Discovering all that the Windy City has to offer will take a number of trips, a funnel of endless dollar bills, and an empty stomach ready to embark on devouring more eats and drinks. There is so much to do, so much to see, and more to experience than what meets the eye. I say, take the time to see the tourist attractions, walk the Magnificent Mile strip, then hightail your butt to the number of rooftops waiting for your special date night.
With a first date that ended after 8 hours, covered 3 locations, and started a relationship in which we now plan every vacation visit around rooftops, this my friends, is our specialty. Let’s get to the best rooftop date night ideas we love in Chicago.
1. LondonHouse Chicago
I remember the days of long lines just to enter this place. This was the second location on the infamous 8 hour first date night. We were full enough from our Mexican meal, but we kept the drinks coming. This place has an irreplaceable view of the Chicago River with a row of buildings on each side. It is the place we saw an NBA player (I don’t remember his name) and we peered into the distance into the night. It was perfect.
2. Streeterville Social
This place is great for a mature evening out. Nested in the best of Streeterville, you see a different angle of Chicago with a view of the NBC tower. It’s a chill vibe, lots of seating, and a grassy area for games on the appropriate evening. If you are looking for a spot for a private event, this is it.
3. IO Godfrey
True memories and magic happened here. Having eaten and drunk our way into lots of smiles, this is where Logan nervously said his first, “I love you.” We shared an unforgettable moment on a beautiful Saturday afternoon with delectable salmon and great champagne. IO Godfrey is the trendy place to enjoy an evening with great music, quality, well-dressed people, Chicago views as the backdrop, and more memories to be made.
4. Cerise Virgin Rooftop
This was a rooftop visit that was cool, but not our absolute fave. Although a decent ambiance, the views are not necessarily stellar. From what I hear though, the nightlife party there is lit, and rightfully so considering the well-known DJs known to spin there.
5. J Parker
I cannot even count how many times we have frequented this place. A go-to location for friends and family visitors in town, J Parker is a gift made to impress. The food is great. The cocktails are phenomenal and the music will keep you on your feet. There aren’t many seats, but who needs seats when you are dancing. Just know, my mom was feeling it here and talks about it still to this day. The views of Lincoln Park and Lake Michigan are unforgettable. To see the span of greenery with the lake behind gives you the serenity to ask for 1 more cocktail!
Looking for another date night idea in Chicago – check this out!
6. Soho House Chicago Rooftop
This is a must-add because of the exclusivity. As a members-only club, if you ever have a chance to be a guest at this place, don’t miss out. The rooftop experience is one to remember. With a pool, poolside service, and food and cocktails to match the mood of options and access, it is worth finding a friend that is a member; just to say, “I’ve been there.”
7. Raised
I fell in love with this destination on the 3rd floor of the Renaissance Hotel. I think I may have been surprised by the view considering its location and level, but it surprisingly did not disappoint. With its circular architecture and bar placed in the center of the rooftop, even while sitting at the bar, your view is pleasing to the eye. Give it a try and report back with some Instagrammable moments to match.
8. The Up Room
Talk about sophistication. The Robey Hotel is in Wicker Park placed on the historic “six corners” intersection. The rooftop is a boutique-like experience on the 13th floor with a pool on one side, and views on both. I love the perspective provided as you look across the city of Chicago from the Northside. The views are vastly different, and you seem to have a greater understanding of the scale of the city while sipping on specialty cocktails. Slide on into the indoor portion and enjoy the refined environment.
9. Whiskey Business
Catch a vibe here. Whiskey Business is in the Wicker Park neighborhood too. When you need a good activity, combined with good tasting bar food and drinks – hit up Whiskey Business. The team here is so creative in making this rooftop all-season friendly. They offer movie nights, tiki-themed events, individual pools to soak in, bocce ball, igloos, curling and so much more! I highly recommend hopping on in and trying a number of whiskeys, or even a tequila (my favorite) beverage. They have a decent selection of both.
10. Roof on The Wit
As one of the first rooftop bars to garner local and national attention, Roof on The Wit set the trend. Having been newly renovated within the past few years, Roof on The Wit is a great place when you want a rooftop experience, without having to be outdoors. Known to have some of the best fashion events, Roof on The Wit is worth making time for.
11. Cindy’s Rooftop
I always tell everyone to go here! We discovered this prized destination years ago after heading out of the Art Institute of Chicago. I looked up and noticed plenty of people standing close to the edge, and told Logan, “We should go see what it is.” Our nosey selves ended up experiencing one of the best rooftop experiences in the city. The view encapsulates the essence of what you need to have a true Chicago experience. From skyscrapers to Millennium Park, Lake Michigan, and even some of the Southside of Chicago; what you get to see is truly unmatched. We absolutely love enjoying the hip, stylish atmosphere while sipping on an array of select craft cocktails. You will adore the view, the seasonal fare, and the service. Get to it!
Added Bonus Restaurant: Mercadito Chicago River North – When my honey bunches of oats, AKA my husband, Logan, took me out on our first date, he asked me what my favorite food was. A sista told him Mexican, and he ended up taking me to my now favorite Mexican restaurant in Chicago. The food was incredibly tasty, so much so, I ate my food so fast, I wanted to cross over to his plate to cop some of what he had. I prevented myself though, but only that one night. It was just our second date! All I remember were the lobster tacos, the hunger I barely quenched because I starved myself waiting for the yummy food, the refreshing watermelon margaritas, and an ambiance that is hip, quaint, but active enough for a first date impression. Cheers!
If you are needing more ideas, experiences, or suggestions of where to go in any city, connect with the Couples Experience CE Circle for all the goods.
