Book Exclusive Illinois Vacation Packages

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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 $1,506, price is now CA $998 per person
CA $998
per person
Jul 31 - Aug 4
found 6 hours ago
Roundtrip non-stop flight included
Calgary (YYC) 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.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $2,236, price is now CA $1,674 per person
CA $1,674
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) 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.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was CA $1,820, price is now CA $1,369 per person
CA $1,369
per person
Aug 12 - Aug 19
found 19 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,405, price is now CA $1,071 per person
CA $1,071
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
Stay at this 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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was CA $1,556, price is now CA $1,218 per person
CA $1,218
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms 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
The price is CA $194 per night
CA $194
CA $231 total
Jun 29 - Jun 30
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 - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Free cancellation
The price is CA $211 per night
CA $211
CA $251 total
Jun 28 - Jun 29
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
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 $188 per night
CA $188
CA $214 total
Jun 28 - Jun 29
includes taxes & fees
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 Rosemont Theatre and Allstate Arena are located nearby.
Free airport shuttle
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 $250 per night
CA $250
CA $336 total
Jun 30 - Jul 1
includes taxes & fees
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
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Free cancellation
Reserve now, pay when you stay
The price is CA $225 per night
CA $225
CA $267 total
Jun 29 - Jun 30
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
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 $255 per night
CA $255
CA $345 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this luxury 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
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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

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 entertainment choices in this vibrant area.

Wrigley Field
Soldier Field

Soldier Field

4.5/5(115 reviews)

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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

Photos of local treasures

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Frequently asked questions

How much are vacation packages to Illinois?
You might be pleasantly surprised — you can vacation in Illinois for a mere CA $998. 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.

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