Top Chicago Proposal Outdoor Spaces

• 1 Proposal Album
• Spaces for 30-100 Guests
• 2 Outdoor Spaces
• 1 Bar
• 4 Total Spaces

Welcome to the Ivy Hotel, one of Chicago’s premiere boutique properties, boasting 63 guest rooms, an outdoor rooftop event space and 2 indoor ballrooms. One block away from the Magnificent Mile and a short walk to the lakefront, the Ivy provides a luxurious setting with modern style tucked away in the center of it all. Hotel Amenities: Non-Smoking Hotel Free Wi-Fi 24-Hour Front Desk Meeting and Event Space (Indoor and Outdoor) In-room Wet Bar and Mini Bar Lobby Lounge and Bar King Suite (Standard Room Type) Amenities: California King Bed Divided Living and Sleeping Area Two TVs Hardwood Floors Work Desk Private Bar & Mini Fridge Switch Powered Drapes Italian Marble Bathroom with: Double Vanity Sinks Rainfall Shower Deep Soak Tub Beekman 1802 Bath Amenities

• 2 Proposal Albums
• Spaces for 15-400 Guests
• 1 Outdoor
• 1 Restaurant
• 7 Total Spaces

Located on Michigan Avenue, Pendry Chicago offers a sophisticated setting for weddings, corporate events, and social celebrations in the heart of downtown. The hotel features art deco-inspired architecture, elegant ballrooms, stylish dining spaces, and polished guest accommodations that create a refined backdrop for gatherings of every size. With flexible event venues, attentive service, and a prime location near Millennium Park and the Chicago River, Pendry Chicago blends historic character with modern hospitality. From intimate dinners to large-scale receptions, the hotel delivers a memorable event experience shaped by timeless design and city energy.

• Spaces for 50-320 Guests
• 2 Outdoor Spaces
• 1 Hotel
• 4 Total Spaces

The Gwen, a Luxury Collection Hotel, Chicago offers an Art Deco-inspired setting along the Magnificent Mile for weddings, corporate meetings, conferences, receptions, rehearsal dinners, and private celebrations. Set within the historic McGraw-Hill building, the hotel features 15,901 square feet of event space across 13 rooms, including The Gallery Ballroom for up to 400 guests, The Grand Salon, intimate boardrooms, and a rooftop terrace overlooking the city. Custom catering, adaptable audiovisual technology, high-speed Wi-Fi, and dedicated event planning support gatherings of varying styles and scales. With art-filled interiors and panoramic city views, The Gwen creates a distinctive backdrop for memorable Chicago events.

• Spaces for 50-700 Guests
• 1 Outdoor
• 2 Ballrooms
• 4 Total Spaces

Host Unforgettable Events at Builders BLDG – A Landmark Chicago Venue Located in one of Chicago’s most iconic landmark buildings, Builders BLDG is a premier private event space operated by Prime & Provisions. This architecturally stunning venue features a dramatic four-story atrium, exposed original brick, elegant marble floors, and a sweeping staircase with ornate gold handrails — offering the perfect backdrop for luxury events in downtown Chicago. Builders BLDG is ideal for a wide range of occasions, including corporate events, networking receptions, fundraising galas, product launches, weddings, mitzvahs, and more. The venue’s flexible floor plan and historic charm allow for creative event design, while the Prime & Provisions team provides world-class catering and seamless planning support. Whether you’re hosting an intimate celebration or a large-scale affair, Builders BLDG delivers timeless elegance, modern amenities, and unmatched service in the heart of the city. Contact us today to plan your next unforgettable Chicago event.

