Big Hotels, Big Discounts, and Enough Room for Your Whole Group

Welcome stranger! Looking for an nice sized Chicago hotel that can host your entire group? These hotels below receive the most booking requests from groups of 25 or more on our booking platform.

Are you planning a trip to Chicago? There are many different reasons people travel here in groups. Sometimes it’s for work, sometimes it’s for leisure, and sometimes it’s a little of both. No matter what brings you to our beautiful city, you’re going to need proper lodging that can accommodate your entire party and offer the types of amenities you’d expect from a major Chicago hotel. 

In this post, we are going to review 10 different hotels that our users most frequently choose for their group stays. Most are big hotel chains you’ve heard of, some are local flavors. All of them will meet your expectations and amenity requirements. Let’s get started!

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#1 - Hotel Chicago West Loop 

• Address: 1622 W Jackson Blvd, Chicago, IL 60612
• 4.0 ⭐⭐⭐⭐1,315 reviews
• Nightly Rate - $119 - $130
• Group Rate - Enter your trip details here to generate your custom group rate.

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Hotel Chicago West Loop is a gorgeous lodging option located in the famed UIC Medical District, just about 2 ½ miles from Downtown Chicago. The hotel is also just across from the United Center which makes accessing events and sports games a breeze. The UI Health Campus is within walking distance just to the South. The hotel offers complimentary WiFi and rooms equipped with memory foam mattresses, flat-screen TVs, coffee machines, microwaves, and workspaces. Deluxe rooms provide additional closet space and a seating area. Amenities include a 24-hour front desk, private on-site parking, and a 24-hour fitness center. Popular attractions such as Willis Tower and the Chicago Board of Trade are nearby

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#2 – Pendry Chicago

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The Pendry is a staple Chicago hotel. Built in 1929 with class and care, the hotel is breathtaking both inside and outside. Further, it is right in the middle of everything Chicago has to offer. Pendry is located a short 19-minute walk from Ohio Street Beach and offers accommodations with free bikes, private parking, and a fitness center. The hotel features a restaurant, 24-hour room service, and a shared lounge, along with free WiFi throughout the property. Rooms are equipped with flat-screen TVs, safety deposit boxes, and coffee machines. Some rooms offer city views, and all include private bathrooms with showers and complimentary toiletries. Guests can enjoy amenities such as a terrace, business center, and an on-site bar. McCormick Place Convention Center, the Chicago Symphony Orchestra, and Cloud Gate are nearby, with Midway International Airport located 11 miles away.

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#3 – DoubleTree by Hilton - Magnificent Mile

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Where to even begin with this beautiful establishment? If you like the Magnificent Mile, this is your hotel. Located at the Southern end of The Magnificent Mile, you have access to everything Chicago has to offer. 

The hotel features an on-site restaurant, HotHouse, which serves breakfast and dinner in a social setting. Each modern room is equipped with a coffeemaker, iPod docking station, and a 50-inch flat-screen TV. Guests also enjoy complimentary toiletries and receive a signature chocolate chip cookie at check-in. The hotel provides a fitness center and offers free WiFi. Millennium Park is less than a mile away.

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#4 - Hilton Garden Inn Chicago Downtown 

• Address: 10 E Grand Ave, Chicago, IL 60611
• 4.1 ⭐⭐⭐⭐ 2,464 reviews
• Nightly Rate – $190 - $220 average
• Group Rate – Enter your trip details here to generate your custom group rate.

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The Hilton Garden Inn Chicago Downtown, just as you may expect from the description, is located right in the middle of Downtown Chicago. This massive hotel most certainly has the space to host your entire group, no matter how large. Sports teams? They got you. Construction crews? A little fancy for a construction crew, but sure. Government contractors, business travelers, church groups? This place has enough space for any group you can imagine. 

