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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
    $1227/person
    $2818
    $2454
    total

    Incl. hotel + flight

    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
    $1467/person
    $3297
    $2933
    total

    Incl. hotel + flight

    Crowne Plaza - Chicago West Loop By IHG Thumbnail
    Crowne Plaza - Chicago West Loop By IHG
    Chicago, 25 S Halsted St
    Moments from the United Center, home of the Chicago Bulls, this hotel offers easy access to downtown attractions along with on-site dining, comfortable guest rooms and a 24-hour fitness center. Accommodations at the Crowne Plaza Hotel Chicago are furnished with large work desks and tea and coffee-making facilities. Guests can also enjoy on-site dining at Dine restaurant, serving unique American cuisine for breakfast, lunch and dinner. The Chicago Crowne Plaza Hotel is a short L-train ride from the Magnificent Mile shopping area and Navy Pier. A number of charming shops, famed restaurants and an exciting nightlife are also nearby. Union Station, with Metra and Amtrak rail lines, is a 12 minute walk from this property.
    8.3 642 Reviews | 3.5-Star Hotel
    $1402/person
    $3167
    $2803
    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
    $1433/person
    $3229
    $2865
    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
    $1506/person
    $3376
    $3012
    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
    $1417/person
    $3197
    $2833
    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
    $1474/person
    $3314
    $2948
    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
    $1445/person
    $3377
    $2889
    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
    $1500/person
    $3366
    $3000
    total

    Incl. hotel + flight

    Arlo Chicago Thumbnail
    Arlo Chicago
    Chicago, 168 North Michigan Avenue
    Located in Chicago, less than a 5-minute walk to Millennium Park and Cloud Gate - The Bean, Arlo Chicago provides a fitness center and an on-site restaurant. The property is set within walking distance to CIBC Theater, Bank of America Theater and Art Institute of Chicago. Chicago Symphony Orchestra and Shops at Northbridge are less than a 10-minute walk from the hotel. All rooms are fitted with a desk, a flat-screen TV and a private bathroom. All rooms will provide guests with a fridge. An American breakfast is available every morning at Arlo Chicago. About Last Knife, the on-site steakhouse restaurant, offers American, seafood and local cuisine. When guests need guidance on where to visit, the reception will be happy to provide advice. DePaul University is less than 0.6 mi from Arlo Chicago , while Chicago Board of Trade Building is a 12-minute walk from the property. The nearest airport is Midway International Airport, 9.3 mi from the property.
    8.7 1373 Reviews | 4-Star Hotel
    $1564/person
    $3492
    $3128
    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
    $1509/person
    $3384
    $3018
    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
    $1459/person
    $3281
    $2917
    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
    $1537/person
    $3437
    $3073
    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
    $1706/person
    $3940
    $3412
    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
    $1591/person
    $3545
    $3181
    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
    $1749/person
    $3861
    $3497
    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
    $1892/person
    $4383
    $3783
    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
    $1696/person
    $3755
    $3391
    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
    $1704/person
    $3771
    $3407
    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
    $1860/person
    $4084
    $3720
    total

    Incl. hotel + flight

    Courtyard by Marriott Chicago at Medical District/UIC Thumbnail
    Courtyard by Marriott Chicago at Medical District/UIC
    Chicago , 625 South Ashland Avenue At Harrison Street
    Located in Chicago, a 15-minute walk from United Center, Courtyard by Marriott Chicago at Medical District-UIC has accommodations with a fitness center, private parking, a shared lounge and a terrace. Among the facilities of this property are a restaurant, a 24-hour front desk and an ATM, along with free WiFi throughout the property. Guests can have a drink at the snack bar. An à la carte, continental or American breakfast is available at the property. There's an in-house bar and guests can also use the business area. Willis Tower is 2.2 miles from the hotel, while Union Station is 2.2 miles from the property. Midway International Airport is 8.7 miles away.
    8.4 197 Reviews | 3.5-Star Hotel
    $1829/person
    $4021
    $3657
    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
    $1858/person
    $4079
    $3715
    total

    Incl. hotel + flight

    Hampton Inn By Hilton Chicago McCormick Place Thumbnail
    Hampton Inn By Hilton Chicago McCormick Place
    Chicago, 123 East Cermak, Suite 100
    In a prime location in the South Loop district of Chicago, Hampton Inn Chicago McCormick Place is located 1.7 mi from Field Museum of Natural History, 1.9 mi from Grant Park and 2 mi from Art Institute of Chicago. With a bar, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The accommodations provides a 24-hour front desk and room service for guests. At the hotel, every room is fitted with a desk. All units at Hampton Inn Chicago are equipped with a seating area and a flat-screen TV with cable channels. Chicago Symphony Orchestra is 2.1 mi from Hampton Inn Chicago McCormick Place, while DePaul University is 2.1 mi away. The nearest airport is Midway International Airport, 8.1 mi from the hotel.
    8.6 777 Reviews | 3-Star Hotel
    $1975/person
    $4313
    $3949
    total

    Incl. hotel + flight

    Best Western Plus Hawthorne Terrace Hotel Thumbnail
    Best Western Plus Hawthorne Terrace Hotel
    Chicago, 3434 North Broadway Avenue
    This historic hotel is within 10 minutes' walk of Wrigley Field and the Red Line train to downtown Chicago. It features a glass-enclosed hot tub and contemporary rooms with free Wi-Fi. A 42 inch flat-screen TV and laptop safe are included in each guest room at Best Western Hawthorne Terrace. A microwave, coffee maker, and refrigerator stocked with free bottled water are provided. A selection of cardio machines is available at the Hawthrone Terrace’s on-site gym. The front desk offers concierge services 24 hours a day and a continental breakfast is served in the mornings. There is a lush and relaxing interior courtyard as well. The shopping at the Magnificent Mile is just 20 minutes' bus ride from the Chicago Hawthorne Terrace Best Western. The Lincoln Park Zoo is 2 miles from the hotel.
    8.6 418 Reviews | 3-Star Hotel
    $1981/person
    $4325
    $3961
    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
    $2011/person
    $4386
    $4022
    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
    $1958/person
    $4282
    $3916
    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
    $2263/person
    $5333
    $4525
    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
    $2137/person
    $4640
    $4274
    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
    $5035/person
    $10433
    $10069
    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
    $5326/person
    $11016
    $10652
    total

    Incl. hotel + flight

    How Far in Advance Customers Book

    Last-minute bookings dominate Charlotte to Chicago trend.

    The peak month for bookings from Charlotte to Chicago is likely within the last week before travel, accounting for 26% of all bookings, coinciding with a significant 36% discount. Conversely, the weakest months appear to be those booked further in advance, likely due to travelers' preference for last-minute deals aligning with spontaneous travel trends or holiday demand.

    Customer Preference by Hotel Category

    4-star hotels lead in bookings from Charlotte.

    In Chicago, 4-star hotels dominate bookings at 61%, offering a competitive 34% discount. Second place is 3-star hotels at 24%, with a similar discount rate of 33%. The gap between the first and second categories is large.

    Average Length of Stay

    3-day trips dominate, reflecting city-break preferences.

    In package bookings from Charlotte to Chicago, the most common trip duration is 3 days, which accounts for 36% of bookings and offers a 33% discount. Short to medium stays dominate, suggesting typical city-break behavior.

    Most Popular Travel Months

    June peak reflects summer travel, February lowest.

    In Chicago, June marks the peak month for package bookings at 14%, possibly due to summer travel demand. Conversely, February sees the lowest at 3%, which may relate to winter weather discouraging travel despite high discounts. Overall, there is distinct seasonality.

    Hotels in Chicago

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