Things to Do

Late May is a beautiful time to visit Chicagoland, with blooming spring scenery, lakefront views, and lively neighborhoods. From iconic city sights and great dining to charming nearby suburbs, there’s plenty to explore while you’re here.

Navy Pier

600 East Grand Avenue, Chicago, IL 60611

A Chicago landmark offering lakefront views, dining, shops, and seasonal entertainment. Enjoy a walk along the pier or ride the Centennial Wheel for skyline views.

Millennium Park and Cloud Gate

201 East Randolph Street, Chicago, IL 60602

Millennium Park & Cloud Gate (The Bean) – Iconic photos and city views

Humboldt Park

Chicago, IL

A beautiful West Side park known for its historic lagoon, walking paths, and iconic boathouse. In late May, the park is especially lively with blooming greenery and a strong Puerto Rican cultural presence nearby, including great food and local shops.

Chicago Riverwalk

Chicago Loop, IL 60601

The Chicago Riverwalk is a 1.25-mile urban trail that lines the Chicago River on the northern side of the Loop. This pedestrian path is one of my favorite ways to sightsee downtown. It’s free, open year-round, and lined with restaurants, bars, cafes, shops, and more.

Skydeck Chicago

233 South Wacker Drive, Chicago, IL 60606

There is a glass balcony observation deck called, The Ledge, with beautiful and terrifying views from the 103rd floor deck!

For all the days along the way