Book Exclusive Illinois Vacation Packages
Search vacation packages deals in Illinois's top destinations
Chicago
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Illinois flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $981, price is now CA $604 per person
CA $604
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,556, price is now CA $879 per person
CA $879
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Art Villa
West Town
Price was CA $1,526, price is now CA $920 per person
CA $920
per person
Jan 21 - Jan 24
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions United Center and Chicago Riverwalk are located nearby.
Grand Royal Hotel O'Hare - Chicago
Price was CA $1,371, price is now CA $844 per person
CA $844
per person
Dec 25 - Jan 1
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Woodfield Mall are located nearby.
Sentral Michigan Avenue
Downtown Chicago
Price was CA $1,586, price is now CA $996 per person
CA $996
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Soldier Field and Millennium Park are located nearby.
Top Illinois hotels deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $152 total
Dec 7 - Dec 8
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $143 per night
CA $143
CA $203 total
Dec 21 - Dec 22
includes taxes & fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pool
Spa
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $117 per night
CA $117
CA $137 total
Dec 7 - Dec 8
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. 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
citizenM Chicago Downtown
80 East Wacker Place Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $150 per night
CA $150
CA $176 total
Dec 8 - Dec 9
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Free WiFi
Restaurant
Warwick Allerton - Chicago
701 North Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $112 per night
CA $112
CA $172 total
Dec 15 - Dec 16
includes taxes & fees
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Free WiFi
Air conditioning
The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $133 total
Dec 8 - Dec 9
includes taxes & 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
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.
Popular places to visit
Wrigley Field
4.5/5(158 reviews)
Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Michigan Avenue
4.5/5(19 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
McCormick Place
4.5/5(141 reviews)
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
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