Chicago city guide: Where to stay and what to do in the Windy City

American are big fans of a nickname, which may explain why Chicago is variously known as the Windy City, the Working City, and the Big Onion. Whatever your preferred moniker, with its extreme seasons, impressive art and culture scene, tales of infamous gangsters in the Roaring Twenties, and position as the starting point of Route 66, there are plenty of reasons to put America’s third-largest city on your radar. Whether you’re visiting Chicago for an extended stay, or to kickstart an epic American road trip, consult our pocket Chicago city guide for art aficionados, thrill seekers, music maestros, foodies and shopaholics to experience it in all its glory.

The hotel: The Emily Hotel

The Emily Hotel in the Fulton Market District is a prime location for exploring, with an array of eateries, bars and boutiques on its doorstep, while bucket list attractions, including the Willis Tower, 360 Chicago and Millennium Park, are around a 30-minute walk away. Not that you need leave the hotel to get in some sights. This boutique stay is adorned with unique artworks as part of its Artist in Residence programme honouring local creatives.

While guests are a stone’s throw away from every cuisine imaginable thanks to downtown Chicago’s vibrant food scene, the Emily Hotel also offers an on-site coffee joint, Flora restaurant, and bar, Selva, on the seventh floor. Add to this 159 rooms and suites, a selection of meeting rooms, and a Rooftop Cinema Club situated on the top floor and you’ll never be left for something to fill your downtime.

Rooms from £150 per night, visit emilyhotel.com

The sights: The Willis Tower and 360 Chicago

Chicago is home to some of the world’s tallest buildings, so a visit to the Willis Tower, and 360 Chicago, are top of the bucket list for sightseers. 360 Chicago – formerly the John Hancock Centre – spans 94 floors, has a sky-high restaurant for swooning over Chicago’s epic vistas, as well as the Tilt. For $9 thrill seekers can stand on a moving glass platform that tilts to a 45° angle – hence the name – to view the East Coast city from 1,000 feet high.

Fearless folk can also get bird’s eye views of Chicago from The Ledge at the Sky Deck, which is suspended 1,353ft in the air on the side of the Willis Tower. You’ll only have 90 seconds in the transparent observation box – but, trust us, that’s plenty.

If you like your feet firmly on the ground, then a trip to the Adler Planetarium – the first planetarium to open in America – the Shedd Aquarium and Navy Pier makes for an educational outing the kids will thank you for. Alternatively, enjoy quality time with your family at Lincoln Park Zoo, a hotspot for families thanks to its remarkable free entry offering. 

The culture: Millennium Park and Art Institute of Chicago

Chicago is an art lover’s heaven; from the architectural buildings and spontaneous sculptures peppered throughout the city to thought-provoking street art, vast art fairs and, of course, the Art Institute of Chicago. The latter is one of the oldest and largest galleries in the world, frequently putting on major exhibitions featuring world-class artworks from seriously famous names.

Alternatively, stroll to Millennium Park to ogle the city’s dwarfed reflection at The Bean, among a mezze of other sculptures, and swoon over the botanical Laurie Garden. Set on the banks of Lake Michigan, taking to the water to explore the city is a must, and there are river tours aplenty. Whether you’re a budding artist, historian, or simply love a boat trip, an architectural river cruise is non-negotiable. Experts explain Chicago’s architectural landscape and the secrets to keeping these multi-storey buildings standing strong in the Windy City. 

The shopping: Magnificent Mile and Fulton Market

Chicago has something for every shopper, including vintage haunts, independent boutiques, high street shops, and designer stores. Looking to splash the cash? Head to the Magnificent Mile and Michigan Avenue for offering from the major fashion houses and luxury department stores, including Nordstrom and Bloomingdales, as well as the much buzzed-about Water Tower Place mall. Elsewhere, venture to Colin Park, Armitage Avenue, Halsted Street or Wicker Park to scour vintage stores, or to the Fulton Market District for an eclectic mix of independent boutiques. 

The fast food joint: Peqoud’s Pizza

Chicago is famed for its deep pan pizza, hot dogs (which must be ordered without tomato ketchup like the local), and roast beef sandwiches. Head to Peqoud’s Pizza for a quintessential deep pan pizza experience, where you can add practically any topping to your doughy delight, and chow down on stuffed crusts guaranteed to rival even the most indulgent cheese toastie. Finish the feast with an evening pit stop at Jeni’s Splendid Ice Creams to satiate the sweetest of teeth with a scoop in a freshly-made warm cone. 

Visit peqoudspizza.com

The restaurants: Monteverde, Girl and the Goat and TimeOut Market

Chicago has a large Italian community and this finds form in Monteverde: a fabulously authentic restaurant in Fulton Market. Send tastebuds on a journey by starting with spicy nduja arancini balls, followed by zesty lemon pasta, washed down with a sweet espresso martini – it’s a winning formula. 

Also in Fulton Market, Girl and the Goat gets booked up fast, so those craving Neo-American cuisine with a difference should get this on their must-visit lists early. From the goat empanadas and chickpea fritters, to the roasted pig face, woodfire lamb ribs and chicken skewers, this is one eatery you will never forget. 

For something a little more casual, Chicago’s TimeOut Market, like most, encourages visitors to sample big flavours from around the globe; from ice cream doughnuts, to spicy pho, traditional Greek dishes, and flavoursome BBQ feasts. The star of the show is Masterchef contestant, Bobby Geetha, who you’ll find serving up samosa chaat, Goan chicken curry and peri-peri fries at Bar Goa, which gathers major queues.

Visit monteverdechicago.com, girlandthegoat.com, timeoutmarket.com

The café: Beatrix

Looking for an elegant brunch spot for business meetings or catching up with friends? Beatrix has an expansive menu to suit all dietary requirements, all day long; from honey-fried chicken sandwiches and fish tacos to whipped feta dips and indulgent steaks – and that’s just the lunch menu. If coffee is called for, Intelligentsia is the place to detour for a caffeine kick. Alternatively, visit the Starbucks Reserve – the largest Starbucks in the world – for a flavoursome coffee created in the most unique ways.

Visit beatrixrestaurants.com and starbucksreserve.com

The hidden gem: The Merchandise Mart

The Merchandise Mart is a talking point in itself as, at 4,000,000 square feet, it was the largest building in the world when it was erected in 1930. It is now used as office space, while also being the canvas for the largest permanent digital art projection on the globe, known as Art on the Mart.

Vornado Realty Trust collaborated with the City of Chicago to provide free public access to contemporary artworks to inspire budding creatives, and as part of the initiative illustrations are projected across the building’s front at 9pm every evening. These, in turn, are reflected in the water, as well as the neighbouring mirrored buildings, and illuminate the city.

Visit artonthemart.com

The bar: Kibbitznest

Kibbitznest is a playful bar you could easily while away hours in. This kooky hangout serves tasty cocktails to be enjoyed among its maze of rooms, while the no Wi-Fi rule makes it the perfect place to leave distractions at the door, unwind in the library or play games in the cosy snug where entertainment options are piled in every corner.

For classy cocktails that pack a punch, the Texan Taco speakeasy is one to have on your radar, not least because it doubles up as a rooftop bar if you know to venture beyond the faux vending machine. Not that you’ll be short on elevated drinking options. The city is laden with skyscrapers reaching record-breaking heights and Nobu, LH rooftop, NoMi at the Park Hyatt, as well as Cindy’s are recommended for a swig at sunset.

Visit kibbitznest.com

Read more: The San Francisco city guide

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