Book Exclusive Illinois Vacation Packages
Search vacation packages deals in Illinois's top destinations
Chicago
Vacations
Illinois flight + hotel packages
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Jun. 14 - Jun. 18
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby. Discover genuine guest reviews for Trump International Hotel & Tower Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Jun. 14 - Jun. 18
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby. Discover genuine guest reviews for Pendry Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Fairmont Chicago at Millennium Park Gold Experience
Downtown Chicago
Save 100% on your flight
per person
Jun. 14 - Jun. 18
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast. Popular attractions Millennium Park and Chicago Riverwalk are located nearby. Discover genuine guest reviews for Fairmont Chicago at Millennium Park Gold Experience, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for The Peninsula Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this business-friendly hotel in Chicago. Enjoy an outdoor pool, a rooftop terrace, and breakfast. Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for DoubleTree by Hilton Chicago - Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.
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 $156 per night
CA $156
per night
Apr. 28 - Apr. 29
Stay at this business-friendly 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 Grant Park and Art Institute of Chicago are located nearby. Discover genuine guest reviews for Congress Plaza Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Breakfast available
Parking available
River Hotel
75 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
per night
Apr. 21 - Apr. 22
Stay at this 4-star 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. Discover genuine guest reviews for River Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Pet-friendly
Parking available
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $207 per night
CA $207
per night
Apr. 23 - Apr. 24
Stay at this 4-star 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. Discover genuine guest reviews for Eurostars Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Spa
Parking available
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
per night
Apr. 21 - Apr. 22
Stay at this 4-star boutique hotel in Chicago. Enjoy a 24-hour health club, onsite parking, 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. Discover genuine guest reviews for Hotel Felix River North/Magnificent Mile, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
per night
Apr. 21 - Apr. 22
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Millennium Park are located nearby. Discover genuine guest reviews for Club Quarters Hotel, Central Loop, Chicago, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
InterContinental Chicago Magnificent Mile, an IHG Hotel
505 N Michigan Ave, Chicago, IL
Free cancellation
The price is CA $274 per night
CA $274
per night
Apr. 21 - Apr. 22
Stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby. Discover genuine guest reviews for InterContinental Chicago Magnificent Mile, an IHG Hotel, in Downtown Chicago neighborhood, along with the latest prices and availability – book now.
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
4.5/5(158 reviews)
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.
McCormick Place
4.5/5(141 reviews)
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.
Navy Pier
4.5/5(459 reviews)
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 theater scene.
- Chicago Vacations
- Champaign Vacations
- Galena Vacations
- Springfield Vacations
- Naperville Vacations
- Mount Vernon Vacations
- Tinley Park Vacations
- Collinsville Vacations
- Waukegan Vacations
- Quincy Vacations
- Elgin Vacations
- Utica Vacations
- Metropolis Vacations
- Fairview Heights Vacations
- Belleville Vacations
- Mattoon Vacations
Book a vacation to Illinois
Most popular
Hotels
Flights
Flights to Texas (DFW)Flights to Florida (ORL)Flights to New Jersey (NYC)Flights to North Carolina (GSO)Flights to California (QLA)Flights to Minnesota (MSP)Flights to South Carolina (MYR)Flights to Alaska (ADQ)Flights to Montana (FCA)Flights to Hawaii (KOA)Flights to Virginia (WAS)Flights to Arizona (LAS)Flights to Michigan (DTT)Flights to Ohio (CLE)Flights to Utah (SLC)
6a94ba5a-ea21-49ba-8038-69c6e8c75c92b22e0359-f25a-43d5-a9bd-e1ba2091d841