Chicago Is My Kind Of Town To Explore This Summer

Chicago Skyline. Photo Jill Weinlein

Listening to the catchy lyrics of 'Chicago' by Frank Sinatra and Nelson Riddle, 'My kind of town, Chicago is my kind of people too, People who smile at you,' might entice you to visit the most populous city in the Midwest. Also known as 'Second City', there are plenty of immersive attractions for visitors to see within a three-day visit in 2024.

Guest Room at Sable Hotel. Photo Jill Weinlein


Late Spring through September is the best time to visit Chicago. Fly into Chicago O'Hare International Airport and rent a car or take a cab or Uber for a 45 minute drive to the epicenter of downtown Chicago.

The new Sable Hotel at the end of Navy Pier offers exciting Lake Michigan and city skyline views. It's the ideal spot to stay, eat, and play while visiting the city. Take in the views up at the rooftop at Offshore Rooftop, a multi-seasonal dining space with a world class kitchen and full-service bar. Offshore Rooftop restaurant, bar and space celebrates the title of 'World's Largest Rooftop' by Guinness World Records. 

To ensure a good night's sleep, guest rooms and suites feature serene design decor, and items from the Hilton Serenity Collection. The comfortable Serenity Bed includes an exclusive Suite Dreams mattress and box springs, Super Topper mattress pad, 250 thread count, down-filled comforter, and Touch of Down pillows. 

Navy Pier. Photo Jill Weinlein

Start your morning at Lirica Restaurant off the lobby for a breakfast buffet or a la carte meal. If the weather is nice, walk outside along the waterfront towards the iconic Chicago high-rise skyline. The historic Navy Pier is also called 'The People's Pier', a popular waterfront venue celebrating over 100 years. It's one of the most visited destinations in the Midwest.

One of the best introductions to Chicago is the new FlyOver Chicago at Navy Pier. Modeled after the FlyOver attractions in Las Vegas, Vancouver and Reykjavik, FlyOver in Chicago is a signature flight ride showcasing the people and places that makes what Sinatra sings  'Chicago is my kind of town.' 

FlyOver Chicago. Photo by Jill Weinlein


FlyOver Chicago is an immersive 9-minute movie and ride that captures the spirit of the city from an entirely new perspective on a 65-foot spherical screen. Ticket holders glide on a state-of-the-art moving platform with six different degrees of motion. With feet dangling, special effects include wind, water sprinkles and location-specific scents to heighten the guests' experience.

As in the lyrics of Sinatra's song 'My kind of razzmatazz and all that jazz', acclaimed composer Elliott Wheeler showcases the city's eclectic musical history that enhances the visuals of FlyOver Chicago.

Learn about the stories of the resilient people who built this city, and how they continue to make it one of the best cities in the world. Part of this emotional journey is the music by Dr. Walt Whitman Jr.'s Soul Children of Chicago Choir. Their vocal talents singing 'Believe Chicago' will touch your soul.

Trumpeter Corey Wilkes' performance at the top of the 36-floor Tribune Tower sets the tone, along with jazz 'razzmatazz', hip-hop and a dynamic house soundtrack. The music connects viewers to the pulsating heartbeat and humanity of the city.

Let FlyOver be your guide to see in person the sights and sounds featured throughout the attraction.

'The Bean'. Photo by Jill Weinlein


See how the Chicago River turns green in honor of St. Patrick's Day festivities, and soar above and in between some of the most famous architecture in the United States. The city's public art featured in FlyOver includes Cloud Gate, known in Chicago as 'The Bean'. This monumental silver bean-looking artwork anchors downtown Millennium Park. Reflections of the city's famous skyline and surrounding park can be viewed on this mammoth sculpture, as the drone flies down and through its center.

Within walking and biking distance from the Navy Pier, Millennium Park is one of the most popular waterfront parks in the heart of Chicago. See 'The Bean' in person and stroll through some colorful gardens. This park is the epicenter to summer cultural programs, interactive fountains and a winter skating rink.

