City Life, Lifestyle, Play, Things to Do in Chicago
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Chicago’s Skyline: Best Places for Viewing

I’m sure you’ve seen numerous pictures of the Chicago Skyline in your social media feeds.  Many may think that these pictures are mostly from tourists but a large portion of them are from locals too.  As a local it’s something that I never tire of.  The skyline is beautiful and each time it comes into sight there’s a certain energy and excitement that infuses me and it hasn’t dulled over time. 

Woman capturing a picture of the Chicago Skyline from the top of the John Hancock Building
Chicago Skyline View from 360 Chicago

Chicago’s skyline is ranked as one of the worlds tallest and most magnificent.  It’s one of the reasons that over 57 million tourists flocked to Chicago in 2018, setting a record!  It should be ogled again and again!

View of John Hancock Building

With and abundance of rooftop bars and patios where should you settle in to take in the Chicago Skyline and other views?  Here’s a list of my favorite spots in the Chicago.

Chicago Riverwalk

Woman sitting at Chicago Riverwalk reading a book
Chicago Riverwalk

The Chicago Riverwalk spans 1.25 miles so there are many great spots to soak in the city whether it’s taking a stroll or relaxing at one of the many bars or eateries along the river.  There’s no shortage of activity with live music, Art on the Mart, and boaters and kayaks passing by.  The Riverwalk is open daily from 6 a.m. until 11 p.m.

Table setting with wine and cocktails at the Chicago Riverwalk
City Winery at Chicago Riverwalk

Cindy’s Rooftop Restaurant

Sitting on the top floor of the Chicago Athletic Association Hotel, Cindy’s Rooftop restaurant and terrace has one of the most enviable views of Chicago with Lake Michigan as a backdrop against Millennium Park.  The panoramic views from the terrace are unmatched.  While one may come for the scenery, you’ll stay for the creative cocktails and food.  Beverage Curator David Morr knows his stuff!  Pro Tip:  make a reservation, this is one of the hottest spots in Chicago!

Aire Chicago

Nestled in the center of The Loop amid skyscrapers, Aire Rooftop Bar on top of the Hyatt Centric gives a magnificent perspective of Chicago’s architecture.  The rooftop bar also curate’s monthly art series featuring local artists for you to enjoy while chilling with cocktails and friends. 

Offshore at Navy Pier

At 36,000 square feet, Offshore, holds the Guinness World Record for the largest rooftop deck in the world!  The all-seasons/all-weather spot at Navy Pier delivers extraordinary sights of Lake Michigan and the Chicago Skyline.  There’s plenty of space for visitors to take in different angles of the beautiful city. You’ll want to linger for awhile.

Interior of Navy Pier Rooftop Bar Offshore
Offshore Rooftop Bar and Restaurant at Navy Pier

Museum Campus

Lakefront Trail with Chicago Skyline as backdrop
Lakefront Trail at Museum Campus

Museum Campus, home to three of the city’s most notable museums, is southeast of downtown. The Lakefront Trail winding through Museum Campus has numerous spots for gazing.  I love hitting the Campus early in the morning to reflect and appreciate the scenery. 

Patio at Cafe Brauer

The Patio sits just south of the main zoo grounds at Café Brauer, a historic Prairie School-style landmark. Overlooking the pond at Nature Boardwalk at Lincoln Park Zoo, the Patio at Café Brauer offers an exceptional observation of Chicago’s skyline and it’s dog-friendly.

London House Hotel

I was blown away the first time I enjoyed the sweeping views of Chicago from the top of London House Hotel. This spot allows you to observe activities on the Chicago River, bustling Michigan Avenue, and Lake Michigan. The night scenes are amazing too!

Night view of Chicago Skyline
Night view of Chicago from London House hotel rooftop

Up Room Lounge at the Robey Hotel

Rooftop lounge overlooking the city of Chicago
Up Room Lounge

Located in Chicago’s Wicker Park neighborhood, the Robey Hotel is the tallest building for miles. The Up Room lounge and terrace on 13th floor delivers an incredibly sexy view of the cityscape. It’s the perfect spot for date night or maybe even an evening with the girls!

360 Chicago

Positioned on the 94th floor of the iconic John Hancock building, 1,000 feet above Michigan Avenue; the observation deck offers stunning 360-degree views of the city’s famous Skyline and scenic Lake Michigan to guests the moment they step off the elevator.  On a clear day, individuals can see as many as four states and as far as 55 miles. In addition, guests can also learn facts about Chicago neighborhoods and architecture through 18 stations of interactive touchscreens and info kiosks. Or take a TILT over the edge of the building, 1,000 feet above The Magnificent Mile

North Avenue Beach

Lake Michigan with Chicago Skyline as backdrop
Chicago Skyline

The popular North Avenue Beach is one of my favorite spots for relaxation and people watching.  There’s an abundance of fun activities to engage in with the beautiful skyline as a backdrop.

Lake Michigan and sandy beach
North Avenue Beach

VU Rooftop Bar

This 13,000 square foot rooftop oasis next to McCormick place in Chicago’s South Loop is a welcome addition in an area where rooftop bars are lacking. With Chef driven fare, fancy cocktails, and TV’s on the outdoor deck, what more could you ask for?

I can’t get enough of the views of this beautiful city, it’s truly a work of art! Where’s your favorite place to soak it in? Let me know in the comments.


  1. What an AWESOME and fun post! We are headed to Chicago in 2 weeks and I absolutely loved reading this post and seeing your great photos!

    • Flo says

      I’m so happy you enjoyed it! So many fun spots to check out!

  2. Pingback: Guided Chicago Bike Tours: A Thrilling Way to Explore the City : Flo's Favorites

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