Walking Date Ideas in Chicago

Choose a stretch of the Chicago Lakefront Trail for a walk together along Lake Michigan. The full 18.5-mile route runs from Edgewater Beach to 71st Street. Break it up with stops at Navy Pier, Museum Campus, or one of four parks along the way.

Strollers, runners, commuters, and rental bikes share the lively trail. Park District repairs are progressing from 63rd Street north to Foster Avenue beach, with possible work zones and closures on some sections.

Follow the Chicago Riverwalk's 1.25-mile path from Lake Street to the lakefront for a walk with a clear start and finish. Its four districts are The Confluence, The Arcade, The Civic, and the Esplanade.

Look for public art, including ART on THE MART and the Vietnam Veterans Memorial Fountain, as you follow the water. Wine and food stops give you places to pause, with weekend afternoons the best time to visit. Path hours are 6am to 11pm.

Walk above the West Side on The 606, a 2.7-mile trail built on a former rail line and opened in 2015. The route links Wicker Park, Bucktown, Logan Square, and Humboldt Park, with changing scenery across the four neighborhoods and art exhibitions along the way.

The trail is open daily from 6am to 11pm.

Take a short, unhurried walk around Promontory Point, where a tree-lined paved loop of just over half a mile sits at the southern end of Burnham Park on the South Side. Fall is when it looks its best.

Reach the southern beach from the Lakefront Trail for skyline views and an autumn picnic. The landscape follows the Prairie School tradition.

Skokie Northshore Sculpture Park holds more than 60 contemporary pieces by nationally known artists, so there is plenty to wander past. The park is north of the city in Skokie, about 40 minutes from downtown Chicago.

Walk the 2-mile paved loop at your own pace, looking for pieces such as Jamie Barber's "Reaper," an alien-like figure made from salvage-yard parts. For a longer outing, begin with the 2-mile walk from Dempster Purple Line station. The park is open seven days a week, closed only from 11pm to 4:30am.

Follow the dedicated walking paths through Millennium Park, a 24.5-acre park in the Loop. Add Grant Park's paths for a 3.5-mile loop together.

Entry is free, with daily hours from 6am to 11pm. Lurie Garden remains open, though its south walkway is closed for improvements.

Cross the BP Pedestrian Bridge from Millennium Park to Maggie Daley Park, a 20-acre downtown stop with a formal garden and picnic groves where you can pause.

A skating ribbon, climbing wall, mini golf, and tennis courts offer ways to make the outing more active. Ice skating requires reservations.

Walk out along Navy Pier and back for more than a mile of lakefront views. The pier is 3,300 feet long, with restaurants and rest areas for stops along the way. The 200-foot Centennial Wheel offers a view from above.

If you like, cap off the walk with a spin on the Wheel. Each year the pier puts on more than 245 free public programs.

Take an easy walk around Humboldt Park's 2.1-mile loop, which takes about 40 minutes and suits beginners or an outing after coffee. The route passes a beach, a Prairie-style boathouse, and a lagoon in the historic West Side park.

Fall is a good season to visit, with leaf color and end-of-season bird watching. Rose beds and an inland beach add to the scenery across the park's more than 200 acres near North and California Avenues.

Wander the 385-acre Chicago Botanic Garden in Glencoe, a suburb north of the city. The 22-mile North Branch Trail connects it with Gompers Park on the North Side.

Nonmembers need tickets, with free admission days for Illinois residents and tickets available up to two months ahead. Parking fees still apply. Hours vary by day.