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  • Chicago

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    Property Types

    • Hotel
    Staypineapple, An Iconic Hotel, The Loop Thumbnail
    Staypineapple, An Iconic Hotel, The Loop
    Chicago, 1 West Washington
    Historic Chicago architecture, designed by world renowned architect Daniel Burnham, with mosaic floors and marble ceilings inspire luxury at this hotel in Chicago’s Loop. Shopping on famed Michigan Avenue and Millennium Park are a short walk away. White and gray colors with mahogany furnishings are balanced by modern amenities like a flat-screen TV and plush bedding in each room. Select suites feature stunning views of Millennium Park and Lake Michigan. Staypineapple, An Iconic Hotel, The Loop has a fitness center and bicycle rental service. Pets receive free bedding and water upon request. Chicago’s entertainment center, Navy Pier, is 1.9 mi from the hotel. The Chicago Theater and Art Institute of Chicago are less than 5 minutes’ walk away.
    8.9 735 Reviews | 4-Star Hotel
    $2292/person
    $4755
    $4583
    total

    Incl. hotel + flight

    Moxy by Marriott Chicago Downtown Thumbnail
    Moxy by Marriott Chicago Downtown
    Chicago, 530 North Lasalle Drive
    Located within 2297 feet of the Magnificent Mile, Moxy Chicago Downtown in Chicago has a number of amenities including a fitness center and a bar. Located around a 10-minute walk from Water Tower Chicago, the hotel with free WiFi is also surrounded by dining and nightlife in River North. Local points of interest like 360 Chicago and CIBC Theater are reachable within 0.7 mi and 0.8 mi, respectively. The units in the hotel are fitted with a flat-screen Smart TV with streaming capabilities. Moxy Chicago Downtown offers certain units with city views, and the rooms include a private bathroom. The restaurant at the accommodations serves Mexican cuisine. Staff at the reception can help guests with any questions that they might have. Bank of America Theater is 0.8 mi from Moxy Chicago Downtown, while Cloud Gate - The Bean is 0.8 mi away. The nearest airport is Midway International Airport, 9.3 mi from the property.
    9.0 453 Reviews | 3-Star Hotel
    $2473/person
    $5177
    $4945
    total

    Incl. hotel + flight

    Aloft Chicago Downtown River North Thumbnail
    Aloft Chicago Downtown River North
    Chicago, 515 North Clark Street
    Located just 3 blocks away from shopping and dining spots on the Magnificent Mile, this boutique hotel offers modern accommodations in Chicago’s River North neighborhood. Free WiFi is available. Every room at Aloft Chicago City Center includes a 42-inch flat-screen TV, small refrigerator and coffee machine. Free bottled water is also provided. The Chicago City Center Aloft has a lounge with a pool table. There is a modern fitness center and business center located on-site. Free dog beds are available at this pet friendly hotel. Beatrix, the on-site neighborhood restaurant, serves unique uniquely inspired cuisine for breakfast, lunch and dinner. River North Bar is located within the restaurant and offers hand-crafted cocktails, along with a carefully selected wine and beer list. Navy Pier, Millennium Park and the Art Institute are all 1 mile from the hotel. O'Hare International Airport is a 30-minute drive away.
    8.8 385 Reviews | 3.5-Star Hotel
    $2484/person
    $5204
    $4968
    total

    Incl. hotel + flight

    Cambria Hotel Chicago Loop - Theatre District Thumbnail
    Cambria Hotel Chicago Loop - Theatre District
    Chicago, 32 W Randolph St
    Just steps away from the famed shopping on State Street, this boutique hotel is located inside the Oriental Theater building in the Chicago Loop Theater District. The hotel features on-site dining, state-of-the-art business services and modern guest rooms with free WiFi. Every room at Cambria Hotel Chicago Loop/Theater District provides a 49-inch flat-screen HDTV and a large work space with a desk and ergonomic chair. Select rooms also offer plush lounge seating. Intermission Restaurant and Bar features local craft beer, signature cocktails and dishes with fresh, local flavors for breakfast, lunch and dinner. A fitness center, games room and banquet space are all available on-site. Business travelers have access to fax and copy services at the hotel business center, which also offers guest computers. Valet cleaning and in-room dining services are offered for guest convenience. Millennium Park is 5 blocks away from the hotel. The Shedd Aquarium and Field Museum are both 2 miles away.
    8.4 1007 Reviews | 4-Star Hotel
    $2390/person
    $4779
    total

