Rooftop Dining Options in Chicago

Rooftop Dining Options in Chicago

    I recently enjoyed a weeklong stay in the windy city, Chicago. With my daughter living in this fun city it doesn’t take much to tempt me to visit. There is so much to see, do, and eat in Chicago. I try to pack as much as possible into my visits. Take a look at my Vlog I made on this trip to see some of the many things I enjoyed.


    With the weather finally feeling a little more like spring we took advantage of the al fresco dining options and tried out 5 rooftop bars.

    Photo Image: Vertigo Facebook Photo Gallery


    Vertigo, 16th floor of Dana Hotel


    This is just a short stroll from my daughter’s apartment in the River North area of downtown. We stopped for a drink on our way out to dinner one evening. As it was early evening, the atmosphere was quite subdued.  But I gather things are quite different later in the evening when there is a DJ. Thre is also a fire pit to keep you warm in the winter and an ice bar for the warmer summer months.


    The outside seating area is quite small.  While it does have a view, it’s not the most inspiring Chicago skyline I have ever seen. A rather gruff bouncer checked our ID upon entering the hotel.  But once up in the bar, the super friendly bar staff made it worth the visit.


    There is a dress code later in the day but during our visit at around 6.30pm there were quite a few guests in gym clothes. This added to the casual atmosphere during daylight hours.


    The Fact Sheet


    Address: Inside the Dana Hotel, 2 West Erie Street

    Phone: 312 202 6060

    Hours: Mon-Fri: 4pm-2am, Sat: 2pm-3am, Sun 2pm-2am Patio closes at 12am on weekends and 11pm on weekdays



    Cindy’s – 13th floor of the Chicago Athletic Association Hotel


    While I cannot say that I’m a fan of the overpriced limited food offering, the view gets a 10 out of 10 so it is well worth a visit – although do as many of my fellow diners did and just enjoy a cocktail on the outside terrace. The picnic tables in the greenhouse-like glass-roofed inside section of the restaurant can be reserved. All other tables are first come first served. The picnic table benches did not have backs,  so don’t expect to be too comfortable. There were a couple of sofa settings, but a group had grabbed them for the entire duration of our stay.


    Outside is the real gem of this location though with fantastic views and a fire pit. Thankfully enough flow of people ensured that you can get a turn at a good photo at the front of the section.


    The food selections are designed to be shared. Some of the dishes are offered in half sizes if you prefer to dine alone (or just not a fan of sharing your food). I thought $60 for a piece of salmon was on the steep side. But $13 for a glass of champagne is par for the course in downtown Chicago. I would visit again, but not to eat, just to enjoy a drink on the terrace.


    The Fact Sheet


    Address: 12 S Michigan Avenue

    Phone: 844 312 2221

    Hours: Mon-Fri: 3pm-2am, Sat: 3pm-3am, Sun: 3pm-midnight










    The Terrace at Trump – Trump Hotel


    Quite a huge terrace, seating for 200 evidently – but then again Trump does everything big 🙂  Most seating is on a first come first served basis. You can reserve the ‘premium tables’ for $100 (which does not include any food or drink evidently). The Terrace offers comfy seating in a contemporary setting with mesmerizing fire pits that are lit once it begins to get dark (or if you need a little additional heat). Prices are on the high side, but the view is unbeatable. We had a very friendly server and were happy to get some amazing photos of downtown Chicago. I would recommend a visit.

    The Fact Sheet


    Address: 401 North Wabash Avenue

    Phone: 312.588.8000

    Hours: Not listed on website so call for info


    But I had a couple of fails due to inclement weather


    Photo Image: Ivy Website

    Ivy Sky Terrace – 16th floor The Ivy Hotel


    During my recent visit I stayed two nights at the Ivy Boutique Hotel located just off Michigan Avenue. I was looking forward to trying out the hotels rooftop bar. But sadly due to the weather, the opening had been postponed. Maybe next time as the photos looked so nice.


    The Fact Sheet


    Address: 233 E Ontario Street

    Phone: 312 335 5444

    Hours: Mon-Fri: 4pm-10pm, Fri-Sat: 2pm-Midnight, Sun: 2pm-10pm




    Photo Image: Peninsular Hotel Website


    Shanghai Terrace at the Peninsular Hotel


    This hotel is just a short stroll from my daughters apartment so I pass it many times whenever I visit. The doormen are always so friendly and actually one gave me a flower on Mothers Day when I walked past. I was very happy to see that there is an outside dining area to enjoy the great views of Chicago. As the weather had been somewhat wet on this recent visit I called to check if the terrace was open. I was told yes, not once, but twice when the gentleman put me on hold to check. Imagine my disappointment when I turned up and it was closed! Another time perhaps…

    The Fact Sheet


    Address: 108 East Superior Street

    Phone: +1 312 573 6695

    Hours: Call as it seems to vary!

    Do you have a favorite rooftop terrace in Chicago? Please share your ideas as I will be returning to Chicago again soon and would love to add to my wish list.

    Happy Dining


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