OK!’s Ultimate Guide to Chicago: Where to Stay, Dine, Drink and Play in the Windy City

Chicago may be famous for deep-dish pizza, towering architecture and a certain very shiny Bean, but spend a weekend in the Windy City and it quickly becomes clear there’s a whole lot more happening here.

Sitting along the shores of Lake Michigan, Chicago manages to pull off that rare combination of big-city energy and surprisingly laid-back charm. One minute you’re sipping cocktails 94 floors above the city, the next you’re kayaking down the Chicago River, catching an improv show or working your way through one of the best restaurant scenes in the country.

And if parts of the city look strangely familiar, there’s a reason. Chicago has become a star of the screen in its own right, providing the unmistakable backdrop to shows including The Bear, Chicago Fire, The Chi and Shameless

From the restaurants and streets of the West Loop to the bridges crossing the Chicago River, sometimes simply wandering around town can feel like stepping onto a TV set.

For those ready to experience it for themselves, OK! has rounded up our favorite places to stay, dine, drink and play in Chicago. Consider this your cheat sheet to doing the Windy City right.

Walking into the Kimpton Gray Hotel feels a little like checking into the Chicago version of a perfectly tailored suit — polished, stylish and just dramatic enough to make an impression.

Set inside the historic former New York Life Insurance Building in the heart of the Loop, the hotel blends its late-19th-century architecture with a much more contemporary personality. Georgia Gray marble, grand staircases and ornate details give the property a sense of old-school Chicago glamour, while the rooms keep things crisp, modern and comfortable.

But this isn't a hotel where you need to retreat upstairs once the sun goes down. Head to Vol. 39, the sophisticated library-inspired cocktail lounge, for drinks surrounded by bookshelves and leather, or make your way up to Boleo, the hotel's rooftop lounge, where Latin-inspired cocktails, music and a retractable roof turn the top floor into one of the property's biggest draws.

With a location that puts much of downtown Chicago within walking distance, Kimpton Gray makes an ideal home base for a weekend of exploring — although with cocktails this close to your room, leaving the hotel occasionally becomes optional.

If your idea of a Chicago getaway includes waking up inside one of the most recognizable buildings in the skyline, the Radisson Blu Aqua Hotel, Chicago delivers.

The hotel occupies the first 18 floors of architect Jeanne Gang's striking Aqua Tower, instantly recognizable for the wave-like balconies wrapping around its exterior. Inside, rooms and suites are sleek and contemporary, with floor-to-ceiling windows and many offering impressive views across downtown Chicago and Lake Michigan.

The real standout, though, is just how much is packed into the property. Indoor and seasonal outdoor pools, hot tubs, a sprawling fitness center, basketball court and running track give the hotel an urban-resort feel, while the huge outdoor recreation deck and green space is a rarity when you're surrounded by downtown skyscrapers.

When hunger strikes, FireLake Grill House & Cocktail Bar serves up Midwestern-inspired dishes and cocktails without having to leave the hotel.

Add a prime location just minutes from Millennium Park and the Chicago Riverwalk, with Navy Pier, Michigan Avenue and River North all within easy reach, and Radisson Blu Aqua strikes a sweet spot between sightseeing and downtime — a stylish home base for packing as much Chicago as possible into one stay.

For travelers who want to drop their bags and immediately start exploring, Cambria Hotel Chicago Loop – Theatre District is all about location.

Sitting on Randolph Street in the heart of the Loop, the hotel puts guests right in the middle of Chicago's Theatre District, making it an ideal base for anyone planning to pack plenty into a Windy City weekend. Restaurants, shopping and public transportation are all close by, while Millennium Park, the Chicago Riverwalk and some of downtown's biggest attractions are within easy reach.

Back at the hotel, the contemporary rooms feature Chicago-inspired décor alongside plenty of space to unwind after a day pounding the pavement. Expect comfortable bedding, refrigerators, workspaces and modern amenities, while the hotel's fitness center is there for anyone who somehow still has energy left after exploring the city.

Downstairs, Intermission Bar and Kitchen keeps the Theatre District theme going, serving American fare alongside cocktails and a daily happy hour. It's an easy spot for a drink before catching a show nearby — or a nightcap when you're not quite ready to call it a night.

Cambria isn't trying to be the attraction itself, and that's part of its appeal. It's stylish, comfortable and incredibly well positioned, giving guests an upscale home base right in the middle of the action. When your Chicago itinerary involves eating, drinking, sightseeing and squeezing as much as possible into a few days, that's exactly what you want.

Plant-based dining has officially entered its main-character era at PLANTA Queen Chicago.

Located in River North, this 100-percent plant-based restaurant takes Asian-inspired favorites and gives them a creative vegan spin — and this isn't somewhere you need to be vegan to appreciate. The menu is built for ordering far too much and sharing everything, with sushi, dumplings, noodles and wok dishes arriving one after another.

The Bang Bang Broccoli has developed a cult following for good reason, while dishes like crispy rice topped with spicy ahi watermelon and inventive vegan sushi make forgetting there's no meat or fish involved surprisingly easy.

Add a stylish dining room, cocktails and a buzzy River North crowd, and PLANTA Queen proves eating your vegetables can actually feel like a night out.

Chicago knows how to do dinner with a view, and RPM Seafood might have one of the best seats in town.

Set directly along the Chicago River, the glamorous River North restaurant comes from celebrity couple Bill and Giuliana Rancic and the Melman siblings of Lettuce Entertain You, pairing serious seafood with a seriously impressive backdrop.

