As the third most-populated city in the United States, Chicago offers families a diverse selection of cultural experiences, world-class museums, food, and fun. Kids will be fascinated by the skyscrapers and attractions, while grown-ups will appreciate the art, architecture, and people that make up the city's vibrant history.
Chicago is known as the Windy City, and indeed, it can be windy -- as well as rainy and foggy -- without much warning. Summer and fall are the high tourists seasons, and unpredictable weather patterns and large temperature ranges mean it's hard to devise a trip itinerary far in advance. That said, plan a mixture of indoor and outdoor activities. If you're blessed with a gorgeous afternoon, take advantage of it by hitting the streets, pier, or parks while it lasts! A jacket is wise even in summer, especially if you plan to be by the lake in the evening. In the fall, the crowds dissipate somewhat, and the weather is likely to be mild throughout September, possibly even into mid-to-late October.
Temperatures average a high of 80 degrees in June, 84 degrees in July, 82 degrees in August, and 74 degrees in September, with low daily averages in the upper 50s/low 60s. Winter is cold, with winds that can take your breath away. Spring can be slow in coming and is often cold, with May showing the first really warm temperatures. Get more weather info.
Chicago has two major airports, Midway (MDW) and O'Hare (ORD). O'Hare is bigger, so you may have more options for cheap flights, but many people prefer Midway's size and proximity to downtown. If you're taking a train, there is Amtrak train service in downtown, and you can also arrive from the suburbs and even surrounding states on one of the commuter trains: Metrarail and NICTD. You'll encounter a lot of traffic if you drive into Chicago, and parking is expensive. There are plenty of shuttles, taxis, buses and other options to get you from the train station or airport to your hotel.
With abundant buses, taxis, and trains servicing the downtown and tourist-centered areas, getting around Chicago is easy. Check out TransitChicago.com for schedules, maps, and an interactive trip planner that'll help you figure out how to get where you want to go. You can also hail a cab from the street. If you have a larger family, ask your hotel concierge to call the taxi company and request a minivan or other roomier vehicle.
About the El Train
Chicago's elevated train system, also known as the "El" (or "L"), is one of the busiest and biggest rapid-transit systems in the United States. With eight lines servicing the city and surrounding suburbs, the El is a convenient way to get around that can also be a fun experience for kids. Make sure to ride it at least once during the day while it's still light outside to get a commuter's view of the city. Avoid rush hour, though -- the train gets very busy. Late morning and early afternoon are the best times during the week; on weekends, other factors (a big game or a festival) may affect how many people are riding at any given time.
The routes are color-coded, so look at a map before you go. The Red Line, the El's busiest train, runs along the lakefront as far north as Evanston. Most attractions' websites will tell you which route to take. Check TransitChicago.com for maps, schedules, and an interactive trip planner.
Chicago always seems to have a festival of some type going on; check the city's official website to see what special events may complement your trip (or turn it into a big hassle). The larger festivals often make getting around downtown nearly impossible, and accommodations very hard to get. You'll definitely want to steer clear of the giant music festival Lollapalooza, and, unless you plan on spending serious time there, avoid the Taste of Chicago weeks in late June/early July.
Consider buying a Chicago City Pass, which gets you into Shedd Aquarium, Adler Planetarium, Field Museum, Museum of Science and Industry, and the Hancock Observatory for one price of $49.50 per adult, $39 per child. Also visit ChooseChicago.com to find out when local museums offer free admission.
If you're interested in seeing how the locals live, one good neighborhood for lolling and strolling is Lincoln Park. Check out our local writer's picks for things to do with kids in this grassy, laid-back area right next to the lake.