Last Updated on August 12, 2025 by Joy Editors
Chicago’s romantic spots create an exceptional honeymoon experience in America’s third largest city. Many couples ask us about Chicago because it perfectly blends urban excitement with intimate moments. The city surprises visitors with more than 20 beaches to choose from for their Chicago honeymoon.
The city lets couples fall in love again with its luxury honeymoon suites and breathtaking rooftop views. The southwestern shores of Lake Michigan make Chicago easily available to visitors, with quick flights from the East Coast and four-hour flights from the West Coast. Couples can enjoy thrilling attractions like Flyover at Navy Pier and The Ledge at Willis Tower. The best time to visit falls between May and October. This piece highlights our favorite romantic dinner spots in Chicago, must-visit attractions, and everything in travel safety tips that will help make your Chicago honeymoon memorable for a lifetime.
Romantic Places to Stay in Chicago
The right place to stay is the foundation of a magical Chicago honeymoon. Chicago’s lodging choices range from cozy bed and breakfasts to luxury suites with stunning views, and each couple can find their perfect romantic haven.
The Publishing House Bed and Breakfast
The Publishing House Bed and Breakfast sits in the heart of the West Loop neighborhood and blends history with modern comfort beautifully. This restored 110-year-old former publishing house stands as one of Chicago’s most charming places to stay. You’ll find a beautiful mix of modern and vintage styles inside, with exposed brick walls, original woodwork, and carefully chosen décor.
The B&B’s cozy communal area with a fireplace makes it special – a perfect spot to unwind after a day in the city. The third floor’s two living spaces connect through a modern fireplace, complete with a grand piano and plenty of dining space. A remarkable 4.9/5 traveler rating puts this unique B&B at #2 among Chicago’s 14 B&Bs.
Conde Naste named The Publishing House among Chicago’s top 25 best hotels, showing that B&Bs can exceed luxury expectations. The breakfast here ranks among the city’s finest, with local ingredients served exclusively to guests.
Luxury Chicago honeymoon suites at The Viceroy and The Peninsula
The Viceroy Chicago gives couples seeking luxury the perfect blend of stylish boutique hotel amenities and a welcoming atmosphere. This 120-year-old landmark building houses 180 guestrooms, including 18 suites. Each room brings mid-century modern glamor to life with bold gold and black accents against floor-to-ceiling windows that frame amazing city views.
The Peninsula Chicago stands out with its exceptional Peninsula Suite. Located on the 18th floor overlooking Michigan and Chicago Avenues, this elegant 3,645 square-foot suite amazes guests. A baby grand piano, dining space for 10, and a private 2,000-square-foot wrap-around terrace with Lake Michigan views make it special. The main bathroom has a soaking tub with a picture window and a separate rain shower.
Unique stays: Boutique hotels and romantic Airbnbs
Chicago’s boutique hotel scene offers many gems for couples. Hotel EMC2, The Guesthouse Hotel, and L7 By Lotte all boast traveler ratings above 4.8/5. These intimate properties blend tailored service with stylish settings that work perfectly for romantic getaways.
Chicago’s romantic Airbnbs give couples more private options. A charming studio apartment catches the eye with its canopy bed, white fluffy linens, and spa-like bathroom. Many spaces feature creative touches like wicker swing chairs hanging from the ceiling – perfect hideaways for couples.
Safety should be a priority when picking your stay. If you rent a car, learn Chicago’s street parking rules and one-way systems before you arrive. Winter visitors should watch weather forecasts since snow affects driving conditions. Chicago’s excellent public transport system offers a great way to avoid parking hassles completely.
Whatever accommodation you choose, each spot sets the stage for creating lasting honeymoon memories in the Windy City.
Where Local Couples Dine for Romance
Chicago’s food scene beats at the heart of every memorable honeymoon. The city welcomes couples with everything from laid-back pizza spots to elite fine dining venues. My years as a Chicago native let me witness countless couples who created lasting memories at these intimate dining spots.
Aba: Mediterranean rooftop magic
The third floor of 302 N. Green Street houses Aba, which brings Mediterranean flavors with a California twist. Trees and plants fill the dining space to create an illusion of outdoor dining even inside. The spacious rooftop patio gives you magnificent skyline views of the iconic Willis Tower.
Chef CJ Jacobson’s modern take on Mediterranean cuisine comes alive through shareable plates. The crispy short rib hummus (USD 18.95) and charred eggplant spread with house yogurt stand out on the menu. The creative cocktails range from USD 12-28, so it’s best to use rideshare services instead of driving.
