Summer in Chicago is the time to find love, or at least someone to shack up with to make sure you always meet the minimum on food delivery orders. The competition is fierce though, as everyone feels the urgency to find a mate before Chicago’s biting cold winter arrives. To make certain that you’ll have someone to cuddle with in front of Netflix this winter, you need to impress them with your dating skills right now. Here are our top ideas for dates in Chicago this summer.
1. Kayaking in the Chicago River
As the Chicago River has gotten cleaner over the years, kayaking downtown has become incredibly popular. What was once unthinkable is now a great way to spend a morning, afternoon, or sunset admiring one of the most beautiful skylines in the world. There are a few companies offering rentals downtown; Wateriders offers a number of different tours and kayak rentals to let you and your date explore the river all by your romantic selves.
2. Walk, jog, or bike on the 606.
The 606 is an old freight train track that’s been turned into an urban garden and running path. Combine a walk along the 606 with a visit to a bar or restaurant in Wicker Park, Logan Square, or Humboldt Park and you’ve created a perfect date.
3. Riverboat tour
Downtown riverboat architecture tours are great for showing out-of-town friends and relatives the city, but they also make for a fun date. The combination of interesting information that you can listen to (or not), plus stunning views of the skyscrapers around you and the green river below, is conducive to in-depth conversations about everyone’s interests and lifestyles. The best tours are done by the Chicago Architecture Foundation. If you want a more intimate tour, take a twilight cruise for the softer light and the cocktails served onboard.
4. Take a picnic by the Lake and watch the sun go down.
Most of Chicago’s lakeshore is public park space, and it’s one of the best spots to be on a beautiful summer evening. Take a picnic out there, find a nice patch of grass, and kick back and relax. One of the best places is out at the tip of Montrose Harbor; being further out into the lake gets you great views over the water to downtown, and the bird sanctuary with native prairie grasses is a lovely place for a short walk in nature.
5. Adler after dark
On the third Thursday of every month, the Adler Planetarium puts on an event called “Adler After Dark.” For just $20 if you buy in advance, you get admission, sky show viewings in any of their three theaters, presentations, and some cool live entertainment. As a bonus, you end your date at the tip of the Museum Campus peninsula with probably the best view of the skyline anywhere in the city.
6. Paddleboarding on the lake
If you just can’t get past the idea of being inches away from the Chicago River, or you want something a bit more challenging, try stand-up paddleboarding on Lake Michigan or in one of the city harbors. Chicago SUP offers rentals, classes, excursions, and even SUP yoga. They have a location at North Avenue Beach and another in Diversey Harbor, where the water is always calm.
7. Millennium Park concert
The pavilion in Millennium Park has a series of free concerts throughout the summer. You can bring your own food and wine and have a picnic as the tunes play and the sun sets over the stunning skyline. For the full schedule, head to the Cultural Affairs and Special Events page on the City of Chicago website.
8. Movie at The Music Box
The Music Box Theatre is a cinema in Lakeview that plays indie and classic films. It’s a fun place to bring a date if you’re looking for a bit of culture. The beautiful interior is a throwback to the golden era of film. Oh, and they serve booze.
9. Lincoln Park Zoo
Chicago has a world-class zoo that happens to be totally free. The Lincoln Park Zoo is also very close to the lakefront, (paddleboarding is an option) and there’s mini golf in Diversey Harbor. Lincoln Park also has some great bars and restaurants, so you can easily pair your visit with other great date activities.
Matador Guide to
Best Travel Credit Cards
Top offers from our partners
Chase Sapphire Preferred® Card
100,000 bonus points
The Platinum Card®
100,000 bonus points
American Express® Gold Card
60,000 bonus points