    Incl. hotel + flight

    Eurostars Magnificent Mile Thumbnail
    Eurostars Magnificent Mile
    Chicago, 660 North State Street
    This boutique Chicago hotel is located in the heart of city, just 5 minutes' walk from the luxury shops of the Magnificent Mile. It features modern rooms with a flat-screen TV and free Wi-Fi. Each room at Eurostars Magnificent Mile offers a mini-bar with chilled wine and floor-to-ceiling windows. A fitness center is located on site, along with concierge services. This hotel is within 10 minutes’ walk of the Museum of Contemporary Art. Navy Pier is 1 mile away.
    8.8 2676 Reviews | 4-Star Hotel
    $2525/person
    $5049
    total

    Incl. hotel + flight

    InterContinental Chicago Magnificent Mile By IHG Thumbnail
    InterContinental Chicago Magnificent Mile By IHG
    Chicago, 505 North Michigan Avenue
    Located on Michigan Avenue’s Magnificent Mile, this historic luxury hotel is located in the heart of downtown Chicago and features renowned on-site restaurants and an indoor pool with elevated bleacher seating. Every room at InterContinental Chicago Magnificent Mile provides a flat-screen LCDTV with premium cable channels and a coffee maker. Some rooms also offers Italian marble bathrooms and upscale luxury bedding. Michael Jordan’s Steakhouse and Bar features prime steak and seafood for lunch and dinner. . For breakfast and lunch, guests can enjoy traditional, fresh dishes at Center Court. Guests can work out in the multi-level modern fitness center or relax at the sauna or spa on-site. A 24-hour business center and historic event space are also available. Navy Pier, Millennium Park and Oak Street Beach are all less than a mile away from InterContinental Chicago Hotel. The Shedd Aquarium and Art Institute of Chicago are both a 15-minute drive away. Newly Renovated Grand Tower Rooms
    8.3 306 Reviews | 4.5-Star Hotel
    $2418/person
    $5401
    $4835
    total

    Incl. hotel + flight

    Doubletree By Hilton Chicago Magnificent Mile Thumbnail
    Doubletree By Hilton Chicago Magnificent Mile
    Chicago, 300 East Ohio Street
    Boasting an outdoor pool in the heart of downtown Chicago, this hotel is located within 5 minutes’ walk of the famous Magnificent Mile. It features 1 on-site restaurant called HotHouse and a flat-screen TV in every room. A coffeemaker is provided in every modern room at DoubleTree by Hilton Chicago Magnificent Mile. Guests can enjoy the convenience of free toiletries and an iPod docking station during their stay. A 50-inch flat-screen TV is provided as well. A well-equipped fitness center is available at Magnificent Mile DoubleTree. Every guest receives a chocolate chip cookie at reception. Hot House is an open concept restaurant with space to socialize and grab a cocktail. It serves breakfast and dinner. Millennium Park is less than 1 mile away. Willis Tower can be reached in 10 minutes’ drive.
    8.2 997 Reviews | 4-Star Hotel
    $2442/person
    $4884
    total

    Incl. hotel + flight

    Le Méridien Essex Chicago Thumbnail
    Le Méridien Essex Chicago
    Chicago, 800 South Michigan Avenue
    Hotel Essex includes a terrace with city views and free high speed WiFi access. Ideally located within steps of the best Chicago experiences, the Essex is 1.4 mi away from the world famous Chicago Museum Campus. An iPod/MP3 dock and a flat-screen cable TV are standard in every guest room with colorful décor and rich wood accents at the Hotel Essex. Rooms include a refrigerator, and a desk as well. At the Hotel Essex you will find a modern fitness center with state-of-the-art cardiovascular equipment. The hotel is 1969 feet from Grant Park, 2625 feet from Chicago Symphony Orchestra, and 2625 feet from DePaul University. Chicago O'Hare International Airport is 16 mi away.
    8.5 269 Reviews | 4-Star Hotel
    $2587/person
    $5173
    total

