Chicago vacation rentals

Frequently Asked Questions

• How is the weather in Chicago?

  Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.

• What are some of the best things to do in Chicago?

  In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.

• What is the best time of year to visit Chicago?

  Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.

• What are the best places to stay in Chicago?

  Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.

• What are the best places to visit in Chicago?

  Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.

• What are some hiking trails in Chicago?

  While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.

• What are some family activities to do in Chicago?

  Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.

• What are some of the best day trip ideas in Chicago?

  For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.

• What types of vacation rentals are available in Chicago?

  Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 6,100 apartment rentals, over 1,080 condo rentals to over 1,900 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

• Are there vacation rentals with a dedicated workspace in Chicago?

  Yes! Work meets play with ease at over 6,910 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.