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, to kickstart an epic American road trip, or your curiosity has simply been peaked by The Bear (which returns to screens this week) consult our pocket Chicago city guide for art aficionados, foodies and shopaholics to experience it in all its glory.

The hotel: The Talbott

A beloved landmark in Chicago’s Gold Coast neighbourhood, The Talbott emerged from a thorough top-to-toe renovation in April, showing off the hotel’s 178 rooms with a whole new look. Marking a new chapter in the hotel’s storied legacy, Studio 11 Design overhauled the inner city address in a palette of soothing caramels and navy hues to create a chic urban retreat for both discerning travellers and locals. Other highlights include the new Mediterranean-inspired restaurant, Laurel, helmed by chef Dino Tsaknis who has created an all-day menu featuring egg and pork belly sandwich, braised lamb shank shawarma and branzino fish and chips which can be enjoyed in the opulent dining room or al fresco on the 100-seater terrace. 

From £160 per night. 

The restaurants: Nadu, Chapel Street Cafe and Crust Tap Room

Fancy Indian food? Nadu is the latest restaurant from Michelin-starred chef Sujan Sarkar who promises to showcase the rich cultural and gastronomic landscapes of India, where every region tells its own story through food. The menu features a symphony of regional cuisines, from the aromatic biryani of Hyderabad to the fiery curries of Kerala, the street snacks of Delhi to the coastal delicacies of Goa – and can be paired with an array of expertly-crafted cocktails (we love the sound of the Old Fashioned-style Til). 

Bringing a taste of down under to the Windy City is Chapel Street Cafe: Chicago’s first Australian-style café that opened on the Magnificent Mile earlier this year. Led by Melbourne native Shawn Uldridge, the cafe consists of a coffee roastery, dine-in restaurant and a take-out bar, offering classic Australian fare such as avocado toast, flat white coffee, meat pies, and Vegemite sandwiches. Plus, Chapel Street roasts gourmet coffee beans on-site and only serves Australian wines – perfect for when you need a pick-me-up during your city break. 

It would be remiss to go to Chicago and not try its buttery, deep-dish pizza – and there are few places serving stand-out slices better than Crust Tap Room. Alongside a draft beer lineup carefully brewed at Crust Brewing in Rosemont, this friendly neighbourhood restaurant offers an array of tavern and deep pizzas, ranging from the The Maple – crispy smoked bacon, rocket and bourbon maple drizzle – to the signature Tap Room Supreme, featuring mozzarella, pepperoni cups, sausage, mushrooms and basil all drizzled in parmesan garlic butter.

The festivals and events: Grant Park Music Festival, Chicago Pride Parade, Windy City Smokeout and Taste of Chicago 

Now in its 90^th season and running until 16 August 2025, Grant Park Music Festival features an extraordinary lineup of classical music in the heart of downtown Chicago throughout the summer. This long-running concert series is the nation’s only free summer outdoor festival dedicated to classical music and includes both historic works and exciting new compositions. Highlights for 2025 include world premieres by Chicago composers, a Rodgers and Hammerstein tribute, classic symphonies, and the popular Independence Day Salute. 

On 29 June 2025, Chicago Pride Parade returns as one of the most popular LGBTQ+ events in the city. A longstanding tradition for more than 50 years, it concludes the city's month-long celebrations with a four-mile procession traversing Northalsted, Uptown, Lakeview, and Lincoln Park. This year’s theme, United in Pride, highlights the power of coming together, embracing diversity, and championing love and equality. 

Foodies will love the Windy City Smokeout from 10-13 July 2025, renowned as the US’ premier outdoor country music and barbecue festival, now in its 12^th year. The star-studded weekend will feature country music’s biggest names – including Kane Brown, Old Dominion, Jon Pardi, Bailey Zimmerman, and Megan Moroney – alongside an impressive roster of up-and-coming talent and more than 25 of the best barbecue teams from across the country. Don’t miss the bottomless brunch which will include a variety of dishes from the Windy City Smokeout’s Pitmaster Buffet, featuring a special bacon bar that's complemented by mimosas and build-your-own Bloody Marys with all the trimmings. 

Another unmissable food fest – which happens to be the world's largest free outdoor food festival – is Taste of Chicago from 5-7 September 2025. A staple in the city’s calendar for more than 40 years, it will take over Grant Park with more than 35 of Chicago’s favorite food vendors, live music performances, community dance lessons, a karaoke competition and more.  

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: Art Institute of Chicago and Intuit Art Museum

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.

Those looking to discover up-and-coming artistic talent needn't look any further than Intuit Art Museum. Renowned for spotlighting lesser-known artists, the newly-renovated museum will exhibit Catalyst: Im/migration and Self-Taught Art in Chicago until early 2026 which features a lineup of up-and-coming, self-taught artists who have created art through the lens of immigrant experience. Featuring works by Carlos Barberena, Pauline Simon, Drossos Skyllas and Derek Webster among others, expect to spot themes include longing for homeland, labour and individual expression, and tendencies toward assimilation. 

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 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.

Read more: Inside the world’s biggest charter yachts