55Doable with Planning
New York City
United States
Americas
NYC is challenging — street level is fine, but the subway will break you.
Best stroller: Compact
United States
Chicago
68/100Stroller-Friendly📊 Medium confidence
Chicago is flat and great for strollers — the lakefront trail is paradise, but winters are brutal.
✅
Bring your stroller
This city is stroller-friendly. Compact strollers work best.
Key Factors
- •Generally manageable
- •Compact stroller recommended
Watch Out For
⚠️Older L stations
📋 The Bottom Line
Chicago is one of the best US cities for strollers. It's completely flat, the lakefront trail stretches for miles, and Millennium Park is a family paradise. The CTA L train has improving accessibility but many older stations still lack elevators. Buses are all accessible. The main challenge is winter — Chicago earns its 'Windy City' nickname, and January wind chills can be dangerous. Summer is glorious though, with outdoor festivals and beaches.
Quick Facts
Overall Score68/100
Best StrollerCompact
Biggest ChallengeOlder L stations
Data Quality📊 Medium confidence
Gear Recommendations
- 🎒Compact stroller works perfectly on flat terrain
- 🎒Extreme cold weather protection for winter visits
- 🎒Rain cover for sudden lake-effect weather
- 🎒Sun shade for summer lakefront walks
Score Breakdown
Terrain20%
8/10Slopes20%
9/10Transit12%
6/10Elevators12%
6/10Facilities12%
7/10Crowding12%
5/10Friendliness12%
7/10Neighborhood Guide
🟢 Where It's Easy ✓
- •Lakefront Trail - 18 miles of flat, paved perfection
- •Millennium Park - Flat, Bean, Crown Fountain, playgrounds
- •Lincoln Park - Zoo, conservatory, flat paths
- •Museum Campus - Field Museum, Shedd, Adler — all accessible
- •North Avenue Beach area - Flat, wide, family-friendly
🟡 Where You'll Struggle ⚠
- •Older L stations - Many lack elevators or escalators
- •Michigan Avenue peak shopping times - Crowded sidewalks
- •Wrigleyville on game days - Not family-friendly atmosphere
- •Winter anywhere outdoors - Dangerous wind chill
🎒 When to Bring the Carrier 👶
- •Navy Pier on summer weekends (packed)
- •Michigan Avenue at holidays (shopping crush)
- •Wrigleyville on game days (bar crowds)
Parent Wisdom
❌ What Parents Wish They'd Known
- ✕Winter visits without extreme cold protection (it's -20°C with wind chill)
- ✕Relying on L trains without checking elevator status
- ✕Navy Pier on summer weekends (wall-to-wall people)
- ✕Not using the lakefront trail (it's the city's best feature)
- ✕Deep dish pizza restaurants — often tiny with no stroller space
⭐ Parent-Recommended Spots
- ★Shedd Aquarium - World-class, fully accessible, amazing
- ★Field Museum - Dinosaurs, accessible, full day activity
- ★Maggie Daley Park - Incredible playground, flat, modern
- ★Lincoln Park Zoo - Free, accessible, excellent
- ★Chicago Children's Museum at Navy Pier - Purpose-built for kids
Similar Destinations
Other cities you might want to explore
38Challenging
San Francisco
United States
Americas
San Francisco's extreme hills make it one of the toughest US cities for strollers — flat areas exist but you have to find them.
Best stroller: Rugged
78Compact Stroller Paradise
Amsterdam
Netherlands
Europe
Amsterdam is stroller paradise — flat terrain and everyone yields to wheels.
Best stroller: Compact
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