Chicago River. Photo Jill Weinlein


The best way to see other attractions featured in FlyOver Chicago is by purchasing a CityPASS. Save up to 48% off the regular admission price for entrance into the Shedd Aquarium or Skydeck Chicago, plus three more famous attractions of your choice.

One of the best ways to see the sights in person that you saw during Flyover Chicago is taking a Shoreline Sightseeing Architecture River Tour. It's one of the most popular CityPASS attractions.

Cruise along the river to witness the skyscraper's birthplace and learn about American Architecture's evolution. Your guide will share stories about ambitious architects who designed 40+ landmarks to withstand the weather elements. Learn about the history of the Tribune Tower, the Wrigley Building, the Willis (Sears) Tower and innovative Marina City towers. 

Discover how architect and designer Jeanne Gang’s wavy Aqua Tower became the tallest building in the world. Designed by a female architect, no floor is alike, and the wavy shape was designed to offset the wind.

The CityPASS allows one-time admission to five different attractions for one price.

Dan Raskin Owner of Manny's Deli. Photo Jill Weinlein


Another iconic place featured in FlyOver Chicago is local favorite Manny's Cafeteria & Deli. Owner Dan Raskin is the fourth generation owner of this beloved family-owned establishment. Since 1942, this authentic Jewish deli and cafeteria has been famous for its pastrami, brisket, matzo ball soup, tuna salads and other comfort foods.

President Barack Obama, Guy Fieri's 'Diners, Drive-Ins and Dives' and Jerry Seinfeld's 'Comedians In Cars Getting Coffee' have all dined at this beloved 'My Kind of Town' restaurant. 

Wrigley Field. Photo Jill Weinlein


As in the lyrics, 'Chicago is The Wrigley Building', Chicago is also Wrigley Field, home to the Chicago Cubs. Featured in FlyOver Chicago, this iconic baseball stadium and field opened in 1914 by chewing gum magnate William Wrigley Jr. Known as the second oldest ballpark in the U.S., with Boston Fenway Park the oldest, the scoreboard was installed in 1937, and continues to be manually operated for every home game.

While in Chicago, one should see a Chicago Cubs game during baseball season. Since the stadium is located in a lively residential area, there are plenty of dining venues for drinks and a meal before or after a game. Directly across from the entrance is Swift & Sons Tavern, a popular eating and drinking spot for burgers, beer pints, oysters, pretzel bites, salads and steak frites.

Since the stadium is located right in the middle of a neighborhood, Cubs fans sit on their rooftop or look out their windows to view baseball games and concerts for free.

Wrigley Field Archives. Photo by Jill Weinlein


While at a Cubs game, walk towards the dugout to view vintage jerseys, bats, awards, baseballs, trophies and other Cubs memorabilia at 'Into the Cubs Archives'.

Notable items include 1984 All-Star Ryan Sandberg baseball cards, and a Kerry Wood  'K' signed bat from the historic 20-strikeout game in 1998.

Wrigley Dugout. Photo Jill Weinlein

Along the memorabilia walk is a large glass window looking into the Chicago Cubs dugout. Located near the third base, fans can peek inside the dugout to watch the action and see their favorite players.

As with the last lines of Sinatra's 'Chicago' song, 'Each time I leave, Chicago is tuggin' my sleeve, Chicago is The Wrigley Building, Chicago is The Union Stockyard, Chicago is one town that won't let you down, it's my kind of town.'

Jill Weinlein

Los Angeles based Jill Weinlein covers travel, food and lifestyle destinations for multiple newspapers, magazines and websites. Her areas of expertise include, luxury travel, culinary reviews, cruising and family travel destinations. Born in Los Angeles, Jill studied Communications and Theatre Arts at UCLA. She has a a Dine and Travel blog - and she writes a weekly restaur...(Read More)

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