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  • Chicago

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    Property Types

    • Hotel
    CLUB QUARTERS HOTEL, CENTRAL LOOP Thumbnail
    CLUB QUARTERS HOTEL, CENTRAL LOOP
    Chicago, 111 West Adams Street
    A short 7-minute walk of the Quincy/Wells Subway Station and Willis Tower Skydeck, Club Quarters Hotel Central Loop, Chicago is located in downtown Chicago and features a restaurant, pub and 24-hour room service. Free WiFi access is available. The contemporary guest rooms provide a flat-screen cable TV, iPod docking station and desk. A coffee machine and complimentary bottled water are provided in each room. Elephant & Castle Pub and Restaurant, an English-style pub, serves British and American cuisine and offers over 100 beers and Scotch whiskeys. A variety of cardio equipment is available to use at Central Loop Club Quarters’ gym. The hotel also has 24-hour concierge service. Club Quarters is less than 1 mile from Chicago Symphony Orchestra, the Art Institute of Chicago and Millennium Park.
    8.2 2340 Reviews | 4-Star Hotel
    $1268/person
    $2861
    $2535
    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
    $1416/person
    $3158
    $2832
    total

    Incl. hotel + flight

    The Allegro Royal Sonesta Hotel Chicago Loop Thumbnail
    The Allegro Royal Sonesta Hotel Chicago Loop
    Chicago, 171 W. Randolph Street
    The Allegro’s storied history as a place of ambition, openness and joie de viver comes to life in modern day in the hotel’s glamorous vibes and refreshing charm. Located at the crossroads of Chicago’s backstory - government, theater, tech - and centered in the city’s beating heart, the hotel itself is well over 100 years old. Our story is rooted in the boldness of spirit that centers Chicago in practicality and ambition. The immigrant Eitel brothers purchased the hotel and, in 1924, acquired the rest of the entire south side of Randolph Street from LaSalle to Wells. With characteristic Chicago bravado, they raised and rebuilt the whole block to match their optimistic vision of the future including a 22-story office building, 2500-seat Palace Opera Theater and a 19-story hotel complete with exquisite details - including our striking marble staircase that still welcomes guests today. This vision of glamor and elegance welcomed all that was novel and new. Our four walls have hosted Vaudeville stars, tapped the first keg post-Prohibition and played headquarters to political change makers, jazz legends and movie stars. This is where you come in. Today, you’ll find no stodgy museum full of dusty historical treasure and tributes to the past. The Allegro is where vintage energy comes alive with Art Deco exuberance. Step up the sweeping staircase into the bustling Grand Lobby and feel the palpable energy of the roaring twenties. A spirit of beauty and optimism is everywhere. The decor. The historic details. The joyful service. Whether it’s champagne and popcorn in the lobby or the evening’s witty ‘Curtain Call’ cart with treasures to help you journey into dreamtime, you’ll find even the most un-thought of needs addressed by our considered details and insightful service. We can't wait to welcome you into our vibrant world to boldly create your own Chicago story, with your stay as the backdrop of the adventure.
    8.4 1065 Reviews | 4-Star Hotel
    $1541/person
    $3407
    $3081
    total

    Incl. hotel + flight

    La Quinta Inn & Suites by Wyndham Chicago Downtown Thumbnail
    La Quinta Inn & Suites by Wyndham Chicago Downtown
    Chicago, 1 South Franklin
    Located in the heart of the Financial District in downtown Chicago, this hotel is located just 2 blocks from Willis Tower and offers contemporary rooms with free WiFi and complimentary full hot breakfast. Every room at La Quinta Inn & Suites Chicago Downtown provides a 50-inch flat-screen TV with premium cable channels and a work desk with an ergonomic chair. A microwave and refrigerator are also featured in all rooms. Guests of the Chicago Downtown La Quinta Inn & Suites have access to the 24-hour on-site fitness center. There is a complimentary business center with free printing services and meetings rooms with top amenities for groups of all sizes. The Washington/Wells transportation rail stop is just 3 blocks away, offering easy access to the city’s famed attractions. The hotel is 1 mile away from the luxury shopping, dining and entertainment on the Magnificent Mile. United Center and Lincoln Park Zoo are both 2 miles away.
    8.2 2684 Reviews | 3-Star Hotel
    $1507/person
    $3340
    $3014
    total

