By Charese David, Chicago Real Estate Broker

Summers in Chicago are amazing and the perfect time to host out-of-town guests. I love showing people this city - it has so much to offer. I have my favorite spots, so I decided to share my perfect 36-hour Chicago itinerary when guests come for a visit. 


Day 1: Late afternoon arrival. Spend the evening locally, starting out in my neighborhood, Roscoe Village. First stop, Lush Wine and Spirits for a nice glass of wine on the outdoor patio. Then stroll along Roscoe Street to visit some of the shops. 


At 7pm, have dinner reservations at Turquoise Cafe to enjoy Turkish food or Le Sud for Southern French cuisine. These are two of my favorite restaurants in Roscoe Village. Dine alfresco on a delicious meal in the beautiful setting of this lovely tree-lined neighborhood. 


After dinner, venture to Southport Corridor for dessert at Jeni’s Ice Cream - a real treat. Wander the street, taking in the evening sights and sounds of Southport Avenue. Then head back to my house for a nightcap in the backyard. 


Day 2: Start the day with a hearty breakfast at my favorite diner, Tempo Cafe in the heart of the Gold Coast. After breakfast, hop on Chicago’s First Lady for a 90-minute architecture boat tour. It’s a great way to learn the history of landmark buildings along the river and a fun way to see the city.  


Once the tour is done, stroll up and down Michigan Avenue to take in the shopping and tourist  scene. Along the way, head south to Millennium Park to see the Chicago Bean, of course, to take a selfie or get a shot of the Chicago skyline in the reflection of the sculpture. The whole area is just wonderful, with so many different things to see and even relax in the gardens. 


Next it's time for a snack and luckily there are a lot of choices in the area. My picks are across the street at either Remington’s or the Gage for a taste of “refined, rustic American fare complemented by innovative libations.” Then it’s off to the Art Institute of Chicago to wander through the amazing and varied art collections. The building itself is fantastic. 


There are a couple of options to choose from after the museum. Either head back to my house to relax or stop by the Lincoln Park Zoo on the way home. The great thing about the zoo is that it is a beautiful area to wander through and it’s free. On the way home, pick up snacks and drinks to hang out in the backyard before dinner. 


For dinner, our choices are either in the West Loop at La Sirena Clandestina for Latin / Brazilian cuisine. Or Mexican food in Andersonville at Octavio Canitna. After dinner, end the evening under the stars in my backyard. 


Day 3: Before the guests leave, wander to John’s Place or Commonwealth for a delicious brunch of American comfort food. And if there’s enough time after brunch, stroll and shop along Roscoe Street before departure. 


There are so many great restaurants, cafes, shops and tourist attractions in Chicago - it’s hard to narrow it down to 36 hours. The cool thing is that there really is something for everyone. That’s why I love it here. And why my guests keep coming back.


If you have questions or comments, please contact us..Cheers to new fun-filled adventures in Chicago!