Chicago is known -- dare we say envied -- for its spectacular skyline and awe-inspiring architecture. Take a stroll along the Magnificent Mile, and you'll know exactly what we're talking about, but don't just look at it from the ground up. Jet up to these great heights to see the city from high above.

Skydeck Chicago in the iconic Willis Tower (formerly the Sears Tower) offers a chance for the truly brave to test their love of heights. Step out onto The Ledge: a collection of glass boxes that extend over 4 feet out from the side of the building, giving you the opportunity to stare over 1,300 feet straight down. Don't forget to breathe once you're out there.

The 875 N Michigan Observatory (formerly the John Hancock Observatory), along the Magnificent Mile, can show you Lake Michigan like no other place in the city. Its 360 degree views also give you the chance to see four states: Illinois, Indiana, Michigan, and Wisconsin. Or take a stroll along the open-air sky walk -- even in the winter!

During the holidays, your little ones can meet Santa and explore the Observatory's Winter Wonderland. And throughout the winter, you can check out these incredible views while gliding along an ice rink that happens to be the highest of its kind in the world.

Having a Chicago date night? Or are you just looking to combine fine dining with spectacular views? Then make reservations at Signature Room at the 95th in 875 N Michigan (formerly the John Hancock Center). They serve lunch and brunch as well, but regardless of when you go, the experience of eating from 95 floors up is one you won't soon forget.

Of course, nobody does it like Donald Trump, and that is definitely true at the Trump International Hotel and TowersSixteen, the hotel's signature restaurant, won accolades in the 2011 Michelin Guide, and its 30-foot windows provide breathtaking views of the Chicago River, Lake Michigan, and the surrounding skyscrapers. In the summer, be sure to have a drink on The Terrace at Trump, which offers the same great view, plus fresh air. Trust us, you won't want to leave.


Related Listings

360 CHICAGO (formerly John Hancock Observatory)
875 N. Michigan Ave.
Chicago, IL 60611
(888) 875-8439

Trump International Hotel & Tower Chicago
401 N. Wabash Ave.
Chicago, IL 60611
(312) 588-8000

Skydeck Chicago
233 S. Wacker Dr.
Chicago, IL 60606
(312) 875-9696

Featured Partners