35 Best Chicago Date Ideas for an Unbelievably Fun Date
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Chicago, Illinois, is a vibrant urban city filled with unique attractions. From high-end restaurants and eclectic bars to famous landmarks and outdoor activities, there's so much to do in this popular city.
You'll also discover an incredible range of romantic things to do in Chicago, IL. Whether you live in the Windy City or are visiting with your partner, these 35 best Chicago date ideas are sure to please everyone!
Planning a last-minute trip to Chicago?
When visiting Chicago, book your accommodations and experiences before you go. Here are some top choices to make your trip enjoyable.
Top Accommodations in Chicago
- Hyatt Place ChicagoDowntown - The Loop (relax by the pool)
- Trump International Hotel & Tower Chicago (5-star rating)
- Level Chicago - Old Town (rated highly)
Top Tours and Experiences in Chicago
- 45-Minute Chicago River Architecture Tour From Magnificent Mile (likely to sell out)
- Chicago Architecture River Cruise (very popular)
- Chicago Crime & Mob Bus Tour (very popular)
- Gangsters & Ghosts Tour in Chicago (very popular)
- Chicago CityPASS
- 35 Chicago date ideas
35 Best Date Ideas in Chicago
Things to Do on a Date in Chicago
- Visit Garfield Park Conservatory
- Explore the Chicago History Museum
- Be amazed at the Chicago Magic Lounge
- Relax at AIRE Ancient Baths
- Watch the fireworks at Navy Pier
- Spend the day at the Lincoln Park Zoo
- Bond over a cooking class
- Check out the best happy hours in the city
- Meet furry friends at a cat cafe
- Enjoy drinks at Adler Planetarium After Dark
- Tackle a rock climb
- Challenge your date to a bowling game
- Explore the Lincoln Park Conservatory
- Go on a brewery tour
- Go Kayaking on the Chicago River
- Watch Chicago's sports teams in action
- Play arcade games at Headquarters Beercade
- Dare to go on the Gangsters and Ghosts tour
- Discover marine life at Shedd Aquarium
- Work together to tackle an escape game
- Luxuriate on a Lake Michigan dinner cruise
- Taste the best dishes in Chicago on a food tour
- See artworks at the Art Institute of Chicago
- Listen to classical music at the Chicago Symphony Orchestra
- Get crafty at a graffiti art workshop
- Hang out and watch a movie at Millennium Park
- Try delicious sweet treats on a donut tour
- Sip drinks and enjoy the views at a rooftop bar
- Share a romantic dinner at Alinea
- Find some unique pieces at Chicago's thrift shops
- Learn something new at the Field Museum of Natural History
- Have brunch together
- Try the best deep dish pizza in the city
- Visit the Chicago Museum of Contemporary Art
- Things to Do Near Chicago on a Date
Chicago Date Ideas Highlights Video
Check out our highlights video of Chicago date ideas.
Chicago Date Ideas Map
A map of Chicago. Use the map to explore all the date ideas.
Things to Do on a Date in Chicago
Visit Garfield Park Conservatory
A visit to Garfield Park Conservatory is an awesome free date idea in Chicago. This stunning indoor botanical garden features an array of stunning plant species, from palms and cacti to ferns and lily pads.
Once you've explored the indoor gardens at this famous Chicago landmark, head outside to wander around the beautiful outdoor gardens.
Not only is this date free, but walking around the gardens together is a great shared experience. You can also take lots of cute photos with stunning tropical plant backdrops!
Explore the Chicago History Museum
If you and your date want to learn more about Chicago, then a trip to the Chicago History Museum is a must. There will definitely be a lot to discuss with your date as you discover various exhibits covering Chicago and Illinois history.
Chicago History Museum additionally hosts events such as walking tours. They occasionally have happy hour socials, too; you can grab a drink and explore the museum at this adult-only event.
Are you interested in visiting Chicago History Museum?
- Select From Two-7 Attractions With go City Chicago Explorer Pass (favorable ratings)
Be amazed at the Chicago Magic Lounge
If looking for unique date ideas in Chicago, then a trip to the Chicago Magic Lounge is a must! The bar has three rooms to check out with a range of magic shows in each.