This hotel offers a wide range of amenities for a comfortable stay. Guests enjoy free WiFi, a fully-equipped kitchen with a microwave and refrigerator, and 24-hour front desk service. The hotel features an indoor pool, a fitness center, and an on-site restaurant and bar. Additional conveniences include a business center, dry cleaning services, and covered parking. For accessibility, the property provides wheelchair-accessible paths, registration desks, fitness centers, and meeting spaces. Other amenities include electric car charging stations, a gift shop, room service, and express check-in/out.

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#5 - Swissotel - Chicago

• Address: 323 E Wacker Dr, Chicago, IL 60601
• 4.7 ⭐⭐⭐⭐⭐ 5,672 reviews
• Nightly Rate – $265 average
• Group Rate – Enter your trip details here to generate your custom group rate.

The Swiss Hotel in Chicago leaves nothing out. Kitchens, double or single beds, living rooms, and AMAZING views of the city. This is for those groups who are looking for a bit more razzle dazzle. If you want to live like a king or queen while in Chicago, this is your place. 

Popular features include a fitness center, business center, 24-hour front desk, on-site restaurant, bar, and smoke-free environment. Rooms are equipped with refrigerators and coffee makers, and room service is available 24 hours. Pet-friendly and featuring recreational activities like nearby hiking, biking, and water sports, the hotel provides services such as concierge, dry cleaning, and banquet facilities.

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#6 - Central Loop Hotel

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Located in the heart of Chicago’s Loop, Central Loop Hotel offers easy access to the Art Institute of Chicago and Millennium Park, both just three blocks away. The hotel features modern amenities like free WiFi, an on-site restaurant, and state-of-the-art workstations. Rooms are equipped with custom-designed furnishings, plush pillow-top mattresses, ergonomic workstations, and optional exercise equipment or air purifiers upon request. The hotel offers a 24-hour concierge, a fitness center, and business services. Guests can dine at the Elephant & Castle Pub, serving British and North American cuisine. The Chicago Board of Trade is a 2-minute walk from the hotel. Your whole group will love this lodging choice. 

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#7 - Hyatt Regency Chicago 

• Address: 151 E Wacker Dr, Chicago, IL 60601
• 4.5 ⭐⭐⭐⭐⭐ 10,675 reviews
• Nightly Rate – $283 - $332 average
• Group Rate – Enter your trip details here to generate your custom group rate.

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The Hyatt Regency Chicago is located just North of Millenium Park and offers breathtaking views of the city, the Chicago River, and Lake Michigan. Some notable amenities include some great on-site features such as car rentals, bar/lounge, restaurant, Conference space, and a spa. This is a favorite stop for many of our business travelers when they hit Chicago. The review count and number of reviews should tell you all you need to know. Highly recommended. 

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#8 - Four Seasons Hotel Chicago 

• Address: 120 E Delaware Pl, Chicago, IL 60611
• 4.7 ⭐⭐⭐⭐⭐ 1,521 reviews
• Nightly Rate – $1100 average
• Group Rate – Enter your trip details here to generate your custom group rate.

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Is any “top hotels” type list really complete without listing The Four Seasons? One of the consistently highest rated hotels in our impressive stable of partners, The Four Seasons is a breathtaking establishment but not for the faint of heart when it comes to spending money. If you’re prepared to shell out the bucks, this hotel will drench you in extravagance and luxury. This is a favorite stop for our executives, CEOs, and similar types of travelers. Your hotel room feels more like a private condo than it does a hotel room, there are no corners cut when it comes to the quality of this accommodation, everyone should experience it once, if they can. 

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#9 - The Peninsula Chicago 

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The Peninsula Chicago is a fabolous choice for large group reservations. Located along the Magnificent Mile, the hotel offers luxury accommodations just a 5-minute walk from the Museum of Contemporary Art. This hotel features a full-service Asian-inspired spa, award-winning dining, and spacious guest rooms with city views. Each room includes a 42-inch flat-screen TV, free Wi-Fi, a temperature and lighting control console, and a soaking tub in the private bathroom. Guests can enjoy a half-Olympic indoor pool with floor-to-ceiling windows, a modern gym with fitness classes like yoga, and an outdoor terrace overlooking the city. The hotel’s restaurants, including The Lobby, serve contemporary American cuisine, and afternoon tea with champagne and chocolate is available. Water Tower Place is located across the street, and Navy Pier is a 15-minute walk from the hotel.