Deep dish with a twist: Lou Malnati’s and Pequod’s
A Chicago honeymoon needs authentic deep dish pizza. Lou Malnati’s, 52 years old, stands among Chicago’s most respected pizza families. Lou’s pizza journey started in the 1940s at Chicago’s first deep dish pizzeria.
Pequod’s Pizza brings something special to classic deep dish with its signature caramelized crust. The pizza makers place mozzarella around the deep dish pan’s rim, which turns golden brown during baking. This method creates a dark rim that’s both crispy and chewy. Wait times can stretch beyond two hours, so advance reservations are essential.
Fine dining at Alinea and romantic dinner places in Chicago
Alinea ranks among Chicago’s finest restaurants. This prestigious venue holds one of only 14 Michelin 3-Star rating spots in the U.S.. Guests can pick from three experiences: the Kitchen Table, The Gallery, and The Salon. Each experience costs between USD 325 to USD 495 per person.
Chef Grant Achatz’s creative approach to modern cuisine has earned Alinea recognition as North America’s Best Restaurant by The World’s 50 Best Restaurants. Fine cuisine meets experimental moments here, making it perfect for special celebrations.
Wine pairings at these romantic spots range from USD 155 to USD 395. Safety comes first, so plan your transportation ahead. Chicago’s excellent public transit system or scheduled rideshare services help you avoid road risks, especially after dark when visibility drops.
Unforgettable Things to Do Together
Chicago gives couples more than just dining and luxury hotels. The Windy City brims with enchanting experiences that create lifelong memories through its serene spas and breathtaking views.
Aire Ancient Baths: A spa like no other
Aire Ancient Baths Chicago sits tucked away in a preserved historic building. Candlelight guides visitors through the dimly lit interior while orange blossom aromas fill the air, creating ultimate tranquility. Couples and honeymooners can pick from several romantic packages:
- “Escape Together” packages let couples enjoy synchronized massages in private rooms before thermal baths. Prices start at USD 495
- “Love Connection” experiences come with basalt stone massages and soothing oils. You’ll spend between USD 515-705 depending on how long you stay
- “Wine Soak” lets you and your partner relax in a private Spanish Ribera del Duero red wine bath for 30 minutes at USD 700
These experiences help strengthen emotional bonds while reducing stress and improving sleep. Booking a rideshare service back to your hotel is a smart safety choice.
Architecture river cruise and The Ledge at Willis Tower
Chicago Architecture Center’s river cruises are among the most romantic ways to see the city’s magnificent skyline. First Lady’s 90-minute tour features expert docents who share compelling stories about the city’s architectural styles and legendary designers. Evening cruises become extra special as the setting sun casts a soft glow on the buildings.
The Ledge at Willis Tower delivers pure excitement with all-glass balconies that stretch 4.3 feet outside the building, 1,353 feet above street level. Crystal-clear glass floors give you unobstructed views across four states on clear days. This unique spot has hosted more than 1,300 proposals, weddings, and vow renewals.
Live music, theater, and jazz lounges
Chicago’s jazz scene sets perfect backdrops for intimate evenings. Andy’s Jazz Club has been a prominent full dining jazz venue since 1977. Nightly performances paired with Cajun-inspired food create unique cultural experiences. The historic Green Mill Cocktail Lounge brings its own charm, entertaining guests for over a century. Al Capone even called it his favorite speakeasy.
Beach day at North Avenue Beach
Lincoln Park’s North Avenue Beach stands out as one of the city’s most scenic spots with Chicago’s skyline creating a stunning backdrop. Lake Michigan’s gentle waves set a peaceful mood that’s perfect for romantic shoreline walks. The beach’s unique 22,000-square-foot beach house looks like an ocean liner, and its upper decks offer magnificent views.
Weather forecasts should guide your beach visit plans. If you rent a car, learn the street parking rules first. Chicago’s excellent public transportation system helps you avoid parking hassles altogether.
Best Views and Rooftop Bars for Sunset Moments
The Chicago skyline turns into a glittering canvas at sunset and creates unforgettable honeymoon memories. Couples can share intimate moments against breathtaking backdrops from the city’s high vantage points.
Cindy’s Rooftop and London House
Cindy’s Rooftop sits on the 13th floor of the Chicago Athletic Association hotel. It gives couples panoramic views of Millennium Park, Lake Michigan, and the stunning cityscape. The glass atrium makes dining comfortable all year round. The open-air terrace has cozy fire pits during winter months. This beloved Chicago spot boasts a stellar 4.1/5 rating from over 2,700 reviewers. You’ll need to book your reservations early.
