Romantic Weekend Getaway in Chicago

Fall in love, once again in Chicago

Let's fall in love all over again and spark some romance in the Windy City. Chicago offers the perfect blend of urban charm and intimate escapes for a dreamy weekend getaway for couples. Whether you're strolling hand-in-hand along the picturesque Riverwalk, indulging in a candlelit dinner with skyline views, or cozying up in a luxurious suite, Chicago has all the ingredients to prepare your romantic meal or say your romantic getaway. From scenic spots to cultural experiences, this vibrant city is ready to make your romantic weekend unforgettable, let’s explore together some of the top places for your Chicago getaway.

Stunning architecture, vibrant culture, and cozy hideaways, yes! You can get all that in Chicago for a memorable escape with your loved one. Here is the list of the best romantic things to do in Chicago.

• Maggie Daley Park Skating Ribbon

If you don't mind sharing the rink with a few young ones, head to Maggie Daley Park's twisting rink in the center of downtown Chicago. Bring out your ice skates or rent some on-site, hold hands with your significant other, and swing around the circular route against the backdrop of the skyline. Remember that visitors must reserve a spot online if they want to get on the ice without any hassle.

• Aire Ancient Baths

Aire Ancient Baths is a unique and rejuvenating spa experience in Chicago that should be enjoyed with a partner. This place carries the old heritage of Greek and Roman bathhouses and also serves the same vibe. Visitors can book and schedule a massage or body treatment for two people, then spend some time indulging in the spa's assortment of baths, which range from cold to scorching hot.

• Visit Comedy Club

It is not a myth that a good sense of humor goes a long way in a relationship and is the perfect key to winning someone over. That's why it's always a smart idea to catch a show at one of Chicago's best comedy clubs. Zanies and the Second City are two of the favorite places to see skits, improv shows, and stand-up routines by some of the best local performers. So, take your partner there, and best of luck!

• Live Jazz at Green Mills

Let's share the universal languages of music and love. Take your partner to a place where both meet! Live jazz is a staple in the area at the Green Mill, which opened its doors in 1907. This historic cocktail lounge has a colorful past—Al Capone has hosted famous performers like Von Freeman and Billie Holiday. Due to its popularity, it is a bit difficult to get past the long line, but once you enter, you may enjoy mean martinis, captivating entertainment, and a wonderful evening with your date.

Weekends and long drives are a perfect combo, how about we combine these two and enjoy more romantic and intimate hideouts near the city on the drive of a few hours? Here we have carefully curated the list of perfect date spots near Chicago for a more fun and adventurous experience for your partner.

• Kohler, WI

Every couple dreams of spending the rest of their lives in the countryside surrounded by mountains and farmlands. Well, no matter how dreamy it sounds, they can now live this dream in reality. Plan your trip to Kohler, a tiny village in Wisconsin, located just west of Sheboygan, and make sure to get reservations at American Club, a century-old luxurious hotel packed with antique charm. Visitors can do yoga by the lake in the morning, or set off on an exploration of a 500-acre forest preserve. Don’t forget to try the food at Lodge Restaurant which is housed inside a cabin, and Horse & Plow Pub a charming greenhouse that is now a café.

• Mackinac Island, MI

Due to its wealth of natural beauty and car-free streets, Mackinac Island is a well-liked wedding location. Take your partner to Original Murdick's Fudge, known for its fudge made from an 1887 recipe. For a romantic sunset view, stroll around the island and find a scenic spot on the west side to enjoy the breathtaking scenery together. How about a romantic sunset view? Walk eight miles around the island and make your way to the west side just in time. This weekend getaway in Chicago is too good to be missed!

• Door County

Whether you like wine testing as a hobby or you just need a good reason for romantic getaways in Chicago, Door County is a place worth visiting. Try some of the 60 different wines and ciders at Door Peninsula Winery. Then, purchase a bottle of your favorite to sip!

• Milwaukee

Couples who eat together stay together! At least Random Cocktail Lounge, a date night staple since 1964, lives by this motto to serve their famous love bowl which couples can share. Apart from that Milwaukee is also popular for its brewery tours, visitors can also opt for peddling a swan boat at Veterans Park Lagoon or enjoy the views of Milwaukee River while slurping delicious hot Oysters at Vaults. No matter what you decide on, Milwaukee is an area full of romantic surprises that will not disappoint you!

• Traverse City

In Traverse City, visit the Sleeping Bear Dunes and enjoy a beach walk with your partner hands in hand along with breathtaking views of Lake Michigan from the bluffs. Next, go to the 26 wineries that make up the Traverse Wine Coast, where you with your partner can taste the wines and have a conversation with the producers.

• Indian Dunes

Calling all thrill-seeking couples! This one's just for you. Visit Indian Dunes and take a plunge at West Beach with your partner, and then stroll around Indiana Dunes National Park's shoreline. Similar in grandeur is the Indiana Dunes State Park, where visitors can hike up a series of hills for 1.5 miles and participate in the 3 Dune Challenge to witness some amazing views. A well-liked wedding location, The Pavilion, serves dinner directly on the beach.