The infamous bar where we met on New Year's Eve, 2019. Unfortunately, it's closed, but the marquee is still there. So take a walk past if you'd like to go down memory lane.
Where we had our first date! A stunning rooftop bar with views of Lincoln Park.
Gabby's personal favorite. You can never go to The Bean too many times. And head over to Cindy's Rooftop after.
A popular rooftop bar with a view of The Bean and Millenium Park
Highly recommend Chicago Riverboat Architecture Tour or The First Lady tours. We have done both a few times.
A gorgeous spot on the river. You can grab a drink, sit on the steps, and people watch. If you're a fan of peeking into the lives of the upper echelon, this is a go to. The yachts park right in front of this bar. Did we already mention people watching?!
This is a frequent route for a walk with Jack. Traipse around and you'll quickly see why it's a favorite.
A less touristy roof top bar. A sure crowd pleaser!
A popular rooftop bar with a view of the river (and we just ignore Trump tower, and occasionally flip it off).
Another frequent Jack walk route. This address is just one of many access points. Look at a map to find a point closest to you. There's nothing better than a walk along Lake Michigan.
ART on THE MART is the largest digital art projection in the world. It runs every night between April and December.
GO EARLY!! Lines build fast, especially on nice days. Hours: 6:30 am – 8 pm Mon – Thu, 8 am – 9:30 pm Fri – Sun
This zoo is FREE! Also has great parks to walk around.
Some of our favorite bars: Sluggers, Old Crow, and Murphy's. Head over to NOLA for a New Orleans vibe.
Hours: 10 am – 8 pm Wed, 10 am – 5 pm Thu – Sun, Closed Mon & Tue | Entrance: Free (online reservations required)
A great place for a peaceful walk at any time of the day. There are several little paths to take, and all lead in similar directions.
Part of Grant Park.
Buckingham Fountain is part of this park. There are so many little paths and gardens. You can walk through here on your way to or from Maggie Daley park.