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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,032, price is now CA $674 per person
CA $674
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Viceroy Chicago
Downtown Chicago
Price was CA $1,638, price is now CA $1,078 per person
CA $1,078
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,558, price is now CA $1,049 per person
CA $1,049
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
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.
SpringHill Suites by Marriott Chicago Southwest at Burr Ridge/Hinsdale
Price was CA $1,092, price is now CA $739 per person
CA $739
per person
Feb 7 - Feb 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Burr Ridge. Enjoy free breakfast, free WiFi, and a 24-hour health club. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Burr Ridge Village Center and Flagg Creek Golf Course are located nearby.
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $2,178, price is now CA $1,480 per person
CA $1,480
per person
Mar 6 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and The Dome at the Parkway Bank Sports Complex are located nearby.
Top Illinois hotels deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $122 per night
CA $122
CA $144 total
Jan 6 - Jan 7, 2026
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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $180 per night
CA $180
CA $245 total
Jan 3 - Jan 4, 2026
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
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
Free WiFi
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. 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
Air conditioning
Hilton Chicago
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $224 total
Dec 30 - Dec 31
includes taxes & fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Pool
Hot tub
Eurostars Magnificent Mile
660 North State Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $129 per night
CA $129
CA $151 total
Jan 22 - Jan 23, 2026
includes taxes & 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
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
Michigan Avenue
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.
Wrigley Field
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.
McCormick Place
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed theater scene and notable monuments in this vibrant area.
Photos of local treasures
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