Book Exclusive Illinois Vacation Packages

Choose one or more items to build your trip:

Search vacation packages deals in Illinois's top destinations

A city skyline with modern skyscrapers and a river with boats and people in the foreground.

Chicago

Vacations
Chicago

Illinois flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was CA $1,930, price is now CA $1,249 per person
CA $1,249
per person
Jul 29 - Aug 4
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
Book a stay at this business-friendly hotel in Wildwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Six Flags St. Louis and Skid Row are located nearby.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 13 hours ago
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $3,867, price is now CA $2,608 per person
CA $2,608
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,422, price is now CA $1,704 per person
CA $1,704
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $2,917, price is now CA $2,084 per person
CA $2,084
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) 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.

Top Illinois hotels deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
per night
Jun 30 - Jul 1
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
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Free cancellation
Reserve now, pay when you stay
The price is CA $181 per night
CA $181
per night
Jun 28 - Jun 29
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
Free airport shuttle
Pet-friendly
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $208 per night
CA $208
per night
Jul 5 - Jul 6
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
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $241 per night
CA $241
per night
Jul 5 - Jul 6
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
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $348 per night
CA $348
per night
Jul 18 - Jul 19
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosemont Theatre and Allstate Arena are located nearby.
Free airport shuttle
Pet-friendly
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
per night
Jul 1 - Jul 2
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
Don't see what you're looking for?
See all available properties in Illinois
View all properties
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

An aerial view of a baseball stadium surrounded by urban buildings and streets.

Wrigley Field

4.5/5(159 reviews)

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.

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
A Ferris wheel and a carousel at a fairground.

Navy Pier

4.5/5(460 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 art scene.

Navy Pier

Photos of local treasures

Browse Illinois vacation photos for more inspiration

A busy city street with tall buildings, a bus, and cars.
Silhouettes of people against a cityscape at night.
Two skyscrapers surrounded by clouds.
A natural cave with a small pond and lush greenery.
A waterfront building with a sign reading "Water Street."

Frequently asked questions

How much are vacation packages to Illinois?
You might be pleasantly surprised — you can vacation in Illinois for a mere CA $1,249. 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.

Explore More Ways to Travel with Travelocity