A first-timer’s guide to Chicago, US

Chicago is a city where cosmopolitan sophistication meets Midwestern warmth, where Michelin-starred restaurants share blocks with classic diners and world-class museums sit steps from vibrant street art. Its skyline dazzles with architectural icons while Lake Michigan offers a serene contrast to the urban buzz. From the historic Loop to the city’s 77 distinct neighbourhoods, Chicago is a mosaic of culture, cuisine and creativity. Whether you’re here on business, a foodie on the trail of The Bear or for the art and the architecture, the Windy City promises something unforgettable in every season.

Where to start – discovering Chicago

Start your journey in the Loop, Chicago’s historic downtown, where world-class architecture meets cultural landmarks. Here, you’ll find the world’s first skyscrapers, the Art Institute of Chicago – home to Grant Wood’s American Gothic – and the elevated train system inaugurated in 1892.

Beyond the Loop, the city’s 77 officially designated neighbourhoods unveil a rich tapestry of identities and experiences. Bronzeville hums with jazz heritage and Black history, Pilsen bursts with colourful murals and authentic Mexican eateries, Andersonville celebrates Swedish roots alongside independent boutiques and Chinatown’s culinary traditions have thrived since the neighbourhood was established in 1912.

How to get around Chicago – transport tips for visitors 

Chicago’s public transport system is among the most efficient in the US, making it easy to explore without a car. The elevated trains – known locally as the “L” – link downtown with neighbourhoods such as Wicker Park, Hyde Park and Logan Square, and the Blue Line runs directly to O’Hare International Airport. For a scenic alternative, hop aboard a Chicago Water Taxi to glide between Chinatown, the Loop and Navy Pier. Cycling is another great option thanks to Divvy Bikes, the city’s bike-share programme with more than 600 stations, perfect for rides along the 29km Lakefront Trail. Ride-share services like Uber and Lyft are widely available, and traditional taxis remain easy to hail downtown.

Where to eat in Chicago

The city's culinary scene is diverse and endlessly creative. For local flavour, head to The Wiener’s Circle in Lincoln Park, a late-night institution famed for its chargrilled Chicago-style hot dogs, cheese fries and cheeky banter. In Bronzeville, Pearl’s Place serves Southern comfort classics such as fried catfish, smothered pork chops and peach cobbler, while Pilsen’s Taqueria El Milagro dishes up authentic Mexican tacos in a no-frills setting.

For the ultimate Chicago experience, head to Lou Malnati’s, widely praised as the city’s best deep-dish pizza spot, thanks to the buttery crust, gooey mozzarella and rich tomato sauce of its pies. This family-owned chain has several locations in the city, but the one at 410 North Michigan Ave is perfectly located for the river and main hotels and attractions.

Feeling fancy? Chicago’s best restaurants are world-class. Alinea in Lincoln Park delivers a multi-sensory tasting menu that feels part-theatre, part-cuisine, while Oriole in the West Loop – a two-Michelin-starred gem tucked in an alley – offers an intimate culinary experience. In the Gold Coast Adalina blends Northern and Southern Italian influences under Michelin-starred chef Soo Ahn, pairing house-made pasta with a thoughtfully curated wine programme. 

Cocktail lovers will find plenty to explore. Nine Bar in Chinatown, the area’s first cocktail bar, hides behind Moon Palace Express and serves yuzu margaritas and baijiu-based creations in a neon-lit space. Scofflaw in Logan Square charms with its gin-forward menu and Victorian-inspired decor, complete with complimentary fresh-baked cookies each night. For a touch of elegance, Bar Kumiko in the West Loop offers spirit-forward drinks crafted with precision by renowned mixologist Julia Momose.

Top things to do in Chicago – must-see attractions

Start at Millennium Park to snap a selfie at Cloud Gate – better known as “The Bean” – before wandering through its gardens and outdoor art installations. The Art Institute of Chicago is a must for art lovers, home to works by Monet, Van Gogh and Grant Wood, and guarded by its iconic bronze lions. For a unique perspective on the skyline, take an Architecture River Cruise – an essential for first-time visitors. The Museum Campus brings together three world-class attractions within walking distance: the Field Museum, Shedd Aquarium and Adler Planetarium. For a thrill, head to the Skydeck at Willis Tower and step onto the glass ledge 103 storeys above the city for a mesmerising view.

Best hotels – where to stay in Chicago

Chicago’s luxury hotels combine impeccable service with stunning views. The Peninsula Chicago , just off the Magnificent Mile, blends Asian-inspired elegance with local sophistication – don’t miss afternoon tea in the lobby or a treatment at its award-winning spa. The Langham, Chicago set in a Mies van der Rohe-designed building along the Chicago River, offers spacious rooms and a dedicated wellness retreat. Four Seasons Hotel Chicago , perched above the Gold Coast, boasts Lake Michigan views and a top-tier restaurant, Adorn, led by chef Richie Farina. For a boutique experience, Nobu Hotel in the West Loop delivers minimalist design, a chic rooftop bar and refined plates.

Chicago travel tips – when to visit and what to pack

Spring brings blooms to Lincoln Park Conservatory, a free oasis of tropical plants and seasonal flowers – visit early for the best light and fewer crowds. In summer, skip Navy Pier and opt for a Lake Michigan cruise for skyline views without the throngs – be sure to book ahead as tours sell out quickly. Autumn is ideal for exploring neighbourhoods beyond the Loop – such as Logan Square, Pilsen and Andersonville – and sampling apple cider doughnuts at farmers’ markets like Green City Market. Winter calls for museum-hopping to stay warm – the Art Institute, Field Museum and Museum of Science and Industry are perfect escapes.

Year-round, dress for the wind as well as the weather. Locals swear by layering, with a light jacket, scarf and comfortable shoes essential for tackling the breezes off Lake Michigan.