The best things do on a Chicago staycation

The city is home to some of the best restaurants in the world, so why not treat yourself to an exceptional meal? From mesmerizing fine-dining institutions, like Alinea and Ever, to the first ever Michelin-Starred Filipino concept, there’s no shortage of acclaimed dining experiences. And you don’t have to break the bank—there are a handful of relatively affordable options.

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 Monteverde 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. 

Whether you’re interested in art, history, science or architecture, Chicago is home to some of the best museums in the world. To make the most of your time, head to the Museum Campus, where you can spend an entire day exploring three different cultural institutions. Check out towering dinosaurs, ancient artifacts and royal Egyptian mummies at the Field Museum, or marvel at the Shedd Aquarium’s captivating world of penguins, whales, sea lions and other marine mammals. If that’s enough, the Adler Planetarium awaits with its dazzling sky shows, exhibits dedicated to astronomy and the largest public telescope in the city.

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 the Purple Pig, Eataly and Shake Shack, you can have a memorable meal (and a drink) without leaving the building. In-house restaurant the Albert crafts contemporary fare like homemade pastas and smoked 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?

Experience the ultimate form of rest and relaxation with a spa day. For a luxurious pampering, book a treatment at Chuan Spa in The Langham or Kohler Waters Spa. Prefer to dip your toes in the water? Then visit hidden oasis Aire Ancient Baths for a peaceful retreat. You can just explore the indoor and outdoor baths—ranging from frigid to hot and incorporating steam, salt and jets—or add on a relaxing massage. The spa also offers packaged experiences for one or two people such as a wine bath, where you’ll take advantage of the antioxidant properties of grapes with a 30-minute soak and an hour-long massage with grapeseed oil.

There’s nothing like a tour with out-of-towners to see your home in a new light—and luckily, Chicago offers options for every interest, whether it's food, running, history or even our favorite pests to hate, rats. For walkers, learn neighborhood history of areas like McKinley Park and West Portage Park with Chicago for Chicagoans or geek out over architecture, construction and, of course, bricks in places like Beverly, Rogers Park and Albany Park with a Brick of Chicago. Runners can admire murals with RunStreet Street Art Tours and Chicago history with Go Running Tours, or talk books with Read & Run Chicago. Hungry? Best to skip breakfast before Steve Dolinsky’s Pizza City USA walking (and eating) tours.

Nestled in the West Loop’s booming Fulton Market District—across from the Google building and steps from the Green Line—The Emily 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. 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 Fora offers globally-inspired brunch and dinner service, while Sushi By Bou delivers an intimate, 60-minute omakase experience. 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 Selva, where you’ll find expertly crafted cocktails and a stunning terrace with knockout views. If you’d rather get out and explore the ‘hood, consider critic-approved spots like Roister, Rose Mary, the Publican or Swift & Sons. (This is just a short list; there are quite literally too many good restaurants in the area.)

Nothing beats a sauna-like greenhouse on a dreary day, and let’s be honest—that’s most of the year outside of summer. The Palm House at Garfield Park Conservatory is the antidote for any tropical wanderlust, all without having to leave Cook County. Wander through more than 70 palms, under 65-foot ceilings, and soak in the humidity and distant sounds of rushing water as you transport yourself (mentally, at least) to tropical forests around the world. After your visit, continue the tropical vibes at Esmeralda’s, a Tiki-themed tropical bar in Humboldt Park.

The Viceroy’s top-notch dining options are what set it apart from the barrage of Gold Coast hotels. Somerset, the lavish, all-American restaurant adjacent to the Viceroy lobby, serves brunch, golden hour and dinner with a side of country club vibes. Upstairs at rooftop bar Pandan, guests can order cocktails and Southeast Asian cuisine. 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. 

With numerous theaters around town, you can catch live performances of plays, musicals and more any night of the week. For the most options, make your way to Chicago’s Theater District to find long-running productions as well as popular touring shows like The Book of Mormon, Harry Potter and the Cursed Child and Les Misérables.

