Solo Travel in Chicago
A river cruise for one, a lakefront trail full of fellow solo walkers, and a show in the dark, the version of Chicago that works when it’s just you.
Chicago is genuinely one of the more solo-friendly American cities, walkable neighbourhoods, friendly locals, and enough parks and river paths to give a solo trip a proper rhythm. Here’s how to spend the time on what actually works solo.
An architecture river cruise
Widely the best orientation any first-time visitor can get, a live guide covers how the city rebuilt itself after the Great Chicago Fire while you simply sit back and take it in. No conversation required, and it makes sense of the skyline in a way craning your neck from the sidewalk never quite does.
A food hall or a food tour
Chicago’s food halls offer an easy solo solution, a wide spread of options under one roof without needing to commit to a single restaurant. A deep-dish pizza tasting tour works well too if the size of a full pie alone feels like too much for one person.
The Riverwalk or the Lakefront Trail
The Riverwalk, a 1.25-mile path along the Chicago River, is properly full of other solo walkers, bikers and readers, free to enjoy and open until 11pm. The Lakefront Trail runs considerably further, 18 miles along Lake Michigan, rent a Divvy bike to cover more ground toward the Museum Campus.
A free walking tour
An easy way to meet other solo travellers, Tours by Foot runs several options including a Loop and Millennium Park tour and a Riverwalk history tour. Sporting events work well too, a single ticket to a Cubs or Bears game often comes at a reasonable price on the day.
A show at a storefront theatre
One of the easiest solo activities anywhere, you spend most of a show sitting in the dark not talking, nobody can tell you’re alone. Chicago’s comedy, independent and storefront theatre scene runs deep, and a rooftop bar or barcade offers a lower-key alternative if a full show feels like too much commitment.
Staying safe
Chicago’s downtown core, the Loop, River North, the Magnificent Mile and Lincoln Park, is broadly safe to walk around alone until roughly 1am, most solo safety concerns here are the usual big-city precautions, pickpocketing and bag snatching rather than anything more serious. Stick to well-lit downtown neighbourhoods at night and avoid empty streets.
Getting around
Chicago is easily walkable, and the L, the city’s elevated train system, runs efficiently and late into the night, one of only three cities worldwide with 24-hour subway service on some lines. A bike rental is a good, flexible alternative if you’d rather cover ground faster.
A few practical notes
A hostel is a reliable way to meet other solo travellers if that’s the goal, several centrally located, affordable options exist across the city. A CityPASS is worth considering if you’re planning several paid museums, it bundles admission at a real saving over buying individually.
That’s everything I’ve got.
A note before you plan around this: prices, opening hours, booking requirements and admission details in this guide were correct at the time of writing, but venues change these often and sometimes without notice. Always check directly with the attraction or its official website before you travel or build a schedule around a specific time or price.
Before travelling to any destination featured on this site, please also check your government’s latest travel advice, as safety situations, entry requirements and travel warnings can change.