London House nearby offers a different but equally magical experience. This tri-level rooftop is one of Chicago’s best open-air bars and features an iconic cupola that serves signature cocktails until midnight. The spot’s magic comes from its location overlooking the Chicago River and the city’s famous landmarks. Sunset makes everything more romantic as golden light washes over the urban scene.
CloudBar at Hancock Tower
CloudBar stands as Chicago’s highest bar on the 94th floor of the former John Hancock Center. This sophisticated venue welcomes guests daily from 9am to 11pm without reservations or dress code. The drink menu celebrates local flavors with Chicago microbrews from Revolution Brewing and delicious cocktails. You should book a rideshare service for your return trip after enjoying these high-altitude drinks.
Evening strolls on the Riverwalk and The 606
The 606 gives couples a more grounded but equally romantic option with its 2.7-mile elevated greenway that’s perfect for evening walks. This transformed former rail line connects several Northwest Side neighborhoods and includes the vibrant Bucktown area. You’ll find an intimate setting here to experience Chicago’s beauty and energy away from the tourist crowds.
These elevated spots give couples the perfect backdrop to create lasting honeymoon memories while they take in Chicago’s magnificent architecture from new points of view.
Travel Tips for a Safe and Smooth Honeymoon
Planning your Chicago honeymoon needs attention to practical details that keep you safe and happy. A good plan lets you focus on making romantic memories instead of handling surprises.
Best times to visit for weather and fewer crowds
The perfect balance of nice temperatures and manageable crowds happens from April through May and September through October during your Chicago honeymoon. Spring brings temperatures between 50s°F and 70°F. These conditions make it perfect to learn about romantic places in Chicago. Fall months showcase spectacular amber and gold foliage, and October stays the driest month.
Navigating the city safely: public transport and walking
Chicago’s extensive public transportation system makes getting around easy and budget-friendly. The CTA’s Blue Line runs 24/7 between O’Hare and downtown and takes about 40 minutes. The Orange Line gets you from Midway to downtown in just 25 minutes. The Chicago Riverwalk stays open daily from 6 a.m. to 11 p.m.. Its well-lit paths create perfect spots for couples to take evening walks.
Road safety and accident prevention tips for car rentals
Renting a car means you should park in well-lit areas and keep your keys ready before walking to your car. Look under the vehicle and check both front and back seats before getting in. Smart travelers ask for rentals without any markers that show they’re visitors.
Emergency contacts and local health services
Dial 911 for immediate police, fire, or medical response during emergencies. City services and non-emergencies need a call to 311. Community Health Centers across Chicago give complete care to everyone whatever their ability to pay. Many centers provide dental services and help in multiple languages.
Conclusion
Chicago stands out as a magical honeymoon spot that blends romance with urban adventure. This piece highlights favorite spots where local couples come back to rekindle their love. Your Chicago honeymoon starts with the perfect place to stay – from cozy boutique spots like The Publishing House to luxury suites at The Peninsula.
Without doubt, the city’s food scene takes any romantic getaway to new heights. Each meal becomes a treasured memory as you savor Mediterranean delights at Aba’s rooftop, taste authentic deep dish at Lou Malnati’s, or treat yourself to a once-in-a-lifetime dinner at Alinea.
Chicago gives couples endless ways to connect. You can unwind in the peaceful setting of Aire Ancient Baths or take architecture river cruises to see the city’s stunning skyline. On top of that, amazing views from rooftop bars like Cindy’s and CloudBar set the perfect scene for sunset toasts and intimate talks.
Your safety matters most when planning a Chicago honeymoon. Check the weather and plan your transportation before evening outings. Couples who rent cars should know local parking rules and might want to use rideshare services after drinks at rooftop bars. Most couples find Chicago’s public transit system affordable and handy to explore the city safely.
Great Chicago honeymoons mix planned activities with spontaneous moments. Book those must-do experiences ahead, but leave room to find unexpected delights – maybe a relaxed walk along the Riverwalk or catching an impromptu jazz show.
Chicago’s mix of Midwestern warmth and world-class attractions creates the perfect setting for newlyweds. The magnificent city by the lake promises unforgettable moments that strengthen your bond, whether you visit during spring’s gentle warmth, summer’s bright energy, or fall’s golden beauty.
