Lara & Tom
Things To Do
Grant Park
Across the street from the hotel room block at Hotel Essex is Grant Park of the Chicago Park District. Are you a fan of Married with Children? Check out the legendary Buckingham Fountain in Grant Park, and enjoy views of Lake Michigan. Within Grant Park is Millennium Park, the Lurie Gardens, the Art Institute of Chicago, the Skate Park of Grant Park, and an amazing array of statues and art work. There is a permanent installment of art by Magdalena Abakanowicz called Agora on the south side of the park near Roosevelt Road. This being important to Lara since she spent years working for Hess Collection Winery in Napa where there was numerous art pieces by Magdalena Abakanowicz. The park has hosted events such as the 2016 MLB Chicago Cubs World Series Championship rally, all 6 NBA Chicago Bulls World Championship rallies (the teams with Michael Jordan), the 2021 WNBA Chicago Sky Championship rally, the Obama Victory rally, Lollapalooza, and multiple softball fields (FYI Bill Remitz).
Wrigley Field
The oldest ballpark in the National League, Wrigley Field has been in operation since 1914. Home of the 2016 World Champion Cubs, it's a must-see stop for anyone in Chicago. Although the Cubbies will be out of town, you can score a tour of the newly renovated ballpark with a chance to walk out on the field. It's a once-in-a-lifetime experience. The ballpark itself is surrounded by the Wrigleyville neighborhood, it's home to many of bars, restaurants and a close walk to the shores of Lake Michigan. From downtown its just a 7 mile L ride to Wrigley via the CTA Redline at the Addison stop and the Clark 22 Bus.
Cloud Gate
Some of the best mirror-image selfies in the world are taken here! Visit the Bean, or "Cloud Gate" sculpture by Indian-born British artist Sir Anish Kapoor, in Millennium Park and take a stroll over to check out the Frank Gehry-designed Pritzker Pavilion amphitheater, which hosts free live music, theatre, and movies throughout the summer months.
The Drawing Room in the Chicago Athletic Association
Walk in to the Chicago Athletic Association Hotel and go to the second floor to experience the Drawing Room where you are greeted with the Harry Potter style carved walls, fireplaces, and lounge area. The Game Room, next to the Drawing Room, offers Bocce, Pool, Shuffle Board and so many more games. The Chicago Athletic Association is both a novel downtown destination on the doorstep of Millennium Park and a historic monument to the big-shouldered spirit that defines our beloved city.
Museum Campus
Chicago’s amazing Museum Campus houses three of the city’s leading institutions all in one place. Spend a day exploring natural history and world cultures at Field Museum, underwater worlds at the Shedd Aquarium, and far-out galaxies at the Adler Planetarium — and all from a breathtaking lakefront vantage point.
Chicago Riverwalk
See the famous Chicago skyline from the picturesque Chicago River's edge and enjoy public art along the way. If you feel so inclined, grab a glass of wine at City Winery, or take a cruise on one of the many boat tours offered along the shoreline.
Chicago's First Lady Cruises
A must-do for visitors to Chicago! The Chicago Architecture Foundation hosts this river cruise, with well-educated docents sharing the history of Chicago through the lens of its architecture as viewed from the water. Learn about the architects, their buildings, and how they fit into Chicago history on this boat that boasts a full bar and snacks.
Magnificent Mile
The Magnificent Mile is Chicago’s premier commercial district. The vibrant, bustling area is home to upscale shops, luxe fashion outlets, cool restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower, the terracotta Wrigley Building skyscraper and the 100-story John Hancock Center, which has a rooftop observation deck with fine dining and panoramic city views.
Willis Tower (Sears Tower)
The Willis Tower (formerly known as and commonly referred to as the Sears Tower) is a 108-story, 1,450-foot (442.1 m) skyscraper in Chicago. The tower has 108 stories as counted by standard methods, though the building's owners count the main roof as 109 and the mechanical penthouse roof as 110. Check out the Skydeck's Ledge and step outside the third tallest building in the Western Hemisphere. At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck. You can see 4 states from this height! Bueller... Bueller... Bueller...
Reckless Records
Take a step back in time when buying and exploring music was an activity. Get lost in the rows of vinyl at this Chicago record shop. "Customer: Hi, do you have the song “I Just Called To Say I Love You?” It’s for my daughter’s birthday. Barry: Yea we have it. Customer: Great, Great, can I have it? Barry: No, no, you can’t. Customer: Why not? Barry: Well, it’s sentimental tacky crap. Do we look like the kind of store that sells I Just Called to Say I Love You? Go to the mall."
