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If your curious kid wants to explore the city on foot, parents often ask: where in Chicago is truly stroller friendly? The good news is there are several paths and neighborhoods built for ease of movement. Below are some of the top picks, how they feel in practice, and what challenges you might still face.
Lakefront Trail: Smooth paths by water
Chicago’s Lakefront Trail runs more than 18 miles along Lake Michigan from north to south, connecting major parks, beaches and attractions. It’s paved, level and wide, which makes it ideal for strollers.
Because it passes by museums, green spaces and rest stops, it’s useful for mixing walking and breaks. You’ll see plenty of families pushing strollers along its length, especially on weekends.
The 606: Elevated strolls through neighborhoods
The 606, also known as the Bloomingdale Trail, is an elevated trail that links four parks on Chicago’s northwest side. It’s flat, scenic and has gentle changes in elevation, making it a favorite for families with strollers.
Because it’s elevated, it avoids street traffic and most sidewalk obstacles. It also connects to family-friendly neighborhoods where you can stop for snacks or a playground break mid-walk.
Chicago Riverwalk: Stroller-friendly riverside walking
The Chicago Riverwalk runs along the Main Branch of the Chicago River and is one of the city’s most stroller-friendly paths, according to the City of Chicago’s official Riverwalk page. It offers seating, public art and plenty of restaurants with space to pause.
Sidewalk widths vary, especially near dining areas, but the mix of calm water views and easy access to downtown makes it a favorite among city parents.
Maggie Daley Park: Smooth paths with skyline views
Maggie Daley Park in downtown Chicago is one of the city’s best stroller-friendly destinations. The park’s wide, winding walkways connect Millennium Park and the Lakefront Trail, offering smooth pavement and plenty of open space to move at your own pace.
The park confirms that it features “wheelchair and stroller-friendly park entrances and paved pathways throughout” that meet or exceed ADA requirements for slope and access, according to the Maggie Daley Park accessibility page. Families can stroll past the playgrounds, picnic areas and climbing walls while taking in skyline and lake views.
Chicago Botanic Garden: Lush paths and stroller access
The Chicago Botanic Garden in Glencoe offers wide, mostly paved trails and garden loops that make it easy for strollers to maneuver. Nearly all areas of the Garden are accessible by wheelchair and stroller, according to the Chicago Botanic Garden’s accessibility page.
The Garden also notes that strollers are welcome during events like Lightscape. Stroller rentals are available through third-party partners.
What to watch for (and avoid)
Even in the best areas, Chicago has its challenges: cracked sidewalks, construction zones and narrow bridge crossings can make maneuvering a bit tricky. When paths merge with bike lanes, keep a close eye for riders.
If your child or stroller needs smoother ground, aim for off-peak hours or well-maintained sections of these trails. After rain or in colder months, some paths can become slippery or partially closed.
How to plan your stroller day
Pick a path close to home or public transit, and plan shorter loops rather than full-length trails. Pack light, bring a small diaper bag, a rain cover and some snacks. Identify restrooms and cafés along your route for quick breaks.
Start in stroller-friendly neighborhoods like Lincoln Park or downtown near the Riverwalk. That way, if your route gets bumpy or the weather shifts, you’ll be close to rest stops and public transportation.
Plan it
- Hours: Varies by location; generally sunrise–10 p.m. for trails and public parks
- Cost: Free (parking fees may apply at Chicago Botanic Garden)
- Parking: Public lots and garages near trailheads; free at suburban parks
- Accessibility: All listed locations are paved and stroller-accessible
- Best for: Families with kids under 6; ideal for daytime walks
Updated October 2025
