Orlando to Chicago Vacation Packages - Flight + Hotel from $1321 per person

This Chicago, Illinois hotel offers free WiFi in the guest rooms. Daley College is minutes from the hotel. The hotel offers a shuttle to the Chicago Midway International Airport 24 hours. The McCormick Place Convention Center is a short drive from the Holiday Inn Chicago Midway Airport S, an IHG hotel Hotel. The United Center, home of the Chicago Bulls and Blackhawks, is also within driving distance of the hotel. Guest rooms at the Holiday Inn Chicago Midway Airport S, an IHG hotel provide a coffee maker and a work desk. Cable TV is also available in every room.

Located one mile from Midway International Airport, this hotel offers complimentary 24-hour airport shuttle services and comfortable guest rooms with free WiFi, along with complimentary parking during the guest's stay. Every room at Hyatt Place Chicago Midway Airport features state-of-the-art media and work centers, a 47-inch flat-screen HDTV and a sofa or sofa bed. A golf putting range and 24-hour fitness center are available on-site. The hotel also offers 2,000 square feet of flexible meeting space. Guests can enjoy Starbucks brewed coffee, along with premium crafted beers, wines and cocktails at Coffee to Cocktails Bar. A 24-hour market featuring grab ‘n go meal options is also available at the hotel for guest convenience. The onsite restaurant serves local beers, cocktails and light meals. The hotel provides complimentary shuttle services to and from the CTA public transportation station, providing easy access to the famed shopping, dining and entertainment in downtown Chicago.

Featuring free shuttle services to O’Hare International Airport, this Chicago hotel is 2 miles away from Donald E. Stevens Convention Center and the Fashion Outlets of Chicago and includes an on-site restaurant and bar, and comfortable guest rooms with free WiFi. Every room at Holiday Inn O’Hare Area provides a 32-inch flat-screen TV with premium satellite channels, along with a microwave, small refrigerator and coffee maker. Select rooms also offer a sofa bed and wet bar. Guests can indulge in one of the restaurant’s signature martinis or grab a bite for breakfast, lunch and dinner at Bar Louie’s, located in the hotel lobby. The restaurant offers free meals for kids. A 24-hour modern fitness center and a fully-equipped business center are available on-site for guest convenience. This hotel is a 4-minute walk away from the Blue Line Metra Train Station, offering easy access to downtown Chicago’s famed shopping, entertainment and dining scene. Allstate Arena is a 9-minute drive away.

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.

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.

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.

In the heart of Chicago city center, and within walking distance to major attractions, this all-suite hotel provides exceptional accommodations, complete with first-class amenities and personalized services. Enjoy a restful nights sleep on the Magnificent Mile Hilton's signature Sweet Dreams bed and take advantage of breathtaking views from the rooftop pool and fitness center. Take a short stroll to the nearby John Hancock Center or beautiful Lakeshore Drive, both located only seconds from the Hilton Chicago/Magnificent Mile Suites. The Museum of Contemporary Art, Navy Pier and the gourmet restaurants and exciting nightlife of State Street are also nearby.

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.

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.

Located among the luxury shopping, dining and entertainment on the famed Magnificent Mile, this downtown Chicago hotel offers a state-of-the-art fitness center, on-site dining and contemporary guest rooms with free WiFi. Every room at Chicago Marriott Downtown Magnificent Mile provides a 32-inch flat-screen LCD TV with premium cable channels and a large work desk with an ergonomic chair. A coffee maker is also included. Rush Street Pantry offers chef-crafted food with gourmet to-go options 24-hours of the day. With 6 plasma screen TVs lining the walls, guests can grab craft cocktails and street food at the hotel’s Reviver – Bar. Harvest – Restaurant offers classic Chicago-style cuisine for breakfast, lunch and dinner. Over 68,000 square feet of flexible meeting and event space is offered at the property. Starbucks Coffee Company is conveniently located in the hotel lobby. 24-hour in-room dining services are offered. Navy Pier and Millennium Park are both a 1-mile walk away from the hotel. The Grand Red Line Subway stop is a 5-minute walk away, offering easy access to the city’s top attractions.