Floor-to-ceiling windows frame the river and skyline, while an expansive waterfront patio becomes prime real estate when Chicago's warmer weather arrives. The menu goes big with crudo, oysters, seafood towers, fresh fish, pastas and seafood steaks, backed by an extensive wine list and cocktail program.

It's polished, lively and made for those dinners where you want the setting to be every bit as memorable as what's arriving at the table. Grab a patio seat, order something from the raw bar and let Chicago provide the scenery.

More than 15 years after opening, Girl & The Goat remains one of those Chicago restaurants that everybody seems to know — and there's a reason people are still trying to get a table.

Chef Stephanie Izard's West Loop favorite helped establish Randolph Street as one of the city's essential dining destinations, serving bold, globally inspired dishes designed to be shared around the table.

The room is bustling, the open kitchen keeps the energy high and the menu jumps between vegetables, seafood and meat without ever playing things particularly safe. Even the green beans have achieved near-celebrity status.

It's fun, loud and packed with personality — the kind of restaurant where ordering "just one more thing" becomes dangerously easy. For a first trip to Chicago, Girl & The Goat still deserves its place on the list.

Head downstairs at Momotaro and suddenly the West Loop starts looking a lot more like Tokyo.

The Izakaya occupies Momotaro's subterranean level, taking inspiration from the yokocho alleyways and post-war markets of Tokyo. Moody neon, vintage street signs, hand-painted menus and narrow lounge-like spaces give the bar an intimate, slightly hidden-away quality that makes simply finding your seat part of the fun.

At the center of it all is a 30-seat bar pouring crafted cocktails alongside sake and an impressive lineup of Japanese whiskies, with shared plates available when drinks inevitably turn into a much longer evening than planned.

Dark, energetic and effortlessly cool, it's exactly where you want to disappear underground for a few hours.

Cocktail hour gets a serious adrenaline boost at the just opened F1 Arcade Chicago.

Located in River North, the huge social gaming venue combines a full bar and restaurant with state-of-the-art Formula 1 racing simulators, meaning your night can go from civilized cocktails to aggressively trying to beat your friends around a virtual racetrack remarkably quickly.

Grab a handcrafted cocktail, pick a race mode and settle into the driver's seat for a little friendly competition — although "friendly" may disappear somewhere around the first corner.

It's part bar, part game night and part Formula 1 fantasy, making it a refreshing alternative when another standard round of drinks just isn't going to cut it.

If Chicago's Prohibition-era history and glamorous nightlife had a very stylish baby, it might look something like Untitled Supper Club.

Hidden away in River North, the sprawling 18,000-square-foot venue leans into 1920s decadence with moody lighting, plush interiors, cocktails and one of the largest selections of American whiskey in the world.

But Untitled isn't just somewhere to grab a drink and leave. Live music, jazz, DJs and cabaret-style performances — including burlesque — turn an evening here into a full night out, and the atmosphere only gets livelier as the hours roll on.

Come for a cocktail, stay for the show and don't be surprised if it's considerably later than planned when you finally emerge back onto Kinzie Street.

Yes, Navy Pier is one of Chicago's biggest tourist attractions — but sometimes the touristy things are popular because they're genuinely fun.

Start with Flyover, an immersive attraction that uses motion, visuals and sensory effects to send guests soaring across Chicago and beyond without ever leaving the Pier. It's dramatic, surprisingly exhilarating and a perfect introduction to the city before heading outside to see the real thing.

Then take things considerably higher aboard the Centennial Wheel. Rising nearly 200 feet above Navy Pier, its enclosed gondolas deliver 360-degree views across Lake Michigan and the Chicago skyline. Time it around sunset and suddenly that Ferris wheel ride becomes one of the best photo opportunities of the entire trip.

Do both back-to-back and you've essentially seen Chicago from the air twice — without needing to book a helicopter.

There are plenty of ways to see Chicago's famous architecture, but paddling directly underneath it is considerably more memorable.

Urban Kayaks launches from the Chicago Riverwalk, putting you right on the river and in the middle of the skyscrapers, bridges and landmarks that define the city. Beginners can opt for an introductory paddle, while guided tours combine kayaking with stories about Chicago's architecture and history.

For something particularly memorable, the Historic Chicago Tour takes paddlers past landmarks including Willis Tower and Marina City, while evening options let you watch the city transform as the skyline lights up around you.

Just accept now that you're probably going to get a little wet but It's definitely worth it.

Chicago looks pretty spectacular from street level. From 94 floors up? Even better.

Located 1,030 feet above the city at 360 CHICAGO, the observation deck serves up sweeping views across Chicago and Lake Michigan from the former John Hancock Center on Michigan Avenue.

And then there's TILT.

The attraction does exactly what its name suggests: guests step against floor-to-ceiling windows that physically tilt outward over the side of the building, leaving you staring straight down at the city more than 1,000 feet below.

It's exhilarating, mildly terrifying and absolutely not the moment to suddenly remember you're scared of heights. Recover afterward with a cocktail at CloudBar — also on the 94th floor — where you can admire the view from the much more reassuring position of a stationary chair.

You can't do Chicago without experiencing some comedy, and there are few places more synonymous with it than The Second City.

The legendary institution has spent more than six decades helping shape American comedy, with alumni including Tina Fey, Steve Carell and Stephen Colbert, and its Chicago stages continue to mix sketch, satire and completely improvised comedy every night.

The best part of improv is that nobody — including the performers — knows exactly where the show is heading. Audience suggestions can send a scene completely off the rails, meaning no two performances are quite the same.

It's unpredictable, fast, occasionally ridiculous and very Chicago. Grab a drink, settle in and prepare to discover why some of the biggest names in comedy got their start right here.