There’s an endless amount of date ideas in Chicago, but these dates are easy to plan. These Chicago date ideas are especially great for active couples looking to get outside and experience Chicago, as well as, people looking for a city adventure that takes them out of their typical neighborhood and day-to-day path.

Whether you’re a Chicago local looking for a new date night idea to change it up from pizza and a movie, or you’re a couple visiting Chicago in search of recommendations for romantic things to do in the city— as local tour guides we’ve got you covered with dates ideas in Chicago!

  1. Take a Romantic Paddle and Go Kayaking on Lake Michigan
  2. Stroll the Lakefront Trail
  3. Play a Board Game
  4. Taste a Chicago Culinary Medley on a Socially Distanced Chicago Food Tour (or make it a Private Dining & Bike Experience!)
  5. Relax at the Spa
  6. Bike through Chicago’s Greatest Neighborhoods
  7. Learn a New Skill Together
  8. Explore the Underwater World of Shedd Aquarium
  9. Drive In to the Movies
  10. Shop at your Local “Toy Store”
  11. Rent a Bike and Travel Anywhere in the City

Date Idea: Romantic Couples Kayak on Lake Michigan

Get outside for your next date in Chicago and go kayaking on Lake Michigan. Now this isn’t for every couple, but for those that enjoy time on the water, being active and want to see how well you and your partner work together in a tandem kayak then this is the perfect date activity.

Paddle around the lake, and take the opportunity to get to know each other better in fun and casual environment. Spend the afternoon on the water cooling off with our couples kayak paddle, go single or rent a tandem kayak. If you’re looking for more of an evening date activity, take a sunset kayak for an even more romantic lake experience.

Date Idea: Stroll the Lakefront Trail

Strolling down the Chicago Lakefront Trail (or any park/neighborhood) is one of the best date ideas for active couples while staying extra protected. Plus by walking alongside each other, there’s no awkward eye contact during a conversation lull!

Strolling the Lakefront Trail is a great Chicago date idea during COVID

Photo by Alan Light


Date Idea: Play a Board Game

Evaluate each other’s smarts with games like Scrabble and Chess, or see how well you collaborate as a team with cooperative games like Forbidden Island and The Mind. Stores like Dice Dojo, Cat & Mouse Games, and Bonus Round Café can help you find a game to fit your interests and your price range (most likely between $15-$45), making the full board game experience a great city date idea. If you’re looking to stay socially distanced, has a fantastic selection of virtual games, making board games a sure bet for a Chicago date idea.

Playing board games at a local bar is a great city date idea

Photo by cottonbros


Date Idea: Taste a Chicago Culinary Medley

Dining out is an obvious choice, but doesn’t that feel a little… uninspired? Switch it up with either our Chicago Favorites food tour or Chinatown food and walking tour! Not only will you get food from multiple restaurants, but you’ll also gain a greater appreciation of this magnificent city from one of our expert storytellers. Transform the hackneyed restaurant date into a Chicago experience with these two contenders for best downtown Chicago date ideas.

Restaurant walk and bike tours are a great thing to do in Chicago for couples

Photo by Bobby’s Bike Hike

Date Idea: Relax at the Spa

2020 was a stressful year, and 2021 hasn’t necessarily been much better. Let go of all your stress at King Spa & Sauna. Relaxing at a spa is also a great date idea for active couples — spa days are a great way to relieve muscle tension. Although the word “spa” can induce not-so-relaxing financial panic, this Korean spa is super affordable without sacrificing quality. Their $50 entrance fee lets you stay all day from 8am-midnight!

Kings Spa in Chicago for Date Ideas

Photo by King Spa

Date Idea: Bike through Chicago’s Greatest Neighborhoods

You ever bike past a cool building, think “That’s neat. Wish I knew more about it,” and then biked onwards? On our bike tours, you and your date will uncover the story behind the pretty views and important looking statues. Talk about a unique date idea for an active couple! Since we know biking might make you hungry, many of our bike tours include food, such as our Westside Foodie Ride and Ultimate Chicago Food Tour by Bike.

Strolling the Lakefront Trail is a great Chicago date idea during COVID

Photo by Bobby’s Bike Hike

Date Idea: Learn a New Skill Together

The pandemic has been all about learning new hobbies (brb, gotta go feed my sourdough starter), which are even more fun when you’ve got someone to share them with! There are all sorts of online tutorials for date activities like cocktail making and painting, as well as other things to do in Chicago for couples. Personally, I’ve been learning origami from Jeremy Shafer’s YouTube series! It’s great having a partner to troubleshoot, commiserate, and then celebrate your achievement with.

Learning a new skill is something Chicago couples can do together

Photo by Carine Felgueiras

Date Idea: Explore the Underwater World of Shedd Aquarium

The Shedd Aquarium has always been one of the best downtown Chicago date ideas, and dare I say it’s even better now? Because of their reduced occupancy, there are significantly fewer crowds, making it easier to submerge yourselves in the aquatic landscapes. Remember, the reduced occupancy and crowds make this a great Chicago date idea. It’s like watching a David Attenborough documentary in person!

Exploring the Shedd Aquarium is a great downtown Chicago date idea

Photo by Allan Henderson

Date Idea: Drive In to the Movies

Yeah, you can always just Netflix and chill at home. But if you’re looking for something a little more special, what about a drive-in movie? It’s so retro that it became cool again! Chitown Movies has a great lineup of bonafide date flicks, plus they’ll cater food directly to your car! Staying safely socially distanced in a trusted vehicle makes this a top Chicago date idea.

Drive In Movies are great Chicago date ideas during COVID

Photo by distelAPPArath

Date Idea: Shop at your Local “Toy Store”

No, we’re not talking about Toys R Us! A trip to the sex shop is a great opportunity to talk about what’s working well and what needs you want to explore. The knowledgeable and affirming staff at Early to Bed, The Pleasure Chest, and Leather 64Ten will help you navigate options without shame or judgment. They know that shopping at their stores is a great thing to do in Chicago for couples, so won’t judge.

Date Idea: Rent a Bike and Travel Anywhere

Biking is one of the best city date ideas because you can cover more area than walking and be more engaged than driving by car. We rent bikes that can handle all kinds of terrain and weather! Or if you’ve got a bike but it needs a little tune-up, we can help with that too. Not sure where to go? Let us help you plot an excursion.

Bike tours are a great Chicago downtown date idea

Photo by Bobby’s Bike Hike



Written by Justin Shannin, Bobby’s Bike Hike Tour Guide
I’ve been a tour guide with Bobby’s Bike Hike since 2019, and I often lead the Chicago Favorites Walking & Food Tour. My favorite neighborhood is Uptown/Edgewater because of the independent eateries, proximity to the beach, and cultural diversity. (Try Sun Wah BBQ’s off-menu Beijing DuckDinner, it’s perfection). My favorite part about being a tour guide is introducing people to this wonderful Windy City, which inspires me to learn more about Chicago every day!


We hope these Chicago date ideas during COVID help you keep the flames alive no matter the temperature and no matter the worldwide crisis. Any date ideas that you’d recommend? Comment below in the name of love!