31 Unique & Romantic Date Ideas in Chicago for Every Couple (2025 Edition)

Looking for the best date ideas in Chicago? From cozy hideaways to big-city adventures, we’ve rounded up dates for every kind of couple as well as the best things to do in Chicago year-round.

Outdoor & Scenic Date Ideas in Chicago

Chicago Riverwalk

Chicago Riverwalk is a place with stunning skyline views and a mix of quiet corners with lively patios. Couples can grab an ice cream, share a drink by the river, or hop on a sunset boat tour.

• Vibe: Scenic, lively, romantic
• Best time to go: Sunset into evening
• Booking tips: Boat tours and restaurant patios fill up in summer—reserve ahead
• Pro Tip: Parking can be tough, so take the train to Clark/Lake or State/Lake.

Promontory Point

Promontory Point sits quietly in Burnham Park, offering one of the most unique skyline views in the city. Locals spread out picnic blankets, while newcomers can’t help but pause and take it all in. If you’re chasing a laid-back anniversary spot or just looking for a cheap date idea in Chicago, few places feel this effortlessly romantic.

• Address: 5491 S. Shore Dr., Chicago, IL 60615
• Price Range: Free
• Vibe: Peaceful, scenic, intimate
• Best time to go: Golden hour or early evening in summer
• Booking tips: No reservations needed, arrive early on weekends for a good spot.

Lakefront Trail

Lakefront Trail stretches along Lake Michigan, linking beaches, parks, and neighborhoods in one seamless path. Cute date ideas involve biking at sunrise, taking a romantic stroll at sunset, or even packing a picnic. It’s no surprise this trail is often part of the best date nights in Chicago.

• Address: Runs 18 miles along Lake Michigan, from Edgewater to South Shore
• Price Range: Free
• Vibe: Scenic, active, laid-back
• Best time to go: Sunrise for biking, sunset for walking, summer evenings for people-watching
• Pro Tip: Stop at North Avenue Beach for skyline views or make a detour into Millennium Park to mix lakefront time with city energy.

Cruise Lake Michigan

Cruise Lake Michigan and you’ll see Chicago from a unique perspective that never gets old. The skyline glows differently from the water, whether you’re on a sunny afternoon ride or a starlit dinner cruise. It’s one of those things to do in Chicago that feels both romantic and unforgettable without having to leave the city.

• Address: Navy Pier, 600 E. Grand Ave., Chicago, IL 60611
• Price Range: $35–$150+ per person, depending on cruise type
• Vibe: Scenic, romantic, celebratory
• Best time to go: Sunset or evening for city lights
• Booking tips: Book ahead in summer, dinner and fireworks cruises sell out quickly
• Pro Tip: Don’t miss the Wednesday and Saturday fireworks cruises for one of the best date nights in Chicago.

Chicago Botanic Garden

Chicago Botanic Garden is a peaceful escape that feels worlds away from the city. It makes a great date spot because it gives you space to walk, talk, and explore without the pressure of a crowded restaurant. For a first date, it’s a relaxed but memorable walk through blooming gardens. There will be conversation starters at every turn.

• Address: 1000 Lake Cook Rd., Glencoe, IL 60022
• Price Range: Free admission; parking $9–$30 depending on time and membership
• Vibe: Tranquil, earthy, restorative
• Booking tips: Timed-entry passes are required on busy weekends—reserve online
• Pro Tip: Don’t miss the Japanese Garden for one of the most romantic spots to pause and take in the view.

Adventurous & Active Dates in Chicago

Adventurous and active dates are great for first-time visitors who want to see the city in a new light or for residents looking to shake up their usual routine.

Urban Kayaks

Urban Kayaks is the place to head for a peaceful kayaking date on the water. Paddling side by side gives you an activity to focus on, which takes the pressure off constant conversation—perfect for a first date. There are even tours available.

• Address: 435 E. Chicago Riverwalk, Chicago, IL 60611
• Price Range: $25–$70 per person, depending on tour or rental
• Vibe: Adventurous, active, energetic
• Best time to go: Evening tours for sunset and city lights
• Booking tips: Weekends fill quickly, reserve online ahead of time
• Pro Tip: After kayaking, walk the Riverwalk for drinks or dinner to extend the date.

