We recommend Wendella or Chicago Architecture Foundation boat tours as a great way to see the city by boat. You can buy drinks at the onboard bar.
The Chicago Lakefront Trail is a 18-mile-long path for walking jogging and cycling, located along the western shore of Lake Michigan. Rent a Divvy bike and check out the different harbors and views. The closest entrance to Ambassador Hotel and Northern Michigan Ave is Oak Street Beach.
Visit the Game Room bar inside Chicago Athletic Association for some drinks and classic games like bocce on their built-in court. Head upstairs to Cindy's rooftop for some food and drinks with an incredible view overlooking Millennium Park. Visit the link for the rest of their restaurants, bars and super hip accommodations.
Head to Wicker Park for some shuffleboard at Royal Palms, where we play in a weekly shuffleboard league (21+ spot). Be sure to grab a griddle burger next door at Small Cheval. http://smallcheval.com
Head to Avec, the brides favorite restaurant for mediterranean and midwest inspired shared plates and a wonderful wine list. The restaurant is small spot with communal tables and limited reservations. They do lunch, brunch and dinner service.
The cubbies are in town playing the Diamondbacks our wedding weekend! Catch a Friday or Sunday game at the historic Wrigley Field in Lincoln Park.
Check out one of our neighborhood staples, Big Star for the best tacos and margaritas. There are lots of restaurants, bars and shopping to walk to from there including the Up Room located on top of The Robey Hotel for city views. Located right off the CTA Blue Line: Damen stop.
Our favorite place to see live blues by local musicians. Doors open at 8 and music starts at 9:30 (get there before 9 to get a seat). $10 cover. If you want more live music, bbq and room to dance, head across the street to Kingston Mines that has two stages and bands playing every night. https://kingstonmines.com
There is always great live comedy to be seen in Chicago. Head to iO (or Second City) for a show and be sure to check out one of our favorite taprooms across the street: Off Color Brewing. http://www.offcolorbrewing.com/taproom. Other local breweries: Half Acre, Begyle, On Tour, Marz Community Brewery, Hopewell (in Logan Square, one of our favorite neighborhoods), Revolution, Metropolitan and more!