Question 1

Where can I find the best vacation rentals for a staycation in Chicago?

Accepted Answer

Whimstay offers a range of staycation rentals, from luxury apartments downtown to cozy homes in neighborhoods like Wicker Park and Lincoln Park.

Question 2

What are the best restaurants to try during a staycation in Chicago?

Accepted Answer

Visit Girl & the Goat for inventive dishes, Pequod’s Pizza for deep-dish pizza, or Au Cheval for one of the best burgers in the city.

Question 3

What are the best local activities for a staycation in Chicago?

Accepted Answer

Explore Millennium Park, visit the Art Institute of Chicago, or take a scenic boat tour along the Chicago River to soak in the city’s architecture.

Question 4

What makes Chicago a great destination for a staycation?

Accepted Answer

Chicago offers world-class museums, diverse neighborhoods, beautiful parks, and a vibrant food scene, making it an ideal city for a staycation.

Question 5

How can I plan a budget-friendly staycation in Chicago?

Accepted Answer

Find affordable rentals through Whimstay, explore free attractions like the Lincoln Park Zoo, and enjoy the city’s many free outdoor festivals and events.

Question 6

What are the top staycation ideas in Chicago?

Accepted Answer

Take a day trip to Navy Pier, enjoy a picnic at Grant Park, or spend an afternoon at the Museum of Science and Industry for a fun local adventure.

Chicago Staycation Rentals

Plan your staycation in Chicago

Top Chicago staycation rentals

Popular features and amenities

What guests are saying

Frequently asked questions