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From ORD airport to Havana
Reaching O'Hare International
CTA Blue Line (24/7, $5 one-way, 40-45 min from Loop/downtown Chicago during normal traffic, often faster than driving)—board at any downtown station, runs directly to all terminals. Rideshare (Uber/Lyft, $28-42 during off-peak, $50-75 during rush hour 6-10am or 3-7pm from downtown, 25-40 min depending on traffic). Taxi flat rate $42 from downtown Loop, 35-50 min. Rental car pickup in Terminal 1 or off-site shuttles available. Best option: CTA Blue Line if traveling light and flexible on time; Uber/Lyft if arriving after 10pm when Blue Line gets sketchy.
Getting from HAV into Havana
José Martí International Airport (HAV) is 11 miles southwest of Habana Vieja. Official yellow metered taxis are the most reliable option — negotiate the price before getting in, expect $25-35 USD to Old Havana or Vedado (30-40 minutes depending on traffic). Private taxi drivers (often in classic American cars) will approach you at arrivals and charge $20-30 USD if you negotiate — perfectly safe and part of the experience. There is no reliable public bus service from the airport for tourists with luggage. Uber does not operate in Cuba. If your casa particular or hotel is sending a pickup, confirm the driver's name and their vehicle before departing the terminal — it typically costs $20-25 and saves negotiation stress after a long flight.
Planning Chicago to Havana
Havana is the most frozen-in-amber city in the Western Hemisphere — a genuine 1950s time capsule where Chevrolet Bel Airs and Buick Roadmasters cruise the Malecón seawall at sunset while crumbling neoclassical mansions slowly return to the earth. For Americans, it remains one of the most legally complicated yet culturally compelling destinations on Earth. The U.S. Treasury still requires travelers to fit into one of 12 authorized categories (the most commonly used being 'support for the Cuban people'), but enforcement is essentially nonexistent under current policy, and hundreds of thousands of Americans visit annually without incident. Flights operate legally from a dozen U.S. cities, and you can book hotels through Airbnb and booking platforms without any real friction.
Local basics
Best-month weather in Havana
February
65–80°F · 4 rain daysThe best month of the year — bone dry, comfortable humidity, and strong sunshine without scorching heat. Essentially perfect.
March
67–82°F · 4 rain daysStill dry season but temperatures begin climbing noticeably. Occasional brief afternoon showers start appearing toward month's end.
The destination guide flags September and August and October as the least favorable months.
Two areas to consider
Habana Vieja (Old Havana)
mid-rangeThe UNESCO World Heritage colonial core is where most first-timers stay and eat, centered on Plaza de Armas, Plaza Vieja, and Plaza de la Catedral. Casas particulares here run $40-80/night and put you within walking distance of the best paladares like La Guarida (book weeks ahead) and San Cristóbal Paladar. It gets noisy and touristy during the day, but evenings when the tour groups leave reveal a genuinely beautiful, lived-in neighborhood.
Vedado
mid-rangeThe mid-century leafy grid neighborhood where Cubans actually live, work, and socialize — far less touristy than Old Havana. The Hotel Nacional and Hotel Riviera are here, along with the famous jazz club La Zorra y El Cuervo on Calle 23 (cover charge about 200 CUP). Casas particulares in Vedado run $35-65/night and you'll get a much more authentic street-level experience of Havana than in the colonial core.
Local planning tip
Bring two wallets. Keep a 'decoy wallet' with $20-30 USD and your expired cards for your back pocket or outer bag — if anything is ever grabbed (rare but possible), you hand that over. Your real cash stash of $200-400 USD should be split: half in a money belt under your clothes, half locked in your casa particular's room safe. More importantly: the best cigar deal in Havana isn't La Casa del Habano (official state store) or a street vendor — it's asking your casa particular host to connect you with a factory worker friend who sells genuine factory-second Cohibas and Montecristos (with minor wrapper imperfections) for 20-40% of retail. This is technically a gray market but universally practiced, the cigars are real Cuban tobacco, and it directly supports a Cuban individual rather than the state monopoly.
Visa and entry notes for US travelers
U.S. passport holders technically require a Cuban Tourist Card (tarjeta del turista) — a pink card required under the 'support for the Cuban people' authorized travel category. As of 2026, airlines operating flights to Cuba (American, JetBlue, Southwest, United) sell these at the departure gate for $50-100 USD — buy it directly from the airline when you check in or at the airport, not from third-party websites that charge markup. You do NOT need a visa through the Cuban consulate for tourist visits. Upon arrival at HAV, immigration is typically smooth (10-30 minutes), though officers may ask about your purpose of travel — 'tourism' or 'visiting cultural sites' is the standard answer. Do not photograph the immigration hall or customs area. Your passport is not stamped (Cuba stopped stamping U.S. passports in 2015, eliminating the old problem of evidence of travel). Travel insurance that includes health coverage is technically required by Cuban law upon entry — carry a printout of your policy. Check OFAC's Cuba travel page within 60 days of your trip as regulations can change with U.S. administrations.