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Unforgettable date night ideas in Chicago for first dates, special occasions, or just to spice up this Saturday. Our guide reveals fun romantic activities for daytime outings or lively nights to be enjoyed all year round, even during Chiberia!
You may also enjoy our unique things to do in Chicago guide.
Things to Do in Chicago as a Couple by Day
Bar Hopping
Irish, sports, craft beer, whiskey, wine, cocktail, rooftop, basement, hidden, swanky, or lowkey, there is no shortage of bars for thirsty couples to visit in this city.
Having a drink or two over multiple bar stops is a great date suggestion for those needing Dutch courage or a canvas that creates conversation, as moving between locations always provides something to discuss.
Clark Street (Andersonville) boasts 20 bars packed into 12 miles, including The Boss Bar, Three Dots and a Dash, and Bamboo Club.
Combine dining with drinking at the West Loop, where Randolph Street, known as Restaurant Row, is located.
You can do more than watch the Cubs on TV in bars in Wrigleyville, but if you do want to, it makes sense to support them at their stomping ground; check out The Sandlot and Budweiser Brickhouse Tavern for more.
Boystown has many LGBTQ+ bars like Roscoe’s Tavern and Kit Kat Lounge.
Or my personal favorite for its hip bars, Wicker Park.
Self-Guided Brewery Tour
Keeping with the booze theme, but don’t worry, if you or your partner prefer less or no alcohol dates, we’ve got many of those suggested below; what about a distillery tour of Logan Square?
Enjoy the hops while hopping between Revolution Brewery, Pilot Project Brewing, and Hopewell Brewing Company.
Rooftop Views
If you prefer taking in the views of the city with a cocktail in hand, head up to one of the many rooftop bars.
VU Rooftop Bar is a popular spot all year round, especially at Christmas; for its igloos, you can practically touch neighboring buildings at Cindy’s Rooftop, and ROOF is known for its elevated indoor seating with floor-to-ceiling views.
Helicopter Tour of Chicago Skyline
If rooftop views aren’t enough for your date, what about a bird’s eye one?
Choose between a ten- or twenty-minute flight that soars above the city’s historic buildings and landmarks.
This would be a cute proposal idea for those searching for engagement locations; think of the photos!
Take a Lovely Stroll
Chicago romantic dates don’t have to involve extravagant gestures; some of the nicest recommendations are free.
Get to know your partner better during a leisurely walk through one of the many parks or gardens.
Some include Chicago’s “front yard,” Grant Park, the city’s largest, Lincoln Park, or Millennium Park, where you will find The Bean.
If dating during autumn, you’ll see fall colors at Humboldt Park and Garfield Park Conservatory.
Hop Aboard the River Cruise
Sure, this 1.5-hour cruise is a tad touristy, but sometimes it’s fun to “visit” your town, and if you are a tourist, there is no shame in seeing the best sights by water.
The activity offers indoor seating, access to the deck, and narration about the Chicago River and surrounding buildings, perfect for architecture fans.
Get to Know Gangster History
One of the most feared gangsters in the US used Chicago as his breeding ground, and you can learn all about Al Capone and his cronies during this 2-hour walking tour.
The local guide also talks about the city’s spooky side and features paranormal stories, so you and your date get a buy-one-get-one-free session.
Plus, ghost tours can equate to cuddling up!
Or, if you prefer your history delivered as you sit on a comfortable bus, check out the Mob Mobile.
Gorge on Deep Pan Pizza
Start a debate: Who has the best deep-pan pizza?
Then, settle it by trying Gio’s, Robert’s, Lou Malnati’s, Giordanos, Eduardo’s, Pequod’s, and Labriola’s over a series of date nights.
Afternoon Tea
OK, this is a unique option for foodies with a sweet or savory tooth.
Afternoon teas consist of sandwiches, pastries like sausage rolls, charming cakes, and warm scones, all of which are served together on layers of trays.
Food is generally served with a teapot of tea, and some establishments allow fizz and cocktails to be added.
Check out Russian Tea Time, The Lobby, or The Allis Chicago for availability.
Pack a Picnic
One of the most romantic things to do in Chicago is very low-budget.
Pack all their favorite food items, or grab tasty takeout, and enjoy a slow lunch in one of the city’s many green spaces or beaches.
In addition to the outdoor spaces mentioned above, there is also Humboldt Park, which has a boathouse, Ping Tom Memorial Park, offering seasonal kayak rentals, and Loyola Park, for a less touristy beach area.
Note: Alcohol is not permitted in parks or on the beach and can result in a fine.
Farmers’ Market
Another food-focused date could be visiting the local farmers market, where you can choose fresh produce to cook at home together.
