If you are first timers in Chicago (or if you live here), this is our number one recommendation to see the city. Relax in a boat in the sun and learn about the history of Chicago. Advanced reservations are recommended.
A must-visit in Chicago, and walking distance from our hotel blocks. Anna loves the modern wing, Brad loves enjoying a coffee the sculpture courtyard.
This is a great way to spend the morning. We recommend grabbing a coffee and walking north on Michigan Ave to the River. Take the steps down to the water near City Winery. From there, you can walk up and down the river.
If you're willing to venture a little farther, or are looking for something to do before our welcome event, this is Chicago's version of the "high-line". It's right near our old neighborhood Ukranian Village. We recommend starting your walk at the Ashland Ave entrance, and walking west on the 606 to North or Milwaukee Ave. Cool off with a coffee from "Ipsento 606", enjoy tacos at "Big Star", or have a burger at our brunch spot below "Mott St".
Chicago’s Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. The conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens. It's one of our favorite escapes from the 'concrete jungle' of the city! Advanced reservations required (but easy to obtain last minute).
Staying through Sunday night and looking for a laugh? This improv comedy club is the origin of many famous stars such as the John Belushi, Bill Murray, Chris Farley, Tina Fey, Steve Carell and many more! Advance reservations recommended for the Sunday night show.
Looking for one last trip to the beach now that summer has passed? Ohio Street Beach is located in the Streeterville neighborhood. The beautiful Lakefront Trail is a great way to get some fresh air and enjoy the intersection of the beach, lake and city skyline.
A bit off the beaten path, but a Melio sibling staple, this pinball bar is a wonderfully divey place to grab a beer, and play some games.
Great spot for a quick coffee and breakfast. Alternatively, stay for a meal and cool off with a beer or glass of wine. Anna loves their lattes, Brad is partial to the dinosaur and spaceship cookies.
The riverfront version of the West-Town original. This is a great place to go for shared-plates and wonderful cocktails, with a fantastic atmosphere. Also tends to be popular, so consider going at slightly off-hours or make a reservation.
From the chef of the "Girl and the Goat", this rooftop spot is one of our favorite Sunday morning places. It's Peruvian inspired shared-plates, and is a fantastic place for brunch. It can fill up on weekends, so grab a reservation if you can.
This place is stunning. It is one of Brad and Anna's favorite places, serving Mediterranean food, with a great rooftop patio. Come for drinks and shared plates, or a dinner if you're staying extra nights.
Another one of chef Stephanie Izard's restaurants, this time it's Chinese-inspired. On Sundays they serve Dim Sum and good brunch cocktails.
One of our absolute favorite places when we were living in Chicago for fried chicken sandwiches. If you are feeling tired from all the celebrations- it's a great place to order take-out from.
Find yourself in Wicker Park or walking the 606? This asian-inspired funky restaurant has delicious food (we love the wings and their burger is famous). There's great outdoor seating if the weather cooperates.
This rooftop bar on at the Chicago Athletic Association Hotel boasts wonderful views of the city, and delicious cocktails. It can be crowded, especially on nice days, but is well worth a visit especially at non-peak hours.
A quick el-ride, or slightly longer walk from the venue, this Fulton Market District market is a great way to sample some Chicago food. There's communal seating, and a rooftop deck. Come for a casual cocktail or bite to eat.
This is our honorable mention because Brad took Anna here on our first date (well, technically, our friend Kyle took Anna and Brad here). They serve a beautiful tasting menu dinner, that is delicious and formal. Advanced reservations required.