• Spaces for 20-79 Guests
• 1 Outdoor
• 1 Restaurant
• 5 Total Spaces

Whether you’re planning a corporate meeting or private event, Hotel Zachary is the perfect location in the heart of the iconic Wrigleyville neighborhood. The Drawing Room is a nontraditional event space ideal for corporate meetings, presentation-style sessions, board meetings, industry conferences and social events of all types. The pool table and adjacent Den lounge space allow for prefunction mingling and networking. Our clean, simple modern design is infused with subtle nods to Wrigley Field architecture, baseball history, our city and its neighborhoods. Hotel Zachary is honored to receive two recognitions on this year's World's Best Awards from Travel + Leisure. Hotel Zachary was named one of the "Best 15 City Hotels in the Continental United States" and came in at No. 2 for the "10 Best Hotels in Chicago." The Word’s Best Awards are among the most prestigious in the travel industry and are selected entirely by Travel + Leisure readers.

• Spaces for 350-750 Guests
• 1 Outdoor
• 1 Rooftop
• 1 Event Space

Host Unforgettable Events at Offshore Rooftop & Bar — Chicago’s Premier Waterfront Venue Located at the iconic Navy Pier, Offshore Rooftop & Bar is one of the top event venues in Chicago for corporate events, client receptions, social activations, product launches, and private parties. As the world’s largest rooftop venue (officially recognized by Guinness World Records), Offshore offers sweeping panoramic views of Lake Michigan and the Chicago skyline — providing an unmatched backdrop for both daytime and evening events. Whether you’re planning a high-impact brand activation, summer networking mixer, company holiday party, or executive dinner, Offshore’s expansive indoor space and surrounding outdoor terraces offer unmatched flexibility and wow factor. Guests can mingle by cozy fire pits, enjoy games in our entertainment zones, and take in the skyline from our breezy open-air decks. Our expert events team will streamline planning with customizable catering packages, full-service bar options, and dedicated support. Offshore is more than a rooftop — it’s where Chicago celebrates.

• Spaces for 40-750 Guests
• 1 Outdoor
• 4 Restaurants
• 4 Total Spaces

NAIA features Greek-Levantine cuisine from the same chef partner, Athinagoras Kostakos, the culinary force behind some of DineAmic Hospitality’s most notable restaurants, including Lyra, Violi, and La Serre. NAIA is 12,000 square feet. The space is thoughtfully designed to host multiple fully private events at the same time. NAIA is divided into two areas: restaurant and lounge. Each area has its own layout, design, full service bar, and river views. An airwall separates the two spaces and can be opened for a seamless flow between the two or closed to create a fully private area. On the restaurant side, the private dining room accommodates up to 40 guests and features a mirrored wall that allows you to see out while maintaining privacy so outside guests cannot see in. The space is situated toward the back of the restaurant, but guests still have a view of the river. There is also a semi-private round table in the main dining room for 8 to 12 guests. The full restaurant seats around 250 guests. The lounge features soft seating and hosts up to 200 to 250 guests for a cocktail style event, or it can be divided into two private spaces using an additional airwall. The lounge can also be set with dining tables upon request. The full venue accommodates upwards of 750 or more guests for a cocktail style event.

• Spaces for 40-250 Guests
• 3 Outdoor Spaces
• 1 Restaurant
• 13 Total Spaces

Waldorf Astoria Chicago is a sanctuary of Parisian-inspired elegance nestled in the heart of the city’s Gold Coast neighborhood. With its chateau-style courtyard, apartment-style rooms and suites featuring private terraces and fireplaces, an award-winning spa, and exceptional dining, the property offers a luxurious escape just steps from Chicago’s finest attractions. Whether you're planning a wedding, reception, birthday celebration, baby shower, corporate meeting, or private dinner, Waldorf Astoria Chicago provides a timeless setting for life’s most memorable moments. From intimate salons to a grand ballroom adorned with jeweled chandeliers, each space is thoughtfully designed to reflect your vision. Our dedicated team, personalized menus, and signature service ensure every event is effortlessly elegant and truly unforgettable. Elegant Venues - From a unique outdoor courtyard to enchanting ceremonies in the Sinclair Ballroom to intimate gatherings in our refined salons, Waldorf Astoria Chicago offers the perfect backdrop for your event. Expert Wedding and Event Planning - Our dedicated team of specialists collaborate with you to infuse personal touches and the signature Waldorf Astoria style and service into every detail. Comprehensive Wedding Packages - Relax as we bring your vision to life. Our thoughtfully designed packages include everything needed for a seamless celebration, delivered with the renowned Waldorf Astoria hospitality.

