How do I get to Chicago?

O'Hare International (ORD) sits 27 km northwest of the Loop and processes roughly 83 million passengers a year. It's a United Airlines hub and a major American Airlines base, with nonstop service to over 200 destinations. The terminal layout trips up first-timers. Terminals 1, 2, and 3 form one connected complex on the east side. Terminal 5, the international terminal, is isolated on the west side and requires a free ATS train ride of about 10 minutes. If you're landing internationally and connecting to a domestic flight, budget 90 minutes for the terminal transfer, customs, and re-screening. Midway (MDW), 16 km southwest of the Loop, is smaller, faster through security, and dominated by Southwest Airlines. If your origin city has a Southwest route to MDW, expect fares $40-80 cheaper than the ORD equivalent. You'll be downtown 20 minutes faster on the Orange Line, too.

From New York, 2.5-hour nonstops on United, American, Delta, JetBlue, and Spirit run $120-250 round-trip. From Los Angeles, it's 4 hours on United or American for $180-350. London Heathrow to ORD is 8.5 hours direct on BA, United, American, or Virgin Atlantic at $600-900 round-trip. From Tokyo Narita, ANA and JAL offer 12-hour nonstops at $900-1,400. Worth noting that Chicago tends to be cheaper to fly into than New York or San Francisco from European origins, sometimes by $100-150 on the same carrier. Low season runs January through March, excluding the holidays, when round-trip fares from Europe drop below $500. Peak pricing hits June through August and the Thanksgiving-to-Christmas corridor. For domestic flights, booking 6-8 weeks out seems to hit the sweet spot. International routes benefit from 3-4 months of lead time.

Amtrak's Union Station at 225 South Canal Street in the West Loop connects Chicago to over 30 cities by rail. The Lake Shore Limited runs to New York Penn Station in 19.5 hours for $60-180 one-way. The Empire Builder heads to Seattle in 46 hours, and the California Zephyr reaches Emeryville (for San Francisco) in 51 hours. The Zephyr's route through the Colorado Rockies, with snow-capped peaks filling every window for 6 straight hours, might be the best train ride in North America. For shorter hops, Megabus and FlixBus run $15-45 routes from Milwaukee (90 minutes), Indianapolis (3.5 hours), and Detroit (5 hours), departing from the Canal Street bus terminal. If you're driving in on I-90/94, expect crawling traffic on the Dan Ryan and Kennedy expressways during rush hours, roughly 6:30-9:30 AM and 3:30-7 PM. Parking downtown runs $35-55 per day in Loop garages.

One thing first-timers tend to get wrong is the airport transfer. O'Hare's CTA Blue Line train to downtown costs $5 and takes 45 minutes to the Loop. That's the right answer for most people. The taxi or rideshare alternative runs $40-60 and saves maybe 10 minutes in light traffic, but at rush hour it can take over an hour on the Kennedy Expressway, so the train wins on both price and time. From Midway, the CTA Orange Line to the Loop costs $3 and takes 25 minutes. The Orange Line runs above ground through Bridgeport and Chinatown, and on a clear afternoon you'll catch the skyline rising over Roosevelt Road. It's one of the better free views in the city. Mind you, both CTA airport stations feel grimy and smell like diesel and warm metal. The signage is adequate but not generous. Follow signs for "Trains to City" and you'll find the platform.