Solo travel in Chicago

Mexican-American street art along 16th and 18th Streets.

Small but world-class gallery of self-taught art — an overlooked gem for curious solo culture-seekers.

Neighborhood blanketed in vivid street murals celebrating Mexican heritage — a must for art-loving walkers.

Two-hour guided walk through history, food or street art — great solo intro to a city.

Walk or kayak past the city's famous architecture on river level.

Elevated rail-trail connecting four neighborhoods — popular with cyclists, joggers and people-watchers.

Waterfront bars and restaurants along the river — the city's liveliest warm-weather outdoor hangout.

Indoor market with local food vendors, coffee and sweets — an easy weekday lunch spot for locals.

Local produce, street food, buskers — easy solo wander or family morning.

Pick a corner, order a coffee — the gentlest 'I'm bored alone' rescue.

American Gothic, Nighthawks and one of the world's great impressionist collections.

Catch a repertory screening or a new release — works solo, on a date or with friends.

Drop-in wheel session or paint-and-sip — easy creative plan with a friend or date.

Anish Kapoor's Bean (Cloud Gate), free concerts at Pritzker Pavilion.

Quiet lakefront beach with protected dunes and birding paths — a local escape from the tourist lakefront.

Hop on the water for an hour — beginner-friendly, great with a friend or date.

Lace up at a city rink — date-night classic and the easiest winter family outing.

Day-pass bouldering with shoe rental — great solo workout or first-date conversation starter.