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.
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!
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
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.
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
Aire Chicago Rooftop 
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.
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 at Cafe Brauer 
Skyline Views
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!
Up Room Lounge at the Robey Hotel
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
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.
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.
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!
I’m so happy you enjoyed it! So many fun spots to check out!
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