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.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,286, price is now CA $925 per person
CA $925
per person
Nov 20 - Nov 23
found 2 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,375, price is now CA $960 per person
CA $960
per person
Dec 19 - Dec 24
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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.
The Emily Hotel
Downtown Chicago
Price was CA $1,320, price is now CA $929 per person
CA $929
per person
Dec 19 - Dec 24
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,494, price is now CA $1,055 per person
CA $1,055
per person
Nov 21 - Nov 23
found 2 hours ago
Roundtrip flight included
Montreal (YMQ) 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.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,361, price is now CA $991 per person
CA $991
per person
Dec 19 - Dec 24
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Top Illinois hotels deals
River Hotel
75 East Wacker Drive Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $263 per night
CA $263
CA $313 total
Oct 25 - Oct 26
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $227 per night
CA $227
CA $270 total
Oct 26 - Oct 27
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.
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 $253 per night
CA $253
CA $301 total
Oct 14 - Oct 15
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.
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $298 per night
CA $298
CA $354 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, 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.
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $228 per night
CA $228
CA $271 total
Oct 25 - Oct 26
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 $227 per night
CA $227
CA $312 total
Oct 24 - Oct 25
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.
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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