Those who have lived in Chicago will agree that it’s quietly becoming one of the most romantic cities in the world. From endless dining options to picture-perfect attractions, the Windy City is a treasure trove of unique date ideas. So if you’re looking for a memorable place to take your date, here are the 10 most picturesque spots for an evening out — or day date — in the beautiful city of Chicago.
During these uncertain times, please keep safety in mind and consider adding destinations to your bucket list to visit at a later date.
1. Lakefront Trail
It's hard to imagine Chicago without the gorgeous Lake Michigan just a stone's throw away. If the weather's nice, head to Lakefront Trail and explore this meandering path for unbeatable views of the Chi-town skyline. The trek is 18 miles long, which means you and that special someone could talk for hours.
2. Promontory Point
Promontory Point is a must-visit spot for any two lovebirds in the Chicago area. This man-made peninsula can be reached via Lakefront Trail and boasts views that will make you feel like the city belongs to you. Address: 5491 S Shore Dr, Chicago, IL 60615.
3. Buckingham Fountain
Forget the Trevi Fountain, because Chicago's Buckingham Fountain is every bit as picturesque (and much easier to get to). Constructed in 1927, this landmark is sculpted out of pink marble and decorative seahorses. And at night, you can expect music and a light show for the perfect after-dinner activity. Address: 301 S Columbus Dr, Chicago, IL 60605.
4. Garfield Park Conservatory
Looking for the perfect rainy-day date idea? Head to Garfield Park Conservatory for a unique display of flora, architecture, and history. This site was built in the early 1900s and remains the largest of its kind in the world. There are no less than 120,000 plants inside, in addition to breathtaking exhibits and other picture-worthy settings. Address: 300 N Central Park Ave, Chicago, IL 60624.
5. Alfred Caldwell Lily Pool
Tucked away inside Lincoln Park, this gorgeous natural area is open from April to November. It's no mystery why this spot is often used as a venue for small weddings. You'll feel like you've stepped inside a Monet painting as you stroll around the lily ponds. Address: 125 W Fullerton Pkwy, Chicago, IL 60614.
6. Le Colonial Chicago
After a full day of exploring Chicago, what could be better than a romantic dinner out? With its French-Vientamese fusion menu, Le Colonial is a go-to spot for food lovers. The view from the upstairs patio is incredible and allows for prime people-watching. Address: 937 N Rush St, Chicago, IL 60611.
7. The Adler Planetarium
You probably knew the Adler Planetarium was the first of its kind in the whole country, but did you know this museum is also one of the most romantic spots in the city? It's here that you and your date can learn about the galaxy while sipping on a drink at the monthly Adler After Hours series. Address: 1300 S Lake Shore Dr, Chicago, IL 60605.
8. Homeslice Wheelhouse
To a true Chicagoan, nothing is more picturesque than a fantastic slice of pizza. That's exactly what you'll find at Homeslice, which features a gorgeous outdoor patio with bistro lights. For a late-night snack and a creative drink menu, this is your spot. Address: 938 W Webster Ave
Chicago IL 60605.
9. Crabtree Nature Center
Want to escape the hustle and bustle of the city for a bit? Taking a stroll along this gorgeous trail in the Forest Preserve District, you'll feel transported to another world. For a short and sweet introduction to this natural wonderland, you can take the 2-mile loop known as Phantom Prairie. You and your date will love checking out the interpretive signs along the way. Address: 3 Stover Rd, Barrington, IL 60010.
10. Lincoln Park Conservatory
Lincoln Park Conservatory has a breathtaking array of plants and flowers from all over the world. Perhaps even more impressive is the glass and iron structure that houses the conservatory. Day or night, this spot could turn just about anyone into a romantic. Address: 2391 N Stockton Dr, Chicago, IL 60614.
11. The waterfront at sunset
This may be an obvious choice, but the magic of the waterfront never fails to amaze...especially at sunset. So whether you're taking a stroll along Navy Pier or enjoying a more remote location, you'll fall in love with Chicago all over again...and maybe your date, too!
Have you ventured to any of these incredible date locations in Chi-town? Be sure to share your experiences with us!