Navy Pier

Navy Pier has plenty to see, with fireworks shows in the summer and live entertainment nearby. You can book a river tour, visit the theatre, stroll through The Butterfly House, and more! The outdoor mini golf course is also an option for a low-pressure way to laugh and compete a little.

If you’re looking for a date that’s straight out of the movies, The Centennial Wheel is a classic choice. You’ll get stunning skyline and lake views. Plus, sharing that quiet time in your own gondola can be a great way to strengthen a connection.

• Address: 600 E. Grand Avenue, Chicago, IL 60611
• Price Range: Centennial Wheel $18–$20 per person | Mini golf around $10–$12
• Vibe: Fun, lively, scenic
• Best time to go: Evening for lights and fireworks; afternoons for a more relaxed vibe
• Booking tips: Buy Wheel tickets online to skip lines, especially on weekends
• Pro Tip: Time your ride on the Centennial Wheel with a sunset or fireworks show for a date you won’t forget.

Wateriders

Wateriders takes kayaking to another level by guiding you right through the heart of downtown Chicago. Unlike a casual stroll, paddling together creates instant teamwork, great for couples who want an active date that feels different.

First-time visitors love the history and architecture tours, while residents often pick the Moonlight Paddle for the city lights. It’s adventurous but still relaxed enough to spark good conversation, making it one of the more memorable things to do in Chicago.

• Address: 500 N. Kingsbury St., Chicago, IL 60654
• Price Range: $45–$70 per person, depending on tour
• Vibe: Adventurous, active, scenic
• Best time to go: Evening for sunset or nighttime skyline views
• Booking tips: Book online early in summer—tours sell out fast
• Pro Tip: Stick around after your paddle to explore nearby spots like the Chicago Riverwalk or have dinner in the West Loop.

Bobby’s Bike Hike

Bobby’s Bike Hike is great for an energetic daytime date. First-time visitors love how much ground they can cover in just a couple of hours. For couples, the mix of movement and discovery makes it feel like an adventure without being overwhelming.

• Address: 540 N. Lake Shore Dr., Chicago, IL 60611
• Price Range: Prices vary depending on tour type
• Vibe: Active, fun, social
• Best time to go: Late afternoon into evening for cooler temps and city lights
• Booking tips: Reserve in advance; popular tours like the Bikes, Bites & Brews food tour often sell out
• Pro Tip: Street parking is limited; use Navy Pier’s garages or public transit.

WhirlyBall Chicago

WhirlyBall Chicago is the kind of date spot that breaks the ice fast. Imagine bumper cars mixed with basketball and lacrosse; it’s chaotic, hilarious, and perfect for couples who don’t take themselves too seriously. For a first date, it’s ideal: you’re moving, laughing, and having fun without the pressure of constant conversation.

• Address: 1825 W. Webster Ave., Chicago, IL 60614
• Price Range: Varies by activity
• Vibe: Playful, energetic, competitive
• Best time to go: Evenings or weekends for a lively atmosphere
• Booking tips: Courts book quickly
• Pro Tip: Free parking is available on-site, a rare perk in Chicago.

Fun & Unique Activity-Based Dates

Penguin Foot Pottery

Penguin Foot Pottery is a hands-on way to break the ice. Unlike your typical sit-down date, you're doing something, which makes those quiet moments feel engaging (so you can skip the awkward first-date small talk). Plus, there's something undeniably charming about learning how people get focused. You’ll even have a souvenir to take home!

• Address: 2514 W Armitage Ave, Chicago, IL 60647
• Price Range: Classes start around $45 per person
• Vibe: Relaxed, creative, cozy
• Best Time to Go: Weeknights for smaller class sizes
• Booking Tips: Reserve 1–2 weeks in advance, especially for weekend spots
• Pro Tip: Grab coffee or dessert at Ipsento 606 around the corner for post-pottery chats.

Bad Axe Throwing

Bad Axe Throwing will inspire a little healthy competition. There’s something bonding about learning a new skill together, especially one that involves a little adrenaline. It’s loud, a little wild, and way more fun than the average dinner date. Plus, you’ll get some good photo opportunities.

• Address: 165 N. Loomis St., Chicago, IL 60607
• Price Range: Starts at $21.99 per person
• Vibe: Energetic, competitive, unconventional
• Best time to go: Evenings or weekends for the liveliest atmosphere
• Booking tips: Walk-ins are possible, but booking ahead guarantees a lane and a coach
• Pro Tip: Make it a full date by grabbing food in the West Loop afterward. It’s one of Chicago’s best dining neighborhoods.

