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 Chicago Downtown, Autograph Collection by Marriott
Downtown Chicago
Price was CA $1,057, price is now CA $760 per person
CA $760
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,324, price is now CA $890 per person
CA $890
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) 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 $1,620, price is now CA $1,144 per person
CA $1,144
per person
Apr 1 - Apr 6
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 $1,723, price is now CA $1,240 per person
CA $1,240
per person
Mar 13 - Mar 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) 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.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,389, price is now CA $1,017 per person
CA $1,017
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
Book a stay at this business-friendly 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.
Top Illinois hotels deals
Hilton Chicago
720 S Michigan Ave Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $181 per night
CA $181
CA $253 total
Feb 1 - Feb 2
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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $198 per night
CA $198
CA $267 total
Jan 28 - Jan 29
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 $112 per night
CA $112
CA $131 total
Jan 25 - Jan 26
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.
Pool
Pet-friendly
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
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 $149 per night
CA $149
CA $175 total
Jan 19 - Jan 20
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
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $219 per night
CA $219
CA $298 total
Feb 1 - Feb 2
includes taxes & 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
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
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
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.
Navy Pier
With a visit to Navy Pier, a favorite shopping spot in Chicago, you can enjoy some retail therapy. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Photos of local treasures
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