Explore Chicago With Someone Who Actually Lives There

Get out of the Loop

Downtown is the architecture and the museums. Pilsen, Logan Square, Andersonville, Chinatown and Hyde Park are where the city lives, and they are a train ride away. A Local Friend knows which ones fit your day.

Eat what Chicagoans eat

Tavern-style thin crust cut in squares, an Italian beef dipped and hot, a hot dog with everything but ketchup, tacos in Pilsen, Polish food on the Northwest Side. Locals eat deep dish less often than visitors do.

Use the lake and the seasons

In summer the whole city lives on the lakefront: the trail, the beaches, the festivals. In winter it moves indoors to bars, music rooms and museums. Someone who lives there knows what each week is good for.

The Loop & River North

Skyscrapers, the river, Millennium Park and the Art Institute. The architecture is the attraction; see it from the water first.

Pilsen

Murals on every block, Mexican bakeries and taquerías, galleries and the free National Museum of Mexican Art. One of the most colourful neighbourhoods in the city.

Logan Square & Wicker Park

Boulevards, bars, live music, vintage shops and some of the city's best restaurants, with the 606 elevated trail running between them.

Hyde Park

The University of Chicago's gothic campus, the Museum of Science and Industry and the Obama family's old neighbourhood, right by the lake on the South Side.

Andersonville

A Swedish-founded neighbourhood on the North Side with independent shops, bakeries, bars and a welcoming LGBTQ+ scene. Pairs well with the Green Mill jazz club in nearby Uptown.

Chinatown

Dim sum, bakeries and hot pot around Wentworth Avenue and the Chinatown Square, with a riverside park and water taxis back to downtown in summer.

Lincoln Park & Wrigleyville

The free Lincoln Park Zoo, the lakefront and beaches, and the bars around Wrigley Field on game days.

May to October. Summer is warm, busy and full of festivals and street fairs, including Lollapalooza in early August. September and October are mild and less crowded. Winter, from December to March, is very cold and windy; January and February are the cheapest months and the city still has plenty to do indoors.

Downtown, the North Side neighbourhoods and the places visitors usually go are busy and generally safe. Most violent crime is concentrated in specific areas away from them. Use normal big-city sense: keep your phone in hand rather than out at the train doors, avoid empty train cars late at night, and stick to busy streets after dark.

The CTA 'L' trains and buses go most places; pay with a Ventra card or by tapping a contactless card or phone. The Blue Line runs from O'Hare to downtown in about 45 minutes and the Orange Line from Midway in about 25. Downtown is very walkable, and Divvy bikes are everywhere. You don't need a car.

In winter: a warm coat, hat, gloves, scarf and waterproof boots — the wind off the lake is no joke. In summer: light clothes, sunscreen and a swimsuit for the lake beaches. A layer in spring and autumn; temperatures swing quickly.

English, with large Spanish-speaking communities, especially in Pilsen, Little Village and Logan Square. Polish is common on the Northwest Side. Chicagoans are friendly and like to give directions and opinions — especially about pizza.

Cheaper than New York or LA. Budget: about $100–150/day before accommodation (CTA, tacos, free parks and museums). Mid-range: about $250–350/day with a hotel. A train ride about $2.50. An Italian beef $10–14. Dinner $35–60 a head. Restaurants expect an 18–20% tip.