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Cities

  • Chicago

Brands

    Property Types

    • Hotel
    Renaissance by Marriott Chicago O'Hare Suites Hotel Thumbnail
    Renaissance by Marriott Chicago O'Hare Suites Hotel
    Chicago, 8500 West Bryn Mawr Avenue
    Less than 4 miles away from O’Hare International Airport, Rivers Casino and the Fashion Outlets of Chicago, this all-suites hotel offers free airport shuttle service and free WiFi in the lobby. Every suite at Renaissance Chicago O’Hare Suites Hotel provides 2 LCD TVs, a separate living room with a sofa bed and a dining area. A desk is also included. Asado Urban Grill offers American fare in a comfortable setting for breakfast, lunch and dinner. R Bar serves artfully crafted cocktails and offers a modern, lively atmosphere. Room service is also available. Guests can swim in the indoor pool and hot tub or work out at the on-site fitness center. A meeting room and event space are also offered at the hotel. The CTA Blue Line Cumberland subway station is less than a mile away, providing easy access to downtown Chicago. Donald E Stephens Convention Center is 3 miles away from the hotel.
    8.0 285 Reviews | 4-Star Hotel
    $1095/person
    $2494
    $2190
    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
    $1563/person
    $3208
    $3126
    total

    Incl. hotel + flight

    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
    $1552/person
    $3103
    total

    Incl. hotel + flight

    The Godfrey Hotel Chicago Thumbnail
    The Godfrey Hotel Chicago
    Chicago, 127 West Huron Street
    Located 3 blocks away from the shopping, dining and entertainment on the Magnificent Mile, this boutique hotel is located in the heart of Chicago’s River North district and offers on-site dining options, 24-hour fitness center, spa and free WiFi. Adorned in stylish contemporary décor, every modern room at Godfrey Hotel Chicago offers a 46-inch flat-screen LCD HDTV, a wet bar and a work desk with an ergonomic chair. Room service is available. IO Urban Rooftop bar and lounge features a retractable roof, offering an indoor bar and outdoor lounge with fire pits. Event space with floor-to-ceiling windows and tech-savvy meeting rooms are offered at Chicago Godfrey Hotel. Laundry services are also available. Millennium Park and the Art Institute of Chicago are both 1.5 miles away from the hotel. Navy Pier is a 12-minute drive away.
    8.3 587 Reviews | 4.5-Star Hotel
    $1658/person
    $3397
    $3315
    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
    $1747/person
    $3494
    total

    Incl. hotel + flight

    Hyatt Regency Chicago Thumbnail
    Hyatt Regency Chicago
    Chicago, 151 E Wacker Dr Chicago
    Off the banks of the Chicago River, this luxurious hotel is conveniently located within 5 minutes' walk of the Magnificent Mile and Millennium Park. As the largest hotel in Chicago, this hotel features numerous of on-site dining options, free WiFi, and a 24-hour fitness center and spa. Each environmentally-friendly room at Chicago Hyatt Regency includes a 37-inch flat-screen TV and an iPod docking station. A desk and seating area are also provided in every room. The hotel offers a wide array of services on site, including car rental, a concierge staff, a babies travel lite program, and ticket services. Stetsons Modern Steak + Sushi serves fine chops and seafood in an elegant atmosphere. Market Chicago, open 24-hours a day, features Starbucks coffee, sandwiches and breakfast items. BIG Bar features views of the city and signature cocktails. American Craft Kitchen and Bar is open for lunch and dinner and serves sandwiches and salads. Chicago Hyatt Regency is a 10 minutes' walk from the Chicago Theater District. The Art Institute of Chicago and Museum of Science and Industry are within 1 mile.
    8.7 1405 Reviews | 4-Star Hotel
    $1826/person
    $3980
    $3652
    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
    $1818/person
    $4212
    $3636
    total

    Incl. hotel + flight

    Hyatt Place Chicago/Downtown - The Loop Thumbnail
    Hyatt Place Chicago/Downtown - The Loop
    Chicago, 28 North Franklin Street
    Located in the heart of the city, Hyatt Place Chicago/Downtown – The Loop is conveniently located near several of the city’s social and cultural landmarks. This hotel offers a restaurant and fitness center. Free WiFi access is available. Each room at the hotel provides a flat-screen cable TV, a sofa and a refrigerator. Private bathrooms come complete with a shower, hairdryer and free toiletries. Extras include a desk and iron. A 24-hour front desk welcomes guests to Chicago/Downtown’s Hyatt Place in the Loop, which features a shared lounge and TV area. Other amenities offered at the hotel include a business center, bicycle rental and baggage storage. The hotel is less than a mile from Millennium Park and 1312 feet from Willis Tower. O’Hare International Airport is 16 miles away.
    8.3 3137 Reviews | 3.5-Star Hotel
    $1838/person
    $3831
    $3675
    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
    $1931/person
    $3861
    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
    $2080/person
    $4159
    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
    $1956/person
    $3912
    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
    $1977/person
    $3953
    total

