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Andersonville
A lovely strip of shops and restaurants very close to the Block Party where Matthew grew up! For those over 21, We love Hopleaf for Belgian ales and food and Simon's Tavern for a classic dive. Women & Children First for books, Paper & Pencil for stationary, Brown elephant for thrifting, Folk for vintage furniture. Can't go wrong.
Lincoln Square
This is our neighborhood! The square has lots of great little shops. Check out Gene's Sausages for meats of all kinds (they also have a kid-friendly rooftop beer garden!) and Merz Apothecary for self care spa treats. If you wander south down Lincoln a ways you'll find Northside Cutlery for knives and other kitchen accessories, L&M for sandwiches, and Cho Sun Ok for Korean BBQ. Maybe even stop by Sunken Garden to see what all the fuss is about.
Lincoln Park
Lincoln Park is a classic old Chicago neighborhood where Tess (Matt's mom) grew up and is a lovely place to spend the day. The zoo is beautiful (and free!) and there are plenty of good place to eat – Cafecito has Cuban favorites near the zoo, or walk to Twin Anchors (where Matt worked in high school) for ribs or Athenian Room (where Tess worked in college) for Greek-American staples. The Chicken Kalamata is one of the finest plates of food you can order in the City, as far as we're concerned.
Montrose Point Bird Sanctuary
Our favorite place on the lakefront. For any bird enthusiast, this is a must see! It's right next to a fabulous sandy beach which is a great place for kids, or jump in the water right off the ledges with an amazing view of the skyline on the horizon. The epitome of summertime in Chicago.
Foster Beach
Foster is an easy stroll from the Block Party and great spot for a family beach day. Bring a picnic and go jump in the lake before we get married at the spot we got engaged!
Jackson Park
No trip to Chicago is complete without a visit to the Southside, and Jackson Park is a great easy option to make it happen. A scenic cruise down Lakeshore Drive delivers you to what is perhaps Chicago's most historic park, the site of the 1893 World's Columbian Exposition and White City (of which the Museum of Science & Industry is the sole surviving building). Home to the Osaka Garden and new Obama Presidential Center (where Ilana has installed work!), Jackson Park is an amazing place to take a walk and think about the Chicago of old and new.
Downtown & Surrounds
Downtown will always be worth exploring, and the Architecture River Tour is a classic for a reason. A variety of tours at different price points and lengths are available – the Architecture Center delivers the longer and more interesting tour, but Wendella has shorter and more affordable options too. Try to get out of downtown to eat, though, Chinatown is just a few short train stops away...