48 hours in CHICAGO
Chicago is often overlooked by travellers to the US but the great Midwestern metropolis is well worth a visit
CHICAGO is one of the USA’s most exciting cities – and, with a population just short of three million, the third largest. Its position on the shore of the vast freshwater Lake Michigan is spectacular, so it feels more like a city on the ocean than a Midwest town. If time is short, concentrate on The Loop. Named after the elevated railway that encircles it, this is the heart of downtown Chicago and home to most of the city’s most famous attractions.
Take the seasons into account when planning your trip. Summers are hot and the beaches on the lake are packed, while winters can be bitterly cold.
DAY ONE
9am Start the day by visiting the Skydeck Chicago in one of the city’s most famous buildings, the 110-storey Willis Tower (233 South Wacker Drive). For many years it was the tallest tower in the western hemisphere and the views from it are spectacular. These are at their best in the morning: arrive early to avoid the queues. Even so, there are stringent security checks, so allow over an hour for your visit.
10.30am Make your way towards the lakeshore and Millennium Park, one of the city’s favourite green spaces. Check out the Cloud Gate, affectionately known by locals as the Bean, a polished metal installation by the British sculptor Anish Kapoor. The centrepiece of the park is the Pritzker Pavilion by Frank Gehry, the architect who designed the Guggenheim museum in Bilbao, an outdoor venue for all kinds of music. Check local listings for concert details, some of which are free.
11.30am Next to the park is the Art Institute of Chicago, one of the world’s greatest museums (111 South Michigan Avenue). If time is short make sure you see its Georgia O’Keeffe collection and its most famous works, including American Gothic by Grant Wood, an iconic 20th-century painting.
1.30pm Chicago is the birthplace of the skyscraper and its skyline is easily as impressive as that of Manhattan. The best way to get a feel of its architectural heritage is the Architecture River cruise that leaves from nearby Navy Pier. The cruise itself takes 75 minutes and travels down both branches of the Chicago River – get there at least 15 minutes before departure. The tour is a unique insight into the city’s history, beginning with the Great Fire of 1871 that destroyed over 17,000 buildings – started, legend has it, when a cow kicked over a kerosene lamp while being milked.
3pm On your return, explore Navy Pier, the city’s most popular attraction, with its giant Ferris wheel and the Amazing Chicago’s Funhouse Maze, as well as shops, bars and restaurants.
6pm For a sundowner go to Cindy’s (12 South Michigan Avenue), a rooftop bar and restaurant above the Chicago Athletic Association Hotel overlooking Millennium Park – aim to get there 30 minutes before sunset. After a couple of cocktails take a stroll down the Chicago Riverwalk, home of the world’s largest digital art projection, as well as restaurants and bars galore. Check out the City Winery (1200 West Randolph Street). Thanks to heated domes, this is a venue that is great all year round.
DAY TWO
10am Start the day with a leisurely brunch as Jojo’s Milk Bar, which opens at 10am (23 West Hubbard Street). This is perhaps most famous for its desserts and ice creams, but there are plenty of savoury plates on offer, too.
12pm Head to the Magnificent Mile, the stretch of Michigan Avenue between North Lake Shore Drive and the Chicago River, and ultimate Midwest retail- therapy destination. This is also home to some of the city’s most interesting buildings, such as the Wrigley Building, the Tribune Tower and the Chicago Water Tower, one of the few Great Fire survivors. For lunch, drop into Ralph Lauren’s RL Restaurant for classic American food.
3pm Jump in a cab to the Chicago Museum of Science and Industry (5700 South Lake Shore Drive), housed in the only remaining building from the World Fair in 1893, which helped put Chicago on the map as one of the world’s great cities. The exhibits will delight both children and adults, including the command module of Apollo 8, a Second World War German submarine, U-505,
and full-size replica coal mine. Allow around three hours for your visit and it is a good idea to book tickets to some of the attractions in advance.
7pm Chicago’s wealth was built on its enormous stockyards, so you can’t leave town before tucking into some of the beef that made the city famous. Head back north to Gibsons Bar and Steakhouse (1028 North Rush Street), a local favourite with good service, huge steaks, heart-stopping desserts and plenty of personality.
9pm To experience Chicago’s hipper side, grab a cab to the Robey, in the city’s Wicker Park neighbourhood (2018 West North Avenue). The building is straight out of Mad Men, so order yourself a martini in the rooftop bar for the perfect end to an evening.
On the shores of vast Lake Michigan, it feels like a city on the ocean