Book Exclusive Illinois Vacation Packages

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Search vacation packages deals in Illinois's top destinations

Chicago showing a high-rise building and a city as well as a family

Chicago

Vacations
Chicago

Illinois flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $842, price is now CA $514 per person
CA $514
per person
Feb 17 - Feb 21
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,170, price is now CA $722 per person
CA $722
per person
Feb 17 - Feb 21
just found
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,188, price is now CA $738 per person
CA $738
per person
Feb 13 - Feb 16
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 a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $937, price is now CA $583 per person
CA $583
per person
Feb 17 - Feb 21
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,643, price is now CA $1,032 per person
CA $1,032
per person
Feb 17 - Feb 21
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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.

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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.

Michigan Avenue
McCormick Place

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.

McCormick Place

Photos of local treasures

Browse Illinois vacation photos for more inspiration

Chicago showing street scenes, a skyscraper and a city
Illinois
Illinois
Starved Rock State Park featuring a cascade
Naperville featuring night scenes and a river or creek

Frequently asked questions

How much are vacation packages to Illinois?
You might be pleasantly surprised — you can vacation in Illinois for a mere CA $514. At Travelocity, we save you money and time with our awesome vacation package deals. With hotels, flights and experiences all ready to be snapped up, why wait any longer?
Where can I get the best vacation package deals for Illinois?
Travelocity has endless ways to score an incredible Illinois package deal. Choose from as many as 400 partner airlines and 1,000,000 hotels worldwide and put together a travel itinerary that suits your style. With so many options at hand, it's easy to plan your next exciting getaway.
Why should I purchase my Illinois vacation package via Travelocity?
Because you'll never wander on your own if you lock in your trip through us, and we offer 24/7 customer support and first-rate service to boot. Add to that our Price Match Guarantee and tons of experiences and destinations to choose from. It's our job to help you jet off on the vacation of a lifetime.
Can I save money on my Illinois car rental if I bundle it with hotels and flights?
Bundling your bookings into an Illinois vacation package will certainly save you money. Combine a car and flight; a flight, hotel and car; or a hotel and car. There's no better way to discover the greater Illinois region than with your own ride. You can also add activities and experiences to your Travelocity package.
Which airport is best for Illinois?
Most visitors get to Illinois via Greater Peoria Regional Airport (PIA) or Central Illinois Regional Airport (BMI). Abraham Lincoln Capital Airport (SPI) is another popular choice.
What is there to do in Illinois?
Illinois boasts hidden gems around every corner, however make sure you plan a trip to Wrigley Field and Six Flags Great America while you're in town. These two attractions can't be missed.