Chicago is a big, bustling city that's popular all year long. Deciding when to visit, and when to book, will determine how much you spend on accommodations and airfare.
Before you begin to plan, take into account Chicago's seasonality, weather, crowds, and hotel options. Then decide when to go based on what you want to do in the city and on your budget.
Chicago is popular throughout the year, mostly due to conventions. June and September are particularly difficult months to find inexpensive accommodations. However, if you're willing to brave cold gusts from Lake Michigan, January, February, and March are less busy than the rest of the year. During winter, you might be able to take advantage of promotions from hotels and low-season airfare.
Like most cities in the U.S., Chicago is particularly popular in the summer vacation months, especially during events such as the Taste of Chicago, and over the December holidays. Leisure travel, coupled with business and convention travel, make the popular tourist areas—the Loop and Near North—book up quickly. You can also expect mid-morning and afternoon crowds at popular attractions and museums, particularly on free days.
- high season: April to December
- low season: January to March
Like many cities in the U.S., Chicago's most pleasant weather is during the spring and fall. Summertime in Chicago usually means comfortably warm, sunny days, but temperatures during heat waves can reach up to 100 degrees with heavy humidity. Winters are notoriously cold, when snowfall and cold air from Canada drive temperatures way down.
Conventions bring many people to Chicago each week during most of the year. This constant visitor influx means hotels, museums, restaurants, attractions, and events tend to be crowded. The annual Taste of Chicago (late June and early July) attracts visitors from the Chicagoland area and from nearby states, and coincides with Fourth of July celebrations.
Chicago's O'Hare airport is the one of the busiest airports in the country, and is prone to delays. Chicago's secondary airport, Midway, is less busy than O'Hare, but you can still expect long lines at the check-in desk and security during peak travel times.
Some attractions may have reduced winter hours, and may be closed, around the December holidays. Public transportation on the Red and Blue lines runs 24 hours, and there is Night Owl service on some bus lines. Service on other train lines closes at various times between midnight and 5 a.m.
When to Save
Hotels may offer reduced rates or special packages during the low-season months of January, February, and March. Admission prices tend to stay the same year-round, but it's a good idea to take advantage of weekly free days, or buy an attractions pass if you plan to visit several museums during your stay.
When to Book
General travel booking rules apply for Chicago. Booking in advance is smart if you need to travel on specific dates. However, because Chicago is home to one of the country's biggest and busiest airports, you might be able to find a low last-minute fare. And, vacation-package providers such as Expedia, Orbitz, Travelocity, and LastMinute.com often feature Chicago packages, even at the last minute. However, if you have your heart set on Chicago at a certain time, it probably isn't worth risking your vacation on a last-minute deal that may or may not come. Book sooner rather than later.
Chicago's O'Hare airport is one of the country's busiest and Midway also sees plenty of traffic from low-fare carriers. It's a good idea to book in advance and allow extra time at the airport.
Because Chicago is a popular convention city, it's smart to book accommodations in advance. The Loop and Near North are the most popular areas to stay, so if you have trouble finding availability, try hotels in the Gold Coast, Old Town, or Wicker Park neighborhoods.
Chicago sees a significant number of business travelers Mondays through Fridays. Weekend rates at business-oriented hotels can be lower than weekday rates to encourage leisure visitors.
Information provided by the Chicago Office of Tourism.