The magic bar shows performances in a close-up setting and allows you to interact with the magician. Alternatively, you can watch a more relaxed show in the music and magic bar.
Of course, tasty food and drinks are on offer to enjoy as you watch the spectacle.
Relax at AIRE Ancient Baths
What better date idea than relaxing with your partner in an urban spa, like AIRE? Found on River West, this Chicago location is just one of six AIRE spas worldwide.
You can simply pay admission to enjoy the baths or choose from a range of experiences. These include massages and salt rubs. They even have experiences for two - an incredible way to spoil and connect with your date.
Watch the fireworks at Navy Pier
You'll discover many things to do at Navy Pier, from checking out restaurants to riding the Centennial Wheel. Additionally, one of the best Chicago date night ideas is to watch the fireworks at Navy Pier.
The fireworks show happens twice weekly on Wednesdays and Saturdays. The show lasts ten minutes, during which time you and your date can enjoy the colorful illuminated display. Checking out the Navy Pier fireworks will surely make your date pop!
Do note that Navy Pier is relatively quiet during January and February. If you're from out of town and want to experience everything Navy Pier has to offer, the best time to visit Chicago for you will be during the spring or summer. November and December are also good times to visit, as there are holiday events at the pier.
Are you looking to join a tour to see Navy Pier?
- 45-Minute Private Helicopter Tour of the Chicago Skyline (widely acclaimed)
- Chicago Architecture River Cruise (a top tour)
Spend the day at the Lincoln Park Zoo
Having a day date with your partner and some cute animals is always a good idea! A trip to the Lincoln Park Zoo will allow you to get up close with a range of creatures. From camels and zebras to snow leopards and even polar bears, you won't get bored as you move between enclosures.
The zoo also hosts some fun events, including a cocktail mixing class and an adults-only night. Check the calendar to see what's on when you and your date visit.
Do you want to see Lincoln Park Zoo on a tour?
- Chicago Night Crimes Bus Tour (highly rated)
- Tour of Chicagos Criminal & Mafia History (well-attended)
Bond over a cooking class
Going on a dinner date is a failsafe idea, but learning to cook incredible dishes together is much more fun! There are many cooking classes in Chicago, most of which are also BYOB.
Cook au Vin is a classy choice for a date. You'll learn how to cook French classics such as Tarte Tatin, souffle, and Coq au Vin. They also have pastry and bread-making classes. If your date loves desserts, also check out Give Me Some Sugar's classes.
Check out the best happy hours in the city
Instead of settling on one bar, try a happy hour bar crawl. This fun date night in Chicago idea allows you to visit multiple spots without breaking the bank. The Press Room, Bernie's Bar, and the The Franklin Room, which has a daily whiskey happy hour, are just a few of the many places to visit.
Meet furry friends at a cat cafe
Is your date an animal lover? Then visiting one of Chicago's cat cafes is a must. Catcade is a downtown Chicago cat cafe that allows you to hang out and play with cute kitties.
The cafe also has retro arcade games that you can play and there's free wifi if you and your date want to get some work or studying done together. All of the cats that live at Catcade are adoptable, so you may end up going home with an additional friend!
Enjoy drinks at Adler Planetarium After Dark
A trip to the Planetarium isn't just for kids! Visiting this astronomical location is a fun date idea any time of the week. However, taking your date to Adler Planetarium during their After Darks event is a great way to keep the date sophisticated.
The event is held on the third Thursday of most months (subject to change) and allows adults-only to explore the Planetarium between 6.30 pm and 10 pm.
Are you looking to discover Adler Planetarium?
- Chicago Hop-On Hop-Off Tour With Big Bus (very popular)
- Chicago CityPASS (rated well)
Tackle a rock climb
If looking for fun date ideas in Chicago and you enjoy adventure activities, then be sure to go to Brooklyn Boulders. This indoor rock climbing venue has two Chicago locations, one near Lincoln Park and one in the West Loop.
