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

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
• 1,315 reviews + 4.0 Rating
• Nightly Rate - $280‍
• 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
• 2,464 reviews + 4.1 Rating
• Nightly Rate – $163 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
• 5,672 reviews + 4.7 Rating
• 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
• 10,675 reviews + 4.5 Rating
• Nightly Rate – $213 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
• 1,521 reviews + 4.7 Rating
• Nightly Rate – $695 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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