Chicago Travel Tips

Chicago is big. You can walk in some areas, but the city spreads across many neighborhoods, with the lake on one side and the expressways on the other. Plan each day by area: the downtown museums and Millennium Park one day, the Lakeview and Lincoln Park North Side another.

Leave extra time at rush hour, about 7 to 9 in the morning and 4 to 6:30 in the evening. That is when the Kennedy, the Dan Ryan and Lake Shore Drive slow to a crawl.

When to visit

Summer is festival season and the busiest time to visit. Fall brings cooler weather, the Chicago Marathon and convention season. Winter is cold but festive around the holidays. See our guide to holiday events in Chicago.

These are the places worth planning a trip around. We drop you at the door, so you skip parking.

The best hotels are on the Magnificent Mile, in the Gold Coast, downtown, and near McCormick Place for convention trips. Here is a mix of picks, all inside our Chicago service areas.

Chicago is a great food city, from deep-dish pizza and Italian beef to Michelin-starred tasting menus. Here is a short list to start. We handle dinner drop-offs and pickups, so nobody has to drive or park.

Chicago is busy in 2026. Here are the big festivals, concerts, games and conventions to plan around. Dates and times can change, so check with the venue or organizer.

Festivals

Major concerts

Sports and big events

Convention centers

Chicago is a top convention city. The two main centers are McCormick Place (2301 S Lake Shore Dr) in the South Loop, the largest convention center in North America, and the Donald E. Stephens Convention Center (5555 N River Rd) in Rosemont, right by O'Hare.

For McCormick Place, the connected South Loop hotels (Hyatt Regency McCormick Place, Marriott Marquis) are the easiest base. For Stephens, the hotels near O'Hare put you minutes from both the show floor and your flight. See our Rosemont car service page for rides there.

2026 conventions at McCormick Place

Corporate car service

Our corporate and executive service covers airport rides for visiting teams, client rides, multi-stop roadshows, convention shuttles between hotels and the show floor, and group trips. You get professional chauffeurs, clean late-model vehicles and on-time service, with billing options for business accounts.

Downtown is laid out on a grid that starts at State and Madison, so it is easier to find your way than in most big cities. The lake runs along the whole east side, and the river splits downtown into clear sections.

Parking and driving

Downtown parking is expensive and street spots are hard to find, especially during events. Many North Side neighborhoods are permit parking only. Lake Shore Drive is scenic but jams at rush hour.

For visitors, a pre-booked flat-rate car service beats driving and parking yourself, and beats rideshare surge on busy nights. No hunting for parking, and your chauffeur knows the shortcuts.

Neighborhoods worth a visit

Outside downtown, make time for Wicker Park (indie shops and nightlife), the West Loop (restaurants), Hyde Park (the University of Chicago and the Museum of Science and Industry), Old Town (Second City and historic streets) and Streeterville (Navy Pier and the lakefront). Each has its own feel and its own food.

Getting to and from the airports

Chicago has two major airports and two executive airports. O'Hare (ORD) is about 17 to 18 miles northwest of downtown, roughly 30 to 55 minutes. Midway (MDW) is about 12 miles southwest, 25 to 45 minutes. We also serve Chicago Executive (PWK) and DuPage (DPA) for private and corporate flights.

For arrivals, we track your flight in real time and adjust to delays at no extra charge. Your chauffeur sets an exact meeting point, and meet-and-greet with a name sign is available. For departures, we plan for traffic and drop you at your terminal curb.

Book as early as you can for busy travel mornings and convention weeks. Your flat rate is confirmed up front, with no surge, even at 5 a.m. or in a snowstorm. Plan to reach O'Hare about two to three hours before an international flight, or follow your airline's advice for domestic flights. Our Chicago airport guide covers terminals, customs and pickup spots.