Book Exclusive Illinois Vacation Packages

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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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to St. Louis (STL)
Stay at this 3.5-star 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.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (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
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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.

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.
Free WiFi
Restaurant
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $239 per night
CA $239
CA $315 total
Aug 22 - Aug 23
includes taxes & fees
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Pool
Spa
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
The price is CA $201 per night
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pet-friendly
Free WiFi
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 $191 per night
CA $191
CA $224 total
Aug 24 - Aug 25
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.
Pool
Pet-friendly
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is CA $239 per night
CA $239
CA $281 total
Aug 24 - Aug 25
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
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 $215 per night
CA $215
CA $253 total
Aug 26 - Aug 27
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.
Free WiFi
Restaurant
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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

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

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

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.

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 $647. 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.