Date ideas for couples in Chicago

Where to go, what to do? Whether you want your date in Chicago to be romantic, fun or adventurous, the city has plenty to offer, from great restaurants and breweries to sightseeing tours and strolling the neighborhoods. We’ve rounded up 15 spots that locals love, plus a few tips for planning ahead, so you can focus on your time together. 

15 top date ideas for couples in Chicago

1. Time Out Market Chicago

Neighborhood: Fulton Market

Time Out Market is a fun Chicago date idea that is both a cultural and dining experience. When you step inside, it looks like a high-end food court, but instead of the restaurants you would typically find in a food court, those in Time Out Market Chicago are hand-selected and among the best in the Midwest. Order from a few stalls so you and your date can try multiple dishes and leave having had a fun shared experience.

2. Swan paddle boat rentals

Neighborhood: Humboldt Park

Looking for an outdoor date idea in Chicago? Pack a picnic and head to Humboldt Park for a fun afternoon on a swan paddle boat ride that will make your inner child smile. Each swan boat comfortably fits two adults, and can be rented for $30 an hour. When you’re done, stroll through Humboldt Park and find a cozy spot to set up your picnic.

3. Metropolitan Brewing

Neighborhood: Avondale

Metropolitan Brewing Company brews authentic German-style lagers — all of which have received rave reviews. At the brewery’s taproom and riverside patio, you can sit down for a meal with your lager, play bingo on Wednesdays or relax with yoga on Sundays. Reservations are not required.  

4. The Neo-Futurists

Neighborhood: Uptown

If you like original theater, The Neo-Futurists Theater is as fresh as it gets. It’s a full-circle creative venue in which the actors are also the writers, directors, producers and stagehands. As you can imagine, each performance is highly personal and honest. It’s often possible to buy tickets at the door, but we suggest buying them in advance to ensure your date night goes smoothly.

5. Bad Axe Throwing

Neighborhood: West Loop or Lakeview

A little friendly competition can be a fun way to spend date night. At Bad Axe Throwing, you can choose to throw axes or knives onto a target — like a large dart board. A private lane can only be reserved if you’re in a group of at least six. So, plan to go during walk-in hours, but check ahead because they vary by day and location.

6. Calumet Fisheries

Neighborhood: South Chicago

From the outside, the building that is home to Calumet Fisheries may not seem like much, but the incredible food makes it one of Chicago’s hidden gems. They specialize in smoked fish  — which includes salmon, trout, herring and even eel — but you can also get delights like crab cakes, stuffed shrimp and clam strips. The seafood is so good that this spot was featured in Anthony Bourdain’s “No Reservations” on the Travel Channel in 2009, making Calumet Fisheries both a date night and bucket list-worthy meal.

7. Koval Distillery

Neighborhood: North Center

Koval Distillery is an award-winning distillery that makes its own whiskey, gin and other craft spirits. You can take your date on a behind-the-scenes distillery tour, join a cocktail class or head to the tasting room for a flight and some bites. Koval also routinely hosts events and experiences, like restaurant pop-ups and comedy shows, making a visit to this distillery a unique Chicago experience. 

8. Navy Pier

Neighborhood: Streeterville

Looking for a romantic Chicago date idea? Navy Pier is the whole package. Go for a sunset ride on the Centennial Wheel, enjoy a lakeside dinner and end the night strolling hand-in-hand along the Lake Michigan waterfront. For something a little different, book two spots on a brunch, lunch or dinner cruise that departs from the pier. Afterward, you can enjoy the pier’s plentiful events and activities if you want to extend your date a little longer.

9. Andy’s Jazz Club

Neighborhood: River North

Andy’s Jazz Club hosts multiple daily live jazz performances in its intimate lounge each evening. You can go just for the show, or plan to have a few appetizers or dinner there too. Andy’s has a full menu of tasty starters, entrées and desserts. Given the venue’s popularity, you’ll want to make a reservation for your preferred night and time through Andy’s website.

