Chicago’s Coolest and Most Romantic Date Ideas

The best first dates are immersive, allowing you to open up and get to know each other in a fun setting. The trouble is, freezing temps in the Northeast, at least mean otherwise great ideas and great outfits —such as grabbing a coffee and strolling through a park—might be impractical. Instead, grab your most stylish boots and a coat that makes you confident , and try one of these fun and inexpensive winter first date ideas that’ll keep the conversation flowing. Candles , a warm soft throw on the floor, a bottle of wine , take out, and a classic holiday movie on the TV : instant picnic! Head to a local holiday festival. Bonnie Winston, Celebrity Matchmaker and Relationship Expert , loves a retro roller skating evening for a first date. Amber Trueblood, marriage and family therapist , suggests playing Groupon Roulette for a rollicking first date. Pick one thing from the first five choices that pop up.

11 Double-Date Ideas You Have to Try

Find out what’s on in Illinois and Chicago with your guide to events, festivals, markets, music, theater, sport and more. Find out how to get to Illinois by plane, train, bus and driving. Getting around Chicago and Illinois is easy with our guide to ways to travel around the state. Visit the History Museums of Illinois. History comes alive at Illinois historical reenactments. Meet Abraham Lincoln in the flesh, experience colonial life, or take a canal boat ride with a period costumed storyteller.

12 Free and Cheap Date Ideas to Try in Chicago · Lincoln Park Zoo · The Signature Lounge at the 96th · Walk the Lakefront Trail · Chicago SummerDance · DIY.

By entering your email address you agree to our Terms of Use and Privacy Policy and consent to receive emails from Time Out about news, events, offers and partner promotions. Thanks for subscribing! Look out for your first newsletter in your inbox soon! Heads up! Singles and long-term couples alike know that brainstorming creative date ideas can range from tedious to excruciating, depending on the willpower and decisiveness of the parties involved. For your romantic consideration, here are our picks for the most unique date ideas in Chicago.

Did you know that swans mate for life? You may not be trying to get hitched, but the elegant birds nonetheless make for pretty symbol of romance, especially in boat form. Paddle around for a while, then take a leisurely stroll to soak in the Prairie-style architecture of the park’s historic boathouse. The stretch of Chicago Avenue bounded by Ashland Avenue and Wood Street is home to some of the city’s best, most innovative galleries, providing the opportunity for a very manageable and not to mention, free walking art tour.

Start at Matthew Rachman Gallery, which showcases sleek mid-century furniture and contemporary art, then head due west. Date ideas hardly get more romantic than stargazing with your sweetheart.

32 Legendary Date Night Ideas in Chicago

I mean, the idea of a sober first date is terrifying to some. Maybe you are sick of having the same date over and over? Regardless of your reasoning behind wanting to get away from the bars, there are many options that are laid back enough, yet entertaining enough to break the ice quickly.

Winter days won’t feel so short when you’re making memories with your partner. Check out these cute winter date ideas.

The most unique date ideas in Chicago You can also tackle the spot sledding hill outside Soldier Field where the fall even creates fake snow in the absence of the real stuff , or try your hand at snowshoeing Northerly Island during the Chicago Park District-hosted Polar Adventure Days. Wholesome, right? Note: Things required. Fireplace ideas are to Chicago winter as outdoor things are to Chicago summer. Read our first rundown of the best date bars in Chicago here.

Get a sampling of the best rooftop things in Chicago here. Get close and personal with the old man winter sport of kings at the Chicago Curling Club yes, this exists — but it’s more expensive for serious suburbs.

Chicago Today

Do you go for plans that are tried and true or try to impress with something more adventurous? There’s so much to do in Chicago. How do you funnel it all down into one perfect evening? Take the pressure off yourself the next time it’s your turn to plan by scanning our suggestions of the best date ideas in the city.

Book a babysitter, grab your honey, and enjoy a one-of-a-kind night out in the Windy City on the cheap. · Museum “Free Days” · Catch a Sports.

Chicago is full of swanky wine bars and lounges. We picked the best for your date night. Choosing from the unlimited restaurants Chicago has to offer is an overwhelming task, especially when you are trying to make a good first impression. Chicagoans swarm patios, rooftops, and beer gardens to soak up the sun in the short summers. Ditch the dinner date routine and jump off the beaten path with these 8 unique date ideas.

Chicago’s best places to eat, drink and enjoy views of the city. Perfect for your date night. If you want to invest in your relationship, you need to invest time spent with that person, and that means planning rewarding and meaningful dates. Tony’s culinary and cultural aptitude combined with Ambiance’s dating expertise is sure to give you the best date night experience.

32 Winter Date Ideas to Cozy Up to Your S.O.

Call the babysitter, grab your couple friends and make plans to go out on one of these awesome dates. Because dinner and drinks can get old, we rounded up 11 of the coolest events, tours and activities you can do in the Chicago area. The Chicago History Museum organizes monthly history pub crawls , where you can hop on a trolley and visit a few historic watering holes. Pop in each stop, grab a drink, and listen as your tour guide shares the history of each bar and surrounding neighborhood.

