Home to mouth-watering culinary delights, a thriving nightlife and a world-famous music and festival scene, Chicago is bursting at the seams with fun and unique experiences that are just waiting to be discovered. Whether you’re stopping in for a brief visit or staying a little longer, we’ve compiled the best that the Windy City has to offer to ensure you don’t miss a minute of the action. From taste-testing local deep-dish pizza to sipping on cocktails at a jazz club or dancing up a storm at one of the many celebrated music festivals, we’ve got you covered!


No visit to Chicago is complete without sampling the local delicacies, with our top picks the iconic deep-dish pizza and Chicago-style hot dogs. For the perfect mix of impressive blues artists and burgers that require two hands, Buddy Guy’s Legends is a must, delivering an impressive dinner and show 7 nights a week! Dubbed one of America’s best, Au Cheval serves up the kind of melt-in-your-mouth burgers that have people lining up for hours, but trust us when we say that the juicy patties, soft buns and selection of gourmet toppings make it well worth the wait. For the mother of all deep-dish pizzas, Lou Malnati’s is a must! The famous creations contain a glorious overload of gooey cheese, rich napolitana sauce and buttery crust that need to be on every must-try list. Be sure to work up an appetite before heading to Swift and Sons, which serves up prime cuts of juicy chargrilled steaks, a selection of succulent seafood and moreish sides that will make you want to order one of everything – and so you should! – It’s safe to say that your belly and soul will always be full in Chicago!


There’s nothing quite like the electric vibe of Chicago at night. Erupting into a lively hub of music, dancing and activity, venturing out to one of the pubs, clubs or bars is the best way to get a true taste of the city. For an unforgettable night of live music and a no fuss, laid-back atmosphere, Empty Bottle is the go-to. Famous for hosting bands before they make it big, you may just watch the ‘next big thing’ without even knowing it. Boasting soulful sounds and a glamorous 1920s-style interior, Green Mill Cocktail Lounge oozes old world charm. Be enticed by the smooth sounds of live jazz and blues, and stay late for the warm atmosphere and bespoke cocktails. If an intimate, low key vibe is more your thing, the Hideout is unmissable. The small balloon-frame house has been a place for hearty drinking, creative musical expression and rebellion for over a century, welcoming everyone with open arms and ice-cold beer. Playing jazz, rock, electronic and soul every night of the week, The Whistler will keep you bopping until the early hours. Wherever your night takes you, you’ll never be far from greats beats!


From world-famous festivals to local neighbourhood street festivals, Chicago is a melting pot of musical creativity and excitement, with artists and music fans from all over the world descending on the city each year to attend the slew of iconic summer festivals. Spanning ten city blocks, Do Division Street Fest is an annual bonanza of food, fashion, family activities and music. Whether you’re bagging a bargain at the sidewalk sale, sampling finger-licking nosh at the local food vendors or grooving to the sounds of the live band, it’s a fun day out for all ages. Showcasing diverse genres and a casual atmosphere, Pitchfork Festival is a truly unique affair. The annual event attracts both up-and-coming artists and megastars, with Chance the Rapper, Tame Impala and Modest Mouse headlining in previous years. Set in Chicago’s Highland Park and running all summer, Ravinia Festival offers rock, pop and classic concerts most nights of the week. Grab a pavillion seat or opt for a picnic on the grass – either way, it’s a guaranteed good time. The highlight of the season and one for the festival bucket list is Lollapalooza. With over 130 bands playing across 8 different stages over 4 days, the cultural extravaganza is a challenge of endurance, but a whole lot of fun! Chicago truly has something to suit all tastes.


Whilst it would be easy to spend your entire trip exploring the inner city, if you venture just a little further, you’re guaranteed to be rewarded with stunning sights, sounds and flavours! A quick trip to Dusty Groove Record Store will land you in vinyl heaven. The store is owned by two seasoned ‘crate diggers’, so you can expect shelves overflowing with classics from all music genres and eras. A scenic 20-minute drive south of Chicago, in the Woodlawn Community area you’ll find Jackson Park. The stunning landmark comprises of over 500 acres of picturesque green space including the Wooded Island, which features a Japanese-style garden, as well as Bobolink Meadow and the stunning Skylanding sculpture by Yoko Ono. Symbolising peace and new beginnings, the park offers an oasis to escape the hustle and bustle of the big city. On your way back to Chicago, stop in at Calumet Fisheries, which is located next to the 95th Street Bridge and was featured in the 1980 film, The Blues Brothers. This rustic white shack serves up generous portions of smoked seafood to go – perfect after you’ve worked up a big appetite from a day of exploring! Albano’s Pizzeria is another must for the foodies. Dishing up all the cheesiness and sauciness you’d expect of a classic pizza only rolled into a convenient, mess free ‘pizza puff’ parcel, it’s a 15-minute drive you’ll be thankful you took. Whether you’re venturing, north, south, east or west, Chicago offers something new to eat, see and do!