Book Exclusive Illinois Vacation Packages
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Illinois flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,603, price is now CA $1,060 per person
CA $1,060
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, 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.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
Price was CA $1,794, price is now CA $1,126 per person
CA $1,126
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
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 United Center and Chicago Riverwalk are located nearby.
The Peninsula Chicago
Downtown Chicago
Price was CA $4,165, price is now CA $2,806 per person
CA $2,806
per person
Jan 22 - Jan 25
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
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 property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 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, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Top Illinois hotels deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $166 per night
CA $166
CA $197 total
Nov 22 - Nov 23
includes taxes & 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 Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $197 total
Dec 1 - Dec 2
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 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.
Pet-friendly
Free WiFi
River Hotel
75 East Wacker Drive Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $141 per night
CA $141
CA $168 total
Dec 15 - Dec 16
includes taxes & fees
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
The Wade
644 N Lake Shore Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $170 per night
CA $170
CA $202 total
Nov 22 - Nov 23
includes taxes & 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 Navy Pier are located nearby.
Pool
Pet-friendly
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $149 per night
CA $149
CA $177 total
Nov 23 - Nov 24
includes taxes & fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. 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
Hilton Chicago
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $193 per night
CA $193
CA $271 total
Nov 22 - Nov 23
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 Grant Park and Millennium Park are located nearby.
Pool
Hot tub
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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