Clearing Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Jul 8 - Jul 12

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    8.8/10 - Excellent (2,174 reviews)
    "Beautiful hotel. Was surprised they didn’t have any usb ports. I forgot a square"
    Reviewed May 31, 2026
    Roundtrip Toronto (YTZ) - Chicago (MDW)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $1,431
    CA $1,028
    per traveller
    found 2 days ago
    Fairmont Chicago at Millennium Park
  • Jul 8 - Jul 12

