Romance is always in the air in Chicago and if you want to take that special someone on a date, there are endless possibilities of things to do.
If the weather's cooperating, nothing beats a scenic stroll hand-in-hand, either through the gorgeous Chicago Botanic Garden or along the city's beautiful lakefront path, with the skyline behind you. Afterward, grab a glass of bubbly and listen to live music at Pops for Champagne, or cozy up in a booth and eat chocolate fondue in one of the cozy, curtain-covered booths at Gejas Cafe.
There is no shortage of entertainment options in Chicago, ranging from live music to comedy clubs and live theater performances. The Green Mill Cocktail Lounge features live jazz almost every night while improv actors keep fans laughing all the way home after a performance at The Second City. Or soar above the city day or night on the new Navy Pier Centennial Wheel.
Seeing Chicago's architectural beauty from the decks of a river cruiser is a must for both locals and visitors. One of the city's most unique tours, the CAF River Cruise takes visitors along the north and south shores of the lake. Guests will learn about more than 50 buildings and their significance to Chicago's architectural landscape as well as general history about Chicago and how it grew from a small back-country outpost to one of the world's most important crossroads of today. Tours are available late April through mid-November and run about an hour and a half in length. Be sure to purchase tickets in advance as they often sell out.
Walk, job, bike, roller blade ... no matter how you travel along this 18.5-mile lakefront path, it's going to be beautiful. It's also going to be congested, especially in the downtown area on summer weekends. But it's worth it. With the Chicago skyline on one side and Lake Michigan on the other, you'll pass by some of Chicago's most famous landmarks, including Buckingham Fountain, Navy Pier, Soldier Field, Lincoln Park Zoo and the Adler Planetarium. Nature lovers will enjoy the gardens and park south of the city, near Northerly Island, and dog lovers will want to stop by the "doggie beach" near Irving Park Road.
A live harpist often performs during the elegant afternoon tea in this historic Chicago hotel - a tradition here for nearly a century. Held in the gorgeous Palm Court room, with a fountain in the center and an enormous chandelier, you feel like royalty here. Choose from a large menu of special tea blends. Everything's served on fine china. And there's a three-tiered dish of chef-made scones, gourmet sandwiches and other dainty desserts. Special teas can be arranged for bridal parties and showers. So can a presentation by a tea sommelier that explains the history of the tea, and the hotel. Pricey, but lovely.
Get lost meandering through any of the Chicago Botanic Garden's 27 gardens and four natural areas that sit within nearly 400 acres of land and around nine islands. Located in a suburb about 25 miles north of Chicago, the gardens are well worth the drive. Visitors will be treated to recreated prairies, Japanese gardens, an English walled garden and giant topiaries. And don't leave without seeing the famous bonsai collection! Afterward, grab lunch or take an ice cream break at the Garden View Café and when the weather cooperates, you can enjoy the tastes of summer on the café decks. Self-guided tours featuring each season as well as nine secret spaces can be downloaded from the website in advance.
Geja's Café has topped Chicago's "Most Romantic Restaurant" lists for years. The fondue dining experience lets you cook your food at the table. Live classical and flamenco guitar add to the ambiance. Diners first walk down a few steps to enter the low-lit dining room of the restaurant filled with small booths and tables with curtains draped throughout to give an even more intimate feel. Premiere Fondue Dinners are a four-course meal with includes its cheese fondue appetizer, Geja's salad, assorted fresh vegetables, eight classic dipping sauces, flaming chocolate dessert fondue and Geja's freshly brewed coffee. You'll leave absolutely stuffed, but in a good way.
The couple that laughs together, stays together. So take your special someone to see the world's premier comedy troupe, The Second City. The improv comedy club has launched some of the biggest names in the business, including John Belushi, Dan Aykroyd, Mike Myers, Steve Carell, Stephen Colbert, Tina Fey and about 500 others. The close seating and small audience provides an intimate vibe. And there are bits that cover all facets of societal satire. After the show, they take ideas from the audience and turn them into an improv sketch - which is no easy task, yet something hilarious to watch.
Trendy folks and jazz aficionados regularly flock to this cool music joint, open till 4 a.m. each night and 5 a.m. on Saturdays. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the place has tons of character. The curvy bar still looks like a speakeasy, setting the scene appropriately for a set by local singers Patricia Barber or Kurt Elling. There's plenty of room for dancing to the fantastic live music. Swing music is offered at least once a week, and Sunday features the long-running, popular Uptown Poetry Slam. Regardless of what night you decide to go, the joint will be jumping. Expect to pay a cover charge from $4-$15, depending on the band.
So many rom-com movies have ice rink scenes where couples fall in love. Perhaps your love story can take place here at Millennium Park's McCormick Tribune Ice Rink. The downtown rink has a gorgeous backdrop of skyscrapers, which looks particularly beautiful at night. And you also skate past an iconic Chicago art piece, the mirrored sculpture known as "The Bean." Admission to the rink is free but skate rental is $12. Rent a locker for $1. Afterward, go for hot chocolate at the adjacent Park Grill. Don't know how to skate? Free skating lessons are held on Fridays, Saturdays and Sundays, an hour before the rink opens (which is usually between 10 a.m. and noon). If it's too crowded, head a bit south and skate along the ribbon-shaped path at Maggie Daley Park.
Opened in May 2016, the Navy Pier Centennial Wheel is a great place for a romantic ride. Located on Navy Pier, the entertainment venue that juts out into the lake, you'll get fantastic views of Chicago's skyline and lakefront. The wheel is 200 feet tall - 50 feet taller than the ferris wheel it replaced. Step into one of the 42 enclosed, temperature-controlled gondolas (or, spend a few more bucks for a VIP gondola with plush seating and glass bottoms) and enjoy the view both day and night. There are also nightly LED light shows from the wheel's spokes and rim.
For a romantic and memorable night in Chicago, take a helicopter tour of the city with Chicago Helicopter Experience, also known as CHE. The hour-long experience, of which about 20 minutes is up in the air, can be done day or night. The flight takes you along the Lake Michigan shoreline and past many of the city's iconic sites, with the pilot sharing some interesting facts about the city. The ride is most romantic on a clear night, when the Chicago skyline sparkles with light. On Wednesday and Saturday nights in summer, you can fly past the Navy Pier fireworks display. While it's a pricey date - prices start around $148 per person - keep an eye out for Groupons. They're regularly offered, and will save you a few bucks.