9. Signature Room at the 95th

If Millennium Park doesn’t do it for you, how about a five-star dinner at the swanky Signature Room at the 95th? The Signature Room is a restaurant located on the one of the top floors of the John Hancock Observatory. The main courses range from $28 to $90, but the view alone is worth the price.

8. Navy Pier Ferris Wheel

If you want something a little easier on the budget, the 150 foot-high Ferris Wheel at Navy Pier is definitely a romantic spot at night to overlook the lake and the city with your sweetheart.

7. The Buckingham Fountain

The Buckingham Fountain in Grant Park is a must-see. During the evening, the Fountain has a light show every 20 minutes with the dancing water display. This romantic spot is a great place to just walk around and take great pictures with your sweetheart.