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#10 - Congress Plaza Hotel

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We have a lot of fancy and upscale hotels on this list but not many options for the budget conscious. So, I figured we better squeeze another one in before we complete this top 10 post. Located directly across from Millennium Park on Michigan Avenue, the Congress Plaza Hotel blends historic charm with modern amenities in the heart of downtown Chicago. This hotel offers stunning city and lake views, free WiFi, and a variety of on-site dining options. Each room features high ceilings, spacious bathrooms, flat-screen TVs, coffee makers, work desks, and ironing facilities. Some rooms offer family-friendly layouts and separate living areas. Guests can dine at Rafael’s for American classics and seasonal dishes or enjoy breakfast at Gazebo. The Congress Lounge provides a relaxed setting with city views and large-screen TVs. Amenities include a 24-hour fitness center, barbershop, same-day dry cleaning, and shoeshine services. The hotel boasts 23 event spaces, including the historic Gold Room. Congress Plaza Hotel is within walking distance of top attractions like the Art Institute of Chicago and Buckingham Fountain, with the Magnificent Mile just a 10-minute walk away.

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#11 - Omni Chicago Hotel - Magnificent Mile

The Omni Chicago Hotel sits at 676 North Michigan Avenue, placing groups in the heart of the Magnificent Mile’s shops, theaters, and restaurants. Housed in a 1993 landmark tower, this all-suite property offers 347 spacious one- and two-bedroom layouts, each with separate living areas, wet bars, and city-scape views. The generous suite count ensures that even sizeable parties, ranging from destination weddings to corporate offsites, can be accommodated under one roof without sacrificing comfort or privacy.

The hotel’s 8,000 square feet of adaptable event space is a major draw; spread across nine breakout rooms and two larger ballrooms, the venues can host everything from board meetings to gala dinners. Group blocks can start as small as ten suites and scale up to 300 rooms, and the in-house sales team handles rooming lists, connecting-suite requests, and customized catering menus to keep logistics seamless.

Omni Chicago’s central location further streamlines group travel logistics. It is a short drive from both O’Hare and Midway airports, and direct access to the Chicago “L” makes neighborhood hopping effortless. After a day of sessions, attendees can gather in the lobby lounge or unwind in the fitness center before reconvening for dinner just steps away.

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#12 - Hotel Felix - River North / Magnificent Mile

Hotel Felix occupies a prime spot at 111 West Huron Street in Chicago’s River North district, just a short stroll from the Magnificent Mile’s shops and restaurants. This eco-certified boutique hotel features 228 guest rooms and suites adorned with natural materials and modern amenities. Room types range from cozy one-bed layouts to multi-bedroom suites that can sleep up to eight, making it easy to house families or small teams together.

For group gatherings, Hotel Felix offers over 1,100 square feet of versatile event space spread across three distinct venues. The intimate Terra boardroom accommodates focused strategy sessions while the Jade and Brook rooms can be configured for classroom-style trainings or cocktail receptions. Group room blocks begin at ten rooms and can expand to more than two hundred, with a dedicated sales team managing rooming lists, connecting-room requests, and tailored catering packages to keep plans running smoothly.

Logistically, the hotel’s central location streamlines group travel. Both O’Hare and Midway airports are within a 30-minute drive and the nearby Chicago “L” provides direct access to downtown destinations. After a day of meetings or excursions, attendees often regroup at the rooftop lounge or in the bright, naturally lit lobby before heading out to explore the city’s nightlife and dining scene.

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#13 - LondonHouse Chicago

LondonHouse Chicago occupies the historic corner of North Michigan Avenue and Wacker Drive in a restored 1923 Beaux Arts landmark paired with a modern glass tower. The hotel features 452 spacious rooms and suites with floor-to-ceiling windows, contemporary decor, and versatile sleeping configurations to accommodate families, small teams, or larger party travel.

