Chicago, United States

• Chicago sits on Lake Michigan in the Midwest. Winters get seriously cold - wind chills can hit -22°F (-30°C) and you'll understand why locals complain about it constantly. Summers are warm and humid, good for the beaches and outdoor spaces along the lake. The architecture ranges from Loop skyscrapers to residential brownstones, depending on which neighborhood you're in.
• Eating alone is common enough that no one will look twice at you dining solo, whether it's a neighborhood taco place or a nicer restaurant. Deep dish pizza is mostly a tourist thing - locals eat thin-crust tavern-style more often. The West Loop has the high-end dining scene, while ethnic restaurants are scattered through various neighborhoods.
• The CTA trains and buses cover most areas you'd want to visit during the day. After 9pm, many women switch to Uber or Lyft instead - the trains still run but feel less safe when they're emptier. North Side areas like Lincoln Park and Wicker Park stay more active at night. The Loop gets very quiet once office workers leave.
• Everyone speaks English. Crime has dropped significantly in 2025-2026 - homicides down about 50%, overall crime decreasing. The city is safer than it's been in decades, though you still need to be aware of which neighborhoods to avoid.

English is spoken everywhere. Spanish is common in some neighborhoods. The emergency service (911) has multilingual operators available. The non-emergency line (311) also offers language assistance for city services.

• Don't put ketchup on a hot dog - locals will notice. Chicago-style comes with mustard, relish, onions, tomatoes, pickles, sport peppers, and celery salt. Deep dish pizza is mostly a tourist thing. Locals eat thin-crust tavern-style more often.
• Stand right on escalators so people can walk on the left. On the CTA, let people exit before you board, and don't block the doors. Keep your bag close on crowded trains.
• Tipping runs 18-20% at restaurants, $1-2 per drink at bars, $2-5 for hotel housekeeping, 15-20% for rideshare. Service workers depend on tips here.
• People are generally friendly and will help if you ask for directions. The city cares about its neighborhoods and sports teams - the Cubs vs. Sox divide is a real thing.

• The CTA 'L' train has eight color-coded lines that cover most tourist areas. Single ride is $2.50 (or $2.75 without a Ventra card). Some lines run 24/7 but feel safer between 8am-9pm. After 9pm, many women switch to rideshare instead.
• Uber and Lyft are everywhere and cheaper than in cities like New York or San Francisco. They're the safer choice after dark. Rides within North Side neighborhoods usually run $8-15.
• You can walk around neighborhoods like Lincoln Park, Wicker Park, and River North easily during the day. Just know that Chicago blocks are longer than in most cities - distances can be deceiving on the grid. The lakefront trail is good for walking or biking when weather's nice.
• Divvy bike-share stations are common. A day pass costs $15 and includes the first 30 minutes of each ride. The Lakefront Trail runs 18 miles along Lake Michigan with no cars.
• If you're planning day trips outside the city, consider renting a car.
• For peace of mind on arrival, book your airport pickup in advance.

Explore Chicago with local guides and curated experiences.