Brooklyn Boulders offers a range of walls to climb for all levels, and you have the option to climb with or without a harness. You and your date can also take a class or have a private climbing lesson.
Challenge your date to a bowling game
Get competitive by challenging your date to a bowling game. Chicago has a range of fun bowling lanes that also offer food and alcoholic drinks.
10pin, for example, offers nightclub-style music and lighting along with a drink menu, martini list, and small plates. Other cool bowling spots to check out include Pinstripes bowling alley and Waveland Bowl. Many of the lanes have billiards, air hockey, and the like too.
Are you looking to join a tour to see 10pin Bowling Lounge?
- 90-Minute Chicago River Architecture Tour (likely to sell out)
Explore the Lincoln Park Conservatory
The Lincoln Park Conservatory is another beautiful indoor botanical garden in Chicago. You'll discover a range of tropical plants such as palm trees and orchids.
There's also a Show Room that hosts an annual flower show and houses beautiful vibrant flowers the rest of the year.
A unique feature here is that you may see a dinosaur! There are dinosaurs hidden all around the conservatory, and you and your date can compete to find the most.
Go on a brewery tour
Going on a brewery tour is one of many super fun things for couples to do in Chicago. You and your date can plan a tour yourselves, hitting all your favorite spots or places you want to try.
Alternatively, you can go on an organized brewery tour. Chicago Beer Experience is a great choice that offers a selection of different brewery tours.
Options to choose from include a Bacon and Brews tour and a Sins and Suds tour that looks at "beer's influence on Chicago's criminal past."
Go Kayaking on the Chicago River
If you and your date love outdoor activities, then kayaking on the Chicago River is the perfect date idea. As you kayak down the river, you'll pass some of Chicago's main attractions.
Places to see include Wrigley Field and the Lyric Opera building. If you're looking for a date night idea, consider kayaking on the river during the Navy Pier fireworks.
Watch Chicago's sports teams in action
Chicago is one of the few cities to have a team in all four major US sports leagues: the Bears in the NFL, Blackhawks in the NHL, Bulls in the NBA, and Cubs in MLB.
Heading to one of these teams' games is a super fun date idea. Even if your partner isn't a major sports fan, grabbing some drinks and cheering for the home team never disappoints.
Are you looking to visit United Center with a tour?
- Chicago Pizza Tour (usually sells out)
Play arcade games at Headquarters Beercade
Located in Chicago's River North neighborhood, HQ Beercade is a super cool date spot. The bar has a fun selection of over 50 arcade games, including Pac-Man and Asteroids. You can also play pinball or challenge yourself and your date to winning their trivia night.
While you explore the arcade, you can enjoy snacks, craft beers, and specialty cocktails. Beercade also has sharing cocktails, perfect for enjoying with your date.
Dare to go on the Gangsters and Ghosts tour
Chicago has a rich but criminal history. Due to this, historical and ghost tours are popular in the city. If you're after some fun couple activities in Chicago, then going on the Gangsters and Ghosts walking tour is a must.
You'll visit a range of haunted buildings and gangster hangouts. Tales involve the city's notorious gangsters, like Al Capone, and the culture of speakeasies during prohibition.
Discover marine life at Shedd Aquarium
Taking your date to Shedd Aquarium is a fun and laid-back idea. Exciting creatures to see include giant octopi, beluga whales, and sharks. You'll also spot otters, penguins, and a colorful array of fish and corals, among many other marine animals.
Once you've seen all the exhibits, check out the pretty gardens or head to the terrace for drinks and views of the pier.
Do you want to join a tour to explore Shedd Aquarium?
- Small Group Tour of Chicagos Lakefront & Museum Campus (highly rated)
Work together to tackle an escape game
A great way to bond is by working together to solve an escape game. The Escape Game Chicago has a selection of themed escape rooms to choose from.
Themes include "Special Ops," "Prison Break," and "The Heist." You and your date will have an hour to solve puzzles in order to break free from the escape room. Even if you don't manage to solve the puzzles in time, you're sure to have fun trying!
