READ MORE FROM OUR 2025 DAY TRIPS FEATURE
Dine Time
Dishes like buttery Hokkaido scallops make John’s Food & Wine a foodie must-stop, and the waitstaff-free setup makes a case for “fast fancy.” Walk in and order at the front counter or, for a splurge, try the five-course tasting menu (which must be reserved through Tock).
Shop Around
Hyde Park’s hub of street style, The Silver Room, has brought the beats to a new location on Michigan Avenue. In addition to DJs, this experimental “lab” offers fashions from international designers and Chicago legends.
It’s time to pick your Milwaukee favorites for the year!
Wow Factor
Sailing and paddling already have their due. It’s time to pontoon. The vessels of Chicago Boat Co. pamper you with plush seating and adjustable canopies. BYOB, pilot and yacht rock. Depart from Marina City and Monroe Harbor.
Stage Antics
Lookingglass Theatre is back at historic Water Tower Water Works after an 18-month hiatus. The company, co-founded by actor David Schwimmer, boasts a new bar and cafe. Iraq, But Funny, running May 29-July 20, is a satire about five generations of Assyrian women.
Staying the Night?
Hunker down at L7 Hotel, a trendy Korean import in the Loop that nods to heritage (patchwork-style “jogakbo” designs appear throughout) and doubles down on clean living (hello, in-room air purifiers).
In early 2026, the Obama Presidential Center will open on 19 acres in Jackson Park, complete with a garden, athletic facility, museum and more.