Why not challenge yourselves to a new recipe or do a course each?
Bagsy dessert!
Seasonal markets are at Logan Square Farmers Market, Independence Park Farmers Market, and Portage Park Farmers Market.
Beach Day
While this city has no ocean, it is blessed with Lake Michigan and sandy shores!
Take advantage of the huge space at North Avenue Beach for a casual walk or an afternoon of tanning.
Pool Day
If you want a chilled drink as you catch some sun during your date, check out hotels with rooftop pools and bars.
Soho House Chicago offers a mix of members and guest passes; avoid early morning as this is when kids can use the pool.
Watersports
During the warmer months, active couples might want to consider renting a kayak or paddleboard and getting out on the water.
You can hire from Chicago SUP at North Avenue Beach and Kayak Chicago Montrose Beach, which also double up as some of the most popular date spots in Chicago.
Rock Climbing
Adventurous dates should check out local climbing walls like Movement Wrigleyville or Brooklyn Boulders Chicago: West Loop.
During guided sessions, new climbers are given equipment and shown how to strategize the most efficient and fun routes to the top of the wall using boulders to get there.
It really is thrilling.
Ice Skating
If gliding is more of your style, hire skates and show off at McFetridge Sports Center or Fifth Third Arena.
Just try not to fall and pull your date down, ha!
Or, if planning a date during winter, the seasonal outdoor rinks at Millennium Park and Maggie Daley Park will be open.
Street Art
Another cheap date idea is to search for the city’s street art, a great option for couples who like modern art and photography.
Start at Art Alley (2424 N Harding Ave), then wander along to Greetings From Chicago Postcard (2226 N Milwaukee Av); next up is the Robin Williams Mural (2051 N Milwaukee Ave), then the Vivian Maier Mural (1651 W North Ave).
If it is raining, you can see a range of street art and graffiti at the Vertical Gallery, which is close to Chicago Truborn and is covered in a huge mural.
Museums and Galleries
Another indoor Chicago date idea is to visit one of the many museums; you can arrange a week’s worth of dates and still not have them all covered.
Choose from The Field Museum of Natural History, the Chicago History Museum, the American Writers Museum, the Museum of Science and Industry, the Chicago Sports Museum, the Museum Of Contemporary Art Chicago, the Art Institute of Chicago, The Institute for the Study of Ancient Cultures, and The DuSable Black History Museum.
Pot Party
Get your hands dirty at a pottery class where experts teach couples how to manage the wheel and mold a souvenir to take home.
Color Cocktail Factory is one of the top-rated.
Please try not to recreate the scene from the 80s movie Ghost.
Vintage Store Shopping
Support local and circular fashion by spending the day shopping at thrift stores.
Not only can you pick up a bargain, you’re guaranteed no one else will have your new outfit.
Entertainment items such as records can also be found on vintage store shelves.
Village Discount Outlet and Out of the Closet – Chicago has rails of pre-loved items looking for new owners.
Couple Spa
You’ll be exhausted from all the above physical and mental pursuits, so why not treat yourself and your partner to a couples’ spa day?
Unwind at The Spa at Palmer House or Spavia Day Spa – Lincoln Park offers couples spa services, so you can both benefit from switching off and zoning out.
A lesser-known item on our list of couple activities in Chicago, ideal for those who work hard and need some rest and relaxation.
Watch a Game
Whether watching a live game together or viewing it on a big TV in sports bars, options are abundant in Chicago.
For baseball, check out the Chicago Cubs; for basketball, check out the Chicago Bulls; for ice hockey, check out the Chicago Blackhawks; and for soccer, check out Chicago Fire FC.
Fun Things to Do in Chicago For Couples at Night
Sunset Spots
Chicago performs a dreamy sunset all year round, so if you are visiting during spring or summer, you can take it all in from outdoors, but during fall and winter, you might want to watch it from the warmth.
The most epic sunset scenes tend to capture Lake Michigan, the skyline with its shiny skyscrapers, or both!
The more obvious vantage points include the Lakefront Trail and Navy Pier, whereas fewer people know about Adler Planetarium.
The tourist attraction, 360 Chicago, is another great option, on the 94th floor of the John Hancock Building, 1000ft up.
Romantic Restaurants
Chicago is a hotbed for cozy restaurants, many of which are titled the “most romantic” in the US by various media outlets.
Bavette’s Steakhouse is known for its ambiance, Geja’s Cafe encourages lovers to lean in close over fondue, and Ciccio Mio offers low-lit dining.
Interactive and Concept Food
Geja’s Cafe isn’t the only culinary experience demanding that you play with your food.