    Incl. hotel + flight

    AC Hotel by Marriott Chicago Downtown Thumbnail
    AC Hotel by Marriott Chicago Downtown
    Chicago, 630 North Rush Street
    Less than a block away from the iconic Magnificent Mile strip, this boutique hotel is located in Chicago’s River North district and features a state-of-the-art fitness center, heated indoor pool and free WiFi. Adorned in European-inspired décor, each room at AC Hotel Chicago Downtown includes a flat-screen TV, small refrigerator and coffee maker. A work desk and in-room safe are also provided. Guests can start the day with breakfast at the AC Kitchen and end with cocktails and cuisine at the AC Lounge, which features an array of Latin-inspired small plates. Business travelers can appreciate the 3,000 square feet of event space at the hotel. Navy Pier and Millennium Park are both 1 mile away from AC Hotel by Marriott Chicago Downtown. O’Hare International Airport is a 30-minute drive away.
    8.3 374 Reviews | 4-Star Hotel
    $1538/person
    $3404
    $3076
    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
    $1579/person
    $4044
    $3158
    total

    Incl. hotel + flight

    Radisson Blu Aqua Hotel Chicago Thumbnail
    Radisson Blu Aqua Hotel Chicago
    Chicago, 221 North Columbus Drive
    Located in Chicago’s Lakeshore East neighborhood, this luxury hotel is located in the modern Aqua building. Free WiFi access is offered in every room, and Millennium Park can be reached in 5 minutes’ walk. Views of Lake Michigan and surrounding parks are provided in every contemporary room at Radisson Blu Aqua Hotel Chicago. A flat-screen cable TV and mini-bar are included, along with deluxe bathroom amenities. The hotel offers an indoor and outdoor pool, and an outdoor track. A seasonal outdoor pool with a sundeck and fire pits is provided at Chicago Aqua Radisson Blu. FireLake Grill House & Cocktail Bar serves American, locally-inspired cuisine for weekday breakfast, lunch, dinner and weekend brunch. Craft cocktails and locally-sourced beers are served at the bar. Shopping and dining on the Magnificent Mile is 5 minutes’ walk away. Museum Campus can be reached in 8 minutes’ drive.
    8.2 1532 Reviews | 4.5-Star Hotel
    $1528/person
    $3756
    $3056
    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
    $1644/person
    $3616
    $3288
    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
    $1720/person
    $3765
    $3439
    total

    Incl. hotel + flight

    The Willows Hotel Thumbnail
    The Willows Hotel
    Chicago, 555 West Surf St
    The Willows Hotel is nestled on a tree-lined street in Chicago's prestigious Lakeview and Lincoln Park neighborhoods. Free WiFi, 24-hour coffee & tea service, and cozy guest rooms featuring modern amenities are included with every stay at the Willows Hotel. With nearby access to public transport systems, guests at the Willows can easily explore popular city center attractions, including the Steppenwolf Theater and Wrigley Field. The Lincoln Park Zoo along with the scenic Lake Michigan coastline is also only minutes away.
    8.1 537 Reviews | 3-Star Hotel
    $1611/person
    $3547
    $3221
    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
    $1598/person
    $3524
    $3196
    total

    Incl. hotel + flight

    Hyatt Centric Chicago Magnificent Mile Thumbnail
    Hyatt Centric Chicago Magnificent Mile
    Chicago, 633 North Saint Clair Street
    Just 1 block away from the famed shopping, dining and entertainment on Michigan Avenue’s Magnificent Mile, this downtown Chicago hotel offers on-site dining, modern business amenities and contemporary guest rooms with free WiFi. Every room at Hyatt Centric Chicago Magnificent Mile features a flat-screen HDTV with plug-in panel media entertainment and an oversize work desk. Select rooms also offer a sofa bed and spa-like bathrooms. Level Two restaurant showcases local flavor in the cuisine, cocktails and craft beer served up each day for breakfast, lunch and dinner. Guests can grab a bite while enjoying live music and entertainment on select nights at the restaurant. An on-site Starbucks coffee restaurant and in-room dining services are offered for guest convenience. Guests can enjoy a swim in the indoor pool and hot tub or work out in the 24-hour state-of-the-art fitness center. The hotel also offers 20,000 square feet of flexible meeting and event space, along with a business center with 3 computers, copy and fax services. Navy Pier and Millennium Park are both within walking distance of this hotel. O’Hare International Airport is 13 miles away.
    8.5 410 Reviews | 4-Star Hotel
    $1760/person
    $3845
    $3519
    total

