What to Do in Chicago in May

••• Photo courtesy of Chicago Cut Steakhouse

May is one of our favorite months in Chicago for so many reasons, from lovely Mother's Day brunches to the return of a number of outdoor attractions. Here is what else is on tap for the month. Have a great time in the city!

May Weather

• Average High Temperature: 69°F (20°C)

• Average Low Temperature: 49°F (9°C)

• Average Precipitation: 3.5"

What To Wear

Dress in layers because Chicago weather can be unpredictable.

It’s also notorious for dramatically dropping or increasing in temperature by 20 degrees or more in one day.

• Don’t forget a lined spring coat, as well as sweaters and scarves. We also recommend checking out Chicagoland shopping malls for additional apparel.

May Perks

• The weather should be finally warm enough to explore outdoors, and Chicago beaches open.

May Cons

• Hotel prices increase due to tourism season heating up. Here are some of Chicago's best hotel room views.

• Chance of flight/travel problems if a storm comes through; here's where to dine and drink if you get stranded at one of the airports.

Good To Know

Millennium Park's Crown Fountain is turned on May 1, weather permitting.

• May is National Burger Month. Here are some of our top picks in Chicago.

• Mother's Day occurs May 14. Here are some of our top brunch recommendations.

• Our recommendations on where to sleep, eat and play if you're in town with kids during Memorial Day weekend, which is May 28-30.

May Highlights/Events

Chicago Kids and Kites Festival

Chicago Underground Film Festival


Chicago Downtown Memorial Day Parade

Bike The Drive

Explore Chicago By Foot or Bike Through These Amazing Culinary Tours

1893 World Columbian Exposition Food Tour: The 1893 World’s Fair a.k.a. 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 of 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 (it was invented at the Palmer House), fruit pies and chili con carne. All guests will receive food from each food stop (Vegetarian options are available, but let the organizers know in advance. Also note that they cannot accommodate vegan or gluten-free dietary restrictions). Get Tickets.

Argyle & Andersonville Ethnic Food Tour: Participants will meet on the Far North Side in what's called "Little Saigon" on Argyle Street and travel by foot for about three-and-a-half hours to historic Uptown and Andersonville. Along the way, they'll visit contemporary dining destinations as well as 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 bar serving Swedish glögg. How To Get Tickets.

Bites, Bikes & Brews Tour: Participants get a good workout during a four-hour cycling tour taking them to popular eating neighborhoods 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. ​Get Tickets.

Chinatown Food Tours: Participants are strongly urged to nosh on something light before taking part in this unique event on the near South Side. Each restaurant's doing full portion sizes, which includes an authentic Beijing Peking duck and Hong Kong-style dim sum. Five restaurants are on the Chinatown walking food tour, including Ten Ren Tea & Ginseng Co. for authentic Chinese loose leaf tea. It's about three hours long. ​Get Tickets.

Savor Historic Gold Coast & Old Town Food Tour. The Gold Coast and Old Town are two of the city's trendiest neighborhoods, yet they also boast a number of cool, vintage, old-world elements.

The Victorian-era buildings, brick alleyways and narrow, tree-lined streets are charming backdrops to a busy main strip of restaurants and bars. Along this three-hour walking tour, guests will sample from four spots, including MORE cupcakes and Five Faces Ice Cream Shop. ​Get Tickets.