    Incl. hotel + flight

    Hilton Garden Inn Chicago Downtown/Magnificent Mile Thumbnail
    Hilton Garden Inn Chicago Downtown/Magnificent Mile
    Chicago, 10 East Grand Avenue
    Just 2 blocks away from the shops and entertainment on the Magnificent Mile, this hotel is located in Chicago’s River North neighborhood and features an on-site restaurant, 24-hour business center and fitness center. Free WiFi is available. Each room at Hilton Garden Inn Chicago Downtown/Magnificent Mile offers a flat-screen HDTV, microwave and refrigerator. A coffee machine is also included. Guests can enjoy a swim in the indoor heated pool, which are enclosed by floor-to-ceiling windows offering iconic city views. There is also a 24-hour snack shop available on-site. The hotel is conveniently located directly across from the Grand-State Red Line subway stop, offering easy access to several of Chicago’s top attractions. Navy Pier is 1 mile away from the hotel.
    7.8 2632 Reviews | 3-Star Hotel
    $2393/person
    $4785
    total

    Incl. hotel + flight

    Ivy Boutique Hotel Thumbnail
    Ivy Boutique Hotel
    Chicago, 233 East Ontario
    Just 2 blocks away from the shopping, dining and entertainment on the Magnificent Mile, this boutique hotel is located in the heart of downtown Chicago and offers spacious rooms with floor-to-ceiling windows and upscale amenities. Featuring modern dark wood furniture and decor, all rooms at Ivy Boutique Hotel offer automatic window drapery, a 42-inch flat-screen TV and an iPod docking station. Select rooms feature a separate living room. A fully-stocked mini-bar, WiFi and in-room spa services are available for an additional fee. DiVine Lounge offers morning breakfast and an array of signature cocktails in the evening. The hotel also offers over 3,000 square feet of meeting and banquet facilities. Navy Pier and Millennium Park are both 1 mile away from the hotel. O’Hare International Airport is 16 miles away.
    8.6 1424 Reviews | 4.5-Star Hotel
    $2647/person
    $5294
    total

    Incl. hotel + flight

    Sofitel Chicago Magnificent Mile Thumbnail
    Sofitel Chicago Magnificent Mile
    Chicago, 20 East Chestnut Street
    Just 2 blocks away from the famed shopping, dining and entertainment on the Magnificent Mile, this luxury Chicago Gold Coast hotel is housed in a 32-floor prism glass building featuring stunning views of Lake Michigan and the city skyline. Adorned in French art de viver furnishings and décor, each room at Sofitel Chicago Magnificent Mile features luxury feathertop duvet bedding and a spacious marble bathroom. A mini-fridge and free WiFi are also included. Café des Architectes offers locally-sourced French-inspired cuisine, a seasonal outdoor terrace and a full bar. Guests can enjoy crafted cocktails and spirits while taking in iconic city views from Le Bar’s floor-to-ceiling windows. Room service is available. The hotel offers over 10,000 square feet of meeting space, a ballroom and a fitness center. Navy Pier and the Art Institute of Chicago are both less than 2 miles away from the hotel. Millennium Park is a 10-minute drive away.
    9.0 1107 Reviews | 4.5-Star Hotel
    $2795/person
    $5589
    total

    Incl. hotel + flight

    Crowne Plaza - Chicago West Loop By IHG Thumbnail
    Crowne Plaza - Chicago West Loop By IHG
    Chicago, 25 S Halsted St
    Moments from the United Center, home of the Chicago Bulls, this hotel offers easy access to downtown attractions along with on-site dining, comfortable guest rooms and a 24-hour fitness center. Accommodations at the Crowne Plaza Hotel Chicago are furnished with large work desks and tea and coffee-making facilities. Guests can also enjoy on-site dining at Dine restaurant, serving unique American cuisine for breakfast, lunch and dinner. The Chicago Crowne Plaza Hotel is a short L-train ride from the Magnificent Mile shopping area and Navy Pier. A number of charming shops, famed restaurants and an exciting nightlife are also nearby. Union Station, with Metra and Amtrak rail lines, is a 12 minute walk from this property.
    8.3 642 Reviews | 3.5-Star Hotel
    $2608/person
    $5215
    total