The property offers over 25,000 square feet of flexible event space across 13 distinct venues, including private boardrooms, meeting rooms, and a grand ballroom with sweeping river views. It can support intimate strategy sessions or gala dinners for up to 300 guests. Group room blocks start at a minimum of ten rooms and can scale up to the full 452-room inventory, and a dedicated events team manages rooming lists, connecting-room requests, and customized catering menus to streamline planning.

Ideal for group arrivals and departures, the hotel is within a 30-minute drive of both O’Hare and Midway airports and adjacent to several “L” train stations for easy access to key business and cultural districts. After meetings or sightseeing, attendees can unwind at the tri-level rooftop lounge, dine riverside at Onyx Tavern, or enjoy the fitness center and spa without leaving the property.

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#14 - Eurostars Magnificent Mile

Perched in Chicago's dynamic River North district, Eurostars Magnificent Mile places you at the epicenter of urban allure, mere moments from the iconic shops and eateries of the Magnificent Mile. This modern boutique hotel offers a striking collection of 216 guest rooms and suites, each thoughtfully designed with expansive floor-to-ceiling windows, luxurious bedding, ergonomic workstations, and the latest in connectivity with high-speed Wi-Fi and smart TVs. Traveling with a group? No problem. Intelligent room layouts, including connecting options, ensure that teams and families can enjoy proximity without compromising on personal space.

For those planning events, the hotel provides over 3,700 square feet of adaptable event space, spread across five distinct meeting rooms. The crown jewel is the largest ballroom, boasting approximately 1,850 square feet of unobstructed space with captivating city vistas. Every venue is naturally lit and equipped with advanced audiovisual technology, modular furniture, and robust internet access. Planning a group stay is effortless, with room blocks starting at ten rooms and the flexibility to reserve the entire 216-room inventory. A dedicated events team is on hand to expertly manage everything from rooming lists and connecting room requests to bespoke catering and on-site logistics, ensuring a flawless experience.

The hotel's prime location simplifies group arrivals and departures, being under three miles from O’Hare International Airport—a quick 15-minute drive or direct CTA ride away. "L" stations nearby offer effortless access to the Loop, Navy Pier, and a myriad of Chicago’s cultural gems. When the day's agenda winds down, attendees can find respite on the open-air rooftop terrace, complete with custom lounge seating and panoramic skyline views, socialize in the chic lobby lounge, or recharge at the fitness center before diving into Chicago’s electric nightlife and culinary landscape.

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#15 - Sofitel Chicago Magnificent Mile

At 20 East Chestnut Street in Chicago’s vibrant Gold Coast, Sofitel Chicago Magnificent Mile stands as a 33-story beacon of French flair woven into the city’s architectural tapestry. The hotel has 415 rooms and 63 suites, each with sweeping windows, customizable sleep setups, and interconnecting options that cater to groups or families seeking both togetherness and private retreats. Its expansive room availability effortlessly accommodates sizable bookings, ensuring every guest enjoys personal space with a touch of refinement.

The property boasts over 10,000 square feet of dynamic venues, including a 4,592-square-foot Grand Ballroom with open designs and breathtaking river views, plus nine compact rooms ideal for strategy sessions, creative seminars, or exclusive gatherings. Groups can reserve as few as ten rooms or the entire hotel, with an expert events crew handling room pairings, connecting suites, and bespoke menus to streamline planning for corporate summits, weddings, or festive occasions.

A quick 30-minute ride from O’Hare or Midway airports and mere steps from “L” train stations, the hotel makes group travel smooth and stress-free. Post-meetings or city adventures, guests can mingle in the sleek Lounge Bar, recharge at SoSPA, or work out in the modern fitness hub before diving into the Magnificent Mile’s nearby shops, cultural spots, and eateries just beyond the hotel’s entrance.

