Timeline
15:59
Grab a beer at Kasey's Tavern. It is a historic dive bar with an extensive selection, perfect for settling in before the walk. Check that it is open; on winter weekdays it opens at 11:00.
16:14
Walk to Dearborn Station. This 1885 landmark was once the first glimpse of Chicago for countless visitors. The rail yard is gone, but the station house remains a solid piece of history. The walk is just two minutes.
16:29
Head to 360 Chicago. The walk takes about 49 minutes north, so leave early. Go up to the 94th floor for a 360-degree view. The sun sets toward the WSW, offering a clear view of the horizon as the light fades.
17:14
End the evening at 900 N Michigan Ave. This building houses 70 specialty shops and is just two minutes from the viewing spot. It is a good place to browse or find a late-night treat, staying open until 19:00 in winter.
Local tip
The walk from the station to the skyscraper is long. Start your drink early and allow plenty of time to reach the top before the sun dips below the skyline.
Check before you go
- Kasey's Tavern is open Mo-Fr,Su 11:00-02:00.
- 360 Chicago hours vary; check the app for evening access.
- 900 N Michigan Ave shops close at 19:00 on Sundays in winter.
Built from places in the Wikivoyage guide to Chicago (CC BY-SA 4.0), with open map data from OpenStreetMap contributors (ODbL).