22 Chicago Hotels with Insane Views — The Most Perfect View (2022)

This is the city where sensual and daring music was born: think about the blues, bring a little soul into your mind, let the jazz swing around your fingers and toes, and you won’t be able to escape all the passion.

This place is an ode to enchantment and grace. The City Beautification Movement (1890-the 1900s) started here, a reform philosophy of North American architecture and urban planning that promoted beauty and monumental grandeur. This movement is the reason for all the lovely pathways, ravishing boulevards, and enchanting gardens that attract every person at first sight.

This is the town to be dazzled, either from the breathtaking views’ splendor or from the eternal snow glare under myriads of Christmas stars.Sensuality, beauty, enchantment, grace, and dazzlement.What could better describe romance...? The word is Chicago, and at The Most Perfect View, we’re determined to make you fall in love with it from the moment you sense the first warm breeze coming from Lake Michigan or at the glimpse of candid winter flakes falling slowly on your beloved’s face.

Introducing you to Chicago

Chicago is located in the Midwestern United States, northeastern Illinois. The city has an eternal and strong liaison with water; in fact, the constant presence of water is definitely an attribute that plays an important role in the city’s appeal.

Chicago lies beside the enormous Lake Michigan. Two rivers flow through town, entirely or partially: the Chicago River, which runs across downtown; and the Calumet River, meandering the industrial far South Side. Also, the city of Chicago nests the saddle point of a very important water gap called the Chicago Portage, the Mississippi and Great Lakes’ connection.

Chicago’s climate is humid Continental, with very well-defined seasons: summers are warm to hot and often humid. In July temperatures may reach an average of 24.3oC but can as well exceed 32oC for a maximum of 21days. On the other hand, winters are cold and snowy with very few sunny days: the normal January high is just below freezing. Spring and autumn are lovely mild seasons gifted with low humidity as a pleasant year’s break. The best time to visit Chicago? It all depends on the kind of stay. You may, for instance, choose winter for a romantic getaway. Yes, it will be cold, but the glimmer of Christmas lights and the city beautifully wrapped in snow will surely invite for intimate dinners and suspended silences in front of one of the marvelous views. On the other hand, if you wish to surprise your beloved one with a longer stay, enjoy Chicago between May and September: it will be passionately alive.

Chicago's Attractions

Chicago’s architecture is absolutely amazing. In fact, the city is considered a rare jewel: Frank Lloyd Wright, Ludwig Mies van der Rohe, Frank Gehry, Zaha Hadid or Anish Kapoor are just a few examples of architects who left their marks in the city. More so, Chicago gave its name to the ‘Chicago School’ and homed the ‘Prairie School’, two influential movements on the field. You will not know the city unless you aim high. There is much to be discovered but don’t worry, we’re here to provide some valuable shortcuts: the first thing you need to know is that Chicago can be divided into four major sections: The Loop (central business district), the North, the South, and West Sides. You can start your romantic journey at Millennium Park: the greatest concentration of 21st-century monuments lies in and around the park. Look for the awesome Frank Gehry’s Jay Pritzker Pavillion (if you’re visiting Chicago in summer do not miss the free opera concerts and dance performances), Anish Kapoor’s reflective-steel Cloud Gate, Jaume Piensa’s monumental 15-meter fountains, or the newest pavilions (one of them was designed by the brilliant Zaha Hadid).

If both of you love architecture, time travel a little more and follow the path up to The Loop and River North. You will meet The Willis (formerly Sears Tower), once the tallest building in the world (after its completion, in 1973, it surpassed The World Trade Center). You may climb up and enjoy the stunning views but we must warn you that waiting in line can be quite annoying... Here’s a nice hint: make better use of time and have a drink at Signature Room’s bar, located on John Hancock Building’s 95th floor. The views are equally astounding and the whole atmosphere is much more intimate and romantic. On your way, try not to miss The Rookery (its beautiful two-story, skylit lobby was redesigned by Frank Lloyd Wright in 1902), the Trump International Hotel & Tower (now the second tallest in the USA),and The Wrigley Building (did you know its tower was modeled on the 16th-century Giralda Cathedral in Seville?). Finally, end up your day by Lake Michigan or take some wonderful shots at Buckingham Fountain. Your sweetheart will love it.

