of year at the J. Parker and a quick brunch and coffee at Elaine's Coffee Call in the morning, all without leaving the building.
—Erin Delahanty
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Palmer House Hotel Lobby
Photograph: Courtesy Palmer House
Experience the classics at Palmer House Hilton
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The Palmer House Hilton that stands quietly on Wabash Avenue beside the El tracks isn’t the first. The original burned down in the Great Chicago Fire—just 13 days after it was completed. What was built afterward became the first fireproof hotel in the world and one of the first hotels with elevators, electric lights and telephones.

Today, the Palmer House retains much of the grandeur of its era: Most of the doors have their original brass knobs and the marble-replete main floor glows with a warm ambience that most lobbies struggle to attain. A weekend here feels like a staycation that also lets you travel back in time. 

Expect all the standard amenities—pool, jacuzzi, fitness center—and extras that go above and beyond what is expected these days. There’s a dedicated bell service and separate concierge, the rooms boast a wide variety of layouts and sizes (the suites are seriously huge), the in-house Balance Spa has an expert staff with a vast array of wellness and relaxation services, the breakfast buffet at Lockwood is positively luxurious, and the hotel itself is an inviting labyrinth—perfect for a post-dinner stroll with a cocktail in hand. The only downside is that depending what floor you’re on, your room may not have the best view of the city. Which is just fine, the interior provides all the views you need. 
—Nick Kotecki
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The Guesthouse
Photograph: The Guesthouse
Get away to The Guesthouse in Andersonville
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With great restaurants and plenty of shopping, Andersonville is one of Chicago’s best neighborhoods for a staycation. Start the weekend by checking into the Guesthouse Hotel, which has two- or three-bedroom suites, each with a kitchen stocked with cookware and glasses, a balcony with a grill and a washer and dryer. That setup (plus free Wi-Fi, fireplaces in the lobby and a small gym) means you can easily spend a great weekend here without even leaving the hotel. Baker & Nosh, River Valley Farmer's Table and Southport Grocery will deliver food, or you can get ingredients delivered if you want to grill or cook for yourself.

When you do venture out, pop over to Cantina 1910 for inventive cocktails, snack on cheese and house-made charcuterie at Appellation or try old-school Swedish fare at Svea. Pick up a souvenir of your mini-vacation at home vintage shop Brimfield or the Women & Children First bookstore.
—Amy Cavanaugh
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Freehand Chicago
Photograph: Courtesy Freehand Chicago
Make friends at The Freehand in River North
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The Freehand Hotel is unlike anything else in Chicago. It’s in the building that was formerly occupied by the Tokyo Hotel, and it's a mix of a hostel and hotel. Guests can choose between a quaint private room and a shared space (there’s also a penthouse option), so you can have a communal experience like you’re backpacking through Europe without even leaving town.

The best part about staying at the Freehand, though, is Broken Shaker—a unique cocktail bar on the first floor. Its drink menu is on-point, and the lounge area is cozy and delightful, especially compared to a lot of the bars River North has to offer. You'll find a solid food menu here, but there’s no shortage of great options nearby, too. You can nibble on an Italian beef at Portillo’s, or hit up Slurping Turtle for a bowl of ramen.

The Freehand is also downtown, which means you can get to pretty much any corner of the city by way of train. Staycationing at the Freehand could change your opinion of River North, which tends to be filled with young men who left their manners at the frat house on the weekends. Not here, though. A night at the Freehand stays classy. 
—Clayton Guse
Renaissance Blackstone
Photograph: Courtesy Renaissance Blackstone
Relax at the Blackstone, Autograph Collection
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For a restful staycation, book a stay at the the Blackstone, Autograph Collection in South Loop. Start your day by grabbing coffee and grabbing a new read at nearby Sandmeyer’s Bookstore, which offers a solid collection of new titles and older classics alike. Then, walk up to the Winter Garden at the Harold Washington Library, a gorgeous atrium space where you can read and study surrounded by greenery. From there, walk down and grab a bottle of your drink of choice for the night at Printers Row Wine Shop.

When it's time to check into your hotel, ask for a room at the end of the east hallway for a great view of Grant Park and the Buckingham Fountain. The rooms have been modernized and are comfy and quiet for a relaxing evening. For dinner, you have a choice of some great South Loop restaurants. The hotel has Mercat a la Planxa, a great choice for tapas, or, if you're a beer nerd, try Villains for its intense craft beer list alongside tasty dishes to sate your palate. Turn in for the night or head a little south to Vice District Brewing, where flights are reasonably priced and sports games rule.

Rooms at the hotel are comfortable enough to hang out for a bit, so enjoy the view. The next morning, breakfast at Mercat a la Planxa is a no-brainer, with dishes like eggs Benedict and shrimp and grits.
—Elizabeth Atkinson
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Loews Chicago O'Hare Hotel
Photograph: Dave Burk
Shop and play in Rosemont and Loews Chicago O’Hare Hotel
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A stay at the Loews Chicago O’Hare Hotel may take you to the suburbs, but the accommodations are comparable (or superior) to lodging within city limits. Located within walking distance of the Rosemont Blue Line station, the luxury hotel boasts rooms outfitted with contemporary furniture, a spacious bathroom, complimentary Wi-Fi, a gigantic flatscreen TV and a well-stocked minibar.

The hotel’s design is equally impressive: Hanging rocks and moss adorn the hotel’s lobby, colorful prints by local artist Jay Ryan hang in each room and a series of halls on the ground floor host a rotating selection of pieces by Chicago artists. 

An on-site restaurant and bar, the Ashburn, serves up stiff cocktails, local craft beer, an all-day menu and a decadent breakfast buffet (including an omelette bar). There’s even more to eat at the nearby MB Financial Park, from authentic German food (and beer) at Hofbrauhaus to Brazilian steakhouse fare at Fogo de Chão. Once you’re full, you can go bowling at the retro-themed Kings alleys, see stand-up comedy at Zanies or experience indoor skydiving at iFly. 

If you prefer to shop, you can spend an entire day searching through racks at the Fashion Outlets of Chicago, an indoor outlet mall that is a short walk away from the Loews. The gigantic two-story building mixes fixtures such as the Gap, American Eagle and Aeropostale with high-end retailers like Barney’s, Coach and Giorgio Armani. Sales are frequent and you can shop while munching on a Wetzel’s Pretzel.
—Zach Long
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