The Architecture Tour on the Chicago River is an absolute MUST do! There are several companies that offer tours - just book the tour that has the best timing for your schedule. I don't know that there are major differences across companies. Chicago is a beautiful city and the tour guides are extremely knowledgeable about the buildings surrounding the river. The Carbide & Carbon building is stunning - and you can see Jordan and Leo's office building as the tour explores the southwestern end of the Loop!
The 606 is an elevated walking path through residential neighborhoods on the west side of Chicago. This path is right in Jordan and Leo's neighborhood. Grab a coffee at Ipsento 606 and hop right on the trail to walk, run, or bike through Wicker Park and Bucktown.
We got engaged here! In this alley there is a very popular (read: very long line) coffee shop called Sawada Coffee or a fast casual barbeque restaurant called Green Street Smoked Meats if you want to add this spot to your itinerary in Chicago.
Lincoln Park is a beautiful area to walk around with views of the city skyline. Route to the Bridge Over South Pond for great views or walk around the free Lincoln Park Zoo!
An ambitious visitor could try to squeeze in the 1:20pm Cardinals vs Cubs game on Friday before the wedding festivities begin! Even without tickets to the game, Wrigleyville will be a lively sight to see on a Friday afternoon.
Horner Park has some of the best drop-in pickleball in the city! It is a beautiful park in a more residential area of Chicago - definitely worth a visit for anyone that wants to get some pickle in over the weekend!