Inner Passionate Chicago

Chicago does not leave anybody indifferent: it can be extremely cold or irresistibly warm, luminous, or introverted. And it may look classical but as well be recklessly extravagant. At The Most Perfect View, we want you to know all the shades of this spectacular place. We have just introduced you to the visible, most well-known side of Chicago. Keep on following us: we’ll take you to some of its better-kept secrets.
Do not limit your visit to downtown, this is a city of rich, vibrant neighborhoods that demand to be explored, hand in hand. The South Side will marvel you with the ethnic communities of Pilsen, Little Italy, and Chinatown. On the North Side, there is charming Andersonville as well as trendy Lincoln Square, the ever-popular triumvirate of Lincoln Park, Wicker Park,and Bucktown, or the hip environs of Logan Square.
Now, pay attention because we have saved the best for last: go even further, outside the city limits, and visit Frank Lloyd Wright Home and Studio, the Chicago Botanic Garden,and Mies Van Der Rohe’s iconic, minimalist Farnsworth House.
The Art Institute of Chicago is another unmissable sight. You will find a fantastic collection of work from the Impressionism movement. Save some of your time to the entire room dedicated to Monet, or sit in silence as you contemplate Seurat’s ‘A Sunday Afternoon on the Island of La Grande Jatte' and Chagall’s America Windows.Can you think of anything more poetic?

Romantic Things to do in Chicago

Chicago reveals its love for water in many ways. At this precise moment, you already know about the breathtaking views you can indulge in from the tallest buildings. Enjoy some of the other well-kept secrets: board the L Train and ride the orange line downtown, towards Midway. It will bring the most surprising view of the city’s buildings. Alternatively, take one of the guided tours run by the Chicago Architecture Foundation.

The river cruise, in particular, offers a wonderful perspective on many of the major landmarks.What about Ohio Beach? Chicago is adorned by 26 lakefront great beaches; we’re particularly fond of Ohio Beach: superb city vistas while swimming in Lake Michigan... how does that sound?

Chicago is also an irresistible place for shopping.Michigan Avenue, also known as The Magnificent Mile dwells high designer shops like Gucci and Louis Vuitton and department stores like Nordstrom or Neiman Marcus. Nevertheless, these are possibly the brands you can as well find at home. Take your dear one to Wicker Park and Bucktown: they are notable areas for independent clothing and jewelry boutiques as well as antique furniture shops. Andersonville is the perfect place for all book lovers whilst Boystown will amaze anyone who is keen on retro styles. We haven’t forgotten the most romantic part of the day: dining, of course. Here’s The Most Perfect View’s list of the top romantic restaurants in Chicago. Number one was mentioned before: the Signature Room at John Hancock Buiding's 95th floor (sighing by just thinking of those jaw-dropping vistas). Number two is Geja’s Cafe, a cozy restaurant where couples’ intimacy is fully respected. Angelina’s Ristorante is our number three. Placed at Lakeview this charming Italian restaurant has a simple romantic feel.Cafe Absinthe, the unique French- American bistro, is in itself a romantic experience you will want to live again.Since we're all about great Chicago views, we couldn't leave out the following Chicago restaurants with a perfect view. Take note:Cite (Lake Point Tower), Riva (Navy Pier), Everest (Chicago Stock Exchange), Sixteen (Trump International Hotel & Tower Chicago), and NoMi Kitchen (Park Hyatt Chicago).

Chicago, Love, and Music

My kind of town, Chicago is | My kind of town, Chicago is | My kind of razzmatazz | And it has all that jazz

This is how Frank Sinatra immortalized our beloved city. And, yes, Chicago has got all the groove, all the soul, all the rhythm and blues, and, for sure, all that jazz. Some of the best American musicians and performers were born or chose to live here: Nat King Cole, Sam Cooke, Muddy Waters, Dinah Washington, Bo Didley, Patti Smith... just to mention a few. The way we see it, it’s impossible to understand Chicago unless you experience music. Save a night for the Green Mill Cocktail Lounge, one of Chicago's iconic bars. And before leaving home (please, please) watch ‘High Fidelity’, a Stephen Frears movie starring John Cusack. It’s all about Chicago, music... and love.
You’d probably ask now what is the most romantic hotel in town... carefully go through our suggestions above; they were all chosen to offer the most UnforgettableChicago stay you can have... Unforgettable as Nat King Cole’s velvety voice would sing.

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