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 $1,202, price is now CA $827 per person
CA $827
per person
May 7 - May 10
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.
Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,264, price is now CA $828 per person
CA $828
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Holiday Inn Chicago SW-Countryside ConfCtr by IHG
Price was CA $1,319, price is now CA $929 per person
CA $929
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Countryside. Enjoy free WiFi, free parking, and room service. Our guests praise the pool and the clean rooms in our reviews. Popular attractions Flagg Creek Golf Course and New Vintage are located nearby.
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $1,645, price is now CA $1,207 per person
CA $1,207
per person
Apr 21 - Apr 25
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Days Inn by Wyndham Waukegan
Price was CA $1,151, price is now CA $850 per person
CA $850
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Chicago (ORD)
Stay at this motel in Waukegan. Enjoy free WiFi, free parking, and a business center. Popular attractions Six Flags Great America and Gurnee Mills 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 $236 per night
CA $236
CA $277 total
Mar 27 - Mar 28
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
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $154 per night
CA $154
CA $219 total
Mar 4 - Mar 5
includes taxes & fees
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.
Breakfast included
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is CA $151 per night
CA $151
CA $177 total
Mar 5 - Mar 6
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $162 total
Mar 5 - Mar 6
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
Eurostars Magnificent Mile
660 North State Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $184 total
Apr 1 - Apr 2
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
Aloft Chicago Mag Mile
243 E. Ontario Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $125 per night
CA $125
CA $147 total
Mar 8 - Mar 9
includes taxes & fees
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk 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.
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 art 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.
McCormick Place
During your trip, find out what's happening at McCormick Place, a top convention center in Chicago. Discover the acclaimed art scene and notable monuments in this vibrant area.
Photos of local treasures
Browse Illinois vacation photos for more inspiration
