Family-friendly hotel - Stay at an accommodation like the Hyatt Regency Chicago which offers spacious rooms for families and is centrally located.
Food
Family-friendly dining - Opt for family-style dining with a mix of Chicago classics like deep-dish pizza, hot dogs, and diverse options offering kids' menus.
Additional Points
Consider purchasing the Chicago CityPASS to save on admission fees to major attractions such as Shedd Aquarium, Skydeck Chicago, and more.
Public transport is convenient in Chicago, consider getting an unlimited ride pass for easy access to attractions.
May can have varied weather; pack layers and check local forecasts to be prepared for both sunny and cooler, windy conditions.