Luxuriate on a Lake Michigan dinner cruise
If you and your partner want to treat yourselves, going on a luxury dinner cruise on Lake Michigan is a must. You'll get to enjoy a three-course meal and drinks, including beer, wine, and cocktails. As you wine and dine, you can admire the views of Lake Michigan and the Chicago skyline.
There's also a DJ aboard so that you can dance to live music, and there's a rooftop deck to hang out on. A Lake Michigan dinner cruise has to be on your Chicago itinerary when visiting with your loved one.
Taste the best dishes in Chicago on a food tour
One of the fun things to do in Chicago for couples that like trying new dishes is going on a food tour. Your guide will take you to a selection of the best eateries in the Windy City. Snacks to try include brownies, hot dogs, deep-dish pizza, and much more. You'll also get to try some local craft beer.
Along the route, you also get to pass a few of the famous landmarks in Illinois. Places to see include Millennium Park and Cloud Gate, the Wrigley Building, and the Magnificent Mile.
See artworks at the Art Institute of Chicago
One of Chicago's best cultural attractions is the Art Institute of Chicago. The museum is one of the oldest and largest art galleries in the world and houses some famous artworks.
Exhibitions at the gallery cover a range of art mediums and feature art from Europe, Asia, the Americas, and more. Some of the renowned artists with pieces on display include Georges Seurat, Claude Monet, and Henri Matisse.
To make admission and exploring the museum a breeze, purchase Art Institute of Chicago skip-the-line and guided tour tickets in advance.
Listen to classical music at the Chicago Symphony Orchestra
Another of the great cultural activities to enjoy with your date is going to see the Chicago Symphony Orchestra. The orchestra was founded in 1891 and generally plays in Orchestra Hall.
You can see a range of classical concerts at the venue and may occasionally be able to see other genres of music. The Chicago Symphony Orchestra is the main act to see here, although other artists and groups do perform too.
Spending an evening at the Chicago Symphony Orchestra is definitely one of the best things to do at night in Chicago.
Get crafty at a graffiti art workshop
One of the most fun Chicago date ideas is going to a graffiti art workshop. During the art class, you'll learn how to create street art murals. Your instructor will teach you different styles and techniques so that you can create your own urban art masterpiece.
This workshop is also BYOB, so you can sip on some drinks while you get creative. The classes are for artists of all abilities, so they're perfect for anyone that enjoys artistic activities. Best of all, you and your date will have a one-of-a-kind art piece to take home.
Hang out and watch a movie at Millennium Park
Millennium Park is an ideal place to hang out with your date and take a romantic walk. In the summer, you can also head to the park to watch an outdoor movie. The movies generally run from July through August.
You can see a different fan-favorite movie at each showing and enjoy the film in the fresh air. Be sure to take a comfy blanket, snacks, and drinks as well so you can relax in style in front of the big screen.
Do you want an easy way to visit Millennium Park?
- Chicagos Tour Featuring Gangsters & Ghosts (a hit among most)
- Chicagos Best Food & Walking Tour (enjoyed by most)
Try delicious sweet treats on a donut tour
For couples who love desserts, a Chicago donut tour can't be missed! This tasty tour will take you and your other half to four of the city's best donut shops, all of which are located around The Loop. Bakeries to stop by are Doughnut Vault, Firecakes Donuts, Stan's Donuts & Coffee, Do-Rite Donuts & Chicken.
At each stop, you'll get to taste some signature donuts. As you walk to each shop, you'll get to see some landmarks and learn some Chicago history and fun facts from your guide. The stores often also have vegan, gluten-free, and nut-free options.
Sip drinks and enjoy the views at a rooftop bar
One of the most fun ways for you and your date to take in the views of Chicago is from a rooftop bar. A popular rooftop bar in the city is found at The Robey Hotel. This stylish drinking spot has both an indoor "rooftop" lounge with views across the city and an outdoor poolside bar.
Drinks on offer include unique cocktails, champagne and sparkling wine, and beer. You can also enjoy bar snacks, like jalapeno wontons or Nashville fried chicken sandwiches. Raised Bar Chicago is another spot to check out that offers food and delicious drinks.