    Incl. hotel + flight

    Hyatt Centric The Loop Chicago Thumbnail
    Hyatt Centric The Loop Chicago
    Chicago, 100 W. Monroe St
    Located in Chicago’s famed Theater District, Hyatt Centric The Loop Chicago is within 10 minutes' walk of State Street shopping and the Art Institute of Chicago. This hotel features a rooftop bar with panoramic views of the city skyline. Each room features modern décor inspired by the character of Chicago and is fitted with Egyptian cotton bedding and a 42-inch flat-screen TV with Bluetooth and personal device streaming connectivity. A coffee maker and refrigerator are included for guests' convenience. The Chicago Hyatt Centric has a 24-hour fitness center with personal TVs on each treadmill. The hotel includes multiple contemporary meeting spaces with state-of-the-art business amenities. The Corner, on the 3rd floor of the hotel, offers a games area, fireplace and a large flat-screen TV in a living area space for guests to relax and play. This historic Hyatt Centric is 656 feet from CIBC Theater, 1312 feet from Willis Tower and an 8-minute walk away from Millennium Park. Chicago O'Hare International Airport is 16 mi away.
    8.5 920 Reviews | 4-Star Hotel
    $2674/person
    $6539
    $5347
    total

    Incl. hotel + flight

    Holiday Inn & Suites Chicago-Downtown by IHG Thumbnail
    Holiday Inn & Suites Chicago-Downtown by IHG
    Chicago, 506 West Harrison Street
    Only a few blocks from the Willis Tower, this Chicago city center hotel features comfortable rooms and thoughtful on-site facilities. The hotel also features a seasonal outdoor swimming pool along with modern fitness facilities. Popular area attractions, including Greek Town and the University of Illinois Chicago Campus are located close to the Chicago Downtown Holiday Inn. Shedd Aquarium, the Magnificent Mile and Navy Pier are also easily accessible with nearby public transport systems.
    8.0 458 Reviews | 3-Star Hotel
    $2578/person
    $5156
    total

    Incl. hotel + flight

    Sports Illustrated Resorts Chicago Thumbnail
    Sports Illustrated Resorts Chicago
    Chicago, 203 North Wabash Avenue
    Steps away from the iconic shopping, dining and entertainment of Michigan Avenue’s Magnificent Mile, this downtown Chicago boutique hotel puts a spin on modern luxury and comfort. Each lifestyle-focused room at Sports Illustrated Chicago is designed with focus and relaxation in mind, offering a large dressing room area separated from the bedroom by sliding door panels. The dressing area features a closet with ample shelving and storage space, a well-lit make-up desk and a luxury walk-in shower with a rainfall shower head. An ergonomic bed and a 42-inch flat-screen LG Smart TV are provided in the bedroom area.
    8.6 1009 Reviews | 4.5-Star Hotel
    $2786/person
    $5571
    total

    Incl. hotel + flight

    City Suites Hotel Thumbnail
    City Suites Hotel
    Chicago, 933 West Belmont Avenue
    Located in the city’s Boystown neighborhood, this Chicago hotel features Art Deco style décor and free WiFi. Every room at City Suites Chicago provides a flat-screen cable TV and a work desk. A fully-stocked mini-bar and small refrigerator are also included. Free access to the nearby fitness center is offered for all guests at Chicago City Suites. The hotel also offers 24-hour coffee and tea services in the lobby. Belmont CTA Station is located next to the hotel, offering easy access to top attractions and entertainment in downtown Chicago. Wrigley Field and Lincoln Park Zoo are both less than a mile away.
    8.1 558 Reviews | 3-Star Hotel
    $2645/person
    $5289
    total

    Incl. hotel + flight

    The Wade Thumbnail
    The Wade
    Chicago, 644 N Lake Shore Dr
    With stunning views of Lake Michigan and moments from the excitement of Navy Pier, this hotel is close to top attractions and features contemporary guestrooms. After a restful nights sleep on the The Wade soft featherbeds, start the morning with an energizing workout in the modern fitness center. Visit Current Chicago, the on-site restaurant specializing in seasonal Italian cuisine. Guests can enjoy lake views while enjoying sipping a microbrew or boutique wine. Enjoy an in-room film on flat-screen TVs. Spend the day relaxing at Ohio Street Beach or explore the campus of Northwestern University, both located only seconds from the "The Wade". Popular Chicago attractions, including Willis Tower and the luxury shops of the Magnificent Mile are also easily accessible.
    8.0 1512 Reviews | 4.5-Star Hotel
    $2686/person
    $5371
    total