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#16 - Loews Chicago Hotel

Loews Chicago Hotel, commanding the lower levels of a striking 52-story glass tower at 455 North Park Drive, offers an exceptional experience for discerning professionals, groups, and business travelers. Conveniently located in the vibrant Streeterville neighborhood, we're just moments from the Chicago River and the iconic Michigan Avenue, placing your team at the heart of the city's dynamic energy. Our 400 meticulously appointed guest rooms, including 25 sophisticated suites, feature expansive floor-to-ceiling windows that frame breathtaking cityscapes. Thoughtfully designed with flexible sleeping arrangements, our accommodations effortlessly cater to individual executives, small teams, or larger corporate groups, ensuring both comfort and productivity.

For your next corporate gathering, conference, or gala, Loews Chicago Hotel provides over 30,000 square feet of versatile event space. This includes two impressive, column-free ballrooms and eleven adaptable breakout rooms, ideal for everything from intimate board meetings to large-scale conventions. The expansive 9,000-square-foot outdoor terrace offers a distinct setting for receptions and networking events with stunning urban backdrops. We simplify group accommodations with room blocks starting at ten rooms, scalable up to our full 400-room inventory. Our dedicated events team provides seamless support, managing rooming lists, coordinating connecting room requests, and crafting customized catering plans to ensure your event's success.

Accessibility is paramount for business travel, and Loews Chicago Hotel excels. We're a convenient 30-minute drive from both O'Hare and Midway International Airports, and direct access to a Red Line L train station further streamlines arrivals and departures for your entire group. Beyond the boardroom, our executive amenities provide the perfect environment for unwinding and networking. Guests can gather at our sophisticated rooftop lounge to enjoy unparalleled skyline views, maintain their routine in our state-of-the-art fitness center, or take a refreshing dip in the indoor lap pool. Our prime location also offers immediate access to world-class dining and entertainment along the Magnificent Mile and Chicago Riverwalk, allowing your attendees to effortlessly transition from business to leisure.

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#17 - Fairmont Chicago at Millennium Park

If you're organizing a substantial group visit to Chicago and need to keep everyone together under one roof, Fairmont Chicago at Millennium Park is your ideal solution. Situated at 200 North Columbus Drive in the heart of downtown, our hotel places your entire contingent just a block from the iconic Millennium and Grant Parks, and steps from the endless shopping and dining experiences of the Magnificent Mile. With an impressive 686 guest rooms and 65 suites, we offer the scale and sophistication necessary to comfortably accommodate even the largest groups. Many rooms provide stunning panoramic city and lake views, and for those seeking an elevated experience, upgrading to the Fairmont Gold level provides personalized service and exclusive access to our executive lounge.

Fairmont Chicago boasts over 60,000 square feet of flexible meeting and event space, spread across 15 distinct venues, ensuring we can cater to every aspect of your group's agenda. Our grand ballroom offers a column-free layout, perfect for major conferences or elaborate gala dinners, while a selection of boardrooms and breakout rooms are available for more intimate strategy sessions and workshops. We specialize in accommodating large groups, with room blocks starting at just ten rooms and the capability to expand to our full inventory of 686 rooms. Our dedicated events team is here to manage all the details, from precise rooming lists and connecting-room requests to customized catering menus, guaranteeing a seamless experience for your entire party.

Getting your group to and from the hotel is straightforward thanks to our central location. O’Hare International Airport is 18 miles northwest and Midway Airport is 12 miles southwest, with multiple CTA stations just an easy walk away, simplifying arrivals and departures for everyone. After a productive day of meetings or exploring the city, your attendees can unwind at the tranquil Leaf Spa, enjoy the skyline views from our rooftop terrace, or take a leisurely stroll through Millennium Park and along the Chicago Riverwalk before rejoining for dinner or evening events. Fairmont Chicago at Millennium Park is committed to ensuring your entire group enjoys a unified, comfortable, and memorable stay.