    Incl. hotel + flight

    Renaissance by Marriott Chicago Downtown Hotel Thumbnail
    Renaissance by Marriott Chicago Downtown Hotel
    Chicago, 1 West Upper Wacker Drive
    Featuring a lobby with a VIP Club Lounge, Artist Studio, coffee bar, this hotel is located in Chicago’s Theater District, directly across from the Chicago River. Providing contemporary décor and modern amenities, each room at the Renaissance Chicago Downtown Hotel includes a private bathroom with marble and wood furnishings, along with a view of the Chicago River or skyline. A cable TV is also provided. Guests can enjoy cocktails and cuisine while taking in the views of the city’s famed architecture from the hotel’s rooftop bar. For guests looking to relax and refresh, the hotel offers an indoor pool on-site. Meeting rooms, a business center and fitness center are also provided at the hotel. Millennium Park is less than a mile away from the Downtown Chicago Renaissance Hotel. Michigan Avenue and Navy Pier are both a 10-minute walk away.
    8.7 293 Reviews | 4-Star Hotel
    $1802/person
    $3930
    $3604
    total

    Incl. hotel + flight

    The Blackstone, Autograph Collection Thumbnail
    The Blackstone, Autograph Collection
    Chicago, 636 South Michigan Avenue
    Located in a historic French Beaux-Arts building, this 4-star Chicago Loop hotel features a tapas restaurant and stylish rooms with 50-inch LCD TVs. Grant Park is across the street and Millennium Park is only a 10 minute walk from the property. Guest rooms at The Blackstone, Autograph Collection feature a desk, refrigerator and streaming services. Marble bathrooms are stocked with a bathrobe, slippers and free bathroom amenities. Selected rooms offer views of the lake. Mercat a la Planxa, the on-site tapas restaurant features Catalan and Mediterranean dishes. Guests have free access to the hotel's 24-hour gym. WiFi access is free in the hotel’s public areas. The Blackstone, Autograph Collection is located in the downtown Chicago loop, a 10 minute walk from the Art Institute of Chicago and the Willis Tower. The Magnificent Mile’s shops, Grant Park, and Museum Campus are less than 1.2 mi away.
    8.5 200 Reviews | 4-Star Hotel
    $1863/person
    $4052
    $3726
    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
    $1914/person
    $4153
    $3827
    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
    $1849/person
    $4444
    $3698
    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
    $2053/person
    $4431
    $4105
    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
    $1786/person
    $3897
    $3571
    total

    Incl. hotel + flight

    Hotel Versey Chicago Lincoln Park Thumbnail
    Hotel Versey Chicago Lincoln Park
    Chicago, 644 West Diversey Parkway
    Just 2 miles away from Wrigley Field and Lake Michigan’s North Avenue Beach, this boutique hotel is located Chicago’s Lincoln Park neighborhood and combines the local culture, music and art of the city to provide a unique lodging experience for travelers. Every room at Hotel Versey Chicago Lincoln Park provides a 50-inch flat-screen TV with premium cable channels and livestream capabilities. A Nespresso coffee machine is also included. Guests can enjoy complimentary access to the LA Fitness facility located next to the property. Complimentary WiFi and daily newspapers can be enjoyed. The famed shopping, dining and entertainment of Chicago’s Magnificent Mile is 3 miles away from the hotel. Lincoln Park Zoo is a 5-minute drive away.
    8.0 714 Reviews | 3-Star Hotel
    $1839/person
    $4006
    $3678
    total

    Incl. hotel + flight

    Hilton Garden Inn Chicago McCormick Place Thumbnail
    Hilton Garden Inn Chicago McCormick Place
    Chicago, 123 East Cermak, Suite 300
    Hilton Garden Inn Chicago McCormick Place features a fitness center, shared lounge, a terrace and restaurant in Chicago. Featuring a bar, the 3-star hotel has air-conditioned rooms with free WiFi. The hotel provides an indoor pool and a 24-hour front desk. Each room is equipped with a desk and a TV, and certain rooms at the hotel have a balcony. Guest rooms will provide guests with a fridge. Hilton Garden Inn Chicago McCormick Place offers a continental or American breakfast. For guests' convenience, the accommodation has a business center. Field Museum of Natural History is 1.6 miles from Hilton Garden Inn Chicago McCormick Place, while Grant Park is 1.9 miles away. Midway International Airport is 9.3 miles from the property.
    8.1 357 Reviews | 3-Star Hotel
    $1872/person
    $4069
    $3743
    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
    $2136/person
    $4838
    $4272
    total

