Situated on the majestic Lake Michigan, Chicago is a bustling city in northeastern Illinois that’s very easy to love. The weather here can be a bit temperamental so we recommend visiting in May, June, September or October to experience all that this big city has to offer unhindered. Made up of 77 distinct neighbourhoods, Chicago has all of the eclectic energy that New York has to offer, but with a laidback and low-key twist. Expect striking architecture, an extraordinary food and brewery scene, innovative art and music spaces and of course, friendly locals (Chicagoans) who are excited to help you get to know their city. Our city guide to Chicago, Illinois takes you to the best hotels, restaurants and attractions in this exciting metropolis.
Housed in a monumental Art Deco masterpiece overlooking a bustling intersection in the Wicker Park district of Chicago, The Robey is the ideal accommodation choice for anyone wanting to experience Chicago from a local’s perspective. The airy 89 room hotel is nestled amongst bars, restaurants and boutiques and is only a short train ride from the Loop. The only skyscraper for miles, it was originally designed as an office building in 1929. Today the boutique hotel embodies a sophisticated balance of slick contemporary design and vintage mid-century touches. Rub shoulders with some of the coolest in the creative industry at the neighbouring Robey Hall rooftop where the pool and lounge are open during the summer season.
In Chicago, you’ll be utterly spoilt for choice when it comes to dining options but sometimes it’s the most simple meals that are the most satisfying. For a slice of pure flavour, it’s hard to beat Spacca Napoli Pizzeria located nearby Montrose. A casual spot with efficient but friendly staff and an outdoor patio to dine on during the warmer months, Spacca Napoli Pizzeria serves brick-oven cooked Neapolitan-style thin crust pizza – the crust a delectable balance of crispy on the outside and chewy on the inside. While the menu offers a range of unique and exciting flavours, we highly recommend opting for at least one Marghertia pizza to really appreciate the master craftsmanship that goes into this base and sauce – simply superb!
Lou Malnati's: Chicago is home to the legendary deep dish pizza and this is the best spot to enjoy it!
Publican Anker: A casual and locally-loved gastropub serving simple yet scrumptious pub fare.
The Publican : A rustic restaurant with a pork-focused menu and international brews. Dine family style on the communal tables and long benches.
Little Goat: Enjoy brunch at this easy-going restaurant specialising in comfort food with a gourmet flair.
Pub Royale: A tap room with a huge array of beers and ciders to enjoy from the busy bar or a more intimate booth.
Twin Anchors: Once a favourite of Frank Sinatra’s this restaurant dates back to 1932 and serves some of the best ribs in the city.
Au Cheval: A dimly-lit upscale diner known for its burgers, foie gras and eggs.
The Purple Pig: Expect Mediterranean-inspired small plates and speciality house-cured meats.
Mott St: Come here for the famous stacked burger – only available at the bar. Get there early for a seat or grab a drink and wait until a bar stool opens up.
The Green Mill: Live jazz music and expertly prepared cocktails, this is one of the last ‘authentic’ speakeasies in the city.
Cindy’s Rooftop: One of the best rooftops in the city, come for a cocktail, the cool crowd and amazing views of the Millennium Park, the Art Institute and Lake Michigan.
The Aviary: An innovative bar serving creative and experimental cocktails in a contemporary cool setting.
Chicago is loved as the best architectural city in the United States. From Frank Lloyd Wright to Ludwig Mies van der Rohe, the city is home to masterpieces from some of the most influential architects of all time. The best way to see and appreciate the architectural scene here is by embarking on the Architecture Boat Tour organised by the Chicago Architecture Foundation Center. Led by engaging experts, on the 90 minute river cruise you will learn the fascinating stories behind 50 of the monumental buildings along the Chicago river and discover how the city came to be one of the largest in America.
Improvised Shakespeare Company: Enjoy fully improvised Elizabethan plays performed by brilliant actors and actresses – a very entertaining evening is guaranteed.
Art Institute of Chicago: An obvious but absolute must, this is one of the most important and influential art museums in the world.
Chicago Riverwalk: An ideal spot to spend the afternoon, walk along the riverside and enjoy some peace by the water.