Jazz fans enjoy local and global jazz stars at the annual Chicago Jazz Festival. Held over Labor Day Weekend, the 2015 Chicago Jazz Festival takes place at the Cultural Center at Millennium Park in Chicago. The Chicago Jazz Festival is ... moreGrant Park / Millennium Park
Between South Michigan Avenue to Lake Michigan and East Roosevelt Road to East Randolph Street.
Party Earth Review Part upscale bar, part restaurant, part club, and part bountiful beer garden, Zella is either the greatest thing since sliced bread or is suffering from multiple-personality disorder – either way, patrons come in droves to drink, flirt, and drink some more. A deceivingly small entrance in the simple brick façade leads ... more
1983 North Clybourn Avenue
Chicago, IL 60614
Taking over Chicago's Union Park every year during Labor Day Weekend, the North Coast Music Festival is a very popular end-of-summer music event that features more than 60 bands and DJs playing everything from electronic to hip-hop to ... moreUnion Park
1501 West Randolph St.
Chicago, IL 60607
Party Earth Review Spanning from the Chicago River at the south end to Oak Street at the north, the Magnificent Mile (“Mag Mile”) is a popular stretch of North Michigan Avenue constantly abuzz with fashionistas, foreigners, families, and finance types out shopping, strolling, or snapping photographs of some of the city’s most famous architecture ... more
400–1000 North Michigan Avenue
Chicago IL 60611
Chicagoans love their food and they love their summer. That’s why it makes sense to say a teary-eyed goodbye to summer at tasty events like the Labor Day at Oak Street Beach. The 2015 Labor Day at Oak Street Beach invites bikini ... moreOak Street Beach
500–1550 North Lake Shore Drive
Chicago, IL 60611
Party Earth Review With lots of glowing flat-screens beckoning to Cubs fans, daily specials luring the budget-minded, and a big seasonal beer garden perfect for open air drinking, Vines on Clark fits right into the Wrigleyville bar scene without being (entirely) about baseball. A long wooden bar with a mirrored back lines the right side ... more
3554 North Clark Street
Chicago, IL 60657
Fashion Event / Party
Stephanie and Adrienne Vendetti are sisters, best friends, natural-born redheads and co-founders of the world’s only redhead brand, How to be a Redhead. How to be a Redhead is empowering every redhead woman to feel confident ... moreOvation
2324 W. Fulton Street
Chicago IL 60612
Party Earth Review Unlike its often status-conscious namesake neighborhood, Lincoln Park itself is a serene escape from the bustling city, providing access to a host of sandy beaches, cultural events, outdoor theater, water activities, and wide open spaces. Spanning nearly six miles, the park runs through the neighborhoods of Lincoln Park ... more
2045 Lincoln Park West
(address of Lincoln Park Cultural Center)
Chicago, IL 60610
Arts Festival / Music Festival
Riot Fest is an annual three-day music festival and carnival that takes place every September at Humboldt Park in Chicago. Started in 2005, Riot Fest is a haven for punk and alternative rock music fans. With more than 30,000 people in ... moreHumboldt Park
Chicago, IL 60622
Bar / Arcade
Party Earth Review Entering Emporium Arcade Bar is like taking a step back into childhood, where frustrations brewed over unsaved princesses, Q*bert blew projectiles out his nose, and the only way to kill monsters was to over-inflate them with a bicycle pump. Anyone who doesn’t get those references should ask their parents. With exposed ... more
1366 North Milwaukee Avenue
Chicago, IL 60622
Food Festival / Street Fair
Chicagoans in need of fine Irish brew and some savory seafood head to the delicious and entertaining Oyster Festival every September. The 2015 Shock Top Oyster Festival features a slew of tents that house fresh seafood and other dishes from ... moreRoscoe Street and Damen Avenue Chicago, IL 60618
Party Earth Review Self-dubbed Chicago’s “lakefront playground,” Navy Pier is one of the city’s busiest tourist destinations, entertaining nearly nine million visitors a year with a plethora of amusement park rides, theaters, boat cruises, and beer gardens. Jutting out a half mile into Lake Michigan, the Pier is busiest during the summer ... more
600 East Grand Avenue
Chicago, IL 60611
The Windy City is a metropolis that is deeply affected by the weather, but regardless of the season, there are plenty of things to do in Chicago year round.
The nightlife scene is mostly indoors in the winter and the city itself is also a subdued beast locked in a deep freeze during the day. This is not to imply that everyone goes into hibernation (certainly not the shirtless Bears fans at Soldier Field) but crowds at most outdoor locales are comparatively scant.
As soon as the April / May thaw arrives, however, residents shake off their cabin fever and make any excuse to soak up the sun. Runners, bikers, and all-around outdoor lovers blanket the city’s nineteen miles of uninterrupted lakefront paths, and popular Lake Michigan beaches like ritzy Oak Street and rowdy North Avenue become a sea of skimpy swimwear and volleyball tournaments.
The city’s network of more than 550 parks – including Grant / Millennium, Lincoln, and Northerly Island – swell with things to do like softball games, sunbathers, dog walkers, and barbecue gods on any warm day. The carnival rides, events, and major promenade at Navy Pier are an obvious choice for first-time visitors, though the area’s cornucopia of cafés and theaters appeals to long-time residents as well.
Even before the thermometer inches past fifty, people head out in the morning to popular brunch spots and fantastic shopping districts to snatch up everything from haute couture along the landmark Magnificent Mile to quirky and trendy wares in Wicker Park.
And even though there are no traditional happy hours in Chicago, no summer would be complete without a day at one of its ballparks, whether in Bridgeport’s Sox country or sitting in the sun behind the ivy walls at historic Wrigley.
Amazing drink deals? Unpretentious crowds? Karaoke with friends? Dancing all night? Then check out these suggestions from Emma: