Find All Inclusive Resorts in Chicago

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Featured Chicago All Inclusive Resorts & Hotels

Pheasant Run Resort

Pheasant Run Resort

2 out of 5
4051 E Main Street West Chicago IL
Pheasant Run Resort features an indoor pool, an outdoor pool, and a gym. You can take advantage of free parking, along with an airport shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, concierge services, and securing valuables. Other amenities at this family-friendly hotel include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
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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.

Featured hotels in Chicago with Free-Breakfast

Hyatt Place Chicago/River North

Hyatt Place Chicago/River North

3.5 out of 5
66 W Illinois St Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $130 total per night
$130 total
per night
Dec 21 - Dec 22
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 coffee shops/cafes. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Free WiFi
Hampton Inn & Suites Chicago Downtown

Hampton Inn & Suites Chicago Downtown

3 out of 5
33 West Illinois Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $107 total per night
$107 total
per night
Jan 4 - Jan 5
Stay at this hotel in Chicago. Enjoy free breakfast, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
Home2 Suites by Hilton Chicago River North

Home2 Suites by Hilton Chicago River North

3 out of 5
110 West Huron St Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $112 total per night
$112 total
per night
Dec 21 - Dec 22
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Pet friendly
Springhill Suites by Marriott Chicago Downtown/ River North

Springhill Suites by Marriott Chicago Downtown/ River North

3.5 out of 5
410 North Dearborn Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $141 total per night
$141 total
per night
Jan 1 - Jan 2
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Breakfast included
Free WiFi
Hyatt Place Chicago Midway Airport

Hyatt Place Chicago Midway Airport

3 out of 5
6550 S Cicero Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $159 total per night
$159 total
per night
Dec 21 - Dec 22
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Pool
Free airport shuttle
Fairfield Inn & Suites Chicago Downtown/River North

Fairfield Inn & Suites Chicago Downtown/River North

3 out of 5
60 W Illinois St Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $114 total per night
$114 total
per night
Dec 23 - Dec 24
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Free WiFi
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $110 total per night
$110 total
per night
Dec 16 - Dec 17
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Pet friendly
Hampton Inn by Hilton Chicago-Midway Airport

Hampton Inn by Hilton Chicago-Midway Airport

2.5 out of 5
6540 S Cicero Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $149 total per night
$149 total
per night
Jan 4 - Jan 5
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SeatGeek Stadium and Chicago Ridge Shopping Mall are located nearby.
Breakfast included
Free airport shuttle
Home2 Suites by Hilton Chicago McCormick Place

Home2 Suites by Hilton Chicago McCormick Place

3 out of 5
123 E. CERMAK ROAD Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $84 total per night
$84 total
per night
Jan 7 - Jan 8
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Pool
Breakfast included
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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.

Featured hotels in Chicago with Free Wi-Fi

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr Chicago IL
Free Cancellation
$162 nightly
The price is $190 total per night
$190 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pool
Pet friendly
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$161 nightly
The price is $189 total per night
$189 total
Dec 28 - Dec 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Free WiFi
Restaurant
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl Chicago IL
Free Cancellation
Reserve now, pay when you stay
$78 nightly
The price is $92 total per night
$92 total
Dec 16 - Dec 17
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Breakfast included
Pet friendly
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive Chicago IL
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $153 total per night
$153 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Spa
Free WiFi
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $110 total per night
$110 total
Jan 13 - Jan 14, 2026
Total with taxes and fees
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Spa
Free WiFi
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free Cancellation
Reserve now, pay when you stay
$100 nightly
The price is $118 total per night
$118 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Free WiFi
Restaurant
Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
20 E Chestnut St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$186 nightly
The price is $218 total per night
$218 total
Dec 17 - Dec 18
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet friendly
Free WiFi
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
800 S Michigan Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $120 total per night
$120 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Pet friendly
Free WiFi
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
401 N Wabash Ave Chicago IL
Free Cancellation
Reserve now, pay when you stay
$296 nightly
The price is $348 total per night
$348 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pool
Spa
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.

Family Friendly Chicago Hotels

    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St Chicago IL
    $136 nightly
    The price is $155 total per night from Dec 21 to Dec 22
    $155 total
    Dec 21 - Dec 22
    Total with taxes and fees
    8.4/10 Very Good! (2,123 reviews)
    Embassy Suites by Hilton Chicago Downtown River North

    Embassy Suites by Hilton Chicago Downtown River North

    600 N State St Chicago IL
    $96 nightly
    The price is $113 total per night from Jan 6 to Jan 7
    $113 total
    Jan 6 - Jan 7, 2026
    Total with taxes and fees
    8.4/10 Very Good! (5,385 reviews)
    Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    511 North Columbus Drive Chicago IL
    $103 nightly
    The price is $120 total per night from Jan 11 to Jan 12
    $120 total
    Jan 11 - Jan 12, 2026
    Total with taxes and fees
    8.2/10 Very Good! (2,741 reviews)

Things to See and Do Near Your Chicago Resort

Sights and AttractionsDistance from City
CIBC Theatre0.1 mi
Symphony Center0.2 mi
Chicago Symphony Orchestra0.2 mi
Montrose Harbor5.8 mi
Oak Brook Golf Course15.7 mi
The Glen Club17.7 mi
Field Museum of Natural History1.2 mi
Chicago Children's Museum1.3 mi
Dave & Buster's1.4 mi

What Airport Should I Fly Into to Get to My Chicago Resort?

You can fly into Chicago Midway Airport (MDW), situated 8.6 mi from the city center. If that airport isn't convenient for your travel schedule, consider booking a flight into Chicago O'Hare Intl. Airport (ORD), which is 15.7 mi away from the city center.

Chicago hotels essential information

Accommodation
5,610 hotels
Lowest Price
$84
Highest Price
$348
Popular hotels
Pheasant Run Resort

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