Known as the “Windy City,” romance sweeps through Chicago with every breeze. This lakeside city bristles with opportunities for perfect moments with your better half. You can share a cuddle with stunning views from Promontory Point, then catch dinner and an epic show at the Chicago Theatre. The next day, enjoy a pleasant stroll and sneak a kiss at the mini oasis of the Alfred Caldwell Lily Pool before spiriting yourselves off to the Adler Planetarium for incredible vistas of the Chicago skyline.

Come evening, go some hearty laughs at The Second City, Chicago’s hottest improv club, where comedy legends like Bill Murray, Amy Poehler, and Steve Carell have gotten their start. You might just catch a show starring the next comedy mega-star! If you prefer your entertainment a bit more high-brow, you can get tickets to see the Chicago Symphony Orchestra for a world-class performance that will leave you flush with emotion from the musicians’ raw talent.

But for a once-in-a-lifetime experience, and some of the most incredible views of any city in the world, head to the top of 360 Chicago — previously known as The John Hancock Building — for dinner and cocktails at sunset. The panoramic views of the Chicago skyline and Lake Michigan will make your jaws drop.

There’s even plenty for active couples here, whether you rent some bikes for a self-guided city tour or go kayaking on the Chicago River. Whatever your preference and style, honeymoons in Chicago will leave you breathless!