May in Chicago: Weather, What to Pack, and What to See

Chicago skyline and Navy Pier from Lake Michigan

Fraser Hall / Getty Images

With the reopening of outdoor attractions and the fun of long holiday weekends, May is a great time of the year to visit Chicago. Even though it's known as the Windy City, Chicago in May is more like summertime. Temperatures rise and the sun breaks through the clouds in a departure from the many blustery days of the preceding months. If you prefer warm temperatures, May is a great month to check out this Midwest hub and enjoy some time outdoors before the summer heat sets in.

Chicago Weather in May

In the state of Illinois, Chicago sits alongside the waters of Lake Michigan, which is responsible for its iconically cold and persistent winds. In May, the weather is much more tolerable as temperatures rise and the sun shines through the clouds—although it can be rainy at this time of year as well. In May, Chicago averages nine hours of sunlight per day and there is an average of eight rainy days during the month.

  • Average high temperature: 70 degrees Fahrenheit (21 degrees Celsius)
  • Average low temperature: 51 degrees Fahrenheit (10 degrees Celsius)
  • Average precipitation: 3.7 inches

What to Pack

Chicago weather can be unpredictable, so you'll need to dress in layers The city is notorious for its dramatic temperature drops, sometimes with daily temperatures that rise or fall by 20 degrees or more in one day. Pack some light sweaters or long-sleeved T-shirts and a pair of jeans. It can still get very cold at night, so you'll want to pack a warm spring coat and maybe a scarf and hat in case the temperature drops a lot. It doesn't rain often in May, but it could still happen so you may want to pack an umbrella just in case.

People visit the Crown Fountain in Chicago's Millennium Park
Jean-Marc Giboux / Getty Images

May Events in Chicago

Chicago's event calendar is full in May, ranging from the celebration of national holidays and seasonal events. In 2021, some events may be canceled so check with official organizers for the latest details.

  •  Millennium Park's Crown FountainOn May 1, the interactive fountain is turned on for the first time of the year, ushering in the summer season.
  • Chicago Kids and Kites Festival: This festival is held at Montrose Harbor in early May. You can make a kite with kids for free, see large-form and sports kites, view arts and crafts, eat a funnel cake, get your face painted, and more. Kites will also be available to purchase. This event has not been rescheduled for 2021.
  • Memorial Day Parade: On this national holiday, the parade typically begins with a wreath-laying ceremony at 11 a.m. at Daley Plaza, then the parade heads south on State Street from Lake Street to Van Buren Street. The parade has not been rescheduled for 2021.
  • Bike the Drive: Enjoy the scenery along iconic Lake Shore Drive on this 30-mile, car-free course. After the ride, hang out in Grant Park for live music, food, and giveaways. The benefit ride is open to all skill levels and abilities. This event will be held virtually in the fall of 2021.
  • Maifest: Celebrate German heritage at Lincoln Square, the heart of Chicago's German Community, with this event which marks the arrival of spring and features a maypole dance, live music, and German food. This event has not been rescheduled for 2021.

May Travel Tips

  • May is when Chicago beaches open, so you may also want to pack a swimsuit, beach towel, hat, and sunscreen just in case you get lucky with a particularly warm day.
  • Hotel prices increase at this time of year due to the tourism season heating up. If you're booking a room for May, check out these places that offer Chicago's best hotel room views.
  • There is a chance of travel problems if a storm comes through. If bad weather does cause a flight delay, there are many places to dine and drink at Midway or O'Hare airports.
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