Book Exclusive Illinois Vacation Packages

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Chicago

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Chicago

Illinois flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,246, price is now CA $808 per person
CA $808
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,395, price is now CA $1,569 per person
CA $1,569
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,617, price is now CA $1,068 per person
CA $1,068
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff 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 $2,423, price is now CA $1,622 per person
CA $1,622
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
Stay at this 5-star 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.
Art Villa

Art Villa

5 out of 5
West Town
Price was CA $2,442, price is now CA $1,665 per person
CA $1,665
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Stay at this 5-star luxury aparthotel in Chicago. Enjoy free WiFi, free parking, and a full-service spa. 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
Get rates
Book a 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 Millennium Park are located nearby.
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $249 per night
CA $249
CA $292 total
Oct 2 - Oct 3
includes taxes & fees
Stay at this 3-star 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 Michigan Avenue and Chicago Riverwalk are located nearby.
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 $222 per night
CA $222
CA $261 total
Oct 20 - Oct 21
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.
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $252 per night
CA $252
CA $295 total
Sep 28 - Sep 29
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
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
Get rates
Stay at this 4-star boutique 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.
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $219 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
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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 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 entertainment choices 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
Navy Pier

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 fascinating museums.

Navy Pier

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 $808. 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.