Zanies Comedy Club

Zanies Comedy Club is a classic Chicago date spot because laughter instantly sets the tone for a fun night. Couples and internet dates alike can relax, share the moment, and let great comics carry the energy. It has an intimate setting and a long history of hosting some of the biggest names in comedy.

• Address: 1548 N. Wells St., Chicago, IL 60610
• Price Range: Ticket prices vary by show
• Vibe: Intimate, lively, entertaining
• Best time to go: Evenings, especially weekends, for headliner shows
• Booking tips: Buy tickets in advance, shows often sell out
• Pro Tip: Arrive early to grab seats closer to the stage—Zanies is an intimate venue. Being up front makes the show feel even more personal and fun for a date.

Fox in a Box Escape Room

Fox in a Box Escape Room is perfect for people who want a date that’s more interactive than sitting across a table. Solving puzzles together builds teamwork and sparks plenty of laughs. It’s a chance to see how well you collaborate under a bit of pressure, which makes it just as fun for new couples as it is for long-time partners.

• Address: 47 W. Polk St., Suite L5, Chicago, IL 60605
• Price Range: Prices vary depending on group size
• Vibe: Interactive, immersive, high-energy
• Best time to go: Evenings or weekends for a lively atmosphere
• Booking tips: Reservations required; popular rooms book fast
• Pro Tip: Don’t rush in; take a few minutes before the clock starts to plan your approach!

Romantic Nights Out in the City

We’ve scoped out the best stops for couples and first-time daters who want to go all out for romance!

Cindy’s Rooftop

Cindy’s Rooftop is a top-tier evening date spot. Overlooking Millennium Park, Lake Michigan, and the city skyline, it’s one of the rare places where Chicago shows off all at once. The atmosphere is lively enough to feel special, but not so loud that you can’t hear each other. It’s one of many must-try Chicago restaurants.

• Address: 12 S. Michigan Ave., Chicago, IL 60603 (inside Chicago Athletic Association Hotel)
• Price Range: Cocktails $16–$20, entrees $25–$40
• Vibe: Romantic, upscale, vibrant
• Best time to go: Sunset for golden-hour views
• Booking tips: Reservations strongly recommended, especially on weekends
• Pro Tip: Check out their live terrace view for a preview of the view.

Odyssey Dinner Cruise

Odyssey Dinner Cruise departs from the Navy Pier and is a great way to sail Lake Michigan with the Chicago skyline glowing behind you. The combination of fine dining, live entertainment, and stellar views makes it ideal for couples who want an experience to remember.

• Address/Location: Navy Pier, 600 E Grand Ave, Chicago, IL
• Price Range: depends on your package
• Vibe: Upscale, romantic, elegant
• Best time to go: Evening cruises for skyline views and sunset
• Booking tips: Book at least 1–2 weeks in advance, especially for weekends and holidays
• Pro Tip: Opt for an outdoor deck seat if the weather allows. The view of the skyline reflecting on the lake is something you don’t want to miss, and it can feel much more private than the main dining area.

Oriole Restaurant

Oriole Restaurant is the kind of place where a date feels memorable by default. With two Michelin stars, it offers a multi-course tasting menu that’s both inventive and intimate. The dining room is sleek and understated, which keeps the focus on the food and the company across the table.

• Address/Location: 661 W. Walnut St., Chicago, IL 60661
• Price Range: Tasting menu from around $215 per person, wine pairings extra
• Vibe: Elegant, intimate, indulgent
• Best time to go: Dinner service, especially weekends
• Booking tips: Reservations required weeks in advance, especially for prime nights
• Pro Tip: Pair your visit with a stroll through the nearby Fulton Market District; perfect for a nightcap or extending the date after dinner.

Cirque du Soleil Chicago

Cirque du Soleil shows in Chicago make for a magical date night. The mix of jaw-dropping acrobatics, live music, and surreal storytelling creates a sense of wonder you can share. If you want a date that feels like an experience instead of just another night out, this is it.

• Address: Varies by season and venue
• Price Range: Tickets usually $60–$150+
• Vibe: Dazzling, theatrical, high-energy
• Best time to go: Evening shows for a true night-out feel
• Booking tips: Buy tickets early, as weekend and prime seats sell fast
• Pro Tip: Pair the show with drinks at a nearby cocktail bar to keep the energy going after the performance.