• Spaces for 15-250 Guests
• 1 Outdoor
• 1 Event Space
• 1 Meeting Space

A rooftop ballroom and open-air terrace, The Penthouse Hyde Park offers Art Deco-inspired design with expansive views of the Chicago skyline and Lake Michigan. Sleek, sophisticated, and simple, our venue acts as a blank slate to make your dream event come to life. Whether you’re planning a seated reception for 150 with dinner and dancing or a cocktail-style gala for 200, The Penthouse Hyde Park provides the perfect setting. A Century in the Making The Penthouse Hyde Park, located atop the former Piccadilly Hotel & Theater, offers an air of refined elegance that nods to its 1920’s roots. Our north and east walls feature 20’ arched windows that showcase skyline and lakefront views, unlike anything you’ve ever seen. Intricate crown molding has been restored to its original glory to provide just a touch of character. The space has been outfitted with modern lighting and a sound system to provide guests with a high-end experience they’ll remember for years to come.

• Spaces for 10-300 Guests
• 1 Outdoor
• 1 Bar
• 11 Total Spaces

Situated along the Chicago River at the juncture of North Michigan Avenue and River North, Trump International Hotel & Tower® Chicago is the city's most enviable address. The lush, contemporary guestrooms start at a spacious 600 square feet, are furnished with kitchenettes and feature 10-foot, floor-to-ceiling windows showcasing breathtaking views of Lake Michigan, the Chicago River and the city skyline. Contemporary, custom-designed furniture grace the living areas and bedrooms. Take your meeting or event to the next level with exceptional views and unparalleled service in each of our Chicago event spaces. Reinventing Chicago meeting space, we offer ideal event venues for both business and pleasure. Whether it's an important meeting, intimate social gathering, or a glamorous formal affair, your event will certainly make the right impression. All of our meeting rooms are easily accessible to guests staying in our Chicago suites and offer a private entrance that is separate from the hotel's main entrance as a convenience for attendees not staying in the hotel, providing a seamless transition between events. With over 26,000 square-feet of function and meeting space, including six salon rooms, several boardrooms, the Skyline Room, Riverside Room, and The Grand Ballroom, we have a space that fits every occasion. Each venue showcases both Chicago’s historic architectural landmarks and spectacular lake, river, and city views. By pairing our spectacularly designed spaces with the hotel's well-appointed amenities and prime location, we ensure that an event at Trump Hotel Chicago is not one to be missed. Going beyond a typical event planning experience, each venue comes equipped with the watchful eye and specialized attention of our team at Trump International Hotel & Tower® Chicago. With experience, expertise, and an endless amount of resources at their disposal, the events specialists at our Chicago Loop hotel will craft your occasion into the incredible affair you’ve always imagined and your guests will never forget. Our culinary team will design a catering menu to accompany the style and mood of your event, offering bold flavors and a brilliant selection and each Chicago conference room comes equipped with top of the line videoconferencing and audiovisual capabilities. Leaving no detail overlooked, our professionals guide you through the entire planning process offering the skills and expertise vital to make your event a success.

• Spaces for 25-999 Guests
• 1 Outdoor
• 4 Museums
• 11 Total Spaces

The Obama Presidential Center is a vibrant community hub, economic anchor, and beacon of democracy on Chicago’s South Side. Designed to inspire, empower, and connect visitors from around the world, the campus creates opportunities for learning, civic engagement, and meaningful community impact. In addition to its cultural and educational offerings, the Center features 11 distinctive event spaces designed for meetings, celebrations, galas, conferences, and special events, making it one of Chicago’s most significant new gathering destinations.

