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  1. Venues & Destinations
  2. United States
  3. Chicago

10 Ideas for Summer Entertaining in Chicago

Jenny Berg
May 3, 2011

Here are new ideas for group outings, catering, client entertaining, gifts, and entertaining summer associates and interns in Chicago.

1. Operating from Memorial Day to Labor Day, Seadog Speedboat Cruises depart from Navy Pier. The 60-minute Fireworks cruise, available every Wednesday and Saturday evening, offers a speedboat ride, tour narration, music, and views of the Navy Pier fireworks. The Seadog fleet comprises four vessels which each carry between 125 and 142 passengers. Hosts can charter an individual boat, or book the entire fleet for a 400-guest event. Pricing begins at $19.95 per head.

2. The new Chicago Brew Bus takes groups of 14 on tours of local breweries, including Goose Island, Wicker Park's Moonshine, and the West Loop's Haymarket. Guests spend about 50 minutes in each spot, and get snacks and samples of beer. The bus is equipped with its own bar, and the tours involve narration on local beer-related landmarks such as Emmit's Pub, which appeared in the movies Backdraft and Uncle Buck. The average ticket price is $49.95 per person.

3. The Chicago Park District offers one-day volunteer opportunities for corporate groups. The outdoor activities, dedicated to improving local parks in a variety of neighborhoods, could include planting gardens or mulching trees. Groups can split up into teams to complete the activities, which typically lasts at least three hours. Hosts can specify which part of the city they'd like to work in, and are asked to submit volunteer applications via the park district's Web site at least three weeks before the requested event date.

4. Real Kitchen Catering, a new firm based in Ravenswood, is headed up by chefs who have worked in such reputable spots as Charlie Trotter's and North Pond. The company caters meetings and events with 4 to 100 guestsโ€”they can also serve larger groups if necessaryโ€” and can prepare picnic meals for summertime functions. The menu changes seasonally, and may include avocado gazpacho, poached-salmon-and-dill-cream-cheese sandwiches, and lemon tarts.

5. Chicago Chocolate Tours' new offerings include private cupcake tasting tours. The tours have accommodated groups with as many as 183 guests, and each group of 15 or more gets its own tour guide. The outings typically last around two hours include local bakeries such as More and Swirlz. Groups can travel by foot, or staffers can arrange for a champagne-stocked limo to pick guests up at the office and shuttle them around. Teambuilding activities include the Cupcake Challenge, in which groups divide into teams to find answers to cupcake-related questions throughout the tour. Pricing starts around $50 per head and group rates are available. 

6. Or, for music lovers, Chicago Detours recently launched its "Our Chicago Sound: Jazz, Blues, and Beyond" tour. Available from June through September, the two-and-a-half hour bus tour can accommodate 34 or fewer guests. Price varies depending on guest count, but the average rate is $60 per person. Tours begin at the Jazz Record Mart, and venture through the city to explore musical landmarks such as the Chess Records Studio. On the bus, videos provide commentary on Chicago's musical history and guests get a blues harmonica lesson; some of the stops include live musical performances.

7. Buddy Guy's Legends opened in a new location last June. The South Loop venue offers live blues every night of the week and has a private party room that can host seated dinners for 60 or receptions for 150. The party space is adjacent to a pool room with three tables and a bar; the lower level is also available for private events and can hold 400. The menu focuses on Cajun fare and offers jambalaya, crawfish etouffรฉe, and catfish tenders.

8. Bottle and Bottega opened in Lincoln Park in March. The studio hosts private painting parties for corporate groups of 5 to 65. Team-building activities include dividing into groups to paint on a large canvas with pre-drawn line art. At the end of the taskโ€”which normally takes two to three hoursโ€”all the canvases combine to form one complete design. Pricing varies depending on the activity, but generally starts at $35 per person for two hours. The venue works with a list of preferred caterers that includes the Hearty Boys and Amazing Edibles.

9. Located across the street from Wrigley Field, the Wrigleyville Rooftops accommodate private Cubs game viewings for groups of 2 to 200. Housed in former residential buildings, the three side-by-side spaces recently underwent slight remodels that resulted in updated decor. Each rooftop viewing area has bleachers and a bar; guests can also sit in an indoor space that offers another bar and classic ballpark fare such as burgers and hot dogs. Prices range from $75 to $200 per head, depending on the game, and include unlimited food and drink.

10. Local artisan candy company Truffle Truffle recently introduced customized gifts. Hosts can personalize packaging to include corporate colors or logos, or integrate invitation graphics into the gift tags. Offerings include summery items such as s'mores, and the new "I Love Chicago" collectionโ€”geared toward visitorsโ€” is a 12-piece tin of truffles decorated to look like the city's flag. Pricing starts at $2 per individually wrapped item.

E20475sa
Photo: Courtesy of Seadog Cruises
Bottles & Bottega hosts arty team-building activities for as many as 65 guests.
Bottles & Bottega hosts arty team-building activities for as many as 65 guests.
Photo: Greg Szoda
Real Kitchen Catering can prepare fare for corporate picnics. The seasonal menu includes summery desserts such as fruit tarts.
Real Kitchen Catering can prepare fare for corporate picnics. The seasonal menu includes summery desserts such as fruit tarts.
Photo: Heather Sperling/tastingtable.com
Real Kitchen Catering can also prepare gourmet sandwiches for picnic lunches.
Real Kitchen Catering can also prepare gourmet sandwiches for picnic lunches.
Photo: Heather Sperling/tastingtable.com
Seadog Cruises operate throughout the summer and depart from Navy Pier. The boats can be rented out for groups with as many as 400 guests.
Seadog Cruises operate throughout the summer and depart from Navy Pier. The boats can be rented out for groups with as many as 400 guests.
Photo: Courtesy of Seadog Cruises
Truffle Truffle can incorporate corporate colors or logos into gift packaging.
Truffle Truffle can incorporate corporate colors or logos into gift packaging.
Photo: Courtesy of Truffle Truffle
The Wrigleyville Rooftops look directly into the ballpark; the game is also aired on TVs in the indoor bar.
The Wrigleyville Rooftops look directly into the ballpark; the game is also aired on TVs in the indoor bar.
Photo: Courtesy of Wrigleyville Rooftops
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