Entertaining Guide to Chicago: Visiting or Hosting



Whether you’re visiting the beautiful city of Chicago or you live here full-time and have to come up with a game plan for your guests, I’ve compiled a fun list of great things to do/check out to make sure your itinerary creates memories for everyone. Just last summer, I had to host a group of 8 people who flew in from all over the country to attend Lollapalooza with us. Talk about stress level 100, but thankfully the itinerary I came up with still gets me mad props when I see those friends months later. Friends and family from Boston, Dallas and even Chicago came along for the ride… literally. Here are a few, yet fun recommendations from personal experience that will make certain you and your guests have a baller time:


Chicago Safari

parked in Lincoln Park


Chicago Safaris

Chicago Safaris takes street cred to another level and is one of the best companies to hit up for visitors or even better for hosts! They customize driving tours around the city to the vibe you’re looking to experience from semi-customizable or fully customized. They have options for sightseeing, food/drink activities and drop-off activities. My crew and I had the pleasure of doing some sightseeing to Wrigley Stadium, a food/drink activity at Bar Cocina in Lincoln Park and a drop off experience at a fun bar called HQ Beercade. The tour guides are extremely knowledgeable and even do a fun trivia during the journey between spots to keep you and your guests engaged the entire time.

Chicago Electric Boat Company

Located downtown on the river across from City Winery, Chicago Electric Boat Company has a variety of boats you can choose from and actually get to captain yourself! At first my guests were shocked that a company has boats on hand we could actually rent for such an affordable price, but the fact we could cruise the river on our own and do what we wanted was the icing on the cake. Being the over achieving hostess that I am, I took responsibility of being captain, aka the DD of the trip. You’re allowed to BYOB for the cruise and other bites you’d like to enjoy on the 2 hour cruise. My guests LOVED this, especially because the boats come with a bluetooth speaker for you to jam your favorite tunes down the river. My biggest recommendation to give on this adventure is to book the boat tour an hour before sunset and watch it along the river as it sets behind the building and literally watch the city light up at night to ride along the lights down the river. Probably one of the best decisions I made that entire weekend because…. well Lollapalooza.

Mobster/Crime Tours

Untouchable Tours

Of course Chicago’s biggest historical draw is for the mobsters and where they used to hang out in the city during the 1920’s & 30’s (prohibition era). With the Untouchable Tours, your tour guides are actual actors playing the part of a 1920’s gangster living in that time of prohibition and giving accurate accounts of happenings during that time. While there aren’t actual stops along the tour to get out and check out, it’s very educational and exciting!

Chicago Crime Tours

Looking for more options so fun it should be a crime? Chicago Crime Tours have anywhere from crime + pizza walk, night crimes tour (seasonally), crime + speakeasy tour (includes grabbing cocktails on stops!) and their standard crime tour. This guided tour through Chicago is more interactive with stops and walking included. The Night Crimes Tour is only offered after dark through spring/summer to allow for adventure under the city’s light!

Millennium Park Events

the best part about the summer in the city is that Chicago host a ton of awesome free events in the park right off of MICHIGAN avenue. from film, music and fitness, they create an awesome line up for people visiting or hosting! below you will find an event to indulge in every day of the week:

Concert in the Park

most Mondays and Thursdays, June 13 to Aug. 15, at 6:30 p.m. at the Jay Pritzker Pavilion.

Workouts in the park

Saturdays, Tuesday and Thursdays, May 25 to Aug. 31 on the Great Lawn,

  • Pilates at 7 a.m.

  • Yoga at 8 a.m. (Weekday Yoga will also be offered on Tuesday and Thursday mornings, May 28 to Sept. 5.)

  • Tai Chi at 9 a.m.

  • Zumba at 10 a.m.

Movies in the park

Tuesdays June 4 to Aug. 20 at 6:30 p.m. at the Jay Pritzker Pavilion.

Melissa HiggsComment