Things To Do

The Art Institute of Chicago

See if you can find our favorite painting which is featured above.

Shoreline Sightseeing Chicago Riverboat Tour

Millennium Park

Close to the Chicago Riverwalk / boat tour, home to "the bean" and Pritzker Pavilion. Definitely worth a walk through!

Shedd Aquarium

If you are feeling brave we recommend taking a divvy (Olivia's preferred mode of transportation) down to Shedd along the lakefront! There is a bike path which is easy to access. The Shedd is close to soldier field with great views of the city.

Untitled Supper Club

Fun to go for live jazz music and a drink! This place was a staple in Nick and Olivia's rotation while living in Chicago. Check the website for the show schedule as they normally only play two shows a night on Friday (no cover required).

Zebra Lounge

Piano bar that is super intimate. Ask Nick about the time he took an entire party bus here.

The Drifter

Hidden speakeasy bar with live burlesque performances. Very small & intimate venue. To access, walk into Green Door Tavern then go down the stairs like you are going to the bathroom. At the bottom of the stairs look at the shelves to the left & open to enter.

Cindy's Rooftop

Overlooking Millennium Park. They serve great cocktails and food - to get food, book a reservation early.

Headquarters Beercade

Free games like pinball, pac man, galaxy and more. Great way to kill time.

Old Crow Smokehouse

The infamous spot that Nicholas and Olivia met. Surrounded by a ton of fun bars & close to Wrigley Field where the Cubs play.

Aba

Some of the best Mediterranean in the city! Book early to get a table here. If you like short rib, get the short rib hummus - it's out of this world.

Chicago Pizza and Oven Grinder Company

The most unique version of Chicago pizza but delicious! Beware cash only.

Hotel Lincoln - JDV by Hyatt

If the weather is nice to go the rooftop for food or a drink for awesome city views.