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Be Spontaneous in Chicago

Find the best hotels in Chicago, as well as the absolute best things to do in the city

By Time Out in association with

After surviving brutal winters, no one knows how to live it up in summer quite like Chicagoans. Explore the city from our newest trails, to our highest thrills and even bring the kids along for the day. With music and street fests happening pretty much every day, there's no excuse to ever be bored in Chicago. Soak up the sun now before another eight months of winter takes over the city.

Chicago blogger's guide

We've all been there. The thought of going on a trip sounds so refreshing and tempting, an escape from our routine, but then reality sinks in as we make arrangements and we have to deal with the hassle of shopping around looking for the best hotels we can afford. Well, I found the cure for that: Spontaneity and the mobile app.

When and Time Out decided to send me on a trip but not tell me the destination till the night before departure, I’ll admit I was skeptical about being able to get the hotel I wanted, but with the app on my side, I had nothing to fear. As soon as they told me I'd be flying to Chicago, I immediately loaded up the app and in minutes, my reservation with The Langham in downtown Chicago, the number one ranked hotel in the city, was confirmed. Oh, did I mention it happened to be 4th of July weekend? and Time Out, you like to live dangerously. I can respect that. 

When I arrived at The Langham, I was immediately struck by how luxurious the property was. Checking in, I was greeted by the super accommodating front desk staff, and the moment I opened the door to my room, I was blown away by the beautiful amenities offered by The Langham. From the gentle strings of Classical music playing as I walked in, to the monogrammed robes perfectly placed on the huge king sized bed, the mood had been set perfectly. 

My first stop after getting freshened up was to the Concierge desk, where the fantastic Timo Nequin had suggestions for places to hit up for a late lunch. I had heard that Chicago is a hub for great restaurants and my first meal in the city certainly lived up to that billing. Siena Tavern was a mere five-minute walk away and the contemporary Italian fare on offer was delicious! Try the spaghetti, you can thank me later.

The rest of my day was spent in the trendy Wicker Park area of Chicago. Teeming with eateries, bars and stores, it was a hive of activity. I stopped into local boutique P45 to check out their delightful wares and later on, indulged my weakness for sweetness at Stan's Donuts & Coffee which, funnily enough, originated in So Cal.

The next morning, I'm not ashamed to say, I slept in. I blame the ridiculously comfortable bed in my room! I headed out to the Lincoln Park area to experience a neighborhood famous for its beautiful homes. Coffee was next on the agenda and luckily Elaine's Coffee Call, located in the lobby of the historic Hotel Lincoln, was just a few minutes’ walk away. Dinner proved to be a particular highlight of our time there: GT Fish & Oyster kept the bar high with amazing small shared plates, and they also make a mean cocktail, so be sure to order a couple.

Day three was spent at the world famous Art Institute, a must-see attraction with amazing architecture, not to mention priceless pieces of art. I couldn't think of a better way to cap off my trip to Chicago, with inspiration and creative energy pouring out of every display. It was the perfect metaphor for my entire time in Chicago, a city bustling with activity that gave me the jolt I needed to take back home with me. And any time I feel a quart low, I know has my back and another shot is just a few clicks away. 

By Sheryl Luke

By Sheryl Luke

Sheryl Luke is a Los Angeles based blogger and creator of Walk In Wonderland which chronicles fashion, food and lifestyle for the modern woman on the go.




Top 10 things to do in Chicago

Since Chicago is home to more than its fair share of great summer music festivals, the real struggle is finding the one that's right for you. Spend countless summer weekends catching the headliners at fests like Lollapalooza, Mamby on the Beach, Riot Fest and a slew of local street festivals.
Now that the old Bloomingdale Trail has been renovated from an unused elevated train line to the six-mile expanse known as The 606, there's plenty of new outdoor space to relax, run or bike in the city. An added perk is all the amazing food, drinks and shopping that can be found just off the path.
Travel back in time
Ditch all forms of technology and head just outside the city to another time and place at the Bristol Renaissance Faire. Get dressed up for the occasion and enjoy an afternoon of jousting, turkey drumsticks and more ye olde fun.
Get to know local farmers by strolling through one of the city's farmers' markets, held pretty much daily throughout Chicago. Get your hands on local produce and take in demonstrations from some of the best chefs in town on a leisurely Saturday morning or run to Daley Plaza in the middle of the workday for a fresh bunch of flowers.
Think you've explored the city from every imaginable angle? You haven't seen anything until you've jumped inside one of Chicago Helicopter Experience's choppers for a high-flying tour of the city, cruising over Lake Michigan to Montrose Harbor and back. Book a sunset cruise for a truly breathtaking look at the city.

Top-rated hotels on

Embassy Suites
Rated 8.7 on

Good things come in threes, as the saying goes, and this downtown hotel packs a triple punch with its all-suite layout, heated indoor pool (plus a hot tub), and soaring 11-story atrium lobby. In short, space isn’t an issue here. You’ll be able to spread out and relax in your two-room suite (hello, separate living room!), and even whip up basic meals in the microwave. Your stay includes free cooked breakfast and a nightly wine reception, which are standard perks in all Embassy Suites, though this location also benefits from an upscale osteria, a pizzeria, a burger joint and a Starbucks.

