Chicago Family Break

Summer is Chicago at its liveliest, with long sunny days and average highs between 24°C and 29°C. This is festival season, with headline events like Lollapalooza and Chicago Blues and Jazz Festivals drawing big crowds. The Navy Pier hosts twice-weekly firework displays over the lakefront, and the city’s beaches, rooftop bars and riverside cafés are in full swing. It’s a popular time to visit, so booking ahead is advised.

Autumn is a fantastic time for a city break, with mild temperatures around 22°C in early September, cooling to 7°C by November. Crisp days and autumn foliage make city walks especially scenic, and cultural events continue throughout the season. Crowds thin out after summer, making it easier to enjoy top attractions at a relaxed pace. It’s also a great time to catch local sports, theatre shows or explore neighbourhood food spots without the heat.

Chicago winters are cold and often snowy, with temperatures ranging from -6°C to 2°C. While not for everyone, winter brings a magical atmosphere with festive lights, ice rinks and cosy cafés. Holiday markets and Christmas displays create a buzz in December, and the city’s museums, jazz clubs and restaurants offer plenty to enjoy indoors. If you’re prepared for the weather, this quieter period can offer excellent value and fewer crowds.