Best Rooftop Views of Chicago for Free

Why stand in those long lines of the observation decks to get a view of Chicago?  This city offers some good rooftop options which are FREE to enter. In this post, I am going to share my five favorite rooftop bars in Chicago with exceptional panoramic views of downtown.

The second most difficult debate between me and my husband, after iOS and Android, is which city has the best skyline in the US – New York City or Chicago? It always ends with both agreeing to disagree since I am forever in love with the beauty of Chicago. Although much smaller in the area compared to NYC’s  Manhattan skyline, it is the architectural beauty of Chicago that makes it so attractive to me. Most all buildings here will tell a story about their appearance. TIP: Highly recommend the architectural boat tour of Chicago to learn these stories. 

This post, however, is all about viewing the phenomenal Chicago skyline from hundreds of feet above. And why not view this concrete jungle from one of the high rises itself? There has been a renaissance of rooftop culture in Chicago since 2015 giving a new meaning to many old heritage buildings. Of course, you can pay and go to the observation decks of some well-known skyscrapers such as Willis Tower (previously Sears Tower) or the John Hancock Tower. But why pay when you can get the same or better view for FREE and that too on top of some significant historic structures in Chicago!

Since some of these are also ranked as top rooftop bars in Chicago, you might just want to get yourself a drink and relax while enjoying the view. I personally make sure to visit a few of these every time I am in the city πŸ™‚

London House

Recently open to the public, London House is located at the corner of Wacker Drive and Michigan Street. The Chicago River bending in front of it gives an interesting perspective to the skyline. There are two lounge areas in London House, one is indoor and the other where you want to be is outdoors a floor above the main level. The outdoor rooftop offers a panoramic view of the city, and wait, it even has a cupola for a higher vantage point.

One of the best rooftop bars in Chicago with the perfect view of Chicago river and the high rises.

As the Chicago river bends, London House rooftop terrace provides a gorgeous look into Chicago skyscrapers in downtown.

The cupola in London House gives a higher vantage point with downtown views on the other side of the river. You can see Wrigley building and NBC tower from top of the cupola.

From the cupola in London House, you get to see the other side of downtown at N. Michigan Street

Cindy’s Rooftop

A contrasting view from other rooftops on this list, Cindy’s Rooftop opens into a vast green space of Grant Park blending into the blues of Lake Michigan. Located on top of Chicago Athletic Association Hotel, Cindy’s restaurant can be a great place for brunch as well. My favorite part of Cindy’s is to see the Bean or Cloud Gate in Millenium Park looking the size of a real bean from an aerial perspective. On the southern side of the terrace, you have the view of other Chicago landmarks such as Art Institute, Buckingham Fountain, Shedd Aquarium and, Adler Planetarium. 

Cindy's rooftop provides a unique view of Chicago downtown. An aerial view of the Bean (aka Cloud Gate) and Jay Pritzker Pavilion

From this rooftop terrace, you are guaranteed a view of Millenium Park you have never seen before. An aerial view of the Bean (aka Cloud Gate) and Jay Pritzker Pavilion

One of the best rooftop bars in Chicago - Cindy's Rooftop, offer a unique view of downtown.

On the southern side, you will see other important Chicago landmarks such as Buckingham Fountain, Lake Michigan, Field Museum and Shedd Aquarium.

Raised Rooftop

My recent find, Raised Rooftop is located on top of Renaissance hotel on Wacker Drive and State Street. Although this rooftop terrace is only on the 3rd floor, the angle at which it opens gives a different view of downtown. I was pleasantly surprised by the spacious outdoor space in Raised and the best part, in my opinion, was the fire pit for winters. According to one of the bartenders, their outdoor space is open all year long!

Looking for a best rooftops to hangout in Chicago with friends? Here it is, Raised bar with gorgeous Chicago skyline views. You can see Trump Tower, Wrigley building from this angle.

Perhaps one of the only rooftops open in winters in Chicago

Raised rooftop bar in Chicago is only at 3rd floor but has beautiful panoramic views of Chicago skyline

The raised rooftop bar has a cozy outdoor sitting area with fire pits to keep you warm in the winter.

Signature Lounge

This one needs to be mentioned here for its legacy. Signature Lounge is one of the oldest lounges in a high rise with 360-degree views. It has been one of my favorite hangouts since my college days almost 10 years ago. The lounge located on the 96th floor of John Hancock Tower, just a floor below the observatory, is an enclosed rooftop bar with glass walls. Since the lounge doesn’t take reservations, you might have to wait to get seated depending on what time of the week you go. TIP: Ladies, you must check out the Women’s restroom here, I haven’t seen a loo with better views. Sorry boys, unfortunately, you don’t have the same glass walls that ladies room does.

