Best Date Ideas in Chicago From a Matchmaker
Looking for the best date ideas in Chicago? While Chicago is arguably one of the most romantic cities in the U.S., planning a special date with your partner is no easy feat. With thousands of venues, activities, and restaurants to choose from, finding the right place for you and your love can seem like a real challenge.
I’ve been a Matchmaker and Dating Coach for over 25 years, so I know a thing or two about love and romance. I would argue that one of the most crucial aspects of healthy, happy relationships is planning great dates that you’ll both enjoy. Date night is an opportunity to strengthen your bond, connect on a deeper level, and create lasting memories.
A few years back, I visited The Windy City to attend a Matchmaking conference. I was immediately captivated by Chicago’s swanky charm and bustling nightlife. One of LUMA’s resident Matchmakers, Michelle Smith, lived in Chicago for many years before moving to warmer weather in the Carolinas. She graciously let me pick her brain for this article and helped me curate some of the best date ideas in Chicago.
Take a Stroll at the Morton Arboretum
There’s something so romantic about taking a stroll in nature. Thankfully, the Morton Arboretum offers a peaceful couple’s retreat right outside of the city. With over 1,700 acres of trees, gardens, and natural landscapes, Michelle says that this arboretum feels like stepping into another world. With so many serene trails to explore, be sure to plan to spend a full day here.
Now and then, even the most urban couples need a break from the concrete jungle. Without the distractions of the bustling city, Morton Arboretum allows couples to connect in a more natural, intimate setting and enjoy quiet, peaceful moments while exploring the gardens and trails.
Dine at Shaw’s Crab House
When I collaborated with Michelle on this list, she said that Shaw’s Crab House was her absolute top pick. Every dish is fresh caught, and they’re best known for their oysters and crab legs. With vintage elegance and top-tier seafood, this restaurant provides a cozy, yet sophisticated backdrop for the perfect dinner date! The classic decor, swanky jazz music, and intimate ambiance are so romantic.
Seafood may not seem like a top pick for a first date, but the inviting atmosphere and fine dining experience make this a great spot for newer couples with refined palates.
Have a Laugh at Second City
I did have the opportunity to catch a show at Second City during my trip, but unfortunately, I was seated up front and was incorporated into a standup bit. Despite my embarrassment, I had a great time! As one of Chicago’s most iconic comedy clubs, Second City is a true must-visit. The relaxed, lighthearted vibe really makes for a great evening and lots of laughs. Just be sure to sit closer to the back unless you want to be made into a joke!
Is there any better way to break the ice than shared humor? As a Matchmaker, I love Second City for newer couples still getting to know each other. The lively, playful, and exciting environment will encourage your date to open up, have a great time, and share a little more about their personality.
Visit Lincoln Park Zoo
Michelle is probably biased, as she’s a donor and member of their community, but she says that Lincoln Park Zoo is arguably one of the most unique zoos in the country. Nestled in the heart of Lincoln Park, this zoo offers free admission, which is rare in today’s economy! This historic zoo offers a mix of indoor and outdoor exhibits and is very walkable. Just be sure to plan your visit in advance so that you can explore all this zoo has to offer!
This is such a cute location for couples still in the early stages of their relationship. Lincoln Park Zoo provides a low-pressure environment that’s sure to be tons of fun!
Explore The Griffin Museum of Science and Industry
If you’re dating a scientist or history buff, there’s no better date idea on our list than The Griffin Museum of Science and Industry. I, unfortunately, did not get the opportunity to visit, however, Michelle has been many times and loves to come at least once a year to see their rotating displays. This world-renowned museum has a little of everything, from immersive displays to hands-on exhibits, to neurons, and even James Bond! Be sure to keep in mind that with the museum’s size, you may not be able to see every section in one day.
Something that a lot of couples miss out on is the experience of learning together. Stimulating, provoking dates like museums and conservatories tend to spark engaging discussions, which fosters a deeper connection among couples.
Have a Picnic at Promontory Point
If you’ve read my other blogs, you’ll know that I love a good picnic date, and Promontory Point does not disappoint. I was able to take a walk on the man-made peninsula when I visited, and I fell in love with the sweeping views of Lake Michigan and the Chicago skyline. Promontory Point can get crowded, but there’s plenty of room to get some space, spread out a blanket, and have a picnic by the water.
Picnic dates are criminally underrated. They make for an idyllic, laid-back date for couples who enjoy natural beauty, small bites, great conversation, and even a bit of wine. This is the perfect location for some privacy, too, as it’s easy to get away from the crowds.
Watch a Show at The Chicago Theatre
If you’re looking for an excuse to dress up the nines, The Chicago Theatre is your perfect venue! Michelle attended a show here earlier this year and already has tickets for another performance. The grandeur, historic architecture, and lavish interiors will make anyone feel classy. They have rotating concerts, Broadway shows, and other live performances, so there’s a show for everyone!