Budget-Friendly & Free Date Ideas in Chicago

The 606 Trail

The 606 Trail is one of those date spots that feels both laid-back and full of surprises. Stretching through several neighborhoods, this elevated path offers a mix of street art, greenery, and city views that keep the walk interesting the whole way.

• Address: Access points across Bucktown, Wicker Park, Humboldt Park, and Logan Square
• Price Range: Free
• Vibe: Active, casual, artsy 
• Best time to go: Late afternoon or sunset for cooler temps and golden light
• Booking tips: No booking required
• Pro Tip: Stop at a nearby café or brewery along the trail to extend the date and keep the conversation going.

Myopic Books

Myopic Books is located in Wicker Park. It’s the perfect spot for a cozy, low-key date. Wandering through its three floors of stacked shelves sparks easy conversation and gives you both a chance to share favorite reads.

• Address: 1564 N Milwaukee Ave, Chicago, IL
• Price Range: Free to browse
• Vibe: Cozy, eclectic, quiet
• Best time to go: Evenings or weekends when the neighborhood is lively
• Booking tips: No booking required
• Pro Tip: Pair your bookstore wander with coffee or drinks nearby in Wicker Park for an easy date flow.

Chicago Cultural Center

The Chicago Cultural Center is a date spot that blends art, architecture, and culture in one inspiring space. We recommend it because it’s free, centrally located, and offers a mix of quiet corners and lively installations that work for both first dates and long-time partners.

• Address: 78 E Washington St, Chicago, IL
• Price Range: Free
• Vibe: Inspiring, artistic, elegant
• Best time to go: Daytime for natural light in the Tiffany Dome, or during rotating exhibitions
• Booking tips: No booking required, but check the calendar for special events or performances
• Pro Tip: Step outside afterward for a quick stroll in Millennium Park—it’s just across the street.

Indoor Dates for Rainy or Winter Days

Chicago winters can be chilly, but there’s no need to put the hold on romance. Let’s review some top indoor activities in Chicago.

AIRE Ancient Baths

AIRE Ancient Baths is for people who want to slow down and connect. Inspired by Roman and Greek traditions, the candlelit pools, salt baths, and steam rooms create a relaxing escape that feels worlds away from the city outside.

• Address: 800 W Superior St, Chicago, IL 60642
• Price Range: Experiences start at $142 and can be upwards of $300
• Vibe: Tranquil, intimate, luxurious
• Best time to go: Evenings for a more romantic atmosphere
• Booking tips: Reserve as far in advance as possible for weekends or evenings. Those time slots go first.
• Pro Tip: Opt for a weekday visit if you can. Sessions are quieter, and the calmer atmosphere makes the experience feel even more private and personal.

Art Institute of Chicago

The Art Institute of Chicago blends world-class art, stunning architecture, and hidden corners perfect for conversation. The Beaux-Arts building sets the tone before you even step inside with its iconic lion statues at the entrance.

Beyond masterpieces like American Gothic, you can wander through the Modern Wing, admire the sweeping glass design by Renzo Piano, or relax in the South Garden tucked behind the museum. The whole area is a great place to discover Chicago's architecture.

• Address: 111 S Michigan Ave, Chicago, IL 60603
• Price Range: $32 for adults
• Vibe: Inspiring, artsy, timeless
• Best time to go: Weekday afternoons for smaller crowds or evenings during extended hours
• Booking tips: Buy tickets online to skip the lines and check if your date falls on a free admission day
• Pro Tip: Head up to the Nichols Bridgeway from the Modern Wing. It gives you a gorgeous view of Millennium Park and the lake, and it’s a great transition into a post-museum stroll.

Maggie Daley Park Skating Ribbon

The Maggie Daley Park Skating Ribbon is one of the most scenic date spots in Chicago. For dates, we love shared activities like skating because they’re a great chance to have a laugh (and, in some cases, help each other stay upright!). It can feel especially magical during the holidays, with lights and festive music.

• Address: 337 E Randolph St, Chicago, IL 60601
• Price Range: Admission free | skate rental extra
• Vibe: Playful, energetic, romantic with city views
• Best time to go: Evenings in winter or mornings in summer for fewer crowds
• Booking tips: Reserve skate rentals online in advance during the peak holiday season.
• Pro Tip: In warmer months, the ribbon transforms into a rollerblading and scooter path, so it’s a year-round date option.

