Chicago is the American city solo travellers skip and then wish they hadn't. It has everything New York has for a person alone, at two-thirds the price, on a lake.
Where to stay alone#
The Loop or River North for the hostel and walking distance to the river, the museums and the lake. Wicker Park or Logan Square for going out. Lincoln Park for the quiet and the lake path. All of them have an L stop, which is what matters.
Things to do alone in Chicago#
| Do | Why |
|---|---|
| The architecture river cruise | Day one, every time; the best introduction to any US city |
| The lakefront path | Eighteen miles, free, the city's living room |
| Cubs bleachers | A single ticket, three hours, conversation guaranteed |
| Jazz and blues | Clubs older than your grandparents, fine alone at the bar |
| A neighbourhood per day | Pilsen, Logan Square, Hyde Park, Andersonville, by L |
| The museums | The Art Institute alone is a day |
Summer or winter#
Summer is Chicago at its best: festivals every weekend, the beaches, patios, everyone outside. Winter is cheap, indoor and honest: museums, bars with fires, the Christkindlmarket. Both work alone; dress for the second.
Eating alone#
Bars. Chicago eats at the bar more than any US city outside New York: tavern-style pizza, Italian beef standing up, a steakhouse bar for the one big dinner. Deep-dish is for a table of four; order it once and move on.
Safety#
Chicago's reputation is real and irrelevant to a visitor: it comes from neighbourhoods you have no reason to enter. In the Loop, the North Side and the neighbourhoods above, the rules are the usual ones. For solo women: rideshare late, know your L stop, busy streets.
Meeting people#
Post your trip on Roavi Community with your dates: travellers heading to Chicago in the same window appear in one place, and Local Friends can reply. Chicago socialises by neighbourhood, so a Local Friend is the way into one: rent a friend in Chicago explains how. Solo travel in the USA covers the other cities.
Going to Chicago alone? Post your trip and meet someone who lives there.
Meet a Local FriendFrequently Asked Questions
Is Chicago good for solo travel?
One of the best in the USA: walkable, excellent transit, bar culture, a lakefront, and prices below New York and San Francisco. The only question is the month.Where should a solo traveller stay in Chicago?
The Loop or River North for the hostel and for walking to everything, Wicker Park or Logan Square for nights out, Lincoln Park for the lake and the quiet. Every one has an L stop.Is Chicago safe for a solo female traveller?
In the areas visitors go, yes, with the usual rules: busy streets at night, rideshare late, know which L stop you're getting off at. Chicago's reputation comes from neighbourhoods a visitor has no reason to be in.How do I meet people travelling alone in Chicago?
The hostel bar, a free walking tour, the bar at any restaurant, the Cubs bleachers, and posting your trip on Roavi Community so travellers heading to Chicago on your dates can find you. A Local Friend shows you their neighbourhood.