Holiday rentals near Chicago

314,038 rentals worldwide

Explore Chicago

A breath-taking modern skyline, music wafting across Millennium Park and the scent of deep-pan pizza will tickle your senses when you visit Chicago. Known as the Windy City of the USA, Chicago has it all, from museums and art galleries to world-class sports teams and award-winning restaurants. Get your giggle on at the Second City Theater, where comedians like Tina Fey and Stephen Colbert learnt their trade, and marvel at the stunning modern architecture towering above you, like the 110-storey Willis Tower (previously known as the Sears Tower). For a truly American experience, head to Wrigley Field to watch the Cubs play baseball, or take in an ice hockey game courtesy of the Blackhawks. There’s so much to see and do you’ll be spoilt for choice.

Renting holiday apartments in Chicago

When staying in apartments in Chicago you can really get a feel for the real city, as you’ll be living amongst locals in a home away from home setting. Take advantage of your neighbours’ local knowledge when you choose Chicago apartments as your holiday accommodation and you’ll be able to find all the hidden gems that tourists in hotels would simply never discover. Browse the selection on HouseTrip and find the holiday rental to suit your needs, then in a matter of clicks you’ll be all booked and ready to take the city by storm!

Where to stay in Chicago

To truly experience Chicago like a local, rent an apartment in Chicago’s residential neighbourhoods. Somewhere like Logan Square will give you easy access to O'Hare Airport and Downtown Chicago, whilst also allowing you to explore the neighbourhood cafes and coffee shops. HouseTrip also has luxury Chicago apartments right in the centre of the city, with stunning views of the skyline and within walking distance of major attractions like Lake Michigan and North Avenue Beach plus the Magnificent Mile and Lincoln Park. Whatever kind of holiday accommodation in Chicago you want, take a look at HouseTrip and start planning your trip to the Windy City knowing your accommodation needs are sorted.

Chicago with the family

Chicago is an amazing destination for a family holiday, with so many places to visit and experiences to enjoy. Take a cruise boat along the Chicago River to get an overview of the city and get your bearings, then take your pick from the huge number of attractions to visit. Stroll through Millennium Park and feast on pizzas al fresco at lunchtime before meeting the animals at Lincoln Park Zoo. If culture is on the agenda, you’ll love a visit to the Art Institute of Chicago, and when it’s time to discover an underwater world get yourselves to Shedd Aquarium. By staying in a holiday rental for the family rather than costly and cramped hotel rooms, you’ll be able to relax together in the evenings after all the daytime excitement.

Sign up

Log-in