    Incl. hotel + flight

    The Royal Sonesta Chicago River North Thumbnail
    The Royal Sonesta Chicago River North
    Chicago, 505 North State Street
    This 4-star boutique hotel is located in the heart of downtown Chicago's River North neighborhood. The eco-friendly hotel offers an indoor pool and sundeck. Featuring designs and décor inspired by the Chicago World’s Fair, every room at the The Royal Sonesta Chicago River North offers a 37-inch flat-screen TV with in-room fitness channels. Rooms also include large bathrooms with designer bathrobes and designer bath amenities. Guests at the The Royal Sonesta Chicago River North can use the 24-hour fitness center with modern equipment. A free morning coffee and tea bar is provided by the The Royal Sonesta Chicago River North. CBR, located next to the hotel, serves regional cuisine for breakfast and dinner. On the weekends a brunch menu is available as well. Just 1 minutes’ walk from the CTA Red Line, this hotel is less than 1 mile from Navy Pier and Millennium Park. O’Hare International Airport and Midway Airport are within 17 miles of this hotel.
    8.7 1173 Reviews | 4.5-Star Hotel
    $3143/person
    $6286
    total

    Incl. hotel + flight

    The Palmer House Hilton Thumbnail
    The Palmer House Hilton
    Chicago, 17 East Monroe Street
    Just 1 block away from Millennium Park and the Art Institute of Chicago, this historic downtown hotel is located in Chicago’s theater and financial district and offers on-site dining options, a modern business center and spa services. A flat-screen HDTV, desk and arm chair are offered in every modern guest room at Palmer House Hilton. t Housekeeping services are available upon request. Guests can work out at the on-site fitness center or visit the on-site spa. Lockwood restaurant offers American cuisine for breakfast, lunch, and dinner. Amid the historic lobby, guests can enjoy dinner & a crafted cocktail at the Lobby Bar. The Monroe Red Line subway station is a 1-minute walk away, providing easy access to Chicago’s top attractions. Navy Pier is 2 miles away from the hotel. Please note Red, Blue, Orange, Pink, Green, and Brown line train lines are all available immediately outside of the hotel for access to attractions and both airports.
    7.9 840 Reviews | 4-Star Hotel
    $2883/person
    $5766
    total

    Incl. hotel + flight

    HOTEL EMC2, Autograph Collection by Marriott Thumbnail
    HOTEL EMC2, Autograph Collection by Marriott
    Chicago, 228 East Ontario Street
    Located alongside the shopping, dining and entertainment of the famed Magnificent Mile, this boutique hotel is located in downtown Chicago and offers on-site dining and expansive meeting space. Featuring modern décor and hardwood floors, every room at Hotel EMC2, Autograph Collection provides a 49-inch flat-screen TV with premium cable channels and a coffee maker. A work desk and safety deposit box are also included. Guests can take in the artistic, creative atmosphere of the hotel while enjoying a crafted cocktail at The Albert Tavern, which offers seasonal cuisine for lunch and dinner. Plated breakfast items are also offered at the hotel and room service. A fitness center and valet dry-cleaning services are offered at EMC2 Hotel. Free WiFi is available in the lobby and public areas. Navy Pier and Millennium Park are both 1 mile away from the hotel. Oak Street Beach is a 15-minute walk away.
    8.9 331 Reviews | 4-Star Hotel
    $3319/person
    $6638
    total

    Incl. hotel + flight

    theWit Chicago, a Hilton Hotel Thumbnail
    theWit Chicago, a Hilton Hotel
    Chicago, 201 North State Street
    Overlooking the Chicago River, this hotel in central Chicago's Theater District offers a spa and on-site dining options, including a rooftop lounge. Guest rooms include a flat-screen cable TV. theWit, a Hilton Hotel Chicago features a state-of-the-art gym. After a workout, guests can relax in the lounge or with a massage at the hotel's full-service spa. Modern rooms boast contemporary amenities such as a 49-inch flat-screen cable TV and iPod docking station at theWit Doubletree. They also include small refrigerators and coffee facilities. State/Lake subway station is steps from the hotel. Millennium Park is a 10-minute walk away and shopping on the Magnificent Mile is a 13-minute walk from the hotel. Roof, the rooftop lounge, offers stunning views of the city as well as wood-burning oven pizza. For a more casual dining experience, State and Lake Restaurant serves American cuisine. Modern rooms boast contemporary amenities such as a 49-inch flat-screen cable TV and iPod docking station at theWit Doubletree. They also include small refrigerators and coffee facilities. *** We are no longer a Doubletree, We are now a Hilton Hotel.
    8.6 478 Reviews | 4.5-Star Hotel
    $3217/person
    $6434
    total

