Fall in Love All Over Again in the Windy City

You won't have to break the bank—the Windy City offers its share of affordable, yet dreamy destinations. Inexpensive Chicago romantic getaways can be as simple as an afternoon stroll through a garden, or as thrilling as a night on the town with music and dancing.

Enjoy Panoramic Views at Promontory Point

Tucked away in Burnham Park, the man-made peninsula of Promontory Point jets out into Lake Michigan offering panoramic views of the Chicago skyline. Take a romantic and leisurely walk along the Point’s open, green spaces and limestone beaches to soak up the sights of the calm waters. Then, snuggle by the fire pits to warm yourself after the sun sets.

Experience the Dazzle of This City Landmark

The Clarence F. Buckingham Memorial Fountain remains one of Chicago’s most iconic images. Nestled inside Grant Park, this lavish 1927 ornamental fountain stages a music and light show from April through October, with water shooting up to 150 feet and dancing across the sweeping skyline.

Offering More than Just a Bouquet

The Garfield Park Conservatory is a charming spot for an inexpensive romantic getaway—and it's open free to the public. The massive eight-room glass house covers two acres and showcases thousands of plants, including ferns, aroids and succulents. A 12-acre outdoor garden is open during the summer and includes an area inspired by Claude Monet’s beloved garden in Giverny, France.

Picnic in the Park

Located in the bustling Loop, Millennium Park is a green space tucked into an urban setting. Pack a picnic and enjoy a free concert offered by the Millennium Park Summer Music Series in the elegant Jay Pritzker Pavilion. You can also roam through the park’s five-acre Lurie Garden, crossing footbridges and walking along colorful flowerbeds with the skyline peeking out from behind.

Go Back in Time at a Nostalgic Theater

The romance of classic Hollywood is alive and well at the Music Box Theater, an ornate, yet cozy 1929 movie theater. When the “stars” on the 800-seat theater’s ceiling begin twinkling, you might think you’re in the great outdoors. Cuddle together as you watch one of the theater’s trademark old Hollywood or foreign films. Discounted matinee prices help keep things affordable. Reserve time to sneak away to the theater's sleek cinema-themed bar featuring leather couches, exposed brick walls, outdoor garden seating and affordable cocktails.

Kick Back with Cocktails

Step back in time with a visit to the Green Mill Cocktail Lounge, an old school jazz club in the heart of Uptown. The club offers a romantic 1930s retro look, complete with cocktail tables and mural-covered walls. The club charges inexpensive covers, particularly after midnight when you can dance into the wee hours of the morning.

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