Chicago staycation ideas
Sometimes you just can’t get away. Maybe you don’t have enough time and money to plan some big, crazy last-minute vacation, or maybe you don’t have the days off. But surely you can find time to relax for at least a day or two. Good thing we live in Chicago—the city that’s full of great restaurants and unbelievable sights and attractions. The next time you’re considering maxing out your credit card for a trip to some far-flung land, take a look at what’s around you. We did, and we discovered this city is home to some truly memorable staycations.
1. Spend a cozy night in Logan Square at Longman & Eagle
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.
2. Enjoy variety at Virgin Hotels Chicago
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 at 7pm 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 Marquee, an elegant venue 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, a spa and even private car service via a Tesla—just call ahead, as it’s first-come, first-served.
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.
3. Live the high life at Chicago Athletic Association
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.
4. Explore impressive options at ACME
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.
5. Make Hotel Lincoln your home base in Old Town
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 Perennial Virant, 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.
6. Experience the classics at Palmer House Hilton
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.
7. Get away to The Guesthouse in Andersonville
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.
8. Find art and decadence at The Gwen
A landmarked building that retains the facade of the former McGraw-Hill building, this lush hotel (formerly Le Meridien and, more recently, the Conrad Hilton) changed hands and rebranded in September 2015 as the Gwen, named for Chicago sculptress Gwen Lux, who designed the distinctive friezes originally featured in that facade. Now part of Starwood Hotels’s Luxury Collection, The Gwen is currently in the midst of a renovation of its fifth-floor lobby, restaurant and bar that will incorporate some of those original friezes; work is projected to be completed in April 2016, in time for the expansive outdoor terrace to open for patio weather.
The Gwen’s rooms are handsomely appointed; if you want to splurge on a staycation to make you feel extra-fancy, this could be your spot. (The suite I stayed in was about three times the size of my actual apartment.) The Gwen is leaning into the artistic connection of its new name; it’s currently partnering with the Art Institute to offer packages for the “Van Gogh’s Bedrooms” exhibit, and my room was furnished with a few extras as part of the hotel’s “Artisti-in-Residence Program.”
At check-in, I found a selection of movie snacks and DVDs of films like Pollock, Frida and Basquiat, as well as a fully set-up easel and canvas with a full complement of watercolors, oil pastels and colored pencils. If you choose to create your own masterpiece, a concierge can hlep arrange to ship it back home.
9. Make friends at The Freehand in River North
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.
10. Relax at Renaissance Blackstone
For a restful staycation, book a stay at the Renaissance Blackstone 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.
11. Shop and play in Rosemont and Loews Chicago O’Hare Hotel
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.
12. Escape to the Gold Coast at Public Chicago Hotel
Nestled in Gold Coast, Public Chicago Hotel is a minimalist’s dream staycation. The beds are low to the ground and the light is dim, with small photos of jazz icons around the room. Head out on the town and grab a drink or dinner at Maple & Ash, the new steakhouse with an upscale vibe. Not in the mood for a steakhouse? Try Spiaggia for Italian. Afterward, grab well-crafted cocktails at Drumbar.
In the morning, brunch at 3 Arts Café in the Restoration Hardware or a super-hearty meal at 3rd Coast Café and Wine Bar won’t disappoint. Then you can enjoy a day of upscale shopping, strolling down Oak Street with high-end boutiques. If you’re looking for a spot that’s a bit easier on the wallet, head to the 900 North Michigan Shops, (and walk down Walton and Rush streets along the way to find Barbour, Madewell, Patagonia and Lululemon) where Bloomingdales, J.Crew and other more cash-friendly shops live.