Chicago is the perfect spot for a romantic weekend getaway. You and your sweetheart can enjoy a scenic bike ride along the lake, bucket-list fine dining at our acclaimed restaurants, cocktails bars with sweeping city views, and so much more. Check out this itinerary for an unforgettable romantic weekend in Chicago.
Friday
Head downtown to Chicago’s iconic The Magnificent Mile, where you’ll find historic sites and tons of shopping. Don’t miss the nearby Gold Coast area, home to luxury boutiques and classic charm.
Have lunch at The Purple Pig, where you can share award-winning small plates right on Michigan Avenue.
If it’s getting dark, grab a spot on the scenic Chicago Riverwalk and watch the night light up with Art on theMART, a massive digital art display that projects stunning, original videos onto the river-facing facade of theMART. While you’re there, grab a pre-dinner drink at City Winery or Tiny Tapp right on the river.
Head to the trendy West Loop, where you’ll find some of the city’s hottest restaurants. The elegant El Che Steakhouse & Bar is the perfect date night spot. The Argentinian-inspired space features traditional platters of rustic flame-finished grilled beef. Or check out Girl & the Goat, the flagship spot of celebrity chef Stephanie Izard, serving innovative small plates on bustling Restaurant Row.
After dinner, walk to BomboBar, a popular walk-up window serving over-the-top desserts all year long.
Saturday
Wake up early and rent a Divvy Bike from the city’s bike share program to pedal down the Lakefront Trail, a paved path that borders Lake Michigan on one side and the soaring skyline on the other. Take leisurely stops to walk on the beach, explore a park, or check out the many museums and attractions all along the trail.
Park your bikes at Maggie Daley Park, where you’ll find more outdoor fun at the all-seasons Skating Ribbon. Hold hands at you ice skate along the icy path in the winter, or challenge for your date to a scooter race in the summer. Afterward, take a quick walk to Millennium Park and snap a picture together in front of Cloud Gate, aka “The Bean”, the ultimate Chicago photo opp.
Just across Michigan Avenue, you’ll find the Chicago Athletic Association. This hip hotel, located in a historic building, is home to several hot spots that are popular with visitors and locals alike. Take the elevators up to Cindy’s, the rooftop bar and restaurant. Order a cocktail and enjoy the sweeping views of Millennium Park and Lake Michigan.
Spend the afternoon with some of the world’s most famous masterpieces at the Art Institute of Chicago, one of the country’s oldest and largest art museums. Don’t miss the extensive Impressionism collection and the striking Modern Wing.
Have dinner at Blue Door Kitchen & Garden, a seasonally focused spot with a vintage vibe and a gorgeous hidden-garden patio. Or head to Geja’s Cafe, a Chicago spot known for romance. Enjoy Swiss gruyere fondue and sizzling meats for dinner, following by chocolate for dessert.
Keep your date night going at Kingston Mines, a legendary blues club that features live music every night of the week. You can see everyone from emerging talent to celebrated musicians hit the stage, and the dance floor keeps going till the early morning hours.
Sunday
Enjoy a mid-day dim sum brunch at MingHin Cuisine in Chinatown. Take your pick from steaming bamboo trays of shrimp dumplings, honey-glazed short ribs, fried spring rolls, pork buns, and more — all perfect for sharing.
Walk off brunch with a stroll through bustling Chinatown. Pop into souvenir shops, gaze at the ornate Chinese architecture adorning the streets, and find some solitude at scenic Ping Tom Memorial Park. Rent a two-person kayak and set off on the Chicago River, where you’ll be rewarded with stunning views of the city skyline.
For an unforgettable date night experience, schedule a private helicopter tour with FlyHeli Tours. These breathtaking tours include unbelievable views of the lake, skyline, and the city’s most iconic landmarks. Schedule a private tour at sunset for a romantic atmosphere.
For dinner, check out the sultry Mama Delia, where you’ll find Spanish tapas downstairs and a secret burlesque bar upstairs.
For a night cap, head to The Violet Hour. The entrance to this acclaimed cocktail spot is hidden behind an ever-changing mural, but the line forming out front usually gives it away. Inside, you’ll find modern speakeasy vibes and next-level mixology — the perfect spot to end your romantic Chicago getaway.