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.

Just 3 minutes’ drive from McCormick Place Convention Center, this boutique hotel is located in Chicago’s South Loop and offers free parking including one parking pass per room and free WiFi. Each room at Chicago South Loop Hotel includes a 32-inch flat-screen LCD TV with cable channels and a private bathroom with a spa bath. An iPod docking station is also provided. A fitness center is available at this hotel, along with a 24-hour business center. Museum Campus and U.S. Cellular Field are both a 5-minute drive away. Millennium Park is 3 miles away from Chicago Hotel South Loop.

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

Directly across from Millennium Park and sitting on the iconic Michigan Avenue, Congress Plaza Hotel offers elegance, luxury, and history in the heart of downtown Chicago. This historic Chicago hotel offers stunning city and lake views, on-site dining options, and free WiFi. Offering a mix of contemporary amenities and classic, historic character, each room at Congress Plaza Hotel features high ceilings, expansive bathrooms and a flat-screen cable TV. Coffee makers, working desks, and ironing facilities are provided in each room. Some rooms offer separate living areas and family-friendly bedding layouts. Rafael’s offers a menu of American classics, coupled with creative seasonal chef specialties for lunch and dinner. For breakfast, guests can start the day off with breakfast at Gazebo or grab a drink and watch a game on the flat-screen TVs at the Congress Lounge, which offers city views and comfortable leather couches and chairs. A 24-hour fitness center, barbershop and same-day dry cleaning and shoeshine services are available on-site. The hotel includes 23 contemporary venue event spaces, including the infamous Gold Room, dating back to early 1920's Chicago. Room service, a business center, and multiple seating areas are also offered. Congress Plaza Hotel is within walking distance from Chicago must-see attractions such as the Art Institute of Chicago, Buckingham Fountain, and Lake Michigan. Shops, dining and entertainment on the Magnificent Mile is only 10 minute's walk. Navy Pier is only 2 miles away.

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

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.

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

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. CDA 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.

Modern Dining Sable At Navy Pier Chicago offers a modern restaurant serving American, Mexican, and Spanish cuisines. Guests can enjoy brunch, lunch, and dinner, complemented by a bar for cocktails. The restaurant features sea views and a comfortable ambiance. Comfortable Accommodations Rooms include air-conditioning, free WiFi, and private bathrooms. Additional amenities include tea and coffee makers, hairdryers, refrigerators, and work desks. Guests can relax in the lounge or stay active in the fitness room. Prime Location Located in Chicago, the hotel is less than 0.6 mi from Ohio Street Beach and a 7-minute walk to Navy Pier. Nearby attractions include the Chicago Museum of Contemporary Art and Millennium Park. Midway International Airport is 13 mi away. An ice-skating rink is also in the surroundings.

Just 5 blocks away from the famed shopping, dining and entertainment of the Magnificent Mile, this hotel is located in downtown Chicago and offers an indoor heated pool and a rooftop deck with views of the iconic city skyline. Hotel rooms offer a flat-screen TV with premium cable channels. A coffee maker is also provided. Guests can get a taste of the city at Pizzeria Ora Restaurant and Lounge, which offers authentic Chicago-style deep-dish pizza and classic Italian fare for breakfast, lunch and dinner. In-room dining services are also available for guest convenience. A fitness center, business center and 24-hour front desk are all available on-site. Navy Pier, Millennium Park and Willis Tower are all 1.5 mi away from the hotel. Wrigley Field is 6 mi away. The hotel is a 35-minute drive away from O’Hare International Airport.

Located in the River North district, this downtown Chicago hotel is 1 mile from Navy Pier. The all-suite hotel features an Italian restaurant, indoor pool and suites with 2 flat-screen TVs. Styled in warm colors and dark wood furniture, the modern suites offer a private bedroom with a spacious living room. A small refrigerator, microwave and an iPod docking station are provided. Osteria Via Stato features a traditional 3-course Italian meal. Embassy Suites Chicago–Downtown offers a daily continental breakfast and a nightly manager’s reception with free snacks and beverages. Guests at Chicago Embassy Suites can workout in the well-equipped gym or visit the gift shop. A concierge desk and a business center are available. The Magnificent Mile shopping area is just 3 blocks from this hotel and the Water Tower Place is a 15-minute walk away. Soldier Field and Shedd Aquarium are 3 miles away.