• Spaces for 40-150 Guests
• 1 Outdoor
• 4 Restaurants
• 4 Total Spaces

The Canvas by Ever is perfect for wedding receptions, ceremonies, rehearsal dinners, family celebrations, company meetings and business dinners. This large room is a blank canvas, a customizable space in which you can create an elegant, unforgettable event. The Canvas is located right next door to Ever restaurant and After lounge in Chicago's West Fulton Market. The Canvas is an extension of two-Michelin-starred Ever and thus pursues Chef Curtis Duffy's vision of unparalleled food, wine, ambiance and service. Our events team will go above and beyond to bring your personal vision to life and help you create a stunning event, whether your celebration is for eight or 100 people. In addition to the main Canvas room, we offer six other luxe private event spaces that can accommodate various aspects of your special event—from private rooms in Ever restaurant and After lounge, to a gorgeous rooftop space with stunning views of the downtown Chicago skyline. All of our spaces are in the same building We are in the business of giving guests once-in-a-lifetime experiences. It would be our honor to host your important event.

• Spaces for 16-1,300 Guests
• 2 Outdoor Spaces
• 4 Restaurants
• 5 Total Spaces

Situated in the heart of the city, with striking views of the Chicago River and city skyline. RR Events offers an impressive setting for your next party or meeting. Run by a successful and seasoned Culinary team, RR Events is a lively social house and gathering place. Experienced event planning and service teams aim to accommodate and anticipate your needs for a flawless event. Whether you’re planning a grand gala for 600 people or an exclusive affair for 8, the delectable, customized menus and exceptional views will impress! The RR Events team offers assistance with all aspects of planning, including booking, menu design and beverage pairing, audio-visual needs, parking, floral and event decor, and additional logistics as requested. With seven event spaces to choose from – each featuring sophisticated decor that pays tribute to the historical landmark building the restaurant is housed in – the options for corporate and social events are endless at RR Events.

• Spaces for 32-900 Guests
• 1 Outdoor
• 4 Restaurants

Host your event in Urban Wine Country. City Winery Chicago provides a full service event program with head to toe planning. Our spaces tailor to any event or occasion. Contact our team today and turn your event into an experience with City Winery Chicago. Offer your guests a unique wine experience to make your event unforgettable. We offer food and wine pairings, wine blending, custom wine labels and more!

• Spaces for 18-225 Guests
• 1 Outdoor
• 1 Restaurant
• 7 Total Spaces

Set along the tree-lined Midway Plaisance and framed by University of Chicago's iconic Gothic architecture, The Study offers a setting for gatherings that feel elevated, timeless, and unmistakably Chicago. Opened in 2021, the hotel features approximately 10,500 square feet of thoughtfully designed event space with on-site catering and seamless indoor-outdoor flow. WINTER GARDEN The heart of the hotel’s event offerings, the Winter Garden is a striking space where art and architecture meet. Guests are welcomed by a dramatic mural by Dean Barger and a sculptural light installation by John Pomp. Expansive windows create an atmosphere that is airy and luminous, while a private walled terrace offers an intimate outdoor extension. The Winter Garden is ideal for weddings, receptions, and large celebrations, accommodating up to 160 guests for a seated dinner or 225 for a standing reception. SECOND FLOOR STUDIOS & TERRACE Accessible via a photo-worthy grand staircase or private elevator, the second floor provides a versatile environment for both social and corporate gatherings. Function spaces include a terrace overlooking the leafy Midway Plaisance, a generous pre-function area with built-in bar, and four studios flooded with natural light from floor-to-ceiling windows. Airy, bright, and fully A/V equipped, these rooms are popular for board meetings, baby showers, and everything in between. GUEST ROOMS & SUITES The property’s 167 guest rooms and suites feature warm wood finishes, curated artwork, and sweeping views of campus, the downtown Chicago skyline, and Lake Michigan. For wedding parties or VIPs, suites boast generous layouts ideal for hosting pre-event preparations or intimate in-room gatherings. TRUTH BE TOLD, The hotel’s British-inspired pub and lounge offers a cozy yet refined setting for rehearsal dinners, farewell brunches, or fireside cocktails. Its inviting atmosphere and approachable menu make it a natural complement to any event.

