Chicago city breaks

Visual arts are everywhere in Chicago too, from the internationally renowned Art Institute to giant public installations like Agora, Crown Fountain and The Picasso. The city’s outdoor spaces come alive in summer, with the sculpture-filled social hub of Millennium Park, the amble-worthy Riverwalk, and the sandy, lakeside beaches among the host of choices.

Travelling with the family? From the aquatic wonders of Shedd Aquarium – where you can ‘hang out’ with beluga whales – and the animals of Lincoln Park Zoo to the fairground rides of Navy Pier, the city has you covered.

Elsewhere, Chicago is recognised for its varied nightlife (live music and comedy are particular highlights), an eclectic food scene that ranges from Michelin star restaurants to food halls and ‘bottomless’ shopping opportunities at places like the Magnificent Mile, the downtown avenue with no less than four shopping centres. If you’re a sports fan, make time for Wrigley Field, the home of the Cubs baseball team.

If you’d prefer to avoid snow, then April and August are good months to travel, with good weather and mid-range prices. April also sees the opening games of baseball season.

Sandwiched between skyscrapers and the lakeshore, Millennium Park is Chicago’s playground. It’s home to the city’s most famous public artwork, Anish Kapoor’s reflective Cloud Gate (also known as The Bean). Summertime sees yet more public art, plus free concerts in the Pritzker Pavilion, a Frank Gehry-designed outdoor venue with a programme of classical, jazz, blues, rock and world music.

Navy Pier

Come rain or shine, there’s entertainment to be found at Navy Pier. Ride the Centennial Ferris Wheel at Pier Park for views across the city and Lake Michigan, then tick off the carousel and the funhouse maze, among other nostalgic fairground rides. Take a speedboat or sailing trip on the lake, and, in summer, linger on for firework shows. If the weather won’t play ball, there’s the Chicago Children’s Museum, the Tony award-winning Chicago Shakespeare Theater and an IMAX cinema to keep you busy.

Willis Tower Skydeck

In a famously high-rise city, it’s only right you head to the highest point. Views from the 103rd floor of the two-block wide Willis Tower are unbeatable – on a clear day, you can see 50 miles over four states. You can also learn about the city’s landmarks and history from the viewing gallery and then test your nerves on the ‘Ledge’, overhanging, glass-floored boxes that ‘pop’ out of the building.

Wrigley Field

Sitting in the bleachers with a hot dog and a cold beer is a true American tradition, and there’s no better place to do it than Wrigley Field, the second oldest ballpark in the US (dating back to 1914). It’s the only major league baseball park with ivy growing on the outfield and a vintage scoreboard still operated by hand. Visit in season – between April and October – to catch a game or take a behind the scenes Wrigley Field Tour, which runs daily.

Chicago River/Lake Michigan

Edged by Lake Michigan and bisected by the Chicago River, Chicago is a city that can be experienced from the water. One of the most popular choices is an architectural river cruise, which gives a whistle-stop tour through the city’s architecture and history, with a particular focus on iconic high-rise buildings. For a more relaxed and romantic affair, consider a brunch, lunch or dinner cruise on Lake Michigan.

On the other side of the centre, South Loop is another quiet residential neighbourhood with excellent value accommodation. Downtown access is easy, but you won’t need to go far for Shedd Aquarium, Adler Planetarium and Field Museum.

For travellers on a budget

There’s no need to stay miles from the centre to nab a cheap holiday to Chicago – River North, just outside The Loop, is packed full of excellent value properties. You’ll find many of the smart, stylish hotel/hostel hybrids that have popped up in the city in recent years here.

Streeterville, between River North and the Lake Michigan, is another good bet, with affordable big brand hotels and hostels on offer. Both these districts keep you in the heart of the action, meaning you’ll also save money by being able to walk to both daytime attractions and your nightlife choices.

For food and drink

A former industrial area, West Loop is considered the undisputed epicentre of the city’s gourmet scene. There’s a choice of boutique hotels near ‘Restaurant Row’, which runs along Randolph Street and Fulton Market. Time Out Market Chicago, a food hall with stalls from well-known chefs, is also located here.

On the lower west side, Pilsen is a lively neighbourhood known for being something of a melting pot of culture. You’ll find authentic Mexican cuisine on every corner, and with Chinatown and Little Italy as neighbours, you won’t go hungry.

For nightlife

River North is where you’ll find Chicago’s mainstream nightlife. A lively area with a host of bars, pubs and clubs that’ll keep you up later than intended, it’s also a good spot for live music or a quiet evening out. It’s also packed with hotels, so it’s not far to stumble home.

For something a little more alternative, Wicker Park is your destination. Located to the west of downtown, this hipster neighbourhood is the place for innovative cocktails and some of the most iconic live music venues in the city. Hotel options are fittingly stylish, too.

For culture

Stay downtown in The Loop you’ll be in the heart of its historic skyscrapers. It’s also home to the Art Institute of Chicago, Millennium Park with the Pritzker Music Pavilion and the Cloud Gate sculpture, as well as the theatre district. It’s also the business district, so hotels here can offer good value on the weekends.

Or, choose the South Loop, where you’ll find plenty more culture. A case in point is the Museum Campus, home to the Shedd Aquarium, Adler Planetarium and the Field Museum. Accommodation here can suit all budgets.