Let’s face the truth: Chicago is the best city in the world but not in winter. The temperature is about 4ºF (-16ºC) and believe me, you don’t want to be outside. However, during snowy days, chances of taking the best skyline pictures increase. So get ready, take your camera and discover some of Chicago’s best sites for photography lovers (winter version)!
1. The Art Institute
Location: 111 South Michigan Ave.
Best Views: Aon Center, Pritzker Pavilion, Millenium Park
Admission: Free to Illinois residents every Thursday from 5:00 to 8:00 p.m. General admission $23, students $17
Description: The Modern Wing is the new home for the museum’s collection of 20th and 21st-century art but also a window to Chicago’s most spectacular skyline view: from Millenium Park. On the other hand, if you feel like it, the Terzo Piano restaurant has amazing views too, but that depends on your budget.
2. The Shedd Aquarium
Location: 1200 S Lake Shore Dr
Best Views: Sears Tower, Lake Point Tower, Aon Center
Admission: General admission $89, children $79
Description: This is one of my favourite spots on earth and although I prefer the views from the outside, the inside ones are good too. On the other hand, the Adler Planetarium views are pretty spectacular too, but it’s further away and remember it’s winter and it’s freezing outside.
3. Hancock Tower
Location: 875 N Michigan Ave.
Best Views: Sears Tower, Lake Point Tower, Aon Center
Admission: Free access to lounge bar, observatory $18
Description: It is the 4th tallest tower in Chicago but it’s the best in my opinion. The observatory’s admission is $18 so you rather go to the signature lounge on the 96th floor, which is free, and spend that money on a drink. Snow storms up here are spectacular, so the worse the weather the better the panorama. Also, if you are lucky enough to be a woman, please check the restroom (and bring your camera here).
4. Whole Foods Market
Location: 1101 S Canal St. #107
Best Views: Sears Tower (south view)
Description: Have you seen these views? Aren’t they amazing? I saw this picture on Instagram and thanks to it I discovered this (not so hidden) spot. No more Dominick’s or Jewel, this is exactly where you need to go on Sundays when you’re running out of milk.
5. Lake Point Tower Restaurant
Location: 505 N Lake Shore Dr.
Best Views: Sears Tower, Trump Tower, Hancock Tower
Description: Did you know Lake Point Tower is the only skyscraper with the privilege to be right next to Lake Michigan? The landowners of the time made some really clever movements to skip the city’s prohibition to build on the Lakefront. Besides the architectural interest of this tower, it has the best views of Hancock Tower as you can see above. This place is not exactly cheap but drinks are affordable and sunsets here are very impressive.
6. Sears Tower Skydeck
Location: 233 South Wacker Drive
Best Views: Chicago 360º
Admission: General admission $18.
Description: You can go up to the top and be amazed by the 360º views of Chicago, Lake Michigan and the Illinois plain, on a clear day you can see up to 50 miles and 4 states! However, you’ll wonder why the glass balconies are faced towards the worst views ever. The reason is because that is the only side of the tower in which elevators go up to the top. In my opinion the Sky Deck is better than The Ledge for this reason.
7. Vertigo Sky Lounge
Location: 2 W Erie St.
Best Views: Trump Tower, Marina Towers
Description: Located on the 26th floor of the Dana Hotel, it’s the only year-round, indoor/outdoor lounge in Chicago which is good if you get a sunny winter day. Views are amazing during day time, at night (unless you take pictures from the outside which is fine) you’ll get horrible glass reflections.
8. The Wit Rooftop
Location: 201 N State St.
Best Views: Marina Towers
Description: This rooftop is absolutely amazing during summer, but also in winter. Sometimes people can be really loud here, especially if there is a party (usually every Sunday) going on but if you come here during weekdays your afternoon can become the best time of your day. The highlight, obviously, is having Marina Towers so close!
9. Trump Tower
Location: 401 North Wabash Ave.
Best Views: Wrigley Building, Hancock Tower
Description: Did you know it was being designed to be the tallest building in the world before 9/11 terrorist attacks which changed the original plans? Anyways is the 2nd tallest tower in Chicago. Its location (downtown by the river) makes this spot an easy place to visit. In my opinion the restaurant is average and quite expensive so I would go for the Lounge instead. I absolutely love how the Wrigley building looks from here!
10. IIT Tower
Location: 10 West 35th Street (Illinois Institute of Technology)
Best Views: Chicago Skyline, Sears Tower
Description: The best for the end, always. Given that you will either arrive by this place or this other one, IIT Tower is just great no matter from which point of view you look at it. So this 20 story tower is the Illinois Institute of Technology less visited part of the campus which makes it the best place to sneak in. Well, not everyone is allowed here but people who love photography aren’t exactly known for their compliance right?
Check these and other amazing buildings of Chicago on the map below or download my Free Architecture Guide of Chicago.