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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
    $2242/person
    $4509
    $4483
    total

    Incl. hotel + flight

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel Thumbnail
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
    Chicago, 172 West Adams Street
    This contemporary hotel is in the heart of the city, steps from Chicago city center's main attractions, including the Skydeck Ledge and the Willis Tower - formerly the Sears Tower. Discover the luxury shops of the Magnificent Mile, enjoy a concert at Millennium Park or stroll along the shores of Lake Michigan, all within walking distance of the recently renovated The Midland Hotel. World-famous restaurants, numerous corporate offices and a vibrant nightlife are also easily accessible from the hotel. Guests can enjoy a wide range of dishes inspired by Chicago's diverse cultures at on-site restaurant Midland Social Club. MSC Bar, also located on-site, offers a variety of signature cocktails and beverages in a cozy and intimate atmosphere. The The Midland Hotel offers a 24-hour fitness center. Relax after a long day with an in-room massage, designed to make all dreams a reality.
    7.6 221 Reviews | 4-Star Hotel
    $2011/person
    $4050
    $4022
    total

    Incl. hotel + flight

    Holiday Inn - Chicago Dwtn - The Mart by IHG Thumbnail
    Holiday Inn - Chicago Dwtn - The Mart by IHG
    Chicago, 350 W Wolf Point Plaza
    Located in Chicago and with Willis Tower reachable within a 14-minute walk, Holiday Inn - Chicago Dwtn - The Mart by IHG has concierge services, non-smoking rooms, a shared lounge, free WiFi and a bar. Offering a restaurant, the property also has a fitness center, as well as an indoor pool and a sauna. The property is a 17-minute walk from CIBC Theatre, and within half a mile of the city center. The hotel will provide guests with air-conditioned rooms offering a desk, a coffee machine, a safety deposit box, a flat-screen TV and a private bathroom with a shower. All rooms feature a closet. The breakfast offers buffet, continental or American options. Guests at Holiday Inn - Chicago Dwtn - The Mart by IHG will be able to enjoy activities in and around Chicago, like fishing. The accommodation also provides a business center and guests can use the on-site ATM machine at Holiday Inn - Chicago Dwtn - The Mart by IHG. Speaking English and Spanish, staff are always on hand to help at the 24-hour front desk. Popular points of interest near the hotel include Millennium Station, Millennium Park and Shops at Northbridge. Midway International Airport is 11 miles from the property.
    7.9 243 Reviews | 3.5-Star Hotel
    $2195/person
    $4415
    $4389
    total

    Incl. hotel + flight

    Embassy Suites By Hilton Hotel Chicago Downtown Thumbnail
    Embassy Suites By Hilton Hotel Chicago Downtown
    Chicago, 600 North State Street
    Located in the River North district, this downtown Chicago hotel is 1 mile from Navy Pier. The all-suite hotel features an Italian restaurant, indoor pool and suites with 2 flat-screen TVs. Styled in warm colors and dark wood furniture, the modern suites offer a private bedroom with a spacious living room. A small refrigerator, microwave and an iPod docking station are provided. Osteria Via Stato features a traditional 3-course Italian meal. Embassy Suites Chicago–Downtown offers a daily continental breakfast and a nightly manager’s reception with free snacks and beverages. Guests at Chicago Embassy Suites can workout in the well-equipped gym or visit the gift shop. A concierge desk and a business center are available. The Magnificent Mile shopping area is just 3 blocks from this hotel and the Water Tower Place is a 15-minute walk away. Soldier Field and Shedd Aquarium are 3 miles away.
    8.2 2312 Reviews | 4-Star Hotel
    $2309/person
    $4646
    $4618
    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
    $2447/person
    $4922
    $4894
    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
    $2278/person
    $4583
    $4555
    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
    $2512/person
    $5052
    $5024
    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
    $2470/person
    $4968
    $4940
    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
    $2667/person
    $5359
    $5333
    total

    Incl. hotel + flight

    The Drake Hotel Thumbnail
    The Drake Hotel
    Chicago, 140 East Walton Place
    Featuring stunning views of Lake Michigan, the Chicago Drake hotel is 3 minutes' walk from Oak Street Beach and 1 mile from Navy Pier. This hotel built in 1920 includes elegantly designed guest rooms and a chance to enjoy an afternoon tea or cocktails at Palm Court. Each spacious room at The Drake provides deluxe bedding and marble bathrooms. Guest rooms offer a flat-screen HD TV with HBO and an iPod docking station. Guests at the Drake Hilton Hotel can explore the shops located on the arcade level of the hotel. A convenience store and foreign currency exchange services are also available. Lincoln Park Zoo is 2.4 miles from this hotel in Chicago. The John Hancock Center is less than 5 minutes' walk away.
    8.4 578 Reviews | 4-Star Hotel
    $2491/person
    $5009
    $4981
    total