Two blocks from the restaurants and shops of Embassy Suites by Hilton Chicago Downtown Magnificent Mile offers a free daily breakfast and evening reception, and is moments from major area attractions. There is also a heated indoor pool at the property. Featuring suites furnished with separate living rooms and bedrooms, each room includes a flat-screen TV as well. Some rooms offer a view of the Chicago skyline. A well-equipped fitness center is on-site for guests' workout needs. The business center and meeting space are perfect for corporate events. The Chicago River Ballroom is available for special events. Guests can enjoy a meal at the 511 North Lounge Restaurant. Only steps from the Embassy Suites Chicago Downtown Magnificent Mile front doors are a number of popular sites. The famous Michigan Avenue, Millennium Park, the Sears Tower and the Shedd Aquarium are all nearby.

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

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.

Just 1 mile away from Millennium Park and the Art Institute Museum, this historic Chicago Loop hotel features renowned architectural designs, a luxury spa and indoor pool in the heart of the city’s financial district. Every room at JW Marriott Chicago features a 42-inch flat-screen LCD TV with Netflix streaming and satellite cable channels. The marble bathroom offers a double vanity, separate bath tub and shower and plush bath robes. Guests can enjoy fine-dining at the on-site restaurant, The Florentine, which features seasonal Italian cuisine. The Lobby Lounge offers a more casual setting, where guests can grab an appetizer during happy hour or gather for drinks after work. In-room dining services are available 24 hours for guest convenience. Navy Pier is 2 miles away from Marriott Chicago JW. The Monroe Public Transit stop is 3 blocks away and offers easy access to several of Chicago’s most popular attractions.

Boasting an ideal location directly connected to the McCormick Place convention center, this hotel offers contemporary accommodations and first-class amenities and services, and is a short drive from Chicago city center. In addition to stunning views of Lake Michigan and central Chicago, guests staying at the Hyatt Regency McCormick Place can enjoy modern business facilities and free WiFi access, along with a 24-hour fitness center. The hotel also offers knowledgeable concierge services. Spacious rooms at the McCormick Hyatt are furnished with all the latest technologies, including iHome iPod and multimedia docking stations and 42-inch flat-screen TVs with expanded cable. Guests will also appreciate in-room coffeemakers and large work desks. With on-site car hire services, guests at the McCormick Place Hyatt Regency can easily explore the surrounding area as well as Chicago city center attractions, including Navy Pier and Soldier Field. Scenic jogging and walking paths along Lake Michigan are also easily accessible.

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.

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.

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.

Experience an abundance of unparalleled facilities and features at The Chicago Hotel Collection Ambassador Gold Coast. Maintain seamless communication using the complimentary Wi-Fi at hotel. Guests can avail parking facilities at the hotel.Reception assistance is offered at the hotel featuring luggage storage. During chilly days and evenings, the hotel provides an in-house fireplace to ensure your warmth. Kindly note that smoking is prohibited in the hotel to ensure fresher air for all visitors.At The Chicago Hotel Collection Ambassador Gold Coast, every guestroom is provided with convenient amenities and fittings to ensure a comfortable stay.A few accommodations within The Chicago Hotel Collection Ambassador Gold Coast offer unique design elements such as a balcony or terrace. Essential restroom facilities are equally significant, and at the hotel, some visitor bathrooms offer a hair dryer to enhance your experience. At the hotel, an assortment of easily accessible and delicious meal choices are available to satisfy your appetite whenever it strikes. Enjoy an entertaining evening with your fellow travelers at the hotel's bar.During your stay at hotel, an array of engaging activities and amenities guarantees a delightful experience.Discover the fitness amenities at hotel to maintain your health and strength during your getaway.