Date Ideas by Chicago Neighborhood

Sometimes the neighborhood can make or break the date. But don’t worry, we’re here to help you out.

Wicker Park

Wicker Park is a great place to browse indie bookstores, hunt for hidden gems in vintage shops, or dive into pinball battles at Replay Arcade Bar. The variety here means your date can be as relaxed or energetic as you want it to be.

• Location: Centered around Damen & North Ave, Chicago, IL
• Price Range: Free to explore
• Vibe: Trendy, artsy, energetic
• Best time to go: Afternoons for shopping, evenings for nightlife
• Pro Tip: Explore vintage shops and indie bookstores during the day, then stay for cocktails or arcade games after dark.

Logan Square

Logan Square has wide boulevards, historic homes, and street art that give you plenty to talk about. It’s a spot where couples can spend hours wandering, eating, and drinking without ever feeling rushed.

If you’re looking for a specific stop, The Whistler is a favorite for its rotating cocktail menu and intimate live music nights.

• Location: Near Logan Square Monument, Logan Blvd & Kedzie Ave
• Price Range: Costs can vary for bars and restaurants
• Vibe: Laid-back, creative, foodie-friendly
• Best time to go: Evenings for live music, cocktails, or dinner
• Pro Tip: Pair dinner with a cocktail bar nearby to turn the date into a relaxed neighborhood crawl.

River North

​​River North architectural tours offer a comprehensive overview of one of Chicago’s most energetic neighborhoods (and maybe learn a thing or two). After that, you can take your date to explore the gallery scene or walk along the river.

Pro tip: If you want a more intimate experience, head to one of the hidden speakeasies tucked between high-rise buildings or settle into a rooftop bar for skyline views.

• Location : North of the Chicago River, south of Division Street, and west of Wabash Avenue
• Price Range: Tour costs can range, but exploring on foot is free
• Vibe: Upscale, lively, stylish
• Best time to go: Nights for dinner and nightlife, afternoons for galleries
• Booking tips: Dinner reservations are a must on weekends
• Pro Tip: Start with an art gallery stroll before heading to a rooftop bar for skyline views.

Andersonville

Andersonville is a neighborhood that’s full of a mix of artsy energy and small-town charm, making it easy to wander without a plan. We love it because it encourages connection without the noise of busier nightlife districts.

You can catch a quirky performance at the Neo-Futurists, then unwind with a cocktail at Simon’s Tavern or another low-lit spot along Clark Street.

• Location: Clark St between Foster Ave & Bryn Mawr Ave
• Price Range: Theatre tickets vary by show
• Vibe: Quirky, cozy, welcoming
• Best time to go: Evenings for indie theater shows or bar-hopping
• Pro Tip: Mix a show at an indie theater with drinks at a nearby cozy bar for a date that feels both cultured and intimate.

Seasonal Date Ideas in Chicago

There’s room for romance all year round! Here are some seasonal spots for unique date nights.

Millennium Park

Millennium Park shines as a summer date spot with free outdoor concerts and movies under the stars. The Great Lawn fills with couples sprawled on blankets, sharing snacks, and soaking in skyline views. There are even concerts and movie nights in the summer! We always suggest arriving early to snag a good spot before the crowd builds.

• Address: 201 E Randolph St, Chicago, IL 60601
• Price Range: Free
• Vibe: Iconic, lively, outdoor
• Best time to go: Summer evenings for concerts or movie nights
• Booking tips: No reservations, but arrive early for good lawn seating on movie nights
• Pro Tip: Bring a blanket and a picnic to enjoy skyline views while watching a free performance.

Garfield Park Conservatory

Garfield Park Conservatory is stunning year-round, but fall makes it a standout date. We love recommending this spot because it mixes beauty with a sense of discovery, making it easy for couples to connect in a relaxed, natural setting.

The FLEUROTICA event in mid-October showcases breathtaking floral garments crafted by leading floral designers!

