Google completes "things to do in chicago alone" with "at night", "free", "downtown", "solo trip" and "reddit". This page is sorted the same way, by someone who lives here.
During the day#
- The Lakefront Trail: 18 miles, from the South Side to Edgewater; walk, run or bike it, alone is the default.
- The Art Institute: the best solo afternoon in the city; Illinois residents get free days.
- The architecture river cruise: an hour and a half on the river with a docent; half the boat is alone.
- Millennium Park and the Bean, early, before the crowd.
- A neighbourhood on foot: Pilsen for the murals and the food, Andersonville, Logan Square, Hyde Park and the Obama Center site, Bronzeville, Chinatown.
- Museum Campus: the Field, Shedd and Adler on free days.
- A matinee at the Chicago Theatre or a Steppenwolf show: single seats are easy.
At night#
- Comedy: Second City, iO, the Laugh Factory, the Annoyance; bar seats and walk-ins, nobody cares that you are alone.
- Blues and jazz: Kingston Mines and B.L.U.E.S. on Halsted (late, every night), the Green Mill in Uptown, Andy's Jazz Club.
- A bar seat at a restaurant in the West Loop, Logan Square or Lincoln Park.
- A Cubs night game at Wrigley or a Sox game: single tickets are easy, and Wrigleyville after is a conversation whether you want one or not.
- The Lakefront at dusk: North Avenue Beach, the Adler planetarium skyline view.
- A repertory cinema: the Music Box.
- Winter nights: the Christkindlmarket, a tavern with a fireplace, a Blackhawks or Bulls game at the United Center.
Where alone does not work#
Clubs in River North, table-service rooftops, and anything that sells bottles; everywhere else in this city being alone is normal and the person next to you at the bar will talk to you.
Or not alone, for an afternoon#
On Roavi you can hire a Local Friend, someone who lives in Chicago, for a few hours at a rate they set (most list $15 to $50), platonic and in public: the food neighbourhood you were going to try anyway, with someone who knows it; a game with a fan; a night out where people actually go. Roavi lists no Local Friends in Chicago yet, which is the honest number and the reason the first people to list here will get every message; messaging is free for the people who write to you. Rent a friend in Chicago.
One afternoon with someone who lives here.
Meet local guides in ChicagoRead next: how to make friends in Chicago and solo travel in Chicago.
Frequently Asked Questions
Is Chicago a good city to visit alone?
Yes. Museums, parks, the food neighbourhoods, comedy, live music, a ball game and a bar seat at a restaurant are all normal solo here; only clubs and table-service rooftops feel awkward alone.What can I do alone in Chicago at night?
Comedy: Second City, iO, the Laugh Factory, the Annoyance; bar seats and walk-ins, nobody cares that you are alone. Blues and jazz: Kingston Mines and B.L.U.E.S. on Halsted (late, every night), the Green Mill in Uptown, Andy's Jazz Club. A bar seat at a restaurant in the West Loop, Logan Square or Lincoln Park.