Michelle Harbi is won over by Chicago’s superlative attractions and fun-loving spirit.

Crossing Michigan Avenue on a Friday night en route to dinner, we were suddenly stopped in our tracks by a flash mob of cyclists. A seemingly endless mass of them whooshed through as they headed up the Magnificent Mile, ringing their bells and calling out, “Happy Friday!”

Chicagoans love their weekends – in fact, in the summer, when I visited, they love every day. It’s no wonder, perhaps, for a city that experiences such long and cold winters. From leisurely lunches on streetside terraces to post-work cocktails atop its rooftop bars, everywhere was buzzing with locals enjoying the sunshine. Even after the baseball at Wrigley Field on a Wednesday afternoon, the surrounding bars were thick with a party crowd, no one looking particularly bothered about heading back to the office.

Even if you are not in town for business, the US’s third-biggest city is a good option for a long weekend, with a flight time of about eight and a half hours from London. And it is, undoubtedly, a place with pretty much everything you would want from a top-notch city break.

It has phenomenal architecture – the world’s first skyscraper was built here in 1885, at a then-dizzying ten storeys, albeit somewhat of a dwarf compared with the city’s tallest building these days, the 110-floor Willis Tower. It is blessed by its fabulous setting on Lake Michigan, offers excellent shopping along the Magnificent Mile and beyond, and has abundant green spaces, world-beating art, great hotels, superb dining and lively bars. And, while being a huge metropolis, it retains a relaxed and friendly Midwestern vibe. Can you tell I liked it?

RIVER VIEW

Taking in Chicago’s soaring architecture can simply be done by wandering the streets of the Loop – the business district – where many of the best examples are located. But if craning your neck gets too much, then take them in from the water.

One of the city’s most popular attractions, and rightly so, is the Chicago Architecture Foundation river cruise aboard First Lady Cruises, which will take you past more than 50 of the city’s finest structures. The foundation’s knowledgeable volunteers share the stories behind the buildings, in doing so providing an insight into the history of Chicago itself.

The river is a great vantage point from which to see the range of architectural styles in close proximity – from the clean lines of Ludwig Mies van der Rohe’s AMA Plaza to the 1960s corncob-shaped Marina City towers and the majestic Wrigley Building. Tours last an hour and a half and run throughout the day (April-November; from US$44; cruisechicago.com).

MASTER OF ART

Back on dry land, take some time to explore the city’s expansive public art collection. In 1967, the huge Cubist sculpture by Picasso on Daley Plaza was gifted to Chicago by the artist; the following decade, the city council ruled that 1.33 per cent of the budget for new public buildings and spaces be set aside for original art. There are now more than 100 works dotted around Downtown, including pieces by Joan Miro, Sol LeWitt and Henry Moore.

Wander through Millennium Park and you’ll discover some more recent landmarks – Frank Gehry’s eye-popping Jay Pritzker Pavilion, Anish Kapoor’s perspective-bending Cloud Gate sculpture, and the Crown Fountain. Designed by Spain’s Jaume Plensa, this comprises two 15-metre-high glass blocks on to which the faces of Chicago citizens are projected; wait long enough and water will spout out of their mouths, gargoyle style, for kids to splash around in.

At the end of Millennium Park, you could easily spend half a day in the Art Institute of Chicago – one of the world’s best galleries, with a collection spanning about 300,000 works. The Impressionism and New Contemporary sections are superb – the latter reopened last year and is home to pieces by Andy Warhol and Roy Lichtenstein – while Edward Hopper’s Nighthawks and Grant Wood’s American Gothic are among the other major draws (open 10.30am-5pm, Thurs 8pm; US$25; artic.edu).

HOME RUN

Still, if the weather is with you, you don’t want to be indoors all day. A stroll, jog or cycle along the Lakefront Trail, which hugs the shoreline for almost 30km, is a must. We spent a glorious Saturday afternoon wandering Navy Pier, where a covers band played Prince classics, before heading northwards past the packed city beaches, taking in the sparkling calm of Lake Michigan and the skyline view back to Downtown.

Ducking into Lincoln Park, we stumbled into a dog show being held by the residents of the Gold Coast – the city’s most gentile neighbourhood, which backs on to this part of the lake. They can’t have been too impressed back in 1959, when one of the grand houses that line its peaceful streets was acquired by Hugh Hefner for his first Playboy Mansion.