    Incl. hotel + flight

    Hilton Chicago Thumbnail
    Hilton Chicago
    Chicago, 720 South Michigan Avenue
    Overlooking Grant Park and Lake Michigan, this hotel is within 5 minutes’ walk of Millennium Park. It features on-site dining, an indoor pool and a 37-inch flat-screen TV with HBO in every room. An MP3 alarm clock and mini-refrigerator are included in every elegant room at Hilton Chicago. Room service is available, and free bathroom amenities are standard. A heated indoor pool and hot tub along with a seasonal sundeck are offered at Chicago Hilton. Guests can work out in the modern fitness center at an extra cost, or make use of the on-site business center. 720 South Bar & Grill serves local cuisine and craft beers for breakfast, lunch, and dinner. Kitty O’Sheas Irish pub provides live entertainment. Herb N' Kitchen offers light fare, meals to go, and coffee. Soldier Field, home to major sporting events and concerts, as well as McCormick Place for city conventions and events are hosted can be reached in 5 minutes' drive. the hotel is located across the street from Grant Park and near the Lakefront bike path that runs along Lake Michigan
    7.9 1037 Reviews | 4-Star Hotel
    $3035/person
    $6070
    total

    Incl. hotel + flight

    Trump International Hotel & Tower Chicago Thumbnail
    Trump International Hotel & Tower Chicago
    Chicago, 401 North Wabash Avenue
    Featuring stunning views from every area of the hotel, this landmark building of stainless steel and tinted glass stands 92-stories above the Loop and North Michigan Avenue along the Chicago River. Luxury spa services, fine dining and upscale amenities are among the unique services offered to guests at the hotel. Floor-to-ceiling windows showcase iconic views of Lake Michigan, Chicago River or city skyline in every spacious room at Trump International Hotel & Tower Chicago. Guests can indulge in the limestone bathroom’s deep soaking bath tub or relax with a movie on the 65-inch flat-screen cable TV. Renowned chef Nick Dostal curates a menu of classic American flavors at the on-site restaurant, Terrace 16, which features a bustling indoor dining room and bar, along with a seasonal outdoor terrace with views of Lake Michigan, the Chicago River and several of the city's iconic landmarks. Guests can enjoy a swim in the 75-foot heated indoor swimming pool or relax on the plush lounge chairs surrounding the pool. A state-of-the-art fitness center and full-service business center are available on-site. The Trump Hotel is a 2-minute walk away from the famed shopping, dining and entertainment on Michigan Avenue’s Magnificent Mile. Navy Pier is less than 2 miles away.
    9.2 989 Reviews | 5-Star Hotel
    $3535/person
    $7511
    $7069
    total

    Incl. hotel + flight

    Kinzie Hotel Thumbnail
    Kinzie Hotel
    Chicago, 20 West Kinzie Street
    Located in Chicago’s River North district, this boutique hotel is within 5 minutes’ walk of shopping and dining on the famous Magnificent Mile. Personalized concierge services are offered, along with a 24-hour business center, 24-hour fitness center and free WiFi. A 42-inch flat-screen LCD HDTV with premium cable channels and a large work desk are included in every room at Kinzie Hotel. Bathrobes and slippers can be found in the private bathroom, along with PURE bath products. Guests can book in-room massage services as well. Guests can enjoy a continental breakfast during their stay. Kinzie Hotel has partnered with the upscale Public House Gastropub offering in-room dining for lunch and dinner. Guests can enjoy tantalizing dishes such as multiple choice Mac N' Cheese or House Sliders in the comfort of their guest room. Every evening guests are welcome to enjoy a nightly reception in the Double Cross Lounge which offers each guest one complimentary drink per night and an assortment of hors d'oeuvres. Millennium Park and The Art Institute of Chicago are within 1 mile of this hotel. The Merchandise Mart is 5 minutes’ walk away.
    8.7 848 Reviews | 4-Star Hotel
    $3507/person
    $7013
    total