EL Ideas gives a front-row viewing of the magic happening, Michelin star Alinea delivers an 18-25 course dinner, and Fairmont’s Le Petit Chef projects an animated show onto the table!
Dine on Dessert
If the conversation is flowing, keep the conversation going over pudding.
Legend Tasty House sells late-night rolled ice cream, Chocolate Shoppe Ice Cream has a rotating roster of gelato, and La Michoacana Premium is a diner cafe with a huge array of popsicles.
Search For Speakeasies
Can you find the following speakeasies in the city?
Hidden behind a stack of books is The Gatsby, enter Through The Record Shop for live music, or go to the Gilt Bar for happy hour.
Did you know that speakeasies were secret illegal bars during the prohibition era?
This level of naughtiness and their ambiance make them some of the most romantic places in Chicago.
Listen To Live Music
Whatever genre of music takes your fancy, you can find it here.
Big international artists play Soldier Field and the United Center, while more casual gigs can be enjoyed at the Bottom Live and The Empty Bottle.
Thalia Hall first opened as an opera hall in 1892, today its stage is donned by pop, indie, rap, country musicians.
See a Drag Show
Catch the Chicago queens slay at Baton Show Lounge, which has been delivering performances for over 50 years, or at the city’s oldest Hispanic drag bar, La Cueva.
Kit Kat Lounge is known for its drag brunches.
Go Dancing
While you might not see many couples doing the Chicago-style steppin’ or Cha Cha Slide, a handful of bars encourage other forms of dancing!
Charlie’s Chicago in Boystown is an all-around entertainment hub offering drag shows, karaoke, and bingo with a Western theme.
The Chicago Scottish Country Dance puts on a weekly ceilidh lesson for couples.
Finally, Ballroom Dance Chicago offers private lessons.
Throwback Arcade Games
Logan Arcade and Emporium Arcade Bar provide one of Chicago’s more casual date night ideas.
Both have a bar and vintage or modern games: challenge accepted.
Boozy Mini Golf
Mini golf, but make it boozy at Big Mini Putt Club!
Tee off with some time off for the drinks packages between play.
This 9-hole mini-golf course is the perfect date idea for couples that prefer to be active while keeping it relaxed, with a healthy dose of competition.
Score at Darts
Show off your aim at Flight Club Chicago, the fun darts bar taking over the world.
This spot allows you to play social darts and enjoy bar snacks and a few cocktails.
Lights, Camera, Movie Action
Spend the evening at one of the city’s independent movie houses, such as The Logan, which also has a weekly movie trivia night.
Alternatively, see one of the latest blockbusters from the comfort of an AMC theater.
Theater Shows
There are over 250 theaters in Chicago and a district dedicated to its art, resulting in a huge variety of shows every night of the week.
You’ll find Broadway at the 1906 CIBC Theatre, the 1926 James M. Nederlander Theatre, or the 1926 Cadillac Palace Theatre.
If you and your date truly love the theater, consider going backstage at the Chicago Theatre during this tour.
Comedy
Escape the frigid temperatures during Chiberia and warm up at one of the following comedy clubs.
Zanies Comedy Night Club (decades old), Laugh Factory (surprise celebrity guests), and UP Comedy Club (full dinner menu available).
Karaoke
Elton and KiKi? Dolly Parton and Kenny Rogers? Marvin Gaye and Tammi Terrell?
Whichever duo you choose, you can belt it out at No.18 Karaoke or Lincoln Karaoke.
Romantic Hotels
If you are planning a Chicago getaway for St. Valentine’s Day, a special occasion, or just because The Publishing House Bed and Breakfast is an 11-bed hotel in the West Loop, some of its rooms have rolltop baths!
The Blackstone Autograph Collection is built in a 1910 beaux-arts building with elegant suites and a spa service.
Romantic Day Trips
Starved Rock State Park
Get into nature and lose a few hours chatting during a Starved Rock State Park walk.
There are 13 miles of trails to explore, and the park features sandstone canyons and waterfalls.
From Chicago:
- 1 hour 30 minutes
- 93 miles
Anderson Japanese Gardens
Travel to Rockford to explore the 12 acres of Anderson Japanese Gardens.
The beloved proposal spot has koi-filled ponds, bridges, streams, and a cafe selling locally sourced organic ingredients.
From Chicago:
- 1 hour 30 minutes
- 85 miles
Final Words
Whether you plan outdoor or indoor romantic dates in Chicago, a spring awakening, summer fling, fall frolics, or cozy cuffing relationships, the city provides all year-round options for locals and visiting couples.
Which is your favorite? Tell us in the comments.