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
$113 nightly
The price is $133 total per night
$133 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$85 nightly
The price is $100 total per night
$100 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$87 nightly
The price is $102 total per night
$102 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
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
$115 nightly
The price is $135 total per night
$135 total
Jan 19 - Jan 20, 2026
Total with taxes and fees
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
$138 nightly
The price is $162 total per night
$162 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
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
$97 nightly
The price is $114 total per night
$114 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$99 nightly
The price is $116 total per night
$116 total
Dec 29 - Dec 30
Total with taxes and fees
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
$139 nightly
The price is $164 total per night
$164 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
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
$76 nightly
The price is $89 total per night
$89 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
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
Reserve now, pay when you stay
$156 nightly
The price is $183 total per night
$183 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
$169 nightly
The price is $198 total per night
$198 total
Jan 20 - Jan 21, 2026
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
$83 nightly
The price is $97 total per night
$97 total
Jan 5 - Jan 6, 2026
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
$135 nightly
The price is $159 total per night
$159 total
Jan 5 - Jan 6, 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
$86 nightly
The price is $101 total per night
$101 total
Jan 25 - Jan 26, 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
$77 nightly
The price is $91 total per night
$91 total
Dec 27 - Dec 28
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
Jan 1 - Jan 2, 2026
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 5 - Jan 6, 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
$319 nightly
The price is $374 total per night
$374 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
    $156 nightly
    The price is $179 total per night from Jan 2 to Jan 3
    $179 total
    Jan 2 - Jan 3, 2026
    Total with taxes and fees
    8.4/10 Very Good! (2,172 reviews)
    Embassy Suites by Hilton Chicago Downtown River North

    Embassy Suites by Hilton Chicago Downtown River North

    600 N State St Chicago IL
    $94 nightly
    The price is $111 total per night from Jan 4 to Jan 5
    $111 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.4/10 Very Good! (5,420 reviews)
    Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    Embassy Suites by Hilton Chicago Downtown Magnificent Mile

    511 North Columbus Drive Chicago IL
    $109 nightly
    The price is $127 total per night from Jan 6 to Jan 7
    $127 total
    Jan 6 - Jan 7, 2026
    Total with taxes and fees
    8.2/10 Very Good! (2,748 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
5,598 hotels
Lowest Price
$89
Highest Price
$374
Popular hotels
Pheasant Run Resort

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