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#18 - Sheraton Grand Chicago Riverwalk

At 301 East North Water Street, poised along the picturesque Chicago Riverwalk and mere steps from the Magnificent Mile’s elite boutiques and dining, Sheraton Grand Chicago Riverwalk redefines luxury for discerning travelers and sophisticated groups. This premier destination offers 1,218 exquisitely appointed guest rooms, revitalized through a multimillion-dollar transformation. Each space boasts expansive floor plans, bespoke ergonomic workstations, and versatile bedding arrangements, effortlessly catering to high-profile families, executive teams, or expansive group reservations with unparalleled elegance.

The hotel commands 125,000 square feet of opulent event space across 43 distinctive venues, including one of Chicago’s grandest hotel ballrooms, accommodating up to 4,600 guests in regal style. Group bookings, starting at just ten rooms and scalable to the entire property, are curated by an elite events concierge team, who orchestrate tailored room assignments, seamless connecting-suite arrangements, and gourmet catering experiences, ensuring flawless execution for high-stakes corporate galas, exclusive weddings, or lavish social soirées.

Conveniently reachable with a swift 18-mile journey from O’Hare International Airport or a 12-mile trip from Midway, and moments from CTA “L” stations, the hotel guarantees effortless arrivals and departures for even the most discerning groups. After productive meetings or curated city explorations, guests can rejuvenate in the state-of-the-art 24-hour fitness center, indulge in a refreshing swim in the indoor lap pool, or savor crafted cocktails on the breathtaking riverfront terrace before immersing themselves in the cultural and culinary riches of downtown Chicago, just beyond the hotel’s doors.

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#19 - The Royal Sonesta Chicago Downtown

Planning to keep your whole crew under one roof in Chicago? The Royal Sonesta Chicago Downtown offers a refined home base that meets the demands of larger parties. Its 381 refreshed guest rooms give everyone plenty of breathing room, and many look directly onto the river or the city skyline to elevate the stay.

Groups will appreciate the hotel’s extensive 16,000 square feet of adaptable event space spread across 18 rooms. High on the 39th floor, the Penthouse Ballroom steals the show with wraparound windows, panoramic city views, and an adjacent 1,600-square-foot terrace perfect for receptions under the open sky. A dedicated events staff coordinates rooming lists, adjoining-room requests, and custom menus, smoothing out every detail from first inquiry to final toast.

Positioned along the Chicago River and only a short stroll from the Magnificent Mile, the property places shopping, dining, and attractions at the doorstep. Both O’Hare and Midway airports are about a half-hour drive, while several CTA lines are within easy walking distance for effortless arrivals and departures. Between outings, guests can recharge in the river-view fitness center or step outside to explore the vibrant downtown scene. The Royal Sonesta Chicago Downtown keeps your group close, comfortable, and connected right in the center of the Windy City.

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#20 - theWit Chicago

As a professional business traveler myself, I gravitate toward venues that double as brand storytellers, and theWit Chicago excels at turning every touchpoint into buzz-worthy content. Rising above the Loop’s theater district, the property delivers a playful, design-forward aesthetic that photographs beautifully, whether you are posting a sneak peek of your kickoff breakfast or a sunset shot from the rooftop lounge.

Inside, just over three hundred refreshed guest rooms and thirty-plus suites give your attendees a comfortable retreat without scattering the group across multiple addresses. Fourteen adaptable meeting rooms, approximately fourteen thousand square feet in total, feature floor-to-ceiling windows, built-in LED walls, and seamless technology that keeps presentations crisp and brand graphics on point. For a show-stopping reception, move the crowd twenty-seven stories up to ROOF, where skyline views and retractable-roof versatility create instant shareable moments. An on-site events team, versed in everything from room-block strategy to custom F&B, keeps logistics tidy so you can focus on event ROI.

The address itself works overtime for your marketing plan. Steps from State and Lake El stations, the hotel places the Riverwalk, Millennium Park, and the Magnificent Mile within an easy walk, simplifying itineraries and reducing transfer costs. Both O’Hare and Midway sit about thirty minutes away by car, so arrivals and departures stay on schedule. Add a spa, a 24-hour fitness studio, and chef-driven dining, and you have a Chicago headquarters that keeps your message cohesive, your attendees comfortable, and your campaign results measurable; all under one roof.

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