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This purpose-built luxury high-rise hotel has 400 rooms in all, with natural light spilling through floor-to-ceiling windows onto modern, clean-lined furnishings done in ivory and gray tones. Higher floors offer spectacular views of Lake Michigan and Navy Pier. Service here gets high marks for the nothing-is-impossible attitude of the staff, and from early summer to late fall the Streeterville Social, the third-floor roof top outdoor terrace, offers craft cocktails and relaxed dining… and views of the city skyline.

Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.

The Wesley G. Usher Memorial Park is one of the many parks located in and around historic downtown Itasca. The adorable pavilion pictured above is a great place to take shelter from the sun, and it overlooks a nice reflecting pool situated on the edge of the property. Take a book, a picnic basket, or just some friends; Usher Memorial Park is great place to spend a relaxing afternoon in Itasca.

Willis Tower—originally known as the Sears Tower—was the world’s tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its “bundled tube” design by architectural firm Skidmore, Owings & Merrill was originally inspired by a handful of cigarettes and the innovative bundling changed the construction of supertall, wind-resistant buildings thereafter. The tower’s height is even more thrilling when measured from the 103rd-floor windows of the Skydeck observatory and the Ledge, a glass-enclosed box which juts more than four feet out from the side of the building so that visitors can (gingerly) walk out and stand 1,353 feet above the street.

This hotel has changed ownership and is now the Ambassador Chicago.

In 2011, hotelier Ian Schrager reopened the iconic but faded Ambassador East Hotel as the Public, instantly infusing Chicago‘s Gold Coast with some flash. Its Pump Room restaurant was the city’s first posh, post-Prohibition, celebrity hangout (everyone from Fred Astaire to John Belushi has come). Keeping its name but little of the old decor, the revitalized Pump Room has a 24-foot bar with a 12-karat white gold–leaf ceiling and a changing menu by Jean-Georges Vongerichten. The high-ceilinged, columned lobby feels both grand and intimate, and it’s now divided into a lounge with a computer-equipped workstation and an elegant library/coffee bar with deep couches and original art, including photos by Hendrik Kersten. Residential high-rises along Lake Shore Drive obscure views of Lake Michigan from the hotel, but drop-dead gorgeous rooms elegantly infuse the pre-WWII architecture with white stuffed couches, bronze textiles, and white sheepskin throws for an effect of lush minimalism befitting one of the city’s oldest and toniest neighborhoods.

In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is different, but all are stylishly simple and feature details such as wood floors, exposed brick, original art work and site-specific installations by local artists, cassette players with mix tapes, well-curated minibars, and Aesop toiletries. For the noise averse, the hotel reminds potential guests that the rooms are located above “an occasionally raucous, whisky-fueled tavern.”

In a world with wine flights and cheese flights, I don’t know why someone hasn’t thought of a pancake flight before. Thankfully Orange filled that gap with delicious fluffy flavorful pancakes before we knew what we were missing. This pancake flight made the perfect breakfast appetizer for my Monday Brunch Group and we even cut each pancake into 4 pieces so we could sample each one. I typically don’t order pancakes as a main order because I prefer savory breakfast to sweet but this pancake flight was the ideal start to a Monday morning. And the orange flavored coffee? That was a tangy cup of delectable right there. Orange, you are full of surprises!

Virgin opened its first U.S. hotel in a 26-story, 1920s art deco tower. Originally a Chicago bank, the building’s high-ceilinged, second-floor hall has been transformed into the Commons Club, a socializing spot divided into a lounge, dining room, and oval-shaped zinc bar with red leather seating and power outlets for tech-addicted travelers. Apartment-like rooms are smartly divided by sliding doors into two sections: a sleeping lounge, and a large dressing and bath area.

One of my favorite discoveries in Chicago is the Empire Ballroom inside The Palmer House. It’s just up the stairs from the hotel’s magnificent lobby and has a rich history most anyone working at the hotel will be willing to tell you more about. This room with its shiny wood floor and opulent chandeliers is where Frank Sinatra used to perform. While the ballroom itself is beautiful, it’s most interesting feature is what’s hidden behind the mirrored wall in its corner. Push on the last panel and you’ll stumble into a dressing room where famous acts - including Sinatra - used to get ready to go on stage. Several autographed pictures are still hanging on the walls.

West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

Restoration Hardware, the upscale home-goods store, made its 2015 Gold Coast debut in style, taking over a building that was created in 1914 as a residence for young women studying music, drama, and the visual arts. Architect James Gillam of Backen, Gillam & Kroeger oversaw the redesign of the 70,000-square-foot structure, creating a six-floor showcase for luxury furnishings. It’s also the first Restoration Hardware to include a culinary element: The ground level features the Three Arts Club Café, where guests can enjoy breakfast, lunch, and dinner while surrounded by heritage olive trees and a refurbished historic fountain.

The sign says “New Antique Store,” which might seem like a misnomer but is in fact a very accurate description of what Urban Remains offers. They sell reclaimed architectural artifacts from old buildings, mostly in the Chicago area and mostly from the 20th century. The Urban Remains warehouse is a giant treasure trove where you’ll find door hardware, industrial furniture, vintage signs, ornamental iron gates and mechanical bits and bobs. If it’s beautiful or functional, Urban Remains probably has it but you might have to dig to find it. Their prices aren’t cheap but sometimes you find just what you weren’t looking for and you simply must have it.

On a quiet residential street one block from the popular vintage shops, bars, and restaurants of Milwaukee Avenue, the Wicker Park Inn is one of the best values in Chicago, attracting an eclectic clientele of older couples, families who book the whole place for weddings and other special occasions, and young travelers eager to live like a local amid the vibrant culture of the Wicker Park and Bucktown neighborhoods.

This place may be small, but its food and drink selection is mighty. Family owned and operated, this cozy local spot is a true gem for authentic Colombian food and drinks in the suburbs of Illinois. The shop and owners are absolutely delightful, and they go out of their way to ensure a wonderful dining experience. You can have breakfast, lunch or dinner, but I’d recommend if you are short on time to at least stop in for a healthy drink. The folks at Colombian’s Taste make wonderful fruit drinks using guanabana, maracuya, lolu and mora. I tried the Colombian lemonade and now am hooked. This place is a true find!

It’s always been about affordable vintage goods at this Wicker Park boutique, which sells contemporary dresses and tops from Amuse, men’s hats from Brixton, denim from skinny-jean pros Just USA, rompers from Los Angeles–based En Crème, and handcrafted leather boots from Red Wing. The popular shop’s homewares and apothecary section is arguably the best place to pick up gifts your friends will love, from grooming and shaving goods to candles, perfumes, and barware like flasks and cocktail shakers.