Updated 5/23/2025
Chicagoland comes alive in the springtime. This season also marks the beginning of what our real estate agents like to call "market season" in Chicagoland, which extends throughout the summer and winds down in the fall. Whether you're looking for arts and crafts, fresh produce, or any other local, handmade goods, you'll find them at these upcoming spring and summer markets and craft fairs in the Chicago area.
With the official start of winter on the horizon, it's what our real estate agents like to call "cozy season" in Chicago. It's the perfect time of year to check into a homey bed and breakfast for a little holiday getaway.
Visitors looking for a place to stay or locals seeking a winter "staycation" will find no shortage of options in each of Chicago's distinct neighborhoods. These are some of our favorite bed and breakfasts in Chicagoland.
Chicago: