The 8 BEST Chicago Hotels for Anniversary Getaways 2026
Discover the top Chicago hotels that promise unforgettable anniversary escapes filled with romance and luxury. Finding the perfect hotel for an anniversary getaway in Chicago can be a daunting task, given the city's vast array of options. This curated list highlights exceptional hotels that provide romance and memorable experiences, making your celebration truly special.
Hotel Saint Clair - Magnificent Mile
162 East Ontario Street
Brings breathtaking city views and a romantic ambiance for an unforgettable anniversary getaway. Imagine toasting your love against the backdrop of stunning Chicago skylines, each moment amplified by an atmosphere that embraces intimacy. The cozy rooms envelop you in warmth, inviting you to unwind as you cherish your time together. Steps away from the vibrant Magnificent Mile, you can explore the city's charm hand in hand before retreating to your haven. Don't let this enchanting experience slip away, book your romantic escape today.
Millennium Knickerbocker Chicago
163 East Walton Place
Brings upscale comfort and farm-to-table dining to your anniversary getaway in the heart of Chicago. Imagine sinking into plush bedding after a day of exploring the city, while a 40-inch flat-screen TV sets the mood. Your evening unfolds over exquisite farm-to-table dishes at NiX, each bite crafted to delight. Sip on classic cocktails from the 1920s at the Martini Bar, where live entertainment adds a touch of magic to your celebration. This is not just a stay; it is a romantic experience waiting to be embraced, so book your unforgettable anniversary escape today.
Freehand Chicago
19 East Ohio Street
Brings a vibrant atmosphere to your anniversary celebration in the heart of River North. Imagine toasting to your love in a uniquely styled space, where every corner exudes creativity and charm. Freehand Chicago envelops you in a lively ambiance that sets the stage for unforgettable memories, with versatile room options catering to your romantic getaway needs. From intimate dinners in its restaurant to dancing the night away at the nightclub, every moment here feels carefully curated just for you. Don't wait to craft your perfect anniversary experience, book your stay now.
The Chicago Hotel Collection River North
312 W. Chestnut St.
Delivers an unforgettable romantic experience with contactless check-in and curated amenity packages. Skip the traditional check-in hassles and dive straight into romance with seamless smartphone room keys that set the tone for your getaway. Indulge in daily drinks and high-speed WiFi, enhancing your time together while enjoying on-site dining options that cater to every craving. Each moment spent here is designed to elevate your connection and create lasting memories. Make your anniversary truly special and book your stay today.
Hotel Felix River North/Magnificent Mile
111 W Huron St
Delivers a romantic atmosphere that enchants couples celebrating their love in the heart of Chicago. As you step into Hotel Felix River North, the elegance and comfort embrace you, creating the perfect backdrop for your anniversary getaway. Luxurious accommodations with plush down comforters and Egyptian cotton sheets invite relaxation after a day exploring the vibrant city. The allure of nearby boat tours adds an element of adventure, allowing you to experience Chicago from a unique perspective. Make this anniversary unforgettable, book your stay at Hotel Felix River North today.
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St
Delivers an enchanting luxury escape in the heart of downtown Chicago. Step into a world where gourmet dining meets intimate ambiance, setting the stage for unforgettable anniversary memories. The Allegro Royal Sonesta Hotel Chicago Loop invites couples to indulge in authentic Italian cuisine, elevating every meal into a celebration of love. After a day of exploring the vibrant city, retreat to your luxurious suite, where comfort blends seamlessly with sophistication. Don't wait, make this enchanting getaway yours and book your stay today.
Godfrey Hotel Chicago
127 West Huron, at LaSalle
Features a stunning rooftop bar with breathtaking skyline views for an unforgettable anniversary getaway. Imagine sipping craft cocktails while taking in the mesmerizing Chicago skyline, the perfect setting to celebrate love. Each stylish room invites you to unwind, equipped with modern comforts to enhance your romantic retreat. With the nearby spa and 24-hour fitness center, every moment is designed for relaxation and connection. Don’t let this incredible experience slip away; book your stay at Godfrey Hotel Chicago today.
Hotel Lincoln
1816 N Clark Street
Offers stunning rooftop views that elevate your anniversary celebration in the heart of Chicago. Imagine sipping cocktails as the sun sets over the skyline, each moment framed by a breathtaking backdrop. The blend of historic charm and modern flair in your chic room sets the stage for intimate evenings, while the proximity to Lincoln Park invites leisurely strolls filled with romance. With every detail thoughtfully designed to enhance your experience, you’ll find Hotel Lincoln to be the ultimate sanctuary for your love story. Book now to secure your unforgettable getaway.
Frequently Asked Questions
What are the best Chicago neighborhoods for a romantic anniversary getaway?
Consider staying in neighborhoods like River North for its vibrant nightlife, or Lincoln Park for its beautiful parks and charming streets. The Gold Coast also offers upscale dining and proximity to Lake Michigan.
Which Chicago hotels offer special anniversary packages?
Look for hotels like The Langham or the Peninsula Chicago, as they frequently offer packages that include champagne, chocolates, or spa treatments designed specifically for couples celebrating anniversaries.
What are some unique romantic activities to do in Chicago?
Take a sunset boat cruise on the Chicago River or visit the Skydeck at Willis Tower for breathtaking views. You can also enjoy a couples' massage at a local spa or a leisurely stroll through the Art Institute of Chicago.
Where can I find the best views of the Chicago skyline?
The rooftop bars at the LondonHouse or Cindy's Rooftop provide stunning skyline views. Alternatively, the 360 Chicago Observation Deck offers an amazing vantage point from the John Hancock Center.
Are there any romantic restaurants near popular hotels?
Yes, restaurants like The Signature Room at the 95th or Gibsons Bar & Steakhouse are excellent options for a romantic dinner. Many hotels in the downtown area are within walking distance to these dining spots.
What is the best time of year to celebrate an anniversary in Chicago?
Spring and fall are ideal for mild weather, making it perfect for outdoor activities. During winter, you can enjoy holiday lights and ice skating, while summer offers festivals and outdoor concerts.
What transportation options are available for getting around Chicago?
The CTA trains and buses provide convenient access to most attractions. Rideshare services like Uber and Lyft are also widely available. Consider renting bikes for a fun way to explore the city together.
Are there any outdoor spaces perfect for a romantic picnic in Chicago?
Yes, Millennium Park and Grant Park offer beautiful settings for a picnic. You can also head to North Avenue Beach for a beachside experience or Lincoln Park for a more secluded atmosphere.
What local events or festivals should we check out during our anniversary?
Depending on the time of year, you might enjoy events like the Chicago Air and Water Show in August or the Chicago Gourmet in September. Always check the city's event calendar for seasonal happenings.
How can we incorporate a cultural experience into our anniversary trip?
Visit the Chicago Cultural Center for free art exhibitions or buy tickets for a performance at the Lyric Opera or Chicago Symphony Orchestra. These experiences can add a special touch to your celebration.
