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

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Oct 30 - Nov 1
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Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Chicago

A grand hotel lobby with a central staircase, ornate columns, and a decorative ceiling.

1. Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,495 reviews)
The price is CA $151
CA $221 total
includes taxes & fees
Nov 27 - Nov 28
Hilton Chicago
A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

2. Hotel 505 River North

Hotel 505 River North
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,989 reviews)
The price is CA $155
CA $230 total
includes taxes & fees
Nov 29 - Nov 30
Hotel 505 River North
A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

3. LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,874 reviews)
The price is CA $201
CA $280 total
includes taxes & fees
Nov 23 - Nov 24
LondonHouse Chicago, Curio Collection by Hilton
A river with buildings on both sides, a bridge, and a pedestrian walkway.

4. River Hotel

River Hotel
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (5,573 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 24 - Nov 25
River Hotel
A swimming pool with lounge chairs and umbrellas, surrounded by tall buildings.

5. DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,580 reviews)
The price is CA $141
CA $168 total
includes taxes & fees
Nov 23 - Nov 24
DoubleTree by Hilton Chicago - Magnificent Mile
A modern interior with a geometric bookshelf filled with books, a bench, and a lamp.

6. Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,416 reviews)
The price is CA $188
CA $267 total
includes taxes & fees
Nov 23 - Nov 24
Arlo Chicago
A modern hotel with a glass facade, multiple floors, and a visible entrance.

7. Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,686 reviews)
The price is CA $165
CA $196 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Place Chicago/Downtown - The Loop
A modern building with a colorful facade and a red circular seating area.

8. citizenM Chicago Downtown

citizenM Chicago Downtown
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,385 reviews)
The price is CA $162
CA $193 total
includes taxes & fees
Nov 23 - Nov 24
citizenM Chicago Downtown
A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.

9. Swissotel - Chicago

Swissotel - Chicago
4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,568 reviews)
The price is CA $163
CA $243 total
includes taxes & fees
Nov 26 - Nov 27
Swissotel - Chicago
A modern lobby with a grey sofa, checkered ottomans, and a coffee table. There are black chairs, a blue sofa, and a TV on a stand.

10. Aloft by Marriott Chicago Mag Mile

Aloft by Marriott Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,328 reviews)
The price is CA $153
CA $182 total
includes taxes & fees
Nov 24 - Nov 25
Aloft by Marriott Chicago Mag Mile
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at all-inclusive hotels in Chicago

Adult-only
5 stars

Find out more about Chicago

Discover top Chicago attractions

For travellers seeking all-inclusive hotels in the greater Chicago area, the vibrant city offers a wealth of engaging experiences. Start your adventure at the stunning waterfront, where you can enjoy picturesque views of the skyline while strolling along the lakeside paths. Families will love exploring the interactive exhibits at a renowned science center, which provides hands-on fun for all ages. For those who appreciate art and culture, the nearby art district showcases a variety of local galleries and unique installations, perfect for an afternoon of inspiration. Don’t miss a visit to the bustling food markets, where you can sample local delicacies and gourmet treats that capture the essence of Chicago's diverse culinary scene. After a day of exploration, return to your all-inclusive hotel, where you can indulge in a variety of dining options, from exquisite multi-course meals to casual bites, all included in your stay. Many properties also offer family-friendly activities, wellness programs, and live entertainment, ensuring a seamless blend of relaxation and excitement. Consider staying in the vibrant downtown area, where you can easily access these attractions while enjoying the luxurious amenities of your hotel, creating the perfect base for your Chicago getaway.

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 $168 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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