Get the best Chicago skyline views from Signature Lounge

View of Chicago downtown skyline from top of John Hancock tower

Sunset in Chicago downtown from Signature Lounge

Get the best Chicago skyline views from Signature Lounge

Restoration Hardware

RH store located in Gold Coast area of Chicago is definitely not a rooftop bar but I don’t want to end my list without a mention of this unique home furnishing retail store. Another Chicago old heritage building restored by this Californian company. RH furniture store is a combination of a restaurant, coffee & pastry shop and a wine bar where you are free to roam anywhere on their five floors with your drink. Yes it’s on my list because of its amazing rooftop but don’t you forget to check out all the other floors as well. I will have to return back here to try out their 3 Arts Club Cafe next time.

Get the best out of furniture store, rooftop and a coffee shop at Restoration Hardware

Restoration Hardware is an old building revamped to a chic furniture store with a cozy rooftop

A hidden gem in Chicago, Restoration Hardware is a must checkout for it's amazing rooftop views

You can take your drinks on any floor in Restoration Hardware including its beautiful outdoor rooftop terrace.

Rooftops Bucket List 

As always, I have my bucket list too. Below are the Chicago rooftops that I want to visit hopefully in better weather. Since you will see a trend of me trying to visit rooftops in Nov to find them closed for the season, I ended up dining there. It also could have been the cold that deterred me from going elsewhere in search of food. Once I visit the below rooftops, I will update this post with new views and reviews. Meanwhile, if you guys go here before me then don’t forget to leave your reviews in the comments section of this post.

  • Noyane –  Gotta go here.
  • Green River – I must mention that I dined in Green River early in Nov but the rooftop was closed for a private party.
  • Joy District – Also dined in Joy District since I heard a lot about their rooftop but it was closed for the season.
  • Aire – I tried visiting Aire as well in early Nov but even that was closed for the season.
  • The J. Parker – Gotta go here.

Looking for free aerial views of downtown Chicago? Here is a list of the top rooftop bars in Chicago with exceptional views

Why pay for rooftop views when you can get them for free? Here are the best rooftops you can view Chicago skyline from.

Hover over the photo to pin it on Pinterest for future reference.

If you do visit any of the above rooftops I mentioned then please leave me a comment on how you liked it! And don’t forget to pin this post and share it with your family and friends πŸ™‚

Happy Traveling!


28 comments on “Best Rooftop Views of Chicago for Free

      • It’s has been a recent thing in Chicago. For the past couple of years, so many open rooftop bars have come up in old heritage buildings. Trust me I have a bucket list in there for a reason πŸ™‚

  1. I’m actually heading to Chicago next January. I absolutely love cityscape views, so this is like heaven to me. The best part, they’re free! Thanks for the fantastic suggestions! Will definitely be building some of these into my itinerary!

    • I am so glad this was of help! I hope you get to check out some rooftops in Jan… in case they don’t shut them coz of snow. Doesn’t harm to ask the bartender to let you out for a quick look/photo πŸ˜‰

    • Thanks Jordan!! I lived in Chicago for many years and I have friends from Michigan who live in the city too πŸ™‚ The rooftop scene in Chicago is bringing its A game on.

  2. I had the pleasure of working in downtown Chicago for 3 months. I lived right on Michigan, and I consider Chicago to have the most iconic cityscape view from the Navy Pier. Your rooftop list is long, and certainly offers opportunities to view this beautiful city in various ways.

    • Chicago has so many cool spots to view the skyline, Navy Pier as you mentioned and The Museum campus too is one of my favs. But rooftops have started becoming a thing here in the last 2-3 years .. so these are pretty unique views that weren’t accessible earlier. πŸ™‚

  3. Wow, you took me down the memory lane. It was more than a decade back that I had seen skylines of both New York and Chicago. I would say between the two I would choose New York but then Chicago is no less. I remember going on top of a building that belonged to a retail chain for the views. Navy pier is another place I loved in Chicago along with its museum.

    • I am pretty sure you are talking about the view from top Sears tower Anu. And about 8 years ago its name changed to Willis tower since that retail chain moved it’s headqtrs in the burbs. You can still go on top to the observation deck, they even have a glass ledge now! check it out online. I am so glad to hear you got to see both the skylines, they are one of the best skylines in the US (maybe the world?) πŸ˜‰ lol

    • You have to see it to believe it Angela! You can even drink throughout the store and all the floors while lounging on the furniture that is on display. True Story!

  4. Chicago has been on my list for quite some time – I’m happy that you gave a breakdown of all the great places to see the cityscape! I’ve been to NYC and the views were spectacular…so now I can actually compare once I make it to Chicago! lol

    • I am so glad I could help. Tbh, I can’t wait to go back to Chicago to check out the remaining rooftops in my list I might be biased since I called Chicago home for many years but Chicago is definitely prettier than NYC although not as big.

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