top of page

Unwind in The Windy City

Unwind in The Windy City by Jenny Cox Holman, Jenny Cox Holman writer

Chicago with its vibrant architecture, trendy restaurants and celebrated events is a captivating city for a fascinating vacation. The picturesque sights and cultural delights of The Windy City creates the perfect place for a romantic getaway or festive family vacation. Explore one of the United States' iconic cities with stops at tourist hotspots, admire artistic traditions at celebrated museums and indulge in savory meals topped off with delectable desserts. We've found the perfect places for selfie-loving sightseers, foodies and art-lovers to ensure an unforgettable vacation in Chicago!

Millennium Park

Millennium Park offers an impressive landscape with inspiring architecture and enjoyable recreation and events where locals and tourists can congregate to enjoy the outdoors. "The Bean," with its massive, reflective presence, showcases the Chicago skyline and is the perfect photo op. In the winter, McCormick Tribune Ice Rink is a great spot to skate under twinkling lights in an unforgettable winter wonderland. The Crown Fountain is a fun, summer spot to cool off or to toss in a penny for a special wish. Events and festivals are also held at Millennium Park from group exercise classes to great concerts.

Skydeck Chicago

Step outside the tallest building in the Western Hemisphere at the Willis Tower on The Ledge, a glass balcony extending four feet outside the 103rd floor! At 1,353 feet in the air, the Ledge’s glass boxes extend out 4.3 feet from the Skydeck offering spectacular views spanning up to four states.

360 Chicago

With its unique location and breathtaking 360° views, the 94th floor observatory originally known as the John Hancock Observatory (JHO) when it first opened in 1969, has enthralled tens of thousands of visitors each year. 360 Chicago offers visitors unique, downward facing views over The Magnificent Mile ® and Chicago's famous skyline from 1,030 feet up.

Bobby's Bike Hike

Bobby's Bike Hike creates one-of-a-kind Chicago bike tours with personable, knowledgeable and fun guides to venture through a trendy and timeless city. Founded in 2002 and consistently ranked as #1 sightseeing tour in Chicago by TripAdvisor, Bobby's Bike Hike provides an insider’s view of the culture, history, architecture, and little known facts that define this phenomenal city. Whether you’re craving a local favorite such as a Chicago-style hot dog washed down with a handcrafted beer or want to explore the city’s unique culinary and ethnic innovations, they have a Chicago food tour that’s perfect for you. Get ready to discover the famous dishes you’ve heard all about as well as delicious hidden gems in off-the-beaten-path neighborhoods.

Maggie Daley Park

Maggie Daley Park's Skating Ribbon is the perfect spot to don a pair of ice skates and enjoy a festive winter activity! During the warmer months visitors can wear roller blades and ride scooters on the Skating Ribbon at Maggie Daley Park.

Stony Island Arts Bank

Stony Island Arts Bank is a book lover's dream with walls filled with a vast collection of books. The Stony Island Arts Bank reopened in 2015 as a hybrid gallery, media archive, library and community center with Chicago's South Side history.

The Art Institute of Chicago

Chicago is an art lover's delight with museums filled with treasured works of art. Make plans to visit The Art Institute of Chicago with works of art of the highest quality, representing the world's diverse artistic traditions.

Museum of Contemporary Art Chicago

One of the nation’s largest facilities devoted to the art of our time, the Museum of Contemporary Art Chicago offers exhibitions of the most thought-provoking art created since 1945. MCA Chicago documents contemporary visual culture through painting, sculpture, photography, video and film, and performance. Located in the heart of downtown Chicago, the MCA boasts a gift store, bookstore, restaurant, 300-seat theater, and a terraced sculpture garden with a great view of Lake Michigan.

Chicago Music Exchange

For more than 25 years, Chicago Music Exchange has been the place where people from all over the world go to buy the finest vintage guitars and amps in the world. Chicago Music Exchange specializes in vintage electric, acoustic and bass, as well as quality new gear from top names like Fender, Gibson, Gretsch, Martin, Taylor, Rickenbacker, Marshall, Orange and Vox to hot boutique lines like Victoria, Divided by 13, Fulltone, Zvex and many more. Everybody loves their famous Gibson Les Paul wall but the Hollowbody is awesome as well. Their Gibson Custom ES-335's will make you feel and sound like a rock star!

Oak Street

Located in the heart of Chicago's Gold Coast, Oak Street is Chicago's most prestigious shopping street with a mix of international couture houses, American luxury brands, and local boutiques. If visiting Chicago in July, Ferraris on Oak is an invitational car show featuring more than 70 rare, vintage and prize-winning specimens of the legendary Italian automobile owned and driven by members of the Ferrari Club of America. During the event, Oak Street, Chicago's luxury shopping destination, closes to regular traffic and rolls out a block-long red carpet to host a unique audience of car collectors and visitors alike!

Chicago Cubs & Chicago Bulls

For avid sports fans, watching the Chicago Cubs or Chicago Bulls play is dream come true. The unforgettable energy and atmosphere of watching their favorite team play is a must-do for visitors to The Windy City.

Pizzeria UNO

A visit to Chicago wouldn't be complete without having a famous deep dish pizza. Pizzeria UNO is the original birthplace of deep dish pizza. Back in 1943, Ike Sewell started the famous pie that is devoured by many loyal patrons located in Chicago and beyond.

I|O Godfrey

From its 4th floor perch, I|O Godfrey is the epicenter of the River North Neighborhood basking in the sunlight throughout the day. As late afternoon yields to evening, uninterrupted views of downtown Chicago radiate to life setting a brilliant backdrop for after-work cocktails. Among the panoramic skyline views, fire pits and shimmering water elements, nighttime revelers feel as if they’ve stumbled upon a glamorous, urban oasis.

RPM Italian

Located in Chicago’s River North neighborhood, RPM Italian is modern in approach and Italian in spirit and features a contemporary, chef-driven menu with dishes meant to be shared. The sister restaurant to RPM Steak, RPM Italian marks the first collaboration between partners RJ, Jerrod and Molly Melman, celebrity couple Bill & Giuliana Rancic and acclaimed chef Doug Psaltis.

Menu highlights include more than a dozen fresh pastas made in-house daily, slow-roasted meats, wild fish and seafood, and celebrated Italian classics with an elevated twist.

The Allis at SoHo House

A relaxed and welcoming social space for meetings, group dining and date nights, The Allis is a restaurant and cocktail bar with an expansive art collection and views of Green Street from floor-to-ceiling windows. The Allis is named after the family that commissioned the building in 1907. It offers all-day dining, serving egg dishes and house-made pastries for breakfast, sandwiches and salads for lunch, and light bites and wood-oven entrees for dinner. Afternoon tea is served daily, along with coffee, wine and craft cocktails.


BomboBar serves up delicious hot cocoa concoctions, coffee, and exquisite Italian pastries, gelato to go. Amongst the delectable dessert options is Executive Chef Fabio Viviani's famous Bomboloni, also known as homeless Italian doughnuts infused with various filling flavors. BomboBar hosts a comfortable outdoor lounge atmosphere during summer months where guests can relax and work remotely while enjoying a morning coffee or tea. In colder temperatures, a cozy heated and enclosed awning equipped with bar seating allows for patrons to warm-up with hot chocolate and an always-fresh, from-scratch bomboloni.


{Blog by: Jenny Cox Holman}

Would you like more great ideas for planning your next vacation? Check out our Lifestyle|Travel section for more exciting ideas!

bottom of page