The Chicago Skyline is truly remarkable, and it is arguably at its best at night when the buildings light up. Because of this, grabbing food and drinks at night at a place that offers a stunning view is a magical experience. Here's a shortlist of places I have gone to with amazing views downtown.
Personally, this is my favorite rooftop in Downtown Chicago. You're in between tons of buildings but your view is not obstructed. This place is perfect for drinks during the day, or for a fun night out in town. We got to enjoy a sunny afternoon here and drank some delicious drinks while soaking in the incredible views of the riverwalk and surrounding buildings. Keep in mind that because of their views, it's a very popular rooftop. You'll want to make a reservation well in advance especially if you want to come at night.
This restaurant offers a similar experience to LondonHouse but from a view much lower. It is located next to the Chicago River a few stories above the streets. During the winter they use globe-like structures so you can still enjoy the views with a fun atmosphere. This place is also very popular and if you want to be outside it's best to make a reservation.
At Cindy's, you'll expect views overlooking Lake Michigan and showcasing Millennium Park (AKA "The Bean". This place is a little more sophisticated and can be pricier, but you have a ton of options for cuisine and drinks. Mostly drinks. It's the perfect place for brunch and drinks with friends, a dinner with colleagues, or you can rent the space for a fun bridal party. The options are endless!