Be Spontaneous in Chicago

The only thing better than admiring Chicago's architecture is admiring it with a drink in your hand on a warm summer day. Head to our favorite rooftop bars for a drink and don't skip out on the hottest new frozen summer cocktails to cool down.

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.

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. 

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.

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.

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. 

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.

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.

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.

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).

Rated 8.6 on Booking.com