Chicago City Breaks 2025

Why go to Chicago

High-rise and high energy, Chicago is big, bold and boisterous – and proudly so. With a striking lakeside setting, a packed sports calendar and a world-class cultural scene – think the blues and deep-dish pizza – a holiday in the Windy City has something for everyone.

Rebuilt extensively after the Great Fire of 1871, Chicago became the home of the first skyscraper – and architects haven’t looked down since. It has four of the tallest buildings in the USA. But it’s not all boring blocks – you’ll also find a mid-century Frank Lloyd Wright house and Frank Gehry’s signature swooping lines at the Pritzker Pavilion.

The city’s museums, meanwhile, are must-visit attractions rather than places to while away a rainy day. See the world’s largest dinosaur at the Field Museum of Natural History, journey to the stars at the Adler Planetarium and ‘experience a tornado’ at the Museum of Science and Industry.

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.

When to go to Chicago

May, June, September and October are the best months to visit Chicago weather-wise, with balmy sunshine and temperatures in the late teens and early 20s bracket. Average temperatures in July and August peak around 28C, giving you the chance to make the most of the city’s lakeside beaches and green spaces. That said, be prepared for humidity and flash showers, which can make sightseeing less comfortable.

Prices from April through to October are significantly higher than the rest of the year, so if you don’t mind the chill, then the winter months are the best time to bag a bargain. December is a good value month, with cheap holidays plus festive treats to enjoy, including a German-style Christmas market and skating rinks.

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.

What to do in Chicago

With a host of world-class museums and attractions catering to a broad range of interests – everything from space and science to sculpture – Chicago is a cultural powerhouse. Be sure to include time on the pier, in a park or two, and, of course, high above in one of its skyscrapers (the TILT experience at 360 Chicago is recommended).

Millennium Park

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.

Where to stay in Chicago

For families

Whether you’re travelling with tots or teens, Lincoln Park is a safe bet for family stays. Calmer and greener than downtown, this district is just a short ride north from The Loop on the L train. Right on the doorstep are the city’s largest park, the zoo, and North Avenue Beach.

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.