Little Village, or La Villita, as it’s commonly called, is Chicago’s ultimate neighborhood for Mexican food and culture. As you enter the main commercial district, a photo of (or with) the terracotta archway stretching across 26th that reads “Bienvenidos a Little Village” is obligatory. Nicknamed the “Mexican Magnificent Mile,” this area is home to over 1,000 businesses, including locally-owned bakeries like El Churro Shop for delicious pastries and stores like Artesanias Elena for shopping. Satisfy your sweet tooth at the impressive megastore Dulcelandia and dine at neighborhood favorite Nuevo Leon or Osito’s Tap for decadent lamb birria grilled cheese and mole rosa. Skip the post-lunch nap and visit the Open Center for the Arts to glimpse works by local artists.

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 89 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 three bars. The Up Room, on the 13th floor, offers stunning views backed by craft cocktails, while The Cabana Club, on the sixth-floor rooftop, lets you sip fruity drinks around a tiny but functional swimming pool.

On the second floor, Clever Coyote serves tiki-inspired concoctions and tasty bites like smoked pork belly steamed buns. Ground-floor restaurant Café Robey dishes out terrific seasonal comfort food 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.

Escape the urban hustle and bustle and take a stroll through Chicago’s numerous green spaces. With more than 600 facilities throughout the city, there’s something for everyone. Take a selfie in front of Anish Kapoor's Cloud Gate sculpture ("The Bean") at Millennium Park or see a variety of animals at Lincoln Park Zoo in Lincoln Park. Plant lovers can explore Garfield Park Conservatory and Osaka Japanese Gardens in Jackson Park for some breathtaking sights.

No matter your musical tastes, your favorite artists are bound to make a stop in Chicago. Thanks to its unofficial status as the capital of the Midwest, the city’s concert calendar is always jam-packed. You can catch the biggest names in the world at venues like the Aragon Ballroom and the Chicago Theatre or up-and-comers at intimate clubs such as the Empty Bottle and the Hideout.

Forget balking at tourists—become one! Navy Pier’s 100 years of history houses more today than just Margaritaville’s blaring music. Book a suite at Sable to gaze upon Lake Michigan’s blue waters—the Pier’s hotel features floor-to-ceiling windows in every room. Summertime guests can pair Wednesday or Sunday fireworks shows with complimentary Champagne and chocolates. Go full staycation mode by dining at one of the many Navy Pier restaurants, or sneak under Lake Shore Drive to Robert’s Pizza and Dough Company for handcrafted crusts topped with farm-to-table ingredients. You may even stumble upon the quirky Robert himself.

The area surrounding the former Union Stockyards wasn’t always a welcome place for everyone—until recently. Today, visitors can step beyond the White Sox stadium and explore colorful breweries, repurposed pork processing plants, art galleries, coffee shops and museums in Bridgeport and Back of the Yards. Start with coffee at Bridgeport Coffee and a yoga class at nearby Yoga in Vogue located inside the Bridgeport Art Center. Browse the exhibition halls or the Maritime Museum and then head south to the Plant for the Packingtown Museum and maybe even a vegan market. Finish in Bridgeport at Maria’s Packaged Goods and Community Bar and adjoining Kimski for brews made by the “Mayor of Bridgeport” himself, Ed Marszewski, and Polish-Korean fusion fare. Try the Maria’s Standard, a Polish sausage topped with a kimchi and sauerkraut hybrid. 

You may be familiar with the city’s gorgeous skyline, but do you know the rich history behind it? The Chicago Architecture Foundation’s renowned boat cruise will take you down the Chicago River and give you the fascinating scoop on more than 50 buildings along the way. If you’d rather head out on the lake, the Seadog Speedboat Tour will get you to a number of noteworthy landmarks in just 30 minutes.

The South Loop has long been a destination for conventions and trade shows at McCormick Place, but the opening of Wintrust Arena (which hosts DePaul’s basketball teams, the Chicago Sky and concerts) has helped 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 lounge 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 or Titanium 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 and snacks until 3pm. In the lobby is the hotel’s restaurant, Woven & Bound, where regional ingredients garnish dishes like Alaskan Halibut and lamb osso bucco. Of course, you’re not far from breweries like Duneyrr Artisan Fermenta, 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.

