Deciding when to travel is an important decision and when planning a trip to Chicago, the types of activities and attractions you can include on your itinerary are affected by the varying weather of the Chicago seasons. The temperature range of highs and lows changes significantly, and visitors planning a trip to Chicago in January, February, or March can expect highs from 32 to 47 degrees and lows from 18 to 32 degrees.

Temperatures begin to rise during April and May and reach moderate levels by June. When planning to travel to Chicago during the summer, July is the month for the heaviest rainfall and also one of the warmest months, with temperatures reaching the mid-80 degree mark. August remains the same, but by September the temperatures begin to fall, with high temperatures only averaging 76 degrees. October temperatures decline to the mid-60 degree range, and by November and December the typical highs in Chicago range from 30 to 40 degrees, and the lows range from 24 to 35 degrees.

Spring and summer travel to Chicago presents visitors with opportunities to enjoy the numerous festivals, outdoor concerts, beaches, and special events including the Air and Water Show, Fourth of July Fireworks event, and music festivals that include the Chicago Jazz Festival, Grant Park Music Festival, and the Chicago Blues Festival, all scheduled for the warmer months of the year.

Chicago Map

A trip to Chicago during the warmer months also allows visitors to experience garden walks, flower shows, boat cruises, the waterfalls and fountains at Millennium Park, a pleasant day at the Navy Pier, sunning at Oak Street Beach, strolling Riverwalk, or having dinner by the river on a restaurant's terrace or deck. Walk down the Magnificent Mile or view the city skyline from the Hancock Observatory. The warm weather also presents an array of options for outdoor tours, including architectural trips and walking tours of the city's neighborhoods.

For visitors planning to travel to Chicago, being aware of the events taking place during the different seasons gives visitors an opportunity to plan their Chicago travel itinerary accordingly. In the spring, there are many scheduled events including the White Sox and Cubs season openers in April. In May and June, visitors can check out Marine Week Chicago, the Division Street Fest and Sidewalk Sale, the Randolph Street Market Fest, Chicago River Day, the Cinco de Mayo Parade, the Millennium Art Festival, the Old Town Art Fair, and the Puerto Rican Day Parade. Those interested in cultural events might consider the Scottish Festival & Highland Games, and for those with an interest in food, there are the Taste of Chicago, Taste of Randolph, and Taste of the Riverwalk events.

A trip to Chicago in the late summer, during July, August, or September, still provides plenty of activities, shows, music, festivals, and parades. The month of July is jammed with activities celebrating Chicago's people, food, music, and cultural traditions found at the Irish American Heritage Festival, Mag Mile Art Festival, Sheffield Garden Walk, Lakefront Venetian Night, Wicker Park Fest, and Lou Gehrig Day at Wrigley Field.

In August, scheduled activities begin to slow down, but the month still has plenty to do, starting with the huge concert featuring multiple singers and bands at Lollapalooza. Cultural festivals include the Latin Music Festival and Greek Festival, and the free Chicago Air & Water show is scheduled as well. September brings the Chicago Jazz Festival, Taste of Polonia, and Celtic Fest Chicago.

In October, November, and December, Chicago travel provides a range of interesting opportunities for vacationers during these last three months of the year beginning with the Country Music Festival, the Chicago Marathon, which begins and ends in Grant Park, and the annual Halloween parade and activities. In November, Chicago celebrates with the Lights Festival & Parade and the Thanksgiving Parade, and the city launches the Daley Plaza Santa's House attraction, which runs through December 24, followed by the Holiday Sports Fest.

When making Chicago travel plans, consider what you would most like to add to your vacation itinerary, and take into account the Chicago seasons to ensure that you have the best vacation possible, regardless of the time of year you visit.