Past themes have included: the best Bloody Mary bars, famous speakeasies and greatest dives.

11 Unusual Date Ideas to Try in Chicago, IL · Toyota Park · iFly Lincoln Park · Chicago Magic Lounge · The Chopping Block · Free Tours by Foot.

Popular Categories Life Skills 18 activities. Dessert 6 activities. Beer 14 activities. Gift Cards. Just Booked View All. What’s the one thing everyone must do in Chicago? Besides eating pizza, you need to see that breathtaking skyline! Traveling along the great Lake Michigan on a cruise vessel, learn about Chicago’s colorful history and famous landmarks. You’ll enjoy the panorama of Chicago’s famous skyline, showcasing all the notable skyscrapers, such as the John Hancock, Trump Tower, and Willis Tower.

Want to Meet Great Chicago Singles? We’re Here to Help!

Visit a ‘real’ neighborhood before it gets the gentrification overhaul of tidy uniformity. Try Bridgeport for old world bakery or Uptown for banh mi. If the weather is not completely Arctic, nothing beats a scenic stroll hand-in-hand along the city’s beautiful lakefront path with the skyline behind you and the future just ahead. Afterward, get close in an alcove at the one-of-a-kind The Darling.

Or soar above the city day or night on the Navy Pier Centennial Wheel.

Have a memorable, dreamy date with the 10 Best Romantic Things to Do in Chicago, picked Chicago is a city full of possibilities and that goes for romance, too. chatter and ideas of Instagramming this sensual, relaxing experience behind.

Culture Trip stands with Black Lives Matter. For extra romance, go at twilight to enjoy beautiful views as the skyline lights up. No one in the know pays for a view in Chicago, and the best free view is undoubtedly from the Signature Lounge on the 96th floor of the John Hancock Center. Again, going at night adds that extra touch of romance. Beautiful coasts are often romantic, evoking memories and ideas of travel and excitement. Ready to wow your date with your moves?

Between June 23 and September 10, , are parties with live music and DJs. For those looking to polish up their footwork, dance lessons take place at selected times throughout the weekend. Choose a theme, and you have a great cheap date ahead.

Date Night Ideas

Culture Trip stands with Black Lives Matter. Kick off your weekend by taking a trip to visit Brussels Beach. For those looking for a different way to cruise around the city — head to Place Poelaert and take part in the Roller Bike Parade kicking off with a pre-party at 7 pm. Halfway through, parade participants will also be invited to skate for a bit at Planet Park. A post shared by Out. The Bourse is a cultural hub this Saturday as BXLove Summer invites various organizations for a fun-filled afternoon of music, games, and acrobatic performances starting at 4 pm.

Our very best date night ideas.

Whether you are a Chicago local looking for different date option or a tourist enjoying a romantic vacation, Chicago has what you are looking for. A city with rich culture, historic architecture, and unique experiences is the perfect place to charm that special person in your life. Each season brings out intriguing places to visit in Chicago, too. With an abundance of sights to see, diverse cuisine to sample, cozy settings, and thrilling activities, your date night will turn into a romantic and captivating moment.

Treat your date to a full day of fun or a traditional evening of dinner and drinks in Chicagoland. Here are 11 Chicago date ideas to make your time together extra special. The tradition of toting food to scenic spots can be dressed up with a luxurious selection of wine and gourmet appetizers tucked into a basket. The historic Humboldt Park, for instance, is home to lagoons, boathouses, an inland beach, and more.

This human-constructed peninsula was the beginning of architect Daniel H. When it opened in , the theatre was seen as a smaller version of the booming movie palaces of Chicago. Now, this theatre attracts large crowds due to its uncommon movies. You and your significant other can select your food directly from your seat. You are no longer limited to buttery popcorn — your choice of cuisine, like sushi, flatbread, and more, is brought right to you, so you can take in the big screen with extra comfort.

50 spots for a first date in Chicago

Everybody knows that the fall season brings perfect cuddle weather. Something about the chilly atmosphere just makes us want to curl up next to a fireplace with our loved one and drink some boozy hot chocolate. And we have all the fall date ideas you need for a perfect night out.

So you’re in a relationship and you’ve run out of ideas on what to do that isn’t Italian & a class guides you through changing your dat.

Jump to navigation. And it’s not just happening in Chicago — online dating is a practice that is becoming increasingly popular all over America. And EliteSingles is here to connect Chicago singles looking for love! If you want lasting love, you need to find a site that can meet your needs. At EliteSingles, we’ve specifically designed our dating site to cater to Americans seeking a long-term relationship. Indeed, our fully mobile-optimized platform is the ideal way for busy single professionals to connect, making it easier for our members to f ind each other online and meet up in real life.

Read more: W ant to make dating in Chicago even smoother? It starts with an easy sign-up process and personality test.

12 AMAZING FIRST DATE IDEAS