A river with a yellow boat, surrounded by tall buildings and a bridge.

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Check availability on Chicago All Inclusive Resorts and Hotels

Tonight
Oct 20 - Oct 21
Tomorrow
Oct 21 - Oct 22
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Chicago

A modern hotel lobby with a curved white sofa, two side tables with lamps, a black coffee table, and a large chandelier.
A hotel room with two beds, a desk with a television, a chair, a desk lamp, and a painting on the wall.
A restaurant interior with wooden tables and chairs, a carpeted floor, and framed pictures on the walls.
A marina with numerous boats docked, surrounded by a cityscape with high-rise buildings and a stadium.

1. Hilton Chicago

Hilton Chicago
Downtown Chicago
CA $234
CA $320 total
includes taxes & fees
Oct 30 - Oct 31
Hilton Chicago
The Intercontinental hotel facade with a large American flag and a floral display.
A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.
A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

2. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
CA $299
CA $405 total
includes taxes & fees
Oct 31 - Nov 1
InterContinental Chicago Magnificent Mile by IHG
A modern restaurant interior with a green wall, hanging lights, and a long dining area.
A modern interior with wooden flooring, black furniture, and large windows offering city views.
A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

3. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
CA $236
CA $326 total
includes taxes & fees
Nov 20 - Nov 21
Hotel 505 River North
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.
A grand ballroom with ornate ceiling decorations, multiple chandeliers, and a central table with a white tablecloth.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.

4. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
CA $147
CA $175 total
includes taxes & fees
Nov 10 - Nov 11
Congress Plaza Hotel
The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.
A bar area with a marble countertop, bar stools, and a variety of bottles.
A spacious lobby with a marble floor, a reception desk, and a glass partition.

5. Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago
CA $221
CA $303 total
includes taxes & fees
Nov 11 - Nov 12
Hotel Riu Plaza Chicago
A spacious bar area with high ceilings and large windows, offering views of a cityscape.
A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.
A cityscape with modern high-rise buildings, a river, and a boat.
A bar with a circular liquor display, seating with stools, and a city view through large windows.

6. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
CA $358
CA $476 total
includes taxes & fees
Oct 31 - Nov 1
Hyatt Regency Chicago
A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

7. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
CA $220
CA $261 total
includes taxes & fees
Nov 1 - Nov 2
L7 Chicago by LOTTE
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.
A cozy room with a patterned carpet, a wooden table, and a green sofa with a white throw blanket.
Transparent igloo-like structures with seating inside, set on a wooden deck with snow on the ground, surrounded by tall buildings.
A hotel reception area with a modern design, featuring a wooden panel wall and a marble reception desk.

8. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
CA $190
CA $226 total
includes taxes & fees
Nov 1 - Nov 2
DoubleTree by Hilton Chicago - Magnificent Mile
A building with a sign reading "111" and "III West Adams Street" indicating a pub and restaurant.
A restaurant interior with brick walls, wooden tables and chairs, and a bar area.
A bar with a brick archway, wooden bar counter, and stools.
A hotel room with a large window, a bed, and a suitcase.

9. Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago
Downtown Chicago
CA $182
CA $216 total
includes taxes & fees
Oct 25 - Oct 26
Club Quarters Hotel, Central Loop, Chicago
A modern interior with a bar area, seating, and decorative wooden panels.
A hotel room with a large bed, a flat-screen TV, a desk with a lamp, and a chair.
A hotel room with a flat-screen TV, a wooden cabinet, a round table, a blue sofa, a desk with a computer, and a large window with curtains.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.

10. Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago
CA $151
CA $180 total
includes taxes & fees
Nov 10 - Nov 11
Best Western Grant Park Hotel
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Choose what matters most at all-inclusive hotels in Chicago

