A Guide to Visiting Chicago in May

Things to Do and What to Pack This Time of Year

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Photo courtesy of Chicago Cut Steakhouse

May is a great time of the year to visit Chicago—from lovely Mother's Day brunches to the re-opening of outdoor attractions. Here is what to expect while visiting Chicago in May plus some activities on tap for the month. Have a great time exploring the Windy City!

May Weather

  • 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 and What to Wear

  • Dress in layers because Chicago weather can be unpredictable. The city is also notorious for dramatically dropping or increasing in temperature by 20 degrees or more in one day.
  • Pack a lined spring coat as well as sweaters and scarves in case it gets chilly at night. 

May Perks

The weather in May should be finally warm enough to explore outdoors. May is when Chicago beaches open, so you may also want to pack a swimsuit, beach towel, hat, and sunscreen.

May Cons

  • Hotel prices increase due to 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, here is where to dine and drink as you wait it out at Midway or O'Hare airports.

Things to Do in May in Chicago

  • Bringing the kids over Memorial Day? Then check out these family-friendly places to sleepeat, and play during this extended holiday weekend at the end of May. Don't forget the Memorial Day Parade through downtown Chicago on Saturday. The day 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.
  • Go for a spin along Chicago's iconic Lake Shore Drive at MB Bike the Drive. Enjoy the scenery along the 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.
  • Celebrate German heritage at Maifest in Lincoln Square, the heart of Chicago's German Community. The event marks the arrival of spring and features a maypole dance, live music, and German food.

Explore Chicago By Foot or Bike on a Culinary Tour

If the events above don't pique your interest, how about learning about the city during an amazing culinary tour? It's a unique way to get to know Chicago, plus the weather in May should be ideal for exploring outdoors.

  • 1893 Chicago World's Fair Food Tour: The 1893 World’s Fair (aka the Columbian Exposition)—one of the most significant events that marked the city's recovery from the Great Chicago Fire—is revisited during this tour of five historic venues. The three-hour walking tour is lead by an actress portraying Bertha Honore Palmer, one of the top socialites at the turn of the century, who will entertain guests with her favorite memories of the era. Guests will enjoy Chicago-style hot dogs, popcorn, brownies (the dessert was invented at the Palmer House), fruit pies, and chili con carne. Guests will get to try something at each food stop. (Vegetarian options are available, but let the organizers know in advance. Vegan or gluten-free dietary restrictions cannot be accommodated.)
  • Saigon to Stockholm Food Tour: This tour meets on the Far North Side in what's called "Little Saigon" on Argyle Street and travels by foot for approximately 3.5 hours to historic Uptown and Andersonville. Along the way, visit contemporary dining destinations and unique independently owned businesses, ethnic markets, and antique shops. Of course, there will be a host of tastings, ranging from authentic banh mi at a pioneering Vietnamese restaurant to a Prohibition-era speakeasy serving Swedish glögg.
  • Bites, Bikes & Brews Tour: Participants get a good workout during this four-hour, 13-mile cycling tour that visits popular eating neighborhoods Streeterville, Gold Coast, Lakeview, Lincoln Park, Old Town, and Wrigleyville. They'll need it because there will be generous tastings of cupcakes, craft beers, hot dogs, and pizza in each neighborhood. And, yes, there are vegetarian options. Wear loose, casual clothing. 
  • Chinatown Adventure Food Tour: Participants are urged to nosh on only something light before taking part in this unique event on the near South Side. Each restaurant prepares full-size portions, which include an authentic Beijing Peking duck and Hong Kong-style dim sum. Five restaurants are on the Chinatown walking food tour, including Triple Crown and the Chiu Quon bakery. The tour lasts about three hours.
  • Savor Historic Gold Coast & Old Town Food Tour: The Gold Coast and Old Town are two of the city's trendiest neighborhoods, boasting a number of cool, vintage, Old World elements. The Victorian-era buildings, brick alleyways, and tree-lined streets serve as the backdrop to a busy main street with restaurants and bars. Along with this three-hour walking tour, guests will sample from seven spots, including More Cupcakes and The Sedgwick Stop. There's also time for shopping. (Vegetarian options are available, but let the organizers know in advance. Vegan or gluten-free dietary restrictions cannot be accommodated.)