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 Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,385, price is now CA $1,025 per person
CA $1,025
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was CA $2,182, price is now CA $1,528 per person
CA $1,528
per person
Oct 26 - Oct 30
found 1 day 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.
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was CA $2,074, price is now CA $1,481 per person
CA $1,481
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Talbott, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was CA $2,004, price is now CA $1,452 per person
CA $1,452
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop 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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was CA $2,411, price is now CA $1,836 per person
CA $1,836
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Top Illinois hotels deals
River Hotel
75 East Wacker Drive Chicago IL
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.
Free WiFi
Restaurant
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 $240 per night
CA $240
CA $286 total
Sep 27 - Sep 28
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.
Pet-friendly
Free WiFi
Hampton Inn Chicago Downtown/Magnificent Mile
160 E Huron Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $293 per night
CA $293
CA $349 total
Oct 15 - Oct 16
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.
Breakfast included
Pet-friendly
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is CA $228 per night
CA $228
CA $271 total
Sep 27 - Sep 28
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
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.
Pool
Hot tub
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.
Photos of local treasures
Browse Illinois vacation photos for more inspiration
Frequently asked questions
Book a vacation to Illinois
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in Carrollton
- 5 Star Hotels in Grand Chain
- 5 Star Hotels in Hamletsburg
- 5 Star Hotels in Kenney
- 5 Star Hotels in Rosemont
- Algonquin Hotels
- Hotels with Waterslides in Aurora
- Aurora Hotels
- La Quinta Inn & Suites Hotels in Belleville
- Bridgeview Hotels
- Cottages in Chicago
- Extended Stay Hotels in Chicago
- All Inclusive Resorts & in Chicago
- Hotels with Hot Tubs in Chicago
- Hotels with smoking rooms in Chicago
- Waterpark Hotels and Resorts in Chicago
- Chicago Hotels
- Motels in Chicago
- Cottages in Fox Lake
- B&B in Northbrook
- La Quinta Inn & Suites Hotels in Ottawa
- Motel 6 Hotels in Ottawa
- Red Roof Inn Hotels in Ottawa
- Waterpark Hotels and Resorts in Ottawa
- Ottawa Hotels
- Motel 6 Hotels in Rosemont
- Hotels with Hot Tubs in Woodstock
- Algonquin Vacations
- Belleville Vacations
- Benton Vacations
- Bloomingdale Vacations
- Carlyle Vacations
- Cave-In-Rock Vacations
- Chana Vacations
- Chenoa Vacations
- Chicago Vacations
- Collinsville Vacations
- Cuba Vacations
- Dupo Vacations
- Elmhurst Vacations
- Elmwood Park Vacations
- Galena Vacations
- Golf Vacations
- Grafton Vacations
- Granite City Vacations
- La Salle Vacations
- Lincolnshire Vacations
- Menard Vacations
- Midlothian Vacations
- Naperville Vacations
- New Windsor Vacations
- Niles Vacations
- Northbrook Vacations
- Peru Vacations
- Quincy Vacations
- Roselle Vacations
- Rosemont Vacations
- Schiller Park Vacations
- Springfield Vacations
- Thebes Vacations
- Tinley Park Vacations
- Waukegan Vacations
- West Chicago Vacations
- West Frankfort Vacations
- Westmont Vacations
- Willowbrook Vacations
- Yorkville Vacations
- Ace Rental Cars in Ottawa
- Auto Rent Rental Cars in Glencoe
- Budget Rental Cars in Ottawa
- Car rentals near Chicago
- Car rental Fidelity
- Car rental Hometown
- Car rental Savoy
- Car rental Wheaton
- Compact Car Rentals in Evanston
- Economy Car Rentals in Chicago
- Island Car Rentals Rental Cars in Riverdale
- National Car Rental Rental Cars in Ottawa
- Premium Car Rentals in Metropolis
- Sports Car Car Rentals in Hoffman Estates
- Suv Car Rentals in Rosemont