Central Loop Hotel
Rated 8.4 on

A solid choice for business travelers with an eye for debauchery, this modern pick is attached to Elephant & Castle, a gastropub with happy hours like “Wine Down Wednesdays.” The down-to-earth rooms are outfitted like grown-up college dorms, with compact desks, microwaves and plush bedding—though we bet your college didn’t hand out loaner iPads and ambient noise machines upon arrival, did they? Upgrade to a superior room or a suite for the added bonus of a kitchenette with granite-top counters and a dining table. If you’re in town for a while, consider a studio apartment with free weekly maid service and a grocery delivery option. 

River Hotel
Rated 8.5 on

The River’s friendly staff are quick to point out the dozens of attractions (Millennium Park and the Chicago Theater, for instance) within walking distance of this conveniently located hotel, sandwiched between North Michigan Avenue (right near the Mag Mile’s southern tip) and the Chicago River.  After cavorting around town, recharge in one of the contemporary rooms, suites and apartments, all with desks, flatscreens and free Wi-Fi. For an easy meal, head downstairs to Bella Bacino’s, a vibrant Midwestern pizzeria with low-hanging chandeliers serving hand-spun deep-dish pies.

Warwick Allerton
Rated 8.1 on

This Jazz Age landmark has attracted a lively scene practically since Day One—first in the 1920s, as a YMCA-style social hub and 1,000-unit residence, and later in the 1950s with its famous Tip Top Tap penthouse lounge. Nowadays, the gorgeously restored rooms feature elegant touches (marble bathrooms, Gilchrist & Soames toiletries, tufted headboards), the black-and-white-tiled restaurant keeps things classy with its seasonal fare and moody cocktail lounge, and there’s a 24-hour gym to get your heart rate up before a night on the town.

Rated 9.2 on

Since opening in 1977, this upmarket hotel has had its share of ups and downs (including a confusing stint as a co-branded Ritz-Carlton/Four Seasons property), but as of summer 2015, it reverts back to a full-time Ritz-Carlton—good news indeed for travelers with accumulated Marriott rewards points burning holes in their pockets. First among its many selling points? Those lake views. Set on the 15th to 30th floors of the Water Tower Palace, guest quarters feature wide, panoramic picture windows; the beds and lounge chairs almost seem added for decoration. There’s not a bad room in the building, though the Michigan Avenue corner suites double the skyline views, and come with enviable soaking tubs. Further perks include a restaurant, spa and four-lane pool. 

Hotel Blake
Rated 8.8 on

The Blake is housed in the recently renovated 19th-century headquarters of the Morton Salt Company in the heart of Printers Row. But the hotel’s historic exterior belies the chic, contemporary digs within—think warm red and gold tones, free Wi-Fi and rainfall showerheads. A complimentary 24-hour business center and fitness room are just a few of the amenities, and if you need a little extra pampering, in-room massages are just a phone call away.

Sofitel Water Tower
Rated 9.2 on

Casting an angular silhouette along the Gold Coast skyline, this wedge-topped tower by Jean-Paul Viguier has garnered accolades since it opened in 2002—no small feat in a city known for innovative architecture. The contemporary lobby exudes design high-mindedness, with its 42-foot-high mirrors and bold custom floral arrangements; and the red-lacquered French restaurant (suitably named Café des Architectes) could be a gallery in its own right. Bright, minimalist rooms keep up the pace with beechwood walls, glass-enclosed showers and Bose sound systems. Suites are worth splurging for, too, with sleek Mies van der Rohe Barcelona chairs and vases of fresh orchids.

Four Seasons
Rated 9.3 on

Even without its impressive tally of celebrity guests—Margaret Thatcher, Stephen King, and Kevin McCallister (a.k.a. Macaulay Culkin, who filmed Home Alone 2 scenes in the hotel pool)—this place manages to stand above the pack. Literally. It occupies the top floors of 900 North Michigan Avenue, a luxury shopping mall and also one of the tallest buildings in the U.S. Pristine Pierre-Yves Rochon–designed rooms show off crisp shades of silver and white (in case those glittering lake views weren’t bright enough for you), and guests can dial up the “Martini Man,” a booze-centric spin on the traditional room service cart. Then there’s the world-class art collection (including works by Warhol and Matisse), the Roman-style sauna and farm-to-table restaurant Allium.

ACME Hotel
Rated 9.1 on

It’s hard to believe you can stay in a boutique hotel just steps from State Street and three blocks from Hubbard’s restaurant row for under $200 a night, but ACME pulls it off by breaking some of the dated conventions of a luxury hotel. For example, morning coffee service is simply a thermos left in a paper bag outside the door. ACME achieves the perfect mix of hip, haute and high-tech: graffiti-style handprints above the bed, giant LED lips on the bathroom mirror, and an HDMI setup that allows you to hook your smartphone or laptop directly into the TV to stream Netflix or Hulu. Off the lobby, a terrazzo-tiled, Edison bulb–lit cocktail lounge serves dishes like pickled shrimp sliders and charcuterie plates, and there’s an offshoot bakery by celebrated pastry chef Chris Teixeira (the elusive “doughssant” has been spotted here).

Fairmont Chicago Millennium Park

Rated 8.6 on

An expansive sense of space pervades the Fairmont’s cushy digs. From standards to suites, all 687 rooms are outfitted with oversize marble bathrooms, separate dressing areas and Starbucks or Nespresso coffee makers; higher-floor quarters come with sweeping city views. If you book a room on the Gold floors (14th–17th), you'll also gain access to a private lounge and a slew of perks. For an even more indulgent stay, spring for a massage at the 11,000-square-foot spa before sushi and cocktails at Asian-inspired restaurant Aria.
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