Chicago is a very lively city and there is a lot to do as lonely expatriate, as an expat couple or as a whole expat family. Everybody will find something fun to do.
The activities you will be able to enjoy will also vary with the weather conditions. During winter, days and night are extremely cold. As a matter of fact, it is impossible to entertain yourself and your family the same way as you would in the warmer months. During the winter, it is important to have indoor activities and entertainment options planned, especially for the children. Thankfully, there are a lot of cultural events and venues that are targeted specifically for them. There are many good restaurants and cafés that are child-friendly, as well as warm, cosy spots for those without kids. During the holiday season, children of all ages will enjoy the famous Christmas parade on Michigan Avenue or attending a special Christmas show in one of the Chicago theaters.
As soon as the weather becomes milder in April-May or as soon as the sunshines a little bit harder, Chicagoans head outdoors. After being inside all winter, outdoor activities, along with restaurants and cafés with patios become immensely popular with Chicagoans. The city of Chicago organizes festivals such as “Movies in the Parks” and “Music in the Parks” that attract a huge segment of the population every year. During the summer, the Jay Pritzker Pavilion is home to the Grant Park Music Festival and other free concerts and events. There is classical music and opera for free in the evening and people are also invited to attend the rehearsal during the day.
The cultural life of Chicago is very rich. One of the best resources to find what to do and entertain the whole family is the magazine Time Out Chicago or check their website: http://chicago.timeout.com/.