    Incl. hotel + flight

    Omni Chicago Hotel Thumbnail
    Omni Chicago Hotel
    Chicago, 676 North Michigan Avenue
    Placed on Chicago’s famed Michigan Ave, the all-suite Omni Chicago Hotel puts you in the heart of The Windy City. Centrally located along the Magnificent Mile, world-class shopping, stunning views and premium culinary destinations are all within reach. As Michigan Avenue’s only all-suite hotel, Omni Chicago Hotel offers luxury hotel suites with a spacious living area set apart from the main sleeping room, plus first-class amenities. Whether you’re here for work or play, the comforts of our city-inspired Chicago hotel provide the ultimate downtown retreat. Explore the best of the city from our downtown Chicago hotel, located near top things to do, including The Harry Potter Shop Chicago, where you can enjoy 15% off your purchase by showing your Omni Chicago Hotel keycard. Chicago’s skydeck, Millennium Park, Navy Pier and multiple museums. After your day in the town, stop by our hotel, 676 Restaurant & Bar to end your perfect day in Chicago, IL.
    8.7 697 Reviews | 4.5-Star Hotel
    $2049/person
    $4098
    total

    Incl. hotel + flight

    Hotel 55 Chicago Downtown Thumbnail
    Hotel 55 Chicago Downtown
    Chicago, 55 East Ontario Street
    Located in Chicago, a 14-minute walk from Ohio Street Beach, Hotel 55 Chicago Downtown provides accommodations with a fitness center, private parking, a restaurant and a bar. With free WiFi, this 4-star hotel offers room service and a 24-hour front desk. The property is 700 yards from the city center and a 6-minute walk from Water Tower Chicago. An à la carte, continental or American breakfast is served at the property. The hotel also provides a business center and guests can use the on-site ATM machine at Hotel 55 Chicago Downtown. Popular points of interest near the accommodation include Shops at Northbridge, 360 Chicago and Chicago Museum of Contemporary Art. Midway International Airport is 11 miles away.
    8.5 400 Reviews | 4-Star Hotel
    $2020/person
    $4039
    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
    $2149/person
    $4297
    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
    $2045/person
    $4089
    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
    $2098/person
    $4196
    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
    $2426/person
    $5133
    $4851
    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
    $2139/person
    $4278
    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
    $2346/person
    $4691
    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
    $2249/person
    $4497
    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
    $2196/person
    $4392
    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
    $2470/person
    $4939
    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
    $2443/person
    $4885
    total

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    Sheraton Grand Chicago Thumbnail
    Sheraton Grand Chicago
    Chicago, 301 East North Water Street
    Located in the heart of the Chicago city center, this hotel features rooms overlooking the river and city skyline. Boasting 5 restaurants and bars, Sheraton Grand Chicago is just a 10-minute walk away from Navy Pier and Millennium Park. A 47" cable TV is offered in every spacious room at Sheraton Grand Chicago. All rooms offer city or river views and come equipped with a mini-bar. For guest convenience, a fitness center and business center are also available. Shula’s Steak House, located on site, serves fresh seafood and steak for dinner each evening. Chicago Burger Company features a casual atmosphere with juicy burgers and icy cocktails. This hotel is 5 minutes' walk from the luxurious shops, entertainment and nightlife of Michigan Avenue. The Museum of Contemporary Art Chicago is less than 1 mile away. Breakfast included rates only cover two people and cost an additional $50 per person after two people
    8.1 714 Reviews | 4-Star Hotel
    $2479/person
    $4957
    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
    $3168/person
    $6336
    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
    $3214/person
    $6724
    $6428
    total

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    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
    $4968/person
    $9936
    total

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    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
    $4923/person
    $9846
    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
    $6093/person
    $12185
    total

    Incl. hotel + flight

    How Far in Advance Customers Book

    Peak bookings observed last-minute due to holiday demand.

    The peak month for package bookings from San Diego to Chicago is likely when travelers book last minute (1 week ahead), benefiting from a 33% discount. The weakest month may be when bookings are made 18 weeks ahead, potentially indicating a lack of early holiday planning. Overall, the trend suggests a strong preference for last-minute travel, likely driven by holiday seasons.

    Customer Preference by Hotel Category

    4-star hotels lead with 49% bookings.

    In Chicago, 4-star hotels are the most popular category, accounting for 49% of bookings with a 27% package discount. 3-star hotels follow as the second most popular at 29% with a 29% discount. The gap is moderate.

    Average Length of Stay

    3-day trips dominate; discounts drive short stays.

    The most common trip duration for package bookings from San Diego to Chicago is 3 days, which may indicate a preference for city breaks. Shorter stays dominate, likely motivated by appealing discounts, particularly the 45% on 1-day trips.

    Most Popular Travel Months

    May peak bookings; January weakest with discounts.

    In Chicago, May saw peak bookings at 15% alongside a 28% discount. January and February had the weakest bookings at 6% and 5%, respectively, despite significant discounts. The overall pattern suggests possible holiday-related travel increases and off-peak season declines.

    Hotels in Chicago

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