Book Exclusive Illinois Vacation Packages
Search vacation packages deals in Illinois's top destinations
Chicago
Vacations
Illinois flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,027, price is now CA $714 per person
CA $714
per person
Apr 3 - Apr 5
just found
Roundtrip flight included
Detroit (DTW) 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.
Waldorf Astoria Chicago
Downtown Chicago
Price was CA $2,992, price is now CA $1,837 per person
CA $1,837
per person
Apr 1 - Apr 6
just found
Roundtrip non-stop flight included
Vancouver (YVR) 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.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,542, price is now CA $1,816 per person
CA $1,816
per person
Apr 1 - Apr 6
just found
Roundtrip non-stop flight included
Vancouver (YVR) 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.
The Peninsula Chicago
Downtown Chicago
Price was CA $3,202, price is now CA $2,293 per person
CA $2,293
per person
Apr 1 - Apr 6
just found
Roundtrip non-stop flight included
Vancouver (YVR) 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.
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 $188 per night
CA $188
CA $221 total
Feb 14 - Feb 15
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 Millennium Park and Chicago Riverwalk are located nearby.
Free WiFi
Restaurant
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 $254 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
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CA $154 per night
CA $154
CA $181 total
Jan 25 - Jan 26
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
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
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $242 total
Jan 24 - Jan 25
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 restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Pet-friendly
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
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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