Chicago, Illinois Vacation Rentals: Houses, Mansions, Apartments, Townhomes, Condos, & More

Your Guide to Chicago

What to do in Chicago

Chicago, one of America’s great cities, rises from the shores of Lake Michigan and beckons travelers with its unique blend of culture, history, and architectural marvels. The iconic Millennium Park, home to the gleaming Cloud Gate (often referred to as "The Bean"), is a must-visit, as is the nearby Art Institute of Chicago, housing an impressive collection of global art. The Navy Pier offers family-friendly entertainment with its festive atmosphere, rides, and eateries. Head to the Willis Tower's Skydeck or the 360 Chicago observation deck for the most breathtaking city views. Or take a famous architectural boat tour along the Chicago River for unique perspectives of the city's legendary skyscrapers. Exploring Chicago’s diverse neighborhoods and culinary scene is a must for travelers. Here are a few popular ways to spend your day:Tour Landmarks by Boat - Chicago's architectural boat tours offer a unique perspective on the city's rich architectural heritage. Gliding along the Chicago River, these tours highlight the majestic skyscrapers and historic buildings designed by renowned architects. The narrated journey provides insights into the city's architectural evolution, making it a must-do for visitors.Explore World-Class Museums - The Art Institute of Chicago is famed for its impressive collection of Impressionist art, while the Field Museum enthralls with natural history exhibits. The Museum of Science and Industry offers hands-on experiences, and the Chicago History Museum delves into the city's past.Enjoy a scenic stroll - The Lakefront Trail offers breathtaking views of Lake Michigan juxtaposed with the city skyline. The Chicago Riverwalk, winding along the river through the heart of downtown, provides a serene urban escape. Meanwhile, Millennium Park and Grant Park showcase beautiful landscapes amidst iconic art installations.

Best Time to Visit Chicago

Chicago enjoys distinct seasons and charms visitors year-round. Winter travelers should prepared well for its often-frigid winters. Spring, from April to June, is a delightful time to witness the city's parks and gardens in bloom, particularly the tulips lining Michigan Avenue. Summer, from June to August, brings lively festivals, open-air concerts, and beach activities along Lake Michigan, though it's also the peak tourist season, resulting in larger crowds. The city's architectural boat tours are especially popular during these warmer months. Fall, from September to November, is characterized by crisp air, vibrant foliage, and the renowned Chicago Marathon. The crowd levels dip, making it a quieter time for exploration. Winter, from December to February, is cold and snowy but offers ice skating in Millennium Park and the magical lights at Lincoln Park Zoo. Visitors should be ready for chilly temperatures and bring warm clothing if visiting during the winter months.

The Weather in Chicago

With four well-defined seasons, Chicago experiences a full range of weather, each with unique appeal. Winter (December-February) is cold, with temperatures ranging from 20°F to 35°F (-6°C to 2°C). Snow and arctic-like weather is typical, so travelers should pack heavy coats, scarves, gloves, and insulated footwear. Spring (March-May) sees temperatures from 40°F to 65°F (4°C to 18°C). We recommend lightweight jackets and layered clothing. Summer (June-August) is warm, sometimes hot, with temperatures from 70°F to 90°F (21°C to 32°C). Light clothing, sun hats, and comfortable shoes are ideal. Fall (September-November) has temperatures from 45°F to 70°F (7°C to 21°C), showcasing the city's beautiful autumn foliage. A medium-weight jacket and layers work well. Regardless of the season, we advise bringing comfortable walking shoes as the city is a joy to explore on foot.

Chicago Vacation Rental FAQs

What are the Different Types of Vacation Rentals in Chicago?

Chicago is a truly diverse city shaped by unique historic neighborhoods, architectural marvels, and vibrant reinvention. As such, visitors enjoy an array of vacation rental options. The selection of vacation home rentals in Chicago varies widely by size and style, from chic lofts to traditional stately homes. Chicago vacation rentals in neighborhoods like Wicker Park, Lincoln Park, or Wrigleyville allow guests to immerse themselves in local culture and ambiance. On bnbfinder, you can easily search for Chicago weekly rentals that offer flexibility for extended stays, whether for business or leisure.In the heart of the city, downtown Chicago vacation rentals are ideal for travelers eager to be close to the main attractions. Check neighborhoods like Streeterville, River North, and West Loop. Here, luxury seekers can find Chicago penthouses for weekend rental that provide breathtaking views of the cityscape and Lake Michigan.For groups or families who prefer the comforts and conveniences of home, vacation rentals in Chicago, like large apartments and houses, are perfect choices. These often come equipped with full kitchens, multiple bedrooms, and other amenities. For those desiring a more spacious and opulent experience, Chicago mansion rental options are available, often nestled in the city's upscale neighborhoods.Regardless of which Chicago vacation home you choose, each lodging option provides a unique lens through which to experience this dynamic city.

What type of amenities should I expect when booking a Vacation Rental in Chicago, IL?

The most popular amenities at Chicago vacation rentals are WiFi, city and lake views, gourmet kitchens, self-check-in, laundry, and free parking.

How can I get to and around in Chicago?

Chicago is a central transportation hub in the U.S., making it easy to reach and navigate. Two major airports serve the city: O'Hare International Airport, one of the busiest in the world, and Midway International Airport, catering to domestic and international flights. Once in the city, the Chicago Transit Authority (CTA) provides an extensive network of buses and the "L" (short for "elevated") trains, offering a convenient way to traverse the city. For those driving, major highways include the I-90, I-94, and I-55, which provide easy access to and from various parts of the city and beyond.

Are there pet-friendly house rentals in Chicago?

Yes, many vacation rentals in Chicago are pet-friendly. Check with each property for details.

How much do Chicago vacation rentals cost?

This varies greatly depending on the size, location, and seasonality. You can find a condo for $150 per night or a Chicago mansion rental for thousands of dollars per night.

How many houses are available for rent in Chicago?

Hundreds of Chicago vacation rentals are available, ensuring everyone can find accommodations they’ll love.

What is the best area to stay when traveling to Chicago?

Popular neighborhoods for vacation rentals in Chicago include Near North Side, Old Town, Ukrainian Village, Wicker Park, Bucktown, and the downtown loop.