Best Times to Visit Chicago
The best times to visit Chicago are April through May or September through October, when the temperatures are warm and hotel rates are reasonable. You'll also find a lot of festivals taking place in spring and fall. Summer marks Chicago's peak tourist season, with travelers from around the country hoping to take advantage of the warm weather. If you're planning to visit the Windy City between June and August, prepare yourself for denser crowds and higher prices on accommodations. Winter is a different story altogether: Chicago experiences bitter temperatures between November and March, but if you can hack it, hotel and airfare deals are easy to find.
There are advantages to staying ahead of the summertime crowds, namely lower room rates and more managable crowds. Temperatures hovering between the high 50s and the low 70s — comfortable conditions for walking around. However, you should come prepared for rain, especially if you're visiting in May.
Summer is the most popular time to visit Chicago, so expect prices to be at their highest and hotel vacancies to be hard to come by. While booking in advance is generally a good rule of thumb for Chicago, it especially applies to this time of year — plan on locking down your hotel reservations at least three or four weeks in advance. Summer temperatures ranging from the mid-70s to the mid-80s. However, the city sometimes experiences heat waves, resulting in triple-digit temperatures and heavy humidity, while nighttime breezes from Lake Michigan can make the later hours feel significantly cooler. Also, expect to encounter some rain in August.
Autumn in Chicago offers a sweet spot for tourism. Cooler weather and the start of the school year means fewer crowds and lower room rates. Daytime highs hover in the 60s and 70s, but evenings can see temperatures drop into the 40s. Keep in mind that some of the city's outdoor attractions — like Navy Pier — may have already reduced their hours or closed for the winter season.
Biting winds and freezing temperatures (daytime highs rest in the low 30s) deter faint-hearted tourists, leaving hotels and flights with plenty of vacancies. If you can stand the wintry weather, you'll find some of the lowest rates during this time. You can seek refuge from the wintry weather in the city's museums, but if you're hoping to visit Millennium Park or shop along the Magnificent Mile, wear your warmest layers.