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 Held the last weekend of the month from February to December, Randolph Street Market is a European-style bazaar with more than two hundred vendors – all hand-picked by festival organizers – hawking an array of antiques, handmade items, and vintage goods. Both an indoor and outdoor event, the market features ... more
1350 West Randolph Street
Chicago, IL 60607
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 Navigating a short stretch between Lincoln Park and Lakeview, the Chicago Beer Experience leads adventurous groups of friends and die-hard beer lovers along a half-mile hops-fueled adventure. Beginning in Lakeview at Vaughan's, a cozy Irish pub, the tour runs most Fridays through Sundays (regardless of the weather) and ... more
2917 North Sheffield Avenue
Chicago, IL 60657
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 Founded in 1968 as one of Chicago’s first blues clubs, Kingston Mines has stood witness to more than a few big players in the industry wailing about how their woman left them. Playbills from past performances, old photos of legendary singers, and vintage murals of African American history dot the room, while mismatched ... more
2548 North Halsted
Chicago, IL 60614
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 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
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
Party Earth Review Set in the swanky area of Chicago known as the Gold Coast, Rush and Division is an odd mix of flashy, loud, and slightly seedy that features a range of venues from the rowdy bars along Division to the fat-cat steakhouses on Rush. The addition of State Street to the west – along with the infamous supply of older men on the ... more
Intersection of Rush Street and Division Street
Chicago, IL 60611
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 Set between the swanky shops of Rush Street and the wild bar scene of Division Street, The Cedar Hotel – a crime-riddled boarding house in the 1920s – now provides a bit of both worlds with its unique combination of historical architecture and energetic sports vibe. Popular with a party crowd of post-grads and sports fans ... more
1112 North State Street
Chicago, IL 60610
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: