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

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Check availability on Chicago All-inclusive Resorts

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Oct 18 - Oct 19
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Oct 19 - Oct 20
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Oct 23 - Oct 25
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Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Chicago

An indoor swimming pool with a glass ceiling, wooden walls, and seating areas.
A formal dining room with a round table set for eight, surrounded by leather chairs, a chandelier, and potted plants.
A person overlooking a cityscape from a high vantage point.
A grand ballroom with ornate chandeliers, round tables with floral centerpieces, and elegant chairs.

1. Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
Downtown Chicago
$215 nightly
$256 total
Oct 31 - Nov 1
Total with taxes and fees
Palmer House a Hilton Hotel
A spacious lobby with a central sofa, multiple seating areas, and a decorative ceiling.
A cityscape with various buildings, including a prominent skyscraper and a classical building with arched windows.
A spacious bar area with a central bar, multiple seating options including bar stools and tables, and a well-lit ceiling with recessed lighting.
Outdoor seating with yellow umbrellas labeled "Twisted Tea," wicker chairs, and tables.

2. Congress Plaza Hotel

Congress Plaza Hotel
Downtown Chicago
$108 nightly
$129 total
Nov 11 - Nov 12
Total with taxes and fees
Congress Plaza Hotel
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 bar area with a high bar counter, multiple stools, and a seating area with booths and tables.
A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

3. InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
$241 nightly
$287 total
Oct 31 - Nov 1
Total with taxes and fees
InterContinental Chicago Magnificent Mile by IHG
A hotel room with two beds, a nightstand, a telephone, and a wall with printed text.
A bar area with a long counter, multiple liquor bottles, and a variety of glasses.
A restaurant with booths and tables, a television on the wall, and a view of the street outside.
A gym with treadmills, elliptical machines, and stationary bikes, large windows with a city view.

4. Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago
$172 nightly
$204 total
Nov 3 - Nov 4
Total with taxes and fees
Hilton Vacation Club Hotel Blake Chicago
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.
A bar area with a long counter, blue bar stools, and a variety of bottles and glasses.
A modern hotel room with a large bed, a desk, a sofa, and a view of the city.
A modern room with a view of a river and high-rise buildings.

5. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
$247 nightly
$294 total
Nov 1 - Nov 2
Total with taxes and fees
LondonHouse Chicago, Curio Collection by Hilton
A modern hotel lobby with large windows, leather sofas, and a view of the cityscape.
A lobby with a checkered floor, an ATM, a potted plant, a reception desk, computers, and a staircase.
A compact kitchen with a microwave, coffee maker, and sink.
A hotel room with a bed, a desk with a chair, a sofa, and a view of a building through the window.

6. Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago
Downtown Chicago
$112 nightly
$131 total
Nov 11 - Nov 12
Total with taxes and fees
Travelodge by Wyndham Downtown 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.

7. Hyatt Regency Chicago

Hyatt Regency Chicago
Downtown Chicago
$294 nightly
$350 total
Oct 31 - Nov 1
Total with taxes and fees
Hyatt Regency Chicago
A modern interior with a bar area, seating, and decorative wooden panels.
A modern hotel with a prominent "Grant Park Hotel" sign and "Best Western" branding.
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.

8. Best Western Grant Park Hotel

Best Western Grant Park Hotel
Downtown Chicago
$107 nightly
$127 total
Nov 10 - Nov 11
Total with taxes and fees
Best Western Grant Park Hotel
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 rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

9. Hotel 505 River North

Hotel 505 River North
Downtown Chicago
$190 nightly
$226 total
Nov 17 - Nov 18
Total with taxes and fees
Hotel 505 River North
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 room with a bed, a window with curtains, a small table with a vase of flowers, and a chair.
A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.
A bar area with a long counter, multiple shelves of bottles, and four bar stools.

10. L7 Chicago by LOTTE

L7 Chicago by LOTTE
Downtown Chicago
$184 nightly
$218 total
Nov 1 - Nov 2
Total with taxes and fees
L7 Chicago by LOTTE
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Choose what matters most at all-inclusive hotels in Chicago

Adult-only
5 stars
Pool
4 stars
Family-friendly

Find out more about Chicago

Discover top Chicago (and vicinity) attractions

Travelers seeking all-inclusive experiences in the greater Chicago area will find a wealth of activities and attractions that cater to both adventure and relaxation. Start your journey at the iconic Millennium Park, where you can enjoy art installations like the Cloud Gate sculpture, often called "The Bean," and take part in seasonal concerts and events that create a lively atmosphere. Just a short walk away, the Art Institute of Chicago offers an expansive collection of artworks, from Impressionist masterpieces to contemporary pieces, making it a perfect cultural stop. For family fun, visit the Shedd Aquarium, where you can explore aquatic life from around the globe, with interactive exhibits that are sure to entertain children and adults alike. After a day of exploration, unwind at Navy Pier, where you can enjoy dining options that range from deep-dish pizza to gourmet seafood, and take a scenic boat ride on Lake Michigan. When it comes to all-inclusive hotels, many properties in the River North area offer packages that include gourmet meals, spa treatments, and guided tours of the city's attractions, ensuring you and your family are pampered throughout your stay. This vibrant neighborhood is known for its luxury shopping and dynamic nightlife, creating an engaging atmosphere that enhances your all-inclusive experience.

Top Chicago Hotel Reviews

Frequently asked questions

What are the most popular all-inclusive resorts in Chicago?
For travellers seeking a convenient and value-driven getaway in Chicago, The Wheeler Mansion is a standout all-inclusive option. This charming 4-star hotel boasts an excellent guest rating of 9.0, making it a favorite among visitors looking for an inclusive experience.At The Wheeler Mansion, guests can enjoy a delightful start to their day with a complimentary cooked breakfast, ensuring you're fueled up for your Chicago adventures. The property also features free WiFi, allowing you to stay connected, and free self-parking, a rare convenience in the city.
How much does an all-inclusive hotel in Chicago cost?
Enjoy staying in an all-inclusive hotel in Chicago, with hotels from $129 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 are the top-rated luxury all-inclusive hotels in Chicago?
For those seeking a luxurious all-inclusive experience in Chicago, the 4-star Wheeler Mansion stands out with an excellent guest rating of 9.0. This boutique hotel offers an intimate atmosphere and is designed to provide a comfortable and memorable stay.At The Wheeler Mansion, you can indulge in a complimentary cooked breakfast each morning, setting the tone for a delightful day ahead. The hotel also offers free Wi-Fi, ensuring you stay connected during your visit.
What are the best Chicago all-inclusive hotels on the beach?
For travellers seeking all-inclusive meal options in Chicago, the 4-star Wheeler Mansion is a standout option, boasting an excellent guest rating of 9.0. While not directly on the beach, it provides a unique all-inclusive stay that includes a delicious cooked breakfast, complimentary toiletries, and free WiFi, ensuring a comfortable and convenient experience for all guests.This historic mansion offers a charming atmosphere with luxurious accommodations, making it particularly appealing for couples looking for a romantic getaway.
Is it cheaper to book a Chicago all-inclusive hotel and flight package?
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 travelers 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.

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