Adult-only
5 stars
Pool
4 stars
Water park

Find out more about Chicago

Discover top Chicago (and vicinity) attractions

For families seeking all-inclusive meal options in the greater Chicago area, there are numerous attractions that blend excitement with relaxation. Start your adventure at the Shedd Aquarium, where you can marvel at diverse marine life and even enjoy interactive exhibits. Just a short drive away, the Field Museum offers a captivating journey through history, with its impressive dinosaur skeletons and ancient treasures that spark the imagination of both young and old. Culture enthusiasts will love the Art Institute of Chicago, housing masterpieces ranging from Impressionist paintings to contemporary works, providing a feast for the eyes. For outdoor enthusiasts, the Lincoln Park Zoo is not only free but also features beautiful gardens and picnic areas, perfect for a day out with the family. After a day of adventure, returning to an all-inclusive hotel often means indulging in a variety of dining options, from classic Chicago deep-dish pizza to gourmet international cuisine, along with activities like guided city tours or family-friendly entertainment. The Lincoln Park area is particularly suited for families, offering a blend of green spaces, museums, and nearby the vibrant North Avenue Beach, which is ideal for relaxation and fun. Staying in this bustling neighbourhood allows for an easy exploration of the city’s rich offerings, ensuring that every day is filled with memorable experiences.

Top Chicago Hotel Reviews

Frequently asked questions

How much does an all-inclusive hotel in Chicago cost?
Enjoy staying in an all-inclusive hotel in Chicago, with hotels from CA $175 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
What area of Chicago is best for all-inclusive hotels?
The Magnificent Mile in Chicago is the premier area for travellers seeking all-inclusive hotels that blend luxury with convenience. This iconic stretch along Michigan Avenue is famed for its upscale shopping, fine dining, and proximity to cultural attractions such as the Art Institute of Chicago and the historic Water Tower. Here, you'll find high-end hotels that often include amenities like spa services, gourmet dining options, and rooftop pools, ensuring a comfortable and memorable STAY.For couples on a romantic escape, the nearby River North district is a delightful option. With its chic atmosphere, art galleries, and intimate restaurants, this area provides a great backdrop for a romantic getaway. Enjoy a leisurely stroll along the Chicago Riverwalk or indulge in a candlelit dinner at one of the many acclaimed eateries, making your trip truly special.Families will appreciate the convenience of staying near Navy Pier, where a wealth of entertainment awaits. From the iconic Ferris wheel to interactive museums like the Chicago Children's Museum, the area is designed to engage visitors of all ages. Many family-friendly hotels offer packages that include meals and tickets to local attractions, ensuring a straightforward experience for parents and children alike.
What is the best time to stay at an all-inclusive hotel in Chicago?
The most popular time to STAY at an all-inclusive hotel in Chicago is during the summer months, particularly in July. This time of year typically brings warm temperatures averaging around 28°C, making it ideal for enjoying the city's outdoor attractions, such as Millennium Park or a boat tour along the Chicago River.With the pleasant weather, tourists flock to the city, and you'll find a bustling atmosphere around popular sites like Navy Pier, where festivals and outdoor concerts often take place. The vibrant summer calendar also includes events like the Chicago Air and Water Show, providing fantastic entertainment for families and groups of friends.If you're looking for a more budget-friendly and relaxed experience, consider visiting in September. The weather remains agreeable, with temperatures ranging from 20°C to 25°C, and it's less busy. This month also offers a great opportunity to enjoy local festivals, such as the Chicago Gourmet, while benefiting from lower hotel rates and better availability.
Is it cheaper to book an all-inclusive hotel and flight package in Chicago?
Booking an all-inclusive hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect all-inclusive travel package.
What all-inclusive amenities should we expect at hotels in Chicago?
All-inclusive hotels are perfect for travellers who want a relaxing, top-value vacation. Most packages include your room, all meals, snacks, unlimited drinks including alcohol and non-alcoholic drinks. Entertainment, kids' clubs, access to pools and fitness facilities are often included in the all-inclusive package as well. Some even cover airport transfers, while extras like spa treatments or premium alcohol may cost more. Knowing most of your expenses are already covered makes for a truly relaxing getaway. For more information, refer to the property details on Expedia.
Can I cancel my all-inclusive hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right all-inclusive hotel in Chicago for you.
How can I save on an all-inclusive hotel in Chicago with Expedia?
There are plenty of ways to save on an all-inclusive hotel in Chicago. Join One Key™, our free travel rewards program, to unlock instant discounts with Member Prices across a range of premium hotels. Typically, booking in advance will help you save on your hotel. If you're feeling spontaneous, be sure to check for last-minute deals.

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