Chicago holiday lettings

Why visit Chicago

• Iconic landmarks: Discover renowned sites like the Willis Tower and Millennium Park, showcasing Chicago's architectural brilliance.
• Cultural experiences: Enjoy world-class museums such as the Art Institute of Chicago and the Field Museum, perfect for culture enthusiasts.
• Beautiful parks and beaches: Relax in urban parks or along the scenic shores of Lake Michigan, ideal for outdoor lovers.
• Diverse dining options: Savor a variety of culinary delights, from deep-dish pizza to upscale dining experiences.
• Charming neighbourhoods: Explore vibrant areas like Wicker Park and Lincoln Park, full of unique shops and local culture.

Popular types of accommodation in Chicago

Planning a getaway to Chicago? The next step is selecting the perfect accommodation. From stylish apartments and private holiday homes to modern condos, Chicago offers a variety of holiday rentals to suit every taste and budget. With our platform, you can explore a range of options for your stay, ensuring transparency and savings throughout your booking process. Discover the best holiday rentals in Chicago and enjoy your trip with peace of mind.

• Apartments: The most sought-after choice for holiday rentals in Chicago, offering comfort and convenience in the heart of the city.
• Houses: A fantastic option for families or groups seeking a home-like atmosphere during their stay.
• Condos: A popular pick, providing modern living spaces with access to amenities and shared facilities.
• Cottages: Charming and cosy, ideal for those looking for a quaint retreat near the city.
• Villas: Luxurious accommodations that offer spacious living and often come with exquisite views.**

Top attractions in Chicago

Chicago is a fantastic destination for families and outdoor enthusiasts, offering a diverse range of attractions. Visitors can explore urban parks, modern universities, and beautiful beaches, ensuring a delightful experience for those seeking culture and city life. Whether you’re travelling with family or on your own, there’s plenty to see and do in and around this vibrant city.

• Six Flags Great America: This vibrant theme park offers a thrilling experience with exhilarating rides, entertaining shows, and family-friendly attractions, making it perfect for visitors of all ages.
• McCormick Place: As the largest convention centre in North America, McCormick Place hosts a variety of significant events and exhibitions, providing a bustling atmosphere for networking and business opportunities.
• Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, dining options, and iconic architecture, embodying the lively spirit of Chicago.

Things to do recommended for couples

Seeking a romantic getaway in Chicago? Indulge in a medieval feast at Schaumburg Medieval Times, dance the night away at Aragon Ballroom, or unwind in luxury at Chevy Chase Country Club. Each venue offers a unique experience perfect for couples looking to create lasting memories.

Things to do recommended for families

Families will love the sports atmosphere at Wrigley Field, the serene wellness vibe of Northerly Island Natural Area, and the thrilling adventure at Great Wolf Lodge Water Park, making Chicago a fantastic destination for a memorable family holiday.

Things to do recommended for groups

Explore the vibrant Woodfield Mall for shopping and entertainment, enjoy a show at the iconic Chicago Theatre, or unleash your creativity at the LEGOLAND® Discovery Center. These activities promise a delightful blend of fun and culture for your group in Chicago.

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

When travelling with a group, family, pets, or seeking extended stays, it’s important to filter your options according to your key priorities. Here are some helpful Vrbo booking tips for you.

• Traveling to Chicago with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
• Traveling to Chicago with young kids: Travelling with young children can present its challenges. It's important to prioritise their comfort and safety, along with suitable amenities for their age, such as a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
• Taking your pets with you to Chicago: For many, a family holiday wouldn’t be the same without their furry companion by their side. If that resonates with you, explore Vrbo 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 seeking holiday rentals with special offers for stays of a month or more, you’ve come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in Chicago

Chicago, known as the Windy City, offers a vibrant mix of urban charm and scenic beauty, perfect for family breaks or romantic getaways. Explore iconic landmarks, enjoy delightful dining options, and wander through friendly neighbourhoods. Nearby cities enhance the experience with their unique atmospheres, catering to both business and leisure travellers alike. With its excellent location and diverse attractions, Chicago is a fantastic holiday destination that promises unforgettable memories.

• Downtown Chicago: As the vibrant core of the Windy City, Downtown Chicago offers an exhilarating blend of culture, shopping, and entertainment. Visitors flock to this bustling area for its family-friendly activities, outdoor spaces, and iconic cityscape. Explore the renowned shopping districts, catch a game at a local sports venue, or take in a captivating performance at one of the many theatres. Key landmarks, including the historic tourist precinct and impressive stadiums, make Downtown a must-visit destination for anyone looking to experience the heartbeat of Chicago.
• Magnificent Mile: Magnificent Mile is Chicago's premier shopping district, where luxury meets accessibility amid a lively urban atmosphere. This neighbourhood is perfect for families and those seeking outdoor experiences, with its tree-lined streets and stunning architecture. Visitors can indulge in retail therapy at high-end boutiques, enjoy diverse dining options, or engage in educational visits at nearby cultural institutions. Key attractions include the bustling tourist precinct and sports facilities, making it an exciting destination for both leisure and exploration.
• The Loop: The Loop is Chicago’s iconic downtown area, known for its impressive skyline and rich history. This neighbourhood is ideal for families and outdoor enthusiasts alike, offering a blend of urban parks, shopping venues, and cultural experiences. Stroll through the picturesque downtown, catch a thrilling performance at a theatre, or relax in one of the many green spaces. With its proximity to major landmarks, including the urban park and vibrant stadiums, The Loop provides an engaging experience for all visitors looking to immerse themselves in the city's dynamic atmosphere.

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 Vrbo is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to craft new travel plans, refine your arrangements, or keep track of your existing bookings. The properties you've saved or reserved are thoughtfully categorised into Potential, Upcoming, and Current Trips for your ease of reference. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.