    Incl. hotel + flight

    LondonHouse Chicago, Curio Collection by Hilton Thumbnail
    LondonHouse Chicago, Curio Collection by Hilton
    Chicago, 85 East Wacker Drive
    Sitting on Michigan Avenue and the Chicago River in a historic landmark building, LondonHouse features Chicago’s only tri-level rooftop bar. The hotel is less than 10 minutes’ walk from Millennium Park. All spacious guest rooms at the LondonHouse Chicago include free WiFi, a large work station and a 55 inch flat-screen TV. Some rooms include Chicago skyline and historic landmark views. The 24-hour fitness center includes stat-of-the-art equipment, ballet bar and more. Professionals will enjoy the flexible meeting spaces while events in the grand ballroom with stunning views are available as well. The on-site LH offers a view with reimagined regional cuisine and cocktails. It includes a one-of-a-kind terrace overlooking the river and dining underneath the 23rd story domed cupola. Navy Pier and the Art Institute of Chicago are each within 1.2 mi of the LoundonHouse Chicago, Curio Collection by Hilton.
    9.0 704 Reviews | 4.5-Star Hotel
    $3888/person
    $7776
    total

    Incl. hotel + flight

    The Royal Sonesta Chicago Downtown Thumbnail
    The Royal Sonesta Chicago Downtown
    Chicago, 71 East Wacker Drive
    Just 4 minutes’ walk away from the shopping, dining and entertainment on the Magnificent Mile, the newly renovated The Royal Sonesta Chicago Downtown at the Riverwalk offers on-site dining, 24-hour fitness center and WiFi. Featuring views of the city or the Chicago River, every room at Royal Sonesta Chicago provides a 48-inch flat-screen TV, small refrigerator. A coffee maker is also included. The Hotel provides the following service for a fee: bottled water. Royal Sonesta Chicago modern Hoyt's Chicago, serves Midwestern-inspired dishes for breakfast, lunch and dinner. It also features views of the Chicago River. A business center, ballroom and meeting space are available on-site . The Art Institute of Chicago and Millennium Park are both less than a mile away from the hotel. The Theater District is a 5-minute walk away.
    8.7 1213 Reviews | 4-Star Hotel
    $3957/person
    $7914
    total

    Incl. hotel + flight

    Loews Chicago Hotel Thumbnail
    Loews Chicago Hotel
    Chicago, 455 North Park Drive
    A rooftop lounge with views of the city skyline, on-site modern restaurant and a large indoor lap pool highlight the Loews Chicago Hotel. Located near the Chicago River, the hotel with free WiFi access is 10 minutes’ walk from Navy Pier. Each guestroom features a distinctly Chicago design and offers city and lake views. Modern amenities like an iPod dock and 42-inch flat-screen TV are equipped in every room. Extras include a mini-bar, Keurig® coffee maker and luxury bedding. Loews Chicago Hotel has multiple spacious meeting facilities, including 1 boardroom with video conferencing capabilities. There is a state-of-the-art fitness center that is open 24 hours a day. The hotel is within 1 mile of Millennium Park, the Magnificent Mile, and Millennium Station. Chicago O'Hare International Airport is 18 miles away from the hotel, while Midway International Airport is just 12 miles away. The Destination Fee will include the following: - $10 Uber credit per stay (valid during hotel stay and only in Chicago area. It is activated at check-in and expires at 4:00PM day of departure) - $10 daily food and beverage credit - 10% off local entertainment at Milk + Honey, Big Bus Tours, and Volare - Daily Premium Wi-Fi The indoor lap pool will be closed for repairs through July 31st. We apologize for any inconvenience at this time and look forward to welcoming guests back once repairs are complete.
    9.1 949 Reviews | 4.5-Star Hotel
    $5331/person
    $10662
    total

    Incl. hotel + flight

    Four Seasons Hotel Chicago Thumbnail
    Four Seasons Hotel Chicago
    Chicago, 120 East Delaware Place
    Just steps away from the luxury shopping, dining and entertainment on Michigan Avenue’s Magnificent Mile, this downtown Chicago hotel features skyline city views, an on-site restaurant and lavish spa. Free WiFi is available. Featuring a stunning remodel and marble bathrooms with Le Labo toiletries, every room at Four Seasons Chicago offers panoramic views of the Chicago skyline or Lake Michigan, a flat-screen LCD TV and iHome clock radio. At Adorn Bar & Restaurant, located on the 7th floor of the hotel guests can enjoy views of Magnificent Mile and downtown skyline. Starring the bounty of the American Midwest, Adorn features globally inspired cuisine and cocktails with best-in-class service in an iconic location. The Spa at Four Seasons offers a 50-foot indoor pool and state-of-the-art fitness center. The hotel offers also on-site business center, open 24-hours and a Kids' Clubroom, which offers video games, foosball, arts and crafts and a movie area. Millennium Park, Art Institute of Chicago and Lincoln Park Zoo are all 1.5 miles away from the hotel. 900 North Michigan Shops is just floors below the Hotel. Navy Pier is a 10-minute drive away.
    9.0 163 Reviews | 5-Star Hotel
    $5288/person
    $10576
    total