• Address: 300 N Central Park Ave, Chicago, IL 60624
• Price Range: Chicago residents get in free, with a suggested donation of $10 for adults and $5 for youth.
• Vibe: Lush, peaceful, and inspiring
• Best time to go: Fall for seasonal displays, weekdays for fewer crowds
• Booking tips: No tickets required, but check their website for special events and programs
• Pro Tip: Pair your visit with a walk through nearby Garfield Park Lagoon for extra scenic views.

Christkindlmarket

Christkindlmarket is a Chicago winter tradition, and one of Chicago’s Chirstmas activities we love. It is a festive spot for a holiday date. Couples can sip hot spiced wine, browse handmade ornaments, and share warm pretzels while wandering through the twinkling stalls. It’s crowded, yes, but that energy is part of the charm. Few places capture the holiday spirit so perfectly.

• Address: Daley Plaza, 50 W Washington St, Chicago, IL, 60602
• Price Range: Free entry, $–$$ for food, drinks, and gifts
• Vibe: Festive, cozy, bustling
• Best time to go: Weekdays or afternoons to avoid weekend crowds
• Booking tips: No booking required, but lines can be long for food and mulled wine
• Pro Tip: Grab a collectible Christkindlmarket It’s a fun keepsake and a great conversation starter.

Planning Tips for Your Chicago Date 

We’ve put together a quick guide to plan your Chicago date night, because you only get one first impression!

Best Neighborhoods for First Dates 

First dates work best in neighborhoods where you can pivot easily. Wicker Park and Logan Square are great because you can grab a casual coffee, browse a bookstore, then wander into a cocktail bar if the vibe is right. River North brings nonstop energy, with restaurants and lounges on nearly every block. 

When to Book Ahead (and When You Don’t Have To) 

When to book ahead really depends on the date style. Fine dining, rooftop bars, and dinner cruises should be reserved weeks in advance, especially on weekends or holidays. But casual outings like walking the Lakefront Trail or exploring a street fair don’t require planning at all.

Pro tip: The sweet spot is knowing when reservations remove stress and when spontaneity makes the night more fun. 

What to Wear Based on Date Type 

Outdoor activities like kayaking or skating need layers and comfortable shoes, while rooftop cocktails and Michelin-starred dinners call for something sharper.

We like reminding people to check the weather; it changes fast here, and nothing kills the mood like being underdressed for the wind off Lake Michigan. 

Transit Tips for Couples Exploring the City 

Getting around Chicago on a date can be part of the fun. Many couples enjoy walking between spots in neighborhoods like Andersonville or the West Loop. We recommend mixing transit modes so you’re never rushing but always keeping things comfortable. 

Chicago Date Etiquette or Seasonal Tips 

A little etiquette goes a long way—arrive on time, dress for the weather (yes, even the wind), and always check if your date is comfortable with the plan. Summertime is for casual picnics and street festivals, while winter dates work better indoors—think comedy clubs, museums, or curling up in a speakeasy.

FAQs About Date Ideas in Chicago

What are the best free date ideas in Chicago?

For a free date in Chicago, you can watch the sun set by the lake along the Lakefront Trail or pack a blanket for a free Millennium Park concert under the stars. Many Chicago museums also have free days.

Where can I take someone for a romantic date in Chicago?

For a romantic date, cruise Lake Michigan at night for the city lights, or sip cocktails at a rooftop bar. For something quieter, the Chicago Botanic Garden offers a setting that feels worlds away from the city. Romantic dates in Chicago shine when you mix atmosphere with a view.

Are there any indoor winter date ideas in Chicago?

Zanies Comedy Club is a great indoor winter date idea for guaranteed laughs and fun. There’s also the option to test your teamwork at an escape room or relax together at the many spas.

Where can I go on a budget date in Chicago?

Picnic at Promontory Point, skate the Maggie Daley Ribbon with your own skates, or catch free days at the Art Institute of Chicago are a few fun free date ideas in Chicago. Even a simple stroll through Logan Square followed by coffee at Lula Café can make for one of the best date nights in Chicago.

Your Chicago Romance Awaits

Make a love connection in the Windy City with date nights that feel unforgettable. Whether you’re planning something for a new connection or a grand evening for a long-term love, Chicago has plenty of experiences that set the mood.

Looking to wow your date with something unforgettable? A Cirque du Soleil performance delivers jaw-dropping acrobatics, mesmerizing visuals, and stories that pull you in together. Grab a ticket to one of our Cirque du Soleil shows in Chicago and enjoy a date night that feels anything but ordinary.