    Incl. hotel + flight

    The Westin Michigan Avenue Chicago Thumbnail
    The Westin Michigan Avenue Chicago
    Chicago, 909 North Michigan Avenue
    Located in the center of the luxury shops, world-famous restaurants and vibrant nightlight of the Magnificent Mile, this luxurious downtown Chicago hotel is located directly across from the John Hancock Center and offers first-class amenities, including a renowned boutique spa and a fine dining restaurant. Every room at The Westin Michigan Avenue Chicago provides a 55-inch flat-screen LCD TV and a large work desk with ergonomic chair. Luxury linen and bedding is also included. Experience the taste of Chicago's Gold Coast at 909 North, our hotel restaurant with a scratch-made kitchen. Open for breakfast, lunch, and dinner, we source fresh ingredients locally from family-owned Midwest farms. Café A La Carte serves freshly brewed Starbucks coffee and fresh baked breads throughout the day. 24-hour room service is offered for guest convenience. Iconic Lake Michigan and Oak Street Beach are also only moments away from the hotel. The Art Institute of Chicago and Navy Pier are both a 10-minute drive away. The Chicago Red Line subway station is 2133 feet away.
    8.5 339 Reviews | 4.5-Star Hotel
    $2569/person
    $5163
    $5137
    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
    $2490/person
    $5008
    $4980
    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
    $2624/person
    $6403
    $5247
    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
    $2414/person
    $4853
    $4827
    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
    $2508/person
    $5044
    $5016
    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
    $2625/person
    $5517
    $5249
    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
    $2754/person
    $5536
    $5508
    total

    Incl. hotel + flight

    Embassy Suites by Hilton Chicago Magnificent Mile Thumbnail
    Embassy Suites by Hilton Chicago Magnificent Mile
    Chicago, 511 North Columbus Drive
    Two blocks from the restaurants and shops of Embassy Suites by Hilton Chicago Downtown Magnificent Mile offers a free daily breakfast and evening reception, and is moments from major area attractions. There is also a heated indoor pool at the property. Featuring suites furnished with separate living rooms and bedrooms, each room includes a flat-screen TV as well. Some rooms offer a view of the Chicago skyline. A well-equipped fitness center is on-site for guests' workout needs. The business center and meeting space are perfect for corporate events. The Chicago River Ballroom is available for special events. Guests can enjoy a meal at the 511 North Lounge Restaurant. Only steps from the Embassy Suites Chicago Downtown Magnificent Mile front doors are a number of popular sites. The famous Michigan Avenue, Millennium Park, the Sears Tower and the Shedd Aquarium are all nearby.
    7.9 1696 Reviews | 4-Star Hotel
    $2564/person
    $5156
    $5128
    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
    $2831/person
    $5690
    $5662
    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
    $2788/person
    $5604
    $5576
    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
    $2909/person
    $5845
    $5817
    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
    $3362/person
    $6752
    $6724
    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
    $2997/person
    $6022
    $5994
    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
    $3494/person
    $7423
    $6987
    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
    $3036/person
    $6100
    $6072
    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
    $3873/person
    $7774
    $7746
    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
    $4315/person
    $8658
    $8630
    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
    $5185/person
    $10398
    $10370
    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
    $4993/person
    $10014
    $9986
    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
    $5494/person
    $11681
    $10987
    total

    Incl. hotel + flight

    How Far in Advance Customers Book

    Spontaneous travel drives peak bookings.

    The peak month for package bookings from Detroit to Chicago occurs with last-minute purchases (0 weeks ahead) at 22% of total bookings, indicating a trend towards spontaneous travel. The weakest month appears to be six weeks ahead with only 6% of bookings. This suggests a holiday demand during peak travel times.

    Customer Preference by Hotel Category

    4-star hotels lead bookings in Chicago

    In Chicago, 4-star hotels dominate bookings at 68%, with a significant 15% package discount. 3-star hotels follow as the second most popular category at 20%, aided by a smaller 9% discount. The gap between these categories is large.

    Average Length of Stay

    2-day trips suggest city-break travel trends.

    The most common trip duration to Chicago is 2 days, representing 43% of package bookings, possibly indicating city-break behavior. The moderate discounts suggest travelers may prefer shorter, budget-conscious trips, while longer stays are less popular.

    Most Popular Travel Months

    August peak; January and October lowest bookings.

    In Chicago, August is the peak month for bookings at 16%, suggesting a strong summer travel season. January and October are the weakest months, correlating with higher discounts. Overall, seasonality likely drives these trends.

    Hotels in Chicago

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