芝加哥規劃完善的棋盤式街道系統，非常適合步行。State 街與 Madison 街的交界是起點，地址會標示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，方便導航。此外，芝加哥 Pedway 地下通道網絡連接了市中心商業區超過 40 個街區，讓大家在惡劣天氣下也能有遮蔽。雖然很多地區步行都很方便，但由於城市幅員廣闊，有些目的地可能需要額外交通工具前往。

在芝加哥踩單車是一個實用的出行方式，因為當地有完善的單車徑和路線網絡。市內提供多條路線，連接不同社區和主要景點，令你較容易以單車到達多個目的地。不過，芝加哥的天氣變化無常，冬天寒冷、夏天炎熱，可能會影響踩單車的情況。此外，市內地勢平坦，普遍令踩單車更容易。如果你想選擇共享單車服務，可以透過熱門應用程式使用相關服務。

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.