Hefner and his Bunnies moved on in 1974, but there is always a party to be found somewhere in the city – and if it’s match day, it’s at Wrigley Field. If the Chicago Cubs are playing while you are in town, do go – even if you know nothing about baseball, it’s tremendous fun. The fans are unstintingly passionate, even though the Cubs haven’t won the World Series for more than a century, and the stadium – one of the oldest major league grounds in the US – is fantastically atmospheric. Grab a Goose Island beer, try to keep the hotdog mustard off your shirt, and pretend you know the words to Take Me Out to the Ball Game – you could almost pass for a local.

DINING AND DRINKING

Signature Room at the 95th

Pay US$20 to access the 94th-floor observation deck of the John Hancock Centre – or skip the queue and spend it in the Signature Room restaurant (pictured above) one floor up, or the Signature Lounge on the 96th. The views are sensational – book a window table in advance – and the contemporary American food is flavoursome and generous.

  • Open 11am-2.30pm, 5pm-10pm (11pm Fri/Sat, from 10am Sat/Sun). 875 North Michigan Avenue; tel +1 312 787 9596; signatureroom.com

Cindy’s

In a prime spot facing Millennium Park, Cindy’s is the lively rooftop bar and restaurant of the Chicago Athletic Association hotel, a luxury conversion of a historic gentleman’s club that opened last year. Located on the 13th floor, its outdoor terrace is a great place to sip one of the expertly mixed cocktails (pictured right) in warmer weather.

  • Weekdays 11am-2pm, 4pm-2am; weekends 10am-3pm, 4pm-3am (Sun 12am). 12 South Michigan Avenue; tel +1 312 792 3502; cindysrooftop.com

The Gage

A few doors down from Cindy’s and well placed for the Art Institute of Chicago, this smart restaurant and bar is popular with the after-work crowd and also serves a superb weekend brunch – the BLT with over-easy egg, provolone and basil-tarragon aioli (US$12) will keep you fed for the day, while the Bloody Mary (US$12), complete with a garnish of corned beef and Irish cheddar, is a meal in itself.

  • Open 11am-2am (until 12am Mon, 10am-3am Sat, 10am-12am Sun). 24 South Michigan Avenue; tel +1 312 372 4243; thegagechicago.com

RPM Italian

A glamorous, buzzing restaurant in the River North district serving high-end Italian cuisine. People-watch over a bellini at the bar (pictured above right) before enjoying deliciously creamy burrata (US$15) and richly flavoured pappardelle Bolognese with short rib ragu (US$14). Sister venue RPM Steak is located two blocks south on West Kinzie Street.

  • Open 4pm-12am (11pm Mon, 12.30am Fri, 3pm-12.30am Sat, 12pm-11pm Sun). 52 West Illinois Street; tel +1 312 222 1888; rpmrestaurants.com

Bavette’s

This elegant French-inspired steakhouse has an atmospheric, jazzy ambience and is located in River North. The cuts of meat (from US$39) are superb, and perfectly cooked – accompany with decadent sides such as creamed spinach with blue cheese and caramelised onions, and charred brussels sprouts with Dijon mustard and parmesan (US$12). The Old Fashioned cocktails are good, too.

  • Open 5pm-11.30pm (12.30am Fri-Sat, 10.30pm Sun). 218 West Kinzie St; tel +1 312 624 8154; bavetteschicago.com

Green River

Located in Streeterville, just north of the Chicago River, this upmarket 18th-floor restaurant and bar opened last year. The cocktails, inspired by the city’s Irish heritage, are creative and well crafted, the seasonal American cuisine is impressive, and the staff are passionate and knowledgeable. Take a seat on the outdoor terrace (pictured below) for lake and skyline views.

  • Open 11.30am-10pm (11pm Thurs/Fri; 11am-3pm, 5pm-11pm Sat; 11am-3pm Sun). 259 East Erie Street; tel
    +1 312 337 0101; greenriverchi.com

United flies from London Heathrow to Chicago three-times daily. united.com

Baseball tickets were provided by the Chicago Cubs. chicago.cubs.mlb.com