• Spaces for 1-275 Guests
• 1 Outdoor
• 3 Event Spaces
• 4 Total Spaces

The Ivy Room is a modern oasis in the heart of River North at Medinah Tree Studios, just two blocks from the Magnificent Mile, and in close proximity to the Loop, Navy Pier, and Millennium and Grant Parks. When you host your event at The Ivy Room, your guests will appreciate the beauty and convenience of such an incredible Chicago venue. The Ivy Room embodies a history of artistic elegance. The ballroom windows offer picturesque views of the courtyard garden, transforming every event into an extraordinary experience. Host your intimate dinner party, engagement party, or shower in our event spaces, or choose The Ivy Room for your luxury wedding ceremony and reception.

• Spaces for 8-550 Guests
• 1 Outdoor
• 5 Event Spaces
• 5 Total Spaces

Bloom Events offers a modern, flexible setting in Chicago’s Avondale neighborhood for weddings, galas, corporate events, mitzvahs, milestone celebrations, and private gatherings. The venue features 10,000 square feet of customizable event space, including The Locus for ceremonies and receptions, the Happy Hour space for cocktails and mingling, a customizable outdoor courtyard, and two private suites. Skylights, vaulted ceilings, gilded chandeliers, built-in audiovisual capabilities, portable bars, lounge furnishings, and on-site parking complement the experience. With capacity for up to 260 seated guests with a dance floor, Bloom Events provides a thoughtfully designed blank canvas for memorable Chicago celebrations.

• Spaces for 100-1,200 Guests
• 3 Outdoor Spaces
• 2 Restaurants
• 3 Total Spaces

Nestled along Chicago's iconic North Avenue Beach, Shore Club Chicago offers a one-of-a-kind lakefront setting for weddings, corporate events, brand activations, and social celebrations. Just minutes from downtown, the venue seamlessly blends coastal-inspired design with the energy of the city, creating a destination that feels like a beachside escape in the heart of Chicago. With versatile indoor and outdoor event spaces, panoramic views of Lake Michigan, and customizable food and beverage experiences, Shore Club accommodates everything from intimate gatherings to large-scale receptions and experiential events. Whether hosting a waterfront wedding, corporate celebration, networking event, or private party, guests enjoy elevated hospitality, vibrant cuisine, and an unforgettable setting that captures the spirit of a Chicago summer.

• Spaces for 20-400 Guests
• 3 Outdoor Spaces
• 5 Restaurants
• 5 Total Spaces

Jake Melnick’s Corner Tap is Chicago’s favorite hangout famous for our wings, great burgers, terrific salads, home-cooked specialties, decadent desserts and an awesome selection of beer and cocktails — all enjoyed in a comfortable and welcoming neighborhood spot. Whether you’re hosting an intimate get together for family and friends, or a corporate reception, our experienced event planner will customize a menu that is sure to satisfy the cravings of 15 to 400 guests. Great for watch parties for any sport, as an official Bears, Bulls, Blackhawks, and Cubs bar, we’re the spot to catch all the games, no matter the season. Great for post wedding brunches, welcome parties, bachelor parties, company happy hours, and everything in between. The crew at Jake’s will make your event a huge success by providing first-class service in a laid back setting, & enough fun to keep the good times flowing and the party goers going! So don’t miss out on everything we’ve got to offer and start planning your next event with us today!

• Spaces for 40-168 Guests
• 2 Outdoor Spaces
• 2 Restaurants
• 3 Total Spaces

Located in Chicago's River North neighborhood, Monty's Chicago and Motel Bar Chicago offer two distinct hospitality experiences under one roof, seamlessly transitioning from a bright daytime café to an intimate evening restaurant and cocktail bar. Guests can gather for everything from morning meetings and casual lunches to private dinners, cocktail receptions, holiday parties, and corporate events. Contemporary interiors, warm wood finishes, vintage-inspired design, and flexible private event options create an inviting backdrop for celebrations of all kinds. Whether hosting a small gathering or a full venue buyout, the space combines thoughtful service, elevated cuisine, and handcrafted cocktails in a welcoming setting.