10. The Second City

Neighborhood: Old Town

If you and your spouse need a good laugh, The Second City improv comedy theater is one of Chicago’s most well-known contributions to American culture. It’s helped propel the likes of Stephen Colbert, Amy Poehler, Tina Fey, John Candy and John Belushi into the spotlight. From improv performances and comedic plays to stand-up acts, it’s impossible to leave without a smile on your face. Walk-ins are possible, but Second City is very popular, so you’ll want to snag tickets ahead of time to ensure you get seats for your preferred date and time. 

11. Garfield Park Conservatory

Neighborhood: East Garfield Park

If you happen to be on a budget, this Chicago date idea is for you, as admission is free! This botanical conservatory’s expansive gardens and indoor habitats, from tropical to desert landscapes, are lovely to walk through with a special someone. Take part in an activity together, like the conservatory’s beekeeping drop-in demonstrations, to learn something new together. All Garfield Park Conservatory visitors are required to make a reservation, and it’s recommended to do so in advance of your visit, as walk-up reservations aren’t guaranteed. 

12. The Violet Hour

Neighborhood: Wicker Park

When you want your date night in Chicago to be a classy one, this creative cocktail bar is the perfect spoke. It’s got speakeasy vibes with an easy-to-miss exterior door. Inside, it’s cozy, sophisticated and chic. While you won’t be able to have a complete dinner at The Violet Hour, its menu of small bites pair perfectly with imaginative drinks that are so tasty you’ll keep wanting one more. Reserve a table to ensure you don’t miss out. 

13. Penguin Foot Pottery

Neighborhood: Logan Square

A hands-on art workshop makes a fun date idea for couples in Chicago. At Penguin Foot Pottery, you can join a three-hour workshop to learn how to work with clay on a potter’s wheel and make your own ceramic piece, like a mug or bowl. Not only do you get to create something together, but you also get to bring home a piece that will bring back fond memories of your visit every time you use it. 

14. Kayaking with Wateriders

Neighborhood: Downtown, Rockwell or Bridgeport

Outdoorsy couples will enjoy hitting the water on a kayak. Explore the Chicago River at your own pace by renting two single kayaks or a double. Alternatively, Wateriders offers a variety of themed kayaking tours, such as a ghosts and gangsters tour and a history and architecture tour. For a more romantic experience, join Wateriders’ sunset or moonlight paddle tour. 

15. Kings Dining & Entertainment

Neighborhood: Lincoln Park

How about a game night? At Kings Dining & Entertainment, you and your date can enjoy a little friendly competition by bowling, shooting pool or playing arcade games. Take a break between rounds to nosh on some pizza or share an ice cream sundae. Or relax at the bar and get to know each other better over cocktails. 

Date night tips

You’ve weighed your options and planned the perfect itinerary. Now all that’s left is to go with the flow, right? Well, there are a couple things you can do in advance to minimize the chance of mishaps. Follow these tips for a smooth start to your date. 

Make a reservation when possible

Whether it’s a top-rated restaurant or a small-capacity ticketed experience, it’s always a smart move to try to reserve your spot in advance. If you aren’t able to make a reservation or buy tickets ahead of time, have a backup plan in mind in case the space is at capacity when you arrive.

Be ready for the weather 

From summer thunderstorms to winter snow, inclement Midwestern weather can dampen the best laid plans. Get ahead of the situation by checking the weather before your date. Then you’ll be totally prepared no matter what the outlook may be. 

Live in the moment

It’s great to be prepared, but also remember to live in the moment and be spontaneous. Don’t be afraid to change plans on a whim when you or your date see something exciting to explore just around the corner. 

Find romance in Chicago with Avail

Once you know where you’re going for your date in Chicago, all that’s left is figuring out how you’re going to get there. When you borrow a car with Avail, you can rest assured you’ll be right on time for your date. Our neighborhood locations throughout Chicago offer self-service pick-up and drop-off, which means no lines and no waiting to hit the road. Plus, we offer affordable daily rates, Allstate insurance protection options and no fee to add a second driver, so you and your date have the option to share driving responsibilities.