Clearing Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Clearing

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,357, price is now CA $849 per person
CA $849
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,964, price is now CA $1,182 per person
CA $1,182
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on Aug. 25, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,638, price is now CA $1,054 per person
CA $1,054
per person
Nov 10 - Nov 17
found 18 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug. 26, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,450, price is now CA $934 per person
CA $934
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug. 21, 2025

Where to stay in Clearing

Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Clearing Hotel Deals

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Sep 2 to Sep 3
CA $208
CA $244 total
Sep 2 - Sep 3
includes taxes & fees
8.2/10 Very Good! (1,226 reviews)
"It was very close to navy pier where it was just a 10 min way. And had a great view from our room. Facing the lake"

Reviewed on Aug. 27, 2025

The Wade
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on Aug. 26, 2025

Congress Plaza Hotel
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
Fully refundableReserve now, pay when you stay
The price is CA $219 per night from Sep 4 to Sep 5
CA $219
CA $257 total
Sep 4 - Sep 5
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on Aug. 27, 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 5,022 properties in Clearing
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.
All Inclusive Vacations
All Inclusive Vacations
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Family Vacations

Frequently asked questions

How much does a Clearing vacation package cost?
Handcraft your Clearing vacation package from an affordable CA $849. Pick from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about for ages. Remember to add on one or two experiences!
How do I get a cheap travel package to Clearing?
Bundle your flights and hotels with Expedia to save big on your next getaway. With more than 550 air carriers and 1,000,000 properties globally, your Clearing vacation package can be customized exactly to suit your budget. With all those extra dollars, why not throw in one or more fun experiences and tours? It's an easy way to unlock even more bargains. The vacation you've always dreamed of in Clearing is closer than you thought!
What are the top hotels in Clearing?
Whether you're staying for one or several nights in Clearing, you'll get a wonderful night's rest at Chicago Marriott Midway. This place is popular with lots of travelers.
How far in advance should I book my Clearing vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months prior to take off. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Clearing sometimes occur in the weeks leading up to departure.
What does an Expedia Clearing travel package include?
Hotels, rental cars and flights, or any combination of them — it's up to you! Whether you're exploring Clearing with the entire family or enjoying a solo break, there's a package to match every style and budget. Once you've made your booking, why not add on a few tours and experiences?
What should I know before booking a Clearing travel package?
Our prices are already low. However, you'll enjoy even better deals if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Clearing Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Just select the airline you want and create your ideal Clearing escape.
If I'm not able to travel, can I cancel my Clearing vacation package?
If your travel plans in Clearing have changed, it's good to know that it is possible to cancel or amend your booking. If you booked in the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more details, visit our Customer Service Portal.

Discover the most popular places to visit in Clearing

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

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

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

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.