芝加哥規劃完善的棋盤式街道系統，使其成為非常適合步行的城市。State 街與 Madison 街的交會處是起點，地址則標示出與這個中心點的距離。全市劃分為多個街區，每八個街區約為一英里，讓導航變得簡單。此外，芝加哥步行道（Pedway）在市中心商業區內提供超過 40 個街區的地下通道網絡，能在惡劣天氣時提供遮蔽。雖然許多地區步行相當便利，但由於城市幅員遼闊，部分目的地仍需搭配其他交通工具前往。

在芝加哥騎自行車是一種實用的城市移動方式，因為這裡擁有完善的自行車道和路徑網絡。市內提供多樣化的路線，連接各個社區與主要景點，讓騎車前往許多目的地相對容易。不過，芝加哥的天氣變化無常，冬天寒冷、夏天炎熱，這些都可能影響騎乘條件。此外，市區地勢平坦，通常讓騎自行車更加便利。若想尋找共享單車選項，也有可透過熱門應用程式使用的服務。

Chicago’s public transportation system is extensive and efficient, making it a convenient way to navigate the city. The Chicago Transit Authority (CTA) operates a vast network of buses and rapid transit rail, covering the city and nearby suburbs. With 140 bus routes and 242 miles of rail track, reaching various destinations is straightforward. Additionally, Metra provides commuter rail services with 11 lines and 241 stations, while Pace offers suburban bus services. The infrastructure supports easy access to many areas, though weather conditions can occasionally impact travel times.

Ferries in Chicago, like the Chicago Water Taxi, offer a scenic way to travel between key locations such as Ogilvie/Union, Michigan Avenue, and Chinatown. These ferries run frequently, with departures every 15 to 30 minutes during peak times. They are pedestrian-friendly and allow bikes, making them a flexible option for travelers. The journey between stops typically takes about 15 to 20 minutes. While ferries provide a pleasant ride, weather conditions can affect service, and they are best suited for short distances along the river rather than city-wide travel.