Keen to see more of Chicago through the eyes of an Intrepid local? Consider this a glimpse into our leaders' little black book of local favourites. Discover some of their number one stops to eat, relax, sip and explore in the place they call home.
1. Shaw’s Crab House, for a Chicago institution that’s been serving up oysters, lobster and – of course – crab for over 40 years
2. Twin Anchors, for slow-cooked baby back ribs served with signature sauces in one of Chicago’s oldest restaurants
3. Purple Pig, for Mediterranean spreads of European cheeses, dips and cured meats at lively communal tables
4. JP Graziano, for a fourth-generation family-owned grocery shop slinging Italian subs
5. La Scarola, for Italian comfort food in a cosy setting where picture frames crowd the walls
1. Do Rite Donuts, for coffee with a side of fried chicken sandwiches – or donuts in sometimes unexpected flavours, if you’ve got a sweet tooth
2. Big Shoulders Coffee, for sustainably sourced coffee in a space designed as an ‘ideal third place’ to sit and relax
3. Starbucks Reserve Roastery, for the biggest Starbucks in the world
4. Momentum Coffee, for a Black-owned coffee shop that's also a co-working space for creatives and entrepreneurs
5. Hexe Coffee Co, for barrel-aged coffees, cold brew and pastries made in-house daily
1. Field Museum, for one of the largest natural history museums in the world
2. Museum of Science and Industry, for an immersive experience for the whole family blending science, technology and engineering – think flight simulators and VR space travel
3. Museum of Contemporary Art, for a collection of over 2000 works of new and experimental contemporary art
4. The Art Institute, for artworks by Van Gogh, Matisse, Warhol, Picasso, Monet and many more
5. Notebaert Nature Museum, for a greenhouse home to more than 1000 butterflies, over 100 regional bird species and nature trails
1. The Green Mill, for cocktails, live music and occasional poetry or comedy in one of America’s most famous jazz bars
2. Second City, for improv comedy at the Chicago institution – the launchpad for the likes of Steve Carell, Tina Fey and Martin Short
3. Andys Jazz Club, for a full-dining jazz club that’s been around since the 1950s
4. The Bassment, for live music and cocktails hidden behind a secret entrance
5. Bottom Lounge, for music, beer and American comfort food in a casual setting with a rooftop deck
1. Millennium Park, for Chicago's emblematic Cloud Gate sculpture (AKA ‘The Bean’) and live outdoor entertainment at the Jay Pritzker Pavilion
2. Lakefront Trail, for a nearly 30 km trail along Lake Michigan perfect for running, walking, cycling and even rollerblading
3. Lincoln Park and Zoo, for almost 200 species of animals, including the critically endangered eastern black rhinoceroses and Jamaican iguanas – admission is free!
4. Garfield Park Conservatory, for 4 hectares of outdoor gardens, indoor garden displays, a water lily pond and children’s play areas
5. Jackson Park, for a Japanese-style garden, cherry blossoms in spring and birdwatching at Bobolink Meadow
1. The Pilsen Neighborhood, for Latin music, food and nightlife, plus the 30 or so galleries that make up the Chicago Arts District
2. Andersonville, for the charming Clarke Street shopping strip, a vibrant LGBTQIA+ community and an array of cuisines
3. Margie’s Candies, for candies, chocolates and an ice cream parlour serving sundaes and banana splits
4. Promontory Point, for a manmade peninsula designed in the Prairie School architectural style by Alfred Caldwell
5. Winter Garden at Harold Washington Library, for an atrium with terrazzo flooring and a 15 m glass dome perched on the ninth floor of the library
Our Urban Adventures daytrips are just the beginning. Intrepid has hundreds of multi-day adventures in over 100 countries. Whether you want to trek Peru’s Inca Trail or spend time in Morocco’s Sahara, we’ve got you covered.