Share a romantic dinner at Alinea
If you and your partner are looking to splurge on a night out, dining at Alinea is highly recommended. The food at Alinea is so renowned, that the restaurant is often named one of, if not the, best restaurants in North America.
When dining at this three Michelin star restaurant, you can enjoy a multi-course tasting menu complete with novel and decadent dishes. The exact dishes you'll be served vary, with seasonal produce often being used.
Along with tasting incredible, each plate looks stunning! No matter what is on the menu when you visit, you're guaranteed to try combinations you've never had before.
Find some unique pieces at Chicago's thrift shops
A great daytime date idea is going thrift shopping. Chicago has a host of thrift stores to choose from in and around downtown. Crossroads Trading is a local favorite. This store has lightly worn name-brand clothes at affordable prices.
Another spot to check out is Green Element Resale. While exploring this thrift shop, you'll discover a host of items, from housewares and books to clothing and accessories. There's also a large Buffalo Exchange close to downtown Chicago, which sells an array of second-hand clothing, including chain store brands and designer and vintage pieces.
Learn something new at the Field Museum of Natural History
Chicago's Field Museum of Natural History is one of the largest natural history museums in the world. The museum was established in 1894 and is one of the most renowned cultural attractions in the city.
During a visit, you and your date can learn about a range of fascinating topics. Exhibitions to see include those on dinosaurs and fossils, cultures of the world, and wildlife and conservation.
You'll also be able to see Sue, the museum's dinosaur skeleton! This skeleton is the biggest and most complete Tyrannosaurus Rex skeleton in the world.
The Field Museum of Natural History is generally open from 9 AM to 5 PM, making it another great spot for a daytime date.
Have brunch together
Another of the most romantic things to do in Chicago for couples is going to brunch together. Chicago residents love going to weekend brunch, so you can find many options across the city.
If you can't decide where to go, consider visiting Another Bite. They serve a great selection of pancakes, waffles, and French toast. Unique dishes include Fruity Pebble French toast and Oreo pancakes.
Alternatively, a great plant-based choice for brunch is Bloom Plant Based Kitchen. You can order brunch on Sundays from 11 AM to 3 PM. Delicious dishes include churro waffles, chickpea frittata, and pancakes with maple syrup and vegan whipped cream.
Try the best deep dish pizza in the city
The Windy City is known for its deep-dish pizza. If you're looking for the best pizzerias in the city to try this local treat, one of the cute date ideas in Chicago to try is going on a pizza tour!
This experience allows you and your date to visit six top deep-dish pizza restaurants. At each stop, you can sample the freshly made pies and may even find a new favorite pizza date spot. The route also takes you past some famous attractions, including Grant Park, Lincoln Park, and the United Center.
Visit the Chicago Museum of Contemporary Art
Another of the best date spots in Chicago for art lovers is the Chicago Museum of Contemporary Art. Located downtown, the museum was opened in 1967. It's one of the largest contemporary art galleries in the world and features works by many famous artists.
Renowned artists with pieces on display include Andy Warhol and Edward Krasinski. You can also see a range of mediums at the gallery, including paintings, drawings, and photographs.
Along with the permanent collection, the Chicago Museum of Contemporary Art has temporary exhibits and hosts voracious events.
Things to Do Near Chicago on a Date
See Chicago from above on a helicopter tour
Why stay on the ground for your Chicago date?! Taking a helicopter tour over the city is a fun and memorable idea that's sure to wow your partner!
Chicago Skyline Helicopter Tour offers private helicopter tours of the city that provide incredible bird's-eye views. The 45-minute tour takes you over a range of well-known spots, including Navy Pier and Millennium Park.
This exciting date idea is sure to create long-lasting memories for you and your partner. Do note that the airport for take-off is located about an hour's drive outside Chicago.
Chicago is a fantastic city, featuring a range of incredible date spots. No matter what you and your partner enjoy doing, you're sure to have a blast when trying any of these Chicago date activities!
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