What is the best time to visit Chicago?

The best times are late spring (May-June) and early fall (September-October) with pleasant temperatures (60-75°F), lower hotel rates, and beautiful lakefront weather. Summer (July-August) is peak season with festivals and outdoor activities but can be hot and crowded. Winter (December-March) is brutally cold with lake effect winds, though holiday decorations are beautiful and hotel rates drop significantly. Avoid late January-February unless you love extreme cold.

How do I get from Chicago O'Hare Airport to downtown?

From O'Hare: CTA Blue Line train ($5, 45 minutes direct to downtown, runs 24/7), airport shuttle services ($25-30), Uber/Lyft ($35-60 depending on traffic/surge pricing), or taxi (flat rate $40-50). The Blue Line is cheapest and often fastest during rush hour. From Midway Airport: CTA Orange Line ($3, 25 minutes to Loop). Both airports have easy train access with luggage storage.

Is Chicago safe for tourists?

Yes, Chicago is safe for tourists in popular areas like Loop, Magnificent Mile, River North, Lincoln Park, and Wicker Park. Crime statistics include areas tourists never visit. Standard precautions: stay aware of surroundings, avoid poorly lit areas late at night, keep valuables secure, use rideshare instead of walking alone late at night. The CTA trains are generally safe during the day. Popular tourist areas have strong police presence.

What's the difference between deep-dish and tavern-style pizza?

Deep-dish is Chicago's famous thick, tall pizza with layers (crust, cheese, toppings, chunky tomato sauce on top), eaten with fork and knife, baked 30-45 minutes. Try at Lou Malnati's or Giordano's. Tavern-style (also called thin crust) is what locals actually eat weekly - thin, crispy, cut into squares, topped edge-to-edge. Try at Pequod's or Pat's Pizza. Both are authentic Chicago styles - don't let anyone tell you otherwise!

Do I need to book the architecture boat tour in advance?

Yes, absolutely! The Chicago Architecture Center River Cruise is extremely popular and sells out days or weeks in advance, especially in summer weekends. Book online 1-2 weeks ahead for best times. First tours (9-10am) often have availability and better lighting for photos. The 90-minute tour is the best way to see Chicago's world-class buildings and learn their history from expert docents. Cost: $48-65, runs April-November. Worth every penny!

How much money do I need per day in Chicago?

Budget travelers: $100-150/day (hostels, casual dining, free museums, CTA pass). Mid-range: $200-300/day (3-star hotels, mix of casual and nice restaurants, paid attractions, occasional taxi). Luxury: $400+/day (4-star+ hotels, fine dining, premium experiences). Key costs: hotels $120-400/night, meals $15-75 per person, museums $15-40 (many free days), CTA day pass $10, architecture boat tour $48. Deep-dish pizza $20-35 per person including drinks.