Chicago travel guide: planning your stay

Getting there and choosing your base

O'Hare International (ORD): About 17 miles north-west, United's main hub and known for delays. The CTA Blue Line runs to the Loop around the clock, so airport-area hotels are only worth it for a missed connection or a dawn flight.
Midway International (MDW): Closer, about 10 miles south-west, more compact and dominated by Southwest Airlines. The Orange Line ends at the airport and runs to the Loop, so a hotel near an Orange Line stop makes an easy transfer.
Union Station: The centre of Amtrak's national network, on the western edge of the Loop; most coast-to-coast rail journeys change trains here, and several downtown hotels are within walking distance.

Areas to consider

The Loop

Suits theatre, architecture tours and first visits, with almost every 'L' line on the doorstep. Rooms facing the elevated tracks can hear trains late at night, so ask for a high floor or a side away from them.

Near North and the Magnificent Mile

Suits shoppers and visitors who want the lakefront, Navy Pier and a wide choice of restaurants. Check the walk to the nearest Red Line station, the quickest link to both the Loop and the North Side.

Near South and McCormick Place

Suits convention delegates and visitors to the lakefront museums. When a large show is on at McCormick Place, rates rise across downtown; check the convention calendar before choosing dates.

Lincoln Park and Lakeview

Suits repeat visitors who want neighbourhood bars, the zoo and Wrigley Field rather than towers. Hotel stock is thin here, so book early for Cubs home games and summer weekends.

When to go

December to March is very cold, and wind chill off the lake makes it feel colder still. Summer is hot and often humid, and Grant Park's festivals (Blues and Gospel in June, Taste of Chicago in July, Lollapalooza in August and Jazz over Labor Day weekend) bring crowds downtown. Major conventions run through the year.

Before choosing a room

Downtown hotels usually charge for parking, often valet-only; if you are driving, compare that with a nearby public garage.
In winter, ask whether the room has its own thermostat; some older buildings run heating centrally and rooms can be too hot or too cold.
Hotels near O'Hare often carry 'Chicago' in their names; check the address before taking a cheap rate that is a long way from downtown.

Sources and planning resources

Facts checked on 30 October 2026. Transport services, taxes and hotel offers can change. Confirm the details for your trip before booking.