Chicago to Washington DC, Best Times to Visit Chicago

  1. By kevin
  2. On May 17, 2018
  3. North America
  4. Travel Tips

Chicago's skyscrapers and public art are absolutely worth admiring: Tag along on a Chicago Architecture River Cruise or pass a few hours in Millennium Park and you'll find yourself spending lots of time looking upward. It's the right season to plan a holiday from Chicago to Washington DC. And here we talk about the best times to visit Chicago.

When to visit Chicago?

The best times to visit Chicago are April through May and between September and October, when the temperatures are warm, a variety of festivals take place and crowds are manageable. Summer marks Chicago's peak tourist and festival season, with travelers from around the country hoping to take advantage of the warm weather and abundant activities.

Chicago to Washington DC, Best Times to Visit Chicago


There are advantages to visiting before or after summer, namely more manageable crowds. Average daytime temperatures hover between the high 50s and low 70s – comfortable conditions for walking around. However, you should come prepared for rain, and be sure to bring a light jacket for those occasional days that fall into the high 30s and 40s.

Key Events:

Chicago Comic & Entertainment Expo (April)

Chicago Improv Festival (March-April)

Mayfest Chicago (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. Average summer temperatures range from the high 50s to the mid-80s. But temperatures can fluctuate significantly if there's a passing heat wave with high humidity or strong breezes from Lake Michigan, so pack a mix of clothes. Also, expect to encounter some rain in August.

Key Events:

Do Division Street Fest & Sidewalk Sale (June)

Chicago Blues Festival (June)

Gay Pride Chicago (June)

Taste of Chicago (July)

Square Roots Festival (July)

Chicago Air and Water Show (August)

Lollapalooza (August)

Chicago Fringe Festival (August-September)