Chicago holiday rentals

Why visit Chicago

• Iconic skyline: Marvel at Chicago's stunning skyline, featuring architectural masterpieces and towering skyscrapers.
• Cultural richness: Experience the city's vibrant arts scene, with museums, galleries, and theatres showcasing diverse cultural expressions.
• Outdoor spaces: Enjoy urban parks and sandy beaches along Lake Michigan, perfect for relaxation and recreation.
• Unique neighbourhoods: Discover charming neighbourhoods, each offering distinctive atmospheres, local shops, and dining experiences.
• Exciting nightlife: Explore a lively nightlife scene with a variety of bars, music venues, and dining options.

Popular types of accommodation in Chicago

Discover the best Chicago accommodation, from private holiday homes to cosy apartments and modern condos, ensuring an unforgettable stay in Chicago, Illinois, United States of America. Enjoy the city's iconic attractions, landmarks, and experiences, all while benefiting from transparent savings and reassurance. Explore friendly hotel options and competitive hotel prices for a truly exceptional holiday rental experience.

• Private Holiday Homes: Enjoy a home-away-from-home experience in Chicago with spacious private residences perfect for families or groups.
• Apartments: Opt for convenient and stylish apartments that offer a blend of comfort and accessibility in the heart of the city.
• Condos: Discover modern condos featuring excellent amenities, ideal for a relaxing urban getaway.
• Villas: Experience the luxury of villas, providing ample space and a touch of elegance for your Chicago stay.
• Cottages: Unwind in charming cottages that offer a quaint and cosy atmosphere, perfect for a peaceful retreat.**

Top attractions in Chicago

Chicago offers a vibrant mix of attractions perfect for family outings and outdoor adventures. Visitors can explore urban parks, relax on sandy beaches, and marvel at iconic skyscrapers. The city's rich culture and family-friendly experiences ensure that there's something for everyone, making it an ideal destination for those seeking a diverse city-themed holiday.

• Michigan Avenue: Embrace the vibrant city vibes along this iconic street, lined with elegant shops, cultural landmarks and buzzing urban energy.
• Navy Pier: Enjoy scenic urban views and a welcoming atmosphere at this jetty, where friendly locals and visitors mingle against the backdrop of the city's sparkling waterfront.
• Millennium Park: Delight in the family-friendly, outdoor ambiance of this urban oasis, featuring art installations, lush greenery and open spaces perfect for leisurely strolls.

Things to do recommended for couples

For a romantic getaway in Chicago, explore the stunning views from the Willis Tower Skydeck or enjoy a leisurely walk along the picturesque Lakefront Trail. Don't forget to take a sunset river cruise for a magical experience of the city’s skyline.

Things to do recommended for families

Families visiting Chicago can explore the interactive exhibits at the Museum of Science and Industry, and enjoy a day out at the Lincoln Park Zoo, offering a delightful experience for children and adults alike.

Things to do recommended for groups

Group travellers in Chicago can enjoy a culinary tour in diverse neighbourhoods, explore art and architecture in Millennium Park, and take a scenic boat ride on the Chicago River to appreciate the city's iconic skyline.

What do I need to keep in mind when booking a vacation in Chicago

Whether you're travelling with a group, as a family, with your pets or seeking extended stays, ensure you apply the appropriate filters. Below are some Stayz booking suggestions for you.

• Traveling to Chicago with a group: Think about how many bedrooms you require, along with amenities like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these features and more on Stayz.
• Traveling to Chicago with young kids: Traveling with young children can prove challenging, as their comfort and safety must be prioritised alongside age-appropriate amenities, such as a private swimming pool. It is also advisable to consider your proximity to attractions that cater to families.
• Taking your pets with you to Chicago: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Chicago: If you're in search of holiday rentals offering discounts for month-long stays or longer, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Chicago

Chicago, a vibrant metropolis, offers an array of attractions perfect for families and outdoor enthusiasts. Explore the iconic downtown area, teeming with lively nightlife and cultural landmarks. Stroll through picturesque neighbourhoods, each boasting its unique charm and friendly atmosphere. From the stunning skyline to scenic waterfronts, Chicago invites you to immerse yourself in its urban energy and diverse experiences, making it an ideal destination for an unforgettable holiday.

• Chicago: As one of the largest cities in the United States, Chicago is renowned for its vibrant culture and stunning architecture. Nestled along the shores of Lake Michigan, the city offers a diverse range of experiences, from family-friendly attractions to outdoor activities. Visitors can enjoy world-class shopping in the Magnificent Mile, catch a thrilling game at one of the city's major sports stadiums, or explore the lush greenery of Millennium Park. Chicago's bustling theatre scene and rich culinary landscape further enhance its allure, ensuring there's something for everyone to enjoy.
• Downtown Chicago: Downtown Chicago serves as the energetic core of the city, where urban life flourishes. This neighbourhood is perfect for families and those seeking an outdoor escape while immersing themselves in the city's vibrant atmosphere. Stroll along the picturesque waterfront, visit iconic landmarks like the Willis Tower, or indulge in shopping at various high-end boutiques. The area is also home to numerous theatres and entertainment venues, making it a hub for culture and nightlife. With urban parks offering a serene retreat amidst the hustle and bustle, Downtown Chicago is a must-visit for any traveller.
• Schaumburg: Located just outside Chicago, Schaumburg is a bustling city known for its blend of family-friendly attractions and business opportunities. The city boasts an impressive shopping centre, where visitors can find everything from designer brands to unique local shops. In addition to its retail offerings, Schaumburg features theatres that showcase both blockbuster films and indie productions. With event conference venues and a convention centre nearby, it's an attractive destination for those travelling for business or leisure. The city's vibrant atmosphere and variety of attractions make it a delightful stop on your journey.

Best time to go to Chicago

If you're planning a trip to Chicago, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like December to February tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Moderately Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Average	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Moderately High	Slightly High
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Moderately Low	Average

Booking with Stayz is a breeze

Are you eager to save on your next holiday? Being flexible with your travel dates can be a smart choice, as prices can vary significantly. Additionally, opting for a longer stay often leads to substantial savings. To discover the perfect Stayz property that fits your budget, utilise our filters to organise options by price, location, and type of holiday rental.

Stayz Trips: Planning as easy as it gets

Stayz’s Trip Board provides you with a dedicated space to plan new trips, continue existing ones, or review and organise your bookings. Your saved or booked properties are now neatly categorised into Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.stayz.com.au/trips.

**Based on Vrbo properties bookings.