Chicago Travel Tips: What to Know Before You Go

Practical tips for Chicago

• Tipping 18–22% at restaurants + auto-gratuity 20% for parties of 6+.

• Deep-dish takes 45–60 min to bake — order first, drink second. Lou Malnati's / Pequod's / Giordano's are the classics.

• Winter (Dec–Feb) requires proper coat + gloves + hat; wind chill off the lake is brutal (–20°C real feel possible).

Staying safe and comfortable

Local emergency number: 911.

• Tourist areas (Loop, Mag Mile, Gold Coast, Lincoln Park, River North, West Loop, Wicker Park) safe day + night.

• Avoid West Side + far South Side at night without local knowledge.

• L is safe day + evening; be alert on late-night Red Line.

• Emergency 911.

Visas and entry

Entry policy: mixed, typically up to 90 days. Same US rules everywhere — VWP need ESTA US$21; Canadians with passport; everyone else B-1/B-2 visa. Apply 72h+ before boarding.

Budgeting your trip

Accommodation is the largest controllable cost in Chicago. Compare live rates for your dates and neighbourhood shortlist before locking in flights — the difference between areas is often larger than the difference between travel weeks.