The best ideas for a Chicago staycation

The best ideas for a Chicago staycation

  • Edited by Jeffy MaiWritten by Time Out Chicago editors
  • 08/24/23

Whether you have extra vacation days to burn or need some time away from your cramped studio apartment, a Chicago staycation is the perfect solution. Without spending a fortune on flights, you'll be able to disconnect and recharge while enjoying the best things to do in Chicago, as well as the city's top restaurants and iconic attractions. We've checked out Chicago's very best hotels and found something for every itch—spas, cocktail bars, free amenities and seriously amazing views. Plus we've highlighted some fun activities to do around town. So what are you waiting for? Pack a bag and check in at these staycation-worthy destinations.

Chicago staycation ideas

Geek out at Hotel EMC2

  • Hotels
  • Streeterville

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 WoodWindEataly 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?

Treat yourself to a spa day

  • Health and beauty
  • Spas

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.

Reach peak coziness at The Publishing House Bed and Breakfast

  • Hotels
  • B&Bs
  • West Loop

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 (ElskeThe 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.
Morgan Olsen
Global Food & Drink Editor

Check out the city's best museums

  • Museums

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.

Sit down to a world-class meal at a Michelin-Starred restaurant

  • Restaurants

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.

Explore Fulton Market at The Emily Hotel
Photograph: Courtesy of The Emily Hotel

Explore Fulton Market at The Emily Hotel

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 RoisterRose Marythe Publican or Swift & Sons. (This is just a short list; there are quite literally too many good restaurants in the area.)

Jaclyn Rivas

Catch a live show at a theatre

  • Theater

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 MJ, Hamilton and The Wiz.

Indulge your senses at Viceroy Chicago

  • Hotels
  • Rush & Division

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 Devereaux, guests can order shareable snacks and cocktails (we always love a frosé). 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. 

Connect with nature at Chicago's amazing parks

  • Things to do

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.

See your favorite musicians in concert

  • Music

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.

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