Even the most unpretentious couples need to feel elegant sometimes. The upscale, elevated atmosphere at The Chicago Theatre is perfect for a date night out on the town, especially for couples who share a love for theater.
Visit Garfield Park Conservatory
Without having someone who spent many years in The Windy City to collaborate with on this list, I probably would have missed the Garfield Park Conservatory. This park is a green oasis, with exotic plants, a fishing lagoon, tennis courts, and over 180 acres to explore! They even have art installations to explore. With so many possibilities and so much space, you can plan the perfect date for you and your date based on your preferences.
This date idea is the best on my list for fitness-loving couples and outdoor enthusiasts alike. Garfield Park Conservatory allows couples to escape the urban hustle and get inspired by nature. The peace and tranquility at this park are perfect for couples who seek privacy away from large crowds.
Have a Drink at The Aviary
Neither I nor Michelle are more than social drinkers. However, we both like to try unique drinks when we have the chance. Out of all the bars in Chicago, Michelle argues that The Aviary takes the art of cocktails to the next level with creative, meticulously crafted drinks. I’m certainly no mixologist, but the upscale ambiance and luxury feel make this the perfect spot to grab a drink.
I’d argue that having a nightcap after a dinner or movie date should be the norm, as it allows couples to unwind before ending their night out. The Aviary is a wonderful choice for your last stop of the night because of its intimate setting and unique offerings.
Take a Chicago Architecture Boat Tour
One of Michelle’s fondest memories of living in Chicago was taking a river cruise at sunset. She recommends the Chicago Architecture Boat Tour because it provides such a unique perspective on Chicago’s rich history and has stunning views of the city’s iconic skyline. This river cruise truly is the perfect blend of education, leisure, and fun!
Group tours aren’t normally something I recommend for couples, however, this boat tour is so unique and romantic that it makes an exception. The leisurely cruise provides plenty of time for couples to admire the views and have meaningful conversations, all while learning about The Windy City’s history.
Stargaze at Adler Planetarium
I think we all collectively forgot about how amazing planetariums are. my local planetarium actually closed because they received so few visitors. Thankfully, one of the best in the world, the Adler Planetarium, is still going strong. This is the perfect date idea in Chicago for a dreamy, awe-inspiring date. With interactive exhibits and opportunities for stargazing, there’s no shortage of learning or conversation.
I frequently plan learning and education-focused dates for my more intellectual clients and their matches. I love the Adler Planetarium because the environment encourages couples to bond over shared wonder and curiosity about the universe, and is honestly pretty romantic!
Take a Stroll on the Chicago Riverwalk
Surprisingly, the first place I stopped during my visit to Chicago was the riverwalk. The Chicago Riverwalk is a truly immersive experience, providing stunning views of the city’s architecture and the Chicago River. The walkway is lined with cafes, bars, and public art installations, and there are plenty of seating areas where couples can relax and enjoy the surroundings.
This is arguably the most versatile location on our list. The Riverwalk is perfect for a daytime stroll, a casual lunch, or an evening walk under the city lights, and it’s one of the best ways for couples vacationing in Chicago to get a taste of the city.
Visit Navy Pier
I absolutely love amusement parks, and although Chicago’s Navy Pier has tons of rides, it’s so much more than another fairground. Featuring restaurants, bars, live entertainment, and beautiful views of Lake Michigan, Navy Pier is iconic for a reason! With such a variety of activities, there’s something for every couple to explore.
Whether you’re looking for a romantic Ferris wheel ride or a quiet moment by the water, Navy Pier has something for your vibe. The lively, yet scenic environment makes it an ideal place for couples looking for a fun, relaxed day together.
Explore The Art Institute of Chicago
With some of the most acclaimed museums and exhibits, Chicago really is a cultural center for the arts. I actually got to explore The Art Institute of Chicago during my visit, and this is Michelle’s favorite museum in the city. This museum provides a world-class collection of pieces from across periods and cultures and also has gallery tours that you’re able to book in advance for a more immersive experience.
Museums have a way of inspiring us, sparking insightful conversations, create moments for contemplation. The Art Institute of Chicago is one of the oldest and largest in the entire US, making this one of the best possible dates for any couple who appreciates the arts.
Plan a Trip to the Shedd Aquarium
Although I didn’t have time to visit, Michelle visited the Shedd Aquarium often when she lived in Chicago. As the third-largest aquarium in the Western Hemisphere, over 32,000 animals from across the globe call the Shedd Aquarium their home. Its stunning aquatic displays and immersive exhibits offer a truly unforgettable experience.
Aside from the crowds, aquariums have such a peaceful vibe. Couples planning a wholesome, education-centered date in a serene environment should put the Shedd Aquarium at the top of their list.
Whether you’re in the heart of Chicago, Illinois or anywhere across the country, LUMA Matchmaking is here to help you find a meaningful, lasting relationship. Our personalized matchmaking approach is designed to connect you with your most compatible matches—successful singles who are equally committed to finding true love. Complete your LUMA profile today and take the first step toward finding your best matches with one of our expert Matchmakers.