The 606 - West Trailhead
The 606 brings together arts, history, design, trails for bikers, runners, and walkers, event spaces, alternative transportation avenues, and green, open space for neighbors, Chicagoans, and the world.
Garden of the Phoenix
On the site of the Chicago's Museum of Science and Industry, the only remaining building of the World's Columbian Exposition of 1893, is Washington Park which has the Garden of the Phoenix, a Japanese Garden. In 1893, on Jackson Park's Wooded Island, the Japanese Government built the Ho-o-den [Phoenix Temple] as its pavilion for the World's Columbian Exposition. The Ho-o-den introduces Japan's artistic heritage to Americans and remained as a gift to Chicago after the fair ended.
Old Irving Brewing Co.
The location of our first date, where we enjoyed the gold medal-winning Beezer, a citra and mosaic doubledry-hopped hazy IPA.
Gino's East
If you’re looking for the OG Gino’s East experience, our famous flagship location is just steps off the bustling Mag Mile. A short walk from some of the best hotels in Chicago, including the Hilton, Four Seasons, Langham, and many more, we are the perfect location to try Chicago Style Deep Dish Pizza. This location boasts three floors full of graffiti tagged walls, a Comedy Bar with weekly shows and a stunning third floor terrace.
Palermo's 95th Italian Cuisine
Tavern style pizza at its best on Chicago's South Side (two locations, 63rd Street and 95th Street).
Pizzeria Uno
The originators of Chicago-style deep dish pizza way back in 1943. When people talk about Chicago-style pizza, they're usually referring to this institution or one of the several others that followed with a similar style (Giordano's, Lou Malnati's). Chicago is also the home of tavern-style pizza, which is a thin, crispy circular pie cut into squares.
Paulie Gee's Logan Square
Our favorite pizza place in Chicago, and where we hosted Tom's surprise 40th birthday party. This pizza shop originated in Greenpoint, Brooklyn, NY and expanded to this Logan Square location. Its specialty, in addition to Neopolitan-style pies, is a Detroit-style pizza (which can also be ordered Gluten and/or Dairy Free).
Gene & Jude's
An ode to Tom's parents who owned a hot dog stand on the South Side of Chicago. One summer day in 1945 Gene set out to join his friends at a baseball game at Wrigley Field. Little did he know that was the day of creation. While at the game, the group ordered some hot dogs and drinks. Looking down at the food in his hands, he felt something was missing. By the time he got home the experiment had begun.
Luke's Italian Beef
Typical Chicago hot dog joint down the street from the Sears Tower. Make sure you get your Italian Beef dipped, with mozzarella, green peppers, and red sauce.
Portillo's Hot Dogs
Portillo's started as a hot dog stand in suburban Chicago in 1963 and has since expanded to more than 60 locations across the US, recently going public. You can get quintessential Chicago fare here, including a Chicago-style hot dog, Italian Beef, and the meaty goodness of an Italian Beef & Sausage Combo. One of Tom's favorite orders is the double cheeseburger with cheese fries. They're also known for a delicious chocolate cake with chocolate frosting and a "Cake Shake" incorporating the cake into a milkshake.
Time Out Market Chicago
Chicago’s innovative eating-and-drinking destination features the city’s top chefs, most-talked-about restaurants and buzziest bars—plus the latest in arts and culture—all together under one roof.
The Second City
The Second City is an improvisational comedy enterprise and is the first ongoing improvisational theater troupe to be continually based in Chicago, with training programs and live theatres in Toronto and Los Angeles.
The Green Mill
Swinging sounds are on tap nightly, from big-name artists to local late-night jam sessions. A former haunt of Al Capone.
Andy's Jazz Club & Restaurant
Our first live music outing post-pandemic shutdown. Includes dinner and live jazz music in an intimate setting
Kingston Mines
Founded in 1968, Kingston Mines is the largest and oldest continuously operating blues club in Chicago. Its two stages have been graced by the likes of Magic Slim, Koko Taylor, Sugar Blue, Billy Branch, Junior Wells, Mike Wheeler, Joanna Connor, and scores of other musical greats.
Guaranteed Rate Field (if you must)
Check out the Southside favorites (if you must since the Cubs are out of town), the Chicago White Sox, as they host the Detroit Tigers on our wedding weekend (Wrigley Field offers tours of the ballpark when the Cubs are out of town).