    Incl. hotel + flight

    Chicago Athletic Association, part of Hyatt Thumbnail
    Chicago Athletic Association, part of Hyatt
    Chicago, 12 South Michigan Avenue
    A rooftop bar overlooking Millennium Park, unique dining options and a social games room awaits at the Chicago Athletic Association, part of Hyatt. This hotel, located in a landmark building in downtown Chicago, promotes a high-spirited, club atmosphere. Elegant rooms feature an athletic style decor with modern amenities like a 42 inch flat-screen cable TV. Brass fixtures and vintage athletic gear fill each guestroom. Egyptian cotton linens, a work desk and complimentary WiFi access are included as well. Chicago Athletic Association, part of Hyatt features a grand ballroom with 19th century stained glass windows and a modern fitness center. There is a business center for professional needs, a bike rental to help guests explore Chicago and an indoor boccie ball court for fun. The ever popular Shake Shack is a featured on-site dining option that guests can also enjoy via room service. Cindy's offers seasonal cuisine and cocktails and features an incredible open-air terrace overlooking Millennium Park and Lake Michigan. Chicago Athletic Association, part of Hyatt is steps away from Chicago staples like the Art Institute of Chicago (328 feet away) and the Chicago Symphony Orchestra (984 feet away). Chicago O'Hare International Airport is 16 mi away.
    8.6 215 Reviews | 4.5-Star Hotel
    $2020/person
    $4366
    $4040
    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
    $2116/person
    $4557
    $4231
    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
    $1980/person
    $4286
    $3960
    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
    $2140/person
    $4608
    $4280
    total

    Incl. hotel + flight

    Majestic Hotel Thumbnail
    Majestic Hotel
    Chicago, 528 West Brompton Avenue
    Near Wrigley Field, home to baseball's Chicago Cubs, the historic Majestic Hotel offers easy access to Chicago attractions. It includes complimentary WiFi access and guestrooms with 32-inch flat-screen TV. Built in the 1920s, the completely nonsmoking Majestic Hotel provides 24-hour coffee and tea service. Guests can also enjoy relaxing in the hotel's sitting area in front of a wood-burning fireplace. The Lincoln Park Zoo, Second City comedy theater and the Steppenwolf Theater are only a short distance from the Majestic Hotel. Popular concert venue, like the Aragon Ballroom and Vic Theater are nearby. Parking is $30/day for standard vehicles under 6ft tall. We do not off parking for pick up trucks or Suv's taller than 6ft. Please contact the property for parking suggestions on those type of vehicles.
    8.1 488 Reviews | 3-Star Hotel
    $2082/person
    $4489
    $4163
    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
    $2535/person
    $5395
    $5069
    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
    $3215/person
    $6756
    $6430
    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
    $3478/person
    $7282
    $6956
    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
    $4174/person
    $8673
    $8347
    total

    Incl. hotel + flight

    How Far in Advance Customers Book

    Last-minute bookings influenced by holiday demand.

    The peak month for package bookings from Atlanta to Chicago is within one week of travel, with a significant 31% discount. The weakest months are beyond 5 weeks, likely due to holiday demand influencing last-minute bookings and discounts.

    Customer Preference by Hotel Category

    4-star hotels lead bookings, offering greater discounts.

    In Chicago, 4-star hotels dominate bookings at 60%, with a notable 31% package discount. 3-star hotels follow at 24% with a 26% discount, indicating a moderate gap between categories, suggesting consumer preference for quality at competitive rates.

    Average Length of Stay

    2-day trips dominate, indicating city-break behavior.

    In package bookings from Atlanta to Chicago, 2-day trips dominate at 36%, likely appealing to customers seeking quick city breaks. Discount percentages suggest price sensitivity, encouraging shorter stays to maximize perceived value and convenience in holiday travel.

    Most Popular Travel Months

    August peaks; November is weakest.

    The peak month for package bookings from Atlanta to Chicago is August at 13%, influenced by a 32% discount. November shows the weakest performance at 5%, possibly reflecting a decline in travel demand post-summer. Overall, there is seasonal consistency.

    Hotels in Chicago

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