This comfortable Gold Coast hotel 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, Laurel, offers solid Mediterranean fare in a cozy space; it almost feels like a living room. Though Laurel isn’t a dining destination in itself, the building is a stone’s throw from buzzy spots like Maple & Ash, Gibsons Bar & Steakhouse and Le Colonial.

Once back inside your room, you'll find plush bedding, handsome furniture and clean, sophisticated 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.

Chicago knows comedy, having launched the careers of legends like John Belushi, Tina Fey, Stephen Colbert and many more. On any given night, you can watch an array of shows and performers at vaunted venues like Second City and Zanies. And who knows—you might just be catching the next Saturday Night Live titan before their big breakout.

There’s a watering hole for every type of drinker, whether it’s a wine bar, cocktail bar or craft brewery. But sometimes, you just want to grab a drink away from the crowds. That’s when Chicago’ best speakeasies come in hand. Hidden beneath restaurants, behind closed doors and in alleyways, these dimly-lit establishments provide the perfect setting for a low-key evening filled with creative libations.

Longman & Eagle is well-known in Chicago for its Michelin-starred restaurant and extensive whiskey collection, 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 rabbit and pork terrine to dry-aged strip steak, or head over to Billy Sunday for beautifully balanced cocktails made with unusual ingredients.

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.

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 and book indulgent treatments at the Cowshed Spa.

If you must venture out, enjoy flame-grilled meats at El Che Steakhouse & Bar, 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.

Even if you don’t have a vehicle, you can still have an adventure in the suburbs thanks to Metra. The reliable commuter train offers convenient trips out to destinations outside city limits. You can go zip-lining at an adventure park, play games at the largest arcade in the U.S., hike through a coastal national park and more.

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 Willis 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 an old fashioned 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 club room. The Gray is the place to lean into luxury, take your mind off things and simply relax.

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.

Kick back at Two Zero Three Coffee, the cozy coffee shop that looks out onto Wabash Avenue, for a pick-me-up. Of course, there’s also Italian-tinged Miss Ricky’s restaurant for brunch, lunch or dinner, and the super hip rooftop bar and nightclub, Cerise, for an evening of dancing. 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 Theatre District. Snag tickets to the Joffrey Ballet or stop by the Divvy station for a quick bicycle ride. Satisfy your sweet tooth at Stan's Donuts or Garrett Popcorn, or have a cold beer at Billy Goat Tavern, just steps away.

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 into 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.

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.

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 pristine pieces of nigiri at Sushi Suite 202 or Sushi by Bou, 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. 

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 Spa at Palmer House has an expert staff with a vast array of wellness and relaxation services, 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. 

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. Bar Roma, Lonesome Rose and Demera will bring you food, or you can get ingredients delivered if you want to grill or cook for yourself.

When you do venture out, pop over to Nobody's Darling for inventive cocktails, grab a pastry at Lost Larson or try old-school Swedish fare at Svea. Pick up a souvenir of your mini-vacation at home vintage shop Andersonville Antiques or the Women & Children First bookstore.

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 Xoco for a torta and churro.

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. 

For a restful staycation, book a stay at the the Blackstone, Autograph Collection in South Loop. Start your day with coffee and a butter chicken croissant at Swadesi, and 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, saunter 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 you can try Chicago Firehouse Restaurant for a classic steakhouse experience set inside a restored firehouse.

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 chorizo baked eggs and Spanish tortilla.

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 breakfast buffet. There’s even more to eat at the nearby MB Financial Park, from barbecue at Bub City to Brazilian steakhouse fare at Fogo de Chão. Once you’re full, you can go bowling at the retro-themed Kings, 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 Gucci, Jimmy Choo and Burberry. Sales are frequent and you can shop while munching on a Wetzel’s Pretzel.