We have updated this list for 2014. Read Summer 2014 Guide to Chicago
Chicago in the summer is a beach town—a crazy thought to the uninitiated who only know the Windy City by its famously, bone-chillingly cold winters. But when the weather heats up, Chicagoans take off to the water to take advantage of the city's natural beauty and also show up in force for neighborhood and city-sponsored activities: Like a picture postcard, Lake Michigan fills ups with sailboats; sun worshipers baste on Oak Street Beach in itsy-bitsy bikinis while bicyclers, volleyball players, and joggers get fit by the shore. What's more, a parade of shoppers indulge their cravings for designer duds on Michigan Avenue; baseball fans commit another summer to rooting for their beloved Cubs and White Sox; foodies feast on some of the best fare the Midwest has to offer via a myriad of festivals; and music lovers revel in the treasure trove of outdoor music offerings. Convinced yet?
Taste of Chicago Food Festival
July 10-14 in Grant Park
Dubbed "the largest food festival in the world", this outdoor fest has been going strong since 1980. Close to beautiful Lake Michigan and showcasing celebrity chefs, food demos, restaurants, food trucks, music, and more. If you're visiting the city this is an even you don't want to miss.
Windy City RibFest
July 5-7 in the Uptown neighborhood
Come for the finger lickin' ribs and stay for the entertainment. The musical lineup was recently announced, with Cracker on Saturday night and The Right Now on Sunday.
Taste of Latin America
August 23 – 25 on Armitage Avenue
Enjoy wine tastings, art, entertainments, cooking demonstrations, and food from more than 25 participating Latin American restaurants including cuisine from Argentina, Brazil, Chile, Columbia, Cuba, Ecuador, Jamaica, Mexico, Peru, and Puerto Rico.
35th Annual Chinatown Summer Fair
July 21st from Cermak to 24th Place
Food, arts, crafts, entertainment, live music—and a dragon and lion dance procession at 12:30 pm. You don't want to miss this annual cultural extravaganza.
Navy Pier Fireworks
From Memorial Day weekend through Labor Day Navy Pier has fireworks complete with musical accompaniment every Wednesday at 9:30 pm and Saturday at 10:15 pm. Watch them from the dock, book an evening cruise, or pack up a dinnertime picnic.
Can't-Miss Summertime Happenings
Bastille Day 5K & 8K Run/Walk & Block Party
July 14th in Lincoln Park
Celebrate French Independence Day at the Peggy Notebaert Nature Museum with music, wine, and, of course, delectable French food.
Chicago Air & Water Show
August 17 & 18. You can see the show along the lakefront from Fullerton to Oak Street.
This 55th annual show is said to be the largest free show of its kind in the United States. You may want to bring a blanket and chairs (and plenty of sunscreen!) to watch the show in comfort.
The Magnificent Mile Shopping Festival
August 23 – September 2
It's a festival. Of shopping. It is 12 days of fashion shows, celebrity appearances, in-store events, and special offers. What more do you need to know?
Grant Park Music Festival
Through August 17th in Millennium Park
This annual summer classical concert series takes place in the Jay Prtizker Pavilion designed by renowned architect Frank Gehry near Chicago's lakefront. The event is ongoing, free and features the Grant Park Orchestra & Chorus.
Pitchfork Music Festival
July 19 – 21 in Union Park
Björk, R. Kelly, Belle & Sebastian, MIA, Solange, and others turn up the heat at this festival that also highlights new and emerging music.
Annual African/Caribbean International Festival of Life
Jul 4–7 Union Park in the West Loop
Gospel, rock, reggae, Latin, and electronica genres are all celebrated here. Also look for children's activities, food, arts, and crafts.
August 2 – 4 in Grant Park
The music extravaganza that's been going strong since 1991.The lineup this year includes The Cure, Mumford & Sons, The Killers, Nine Inch Nails, New Order, Queens of the Stone Age, The Lumineers, Thievery Corporation, and a multitude of other acts.
Chicago Jazz Festival
August 29 – September 1 in Millennium Park
Since 1979 music lovers have enjoyed free, world-class jazz over Labor Day.
World Music Festival
September 12-22, multiple venues across the city
The City of Chicago and Chicago Department of Cultural Affairs present 600 artists and groups from over 80 countries at this festival every year.
Randolph Street Market Festival
July 27 & 28, August 24 & 25, September 28 in the West Loop
An indoor/outdoor shopping extravaganza where more than 200 vendors sell antiques, housewares, vintage clothing, jewelry, and collectibles.
African Festival of the Arts
August 30 - September 2 in Washington Park
Look for an art market, "drum village," African folk music, dance, and other traditional and cultural highlights at this Labor Day weekend fest.
Northalsted Market Days
August 10-11 in the neighborhood dubbed as "Boystown"
This is said to be the largest two-day street fair in the Midwest. Think food, arts, crafts, and musical acts including Wilson Phillips.
Where to Stay Now
The Hyatt Regency McCormick Place has completed its $110 Million Dollar Renovation; Langham Chicago Hotel is scheduled to open in July within the landmark Mies van der Rohe building along the Chicago River; The Godfrey Hotel Chicago opens in the River North neighborhood this summer with a rooftop lounge with views of the dazzling Chicago skyline; Aloft Chicago City Center opens in downtown Chicago. It's even a Certified LEED hotel (Leadership in Energy and Environmental Design). Sir Richard Bran is bringing his first U.S. Virgin Hotel to downtown Chicago but for that we have to wait until fall.
Where to Eat and Drink Now
At Curtis Duffy's new and highly anticipated restaurant Grace, you have a choice between two $185 nine-course menus: "Flora" or "Fauna"; Oon Chicago opens later this summer offering contemporary American with a Southeast Asian influence. The Dec Rooftop Lounge + Bar recently opened at the Ritz-Carlton Hotel; Chicago's first distillery and cocktail bar, CH Distillery, opens in the West Loop later this summer too.
Photo Credits: Chicago Summer Festivals: Courtesy of Taste of Chicago; July 4th: Kunal Mehta/Shutterstock; Other Happenings in Town: Woohoopepper | Dreamstime.com; Music: Norman Timonera; Arts: yuan2003/Flickr (CC BY-NC 2.0); New Hotels: Hyatt Corporation; New Bars & Restaurants: Grace Restaurant, Inc.