    Incl. hotel + flight

    Waldorf Astoria By Hilton Chicago Thumbnail
    Waldorf Astoria By Hilton Chicago
    Chicago, 11 East Walton
    Located in Chicago's prestigious Gold Coast neighborhood, Waldorf Astoria Chicago offers a sophisticated retreat with timeless French-inspired elegance. Guests are welcomed by a stunning private courtyard reminiscent of a French château. This luxury hotel features an on-site spa and wellness center, a refined restaurant, and a stylish speakeasy cocktail lounge. High-end shopping at Oak Street and The Magnificent Mile is just a 5-minute walk away. Each room is thoughtfully designed with contemporary style and luxurious details, featuring a mini-bar and a marble-tiled bathroom with deep soaking tubs. Suites offer added indulgences, including cozy fireplaces and private terraces. Select accommodations include a terrace or sofa bed, perfect for elevated relaxation. Unwind at the serene spa and health club with rejuvenating treatments or enjoy a refreshing dip in the indoor pool. A modern fitness center is also available to meet all wellness needs. The Brass Tack, an upscale American brasserie, delights with an extensive wine list, fashionable cocktails, and flavorful dishes crafted with care. The intimate speakeasy, Bernard's offers innovative cocktails and shareable nosh in an effortlessly chic setting. Discover top attractions nearby, including Navy Pier, just 1.2 miles away, and Millennium Park, located 1.3 miles from the hotel.
    8.6 224 Reviews | 5-Star Hotel
    $5113/person
    $10225
    total

    Incl. hotel + flight

    The Ritz-Carlton Chicago Thumbnail
    The Ritz-Carlton Chicago
    Chicago, 160 East Pearson Street
    Located atop the famous Water Tower Place in Chicago’s Gold Coast district, this hotel offers artfully decorated guest rooms that feature city of lake views from large picture windows. The luxury shops and restaurants of the Magnificent Mile are just steps from this hotel. A flat-screen TV is included in every room at Ritz-Carlton, Chicago. Wifi in the room is provided for a fee of USD 14.95. Each room also includes a spacious marble bathroom with free deluxe toiletries. Guests can enjoy an aquatic workout in the temperature-controlled, four-lane lap pool or relax in the on-site spa. The hotel features 24-hour concierge services and 2 restaurants, cafe and bar on site: Torali Italian-Steak, Rooftop at Torali, The Cafe, Torali Bar. Guests can also use the modern fitness center or the 24-hour business center at the Chicago Ritz Carlton. This hotel is less than 1 mile from the Navy Pier entertainment area. The Chicago Museum of Contemporary Art is adjacent to the hotel.
    8.8 78 Reviews | 5-Star Hotel
    $5533/person
    $11735
    $11065
    total

    Incl. hotel + flight

    How Far in Advance Customers Book

    Peak bookings 1 week ahead; low early demand.

    In Chicago, peak package bookings occur 1 week prior to travel, coinciding with an average 31% discount, indicating last-minute travel incentives. Conversely, early bookings (21 weeks ahead) show negligible engagement, suggesting low demand during off-peak periods. Overall, this reflects seasonal travel behavior.

    Customer Preference by Hotel Category

    4-star hotels most popular; moderate gap with 3-star.

    In Chicago, 4-star hotels dominate bookings at 58% with a 24% discount, followed by 3-star hotels at 26% with a 20% discount. The gap is moderate, indicating strong preference for higher-rated accommodations influenced by discounts.

    Average Length of Stay

    Short stays dominate, indicating city-break behavior.

    The most common trip duration for package bookings to Chicago is 2 days, representing 36% of total bookings with a 26% discount. Short and medium stays dominate, suggesting customer preference for city breaks over longer holidays.

    Most Popular Travel Months

    April peak; January weakest due to off-season.

    April exhibits the highest bookings (15%), likely due to spring travel demand and holidays. January and February show the weakest performance (5% and 3% respectively), possibly attributed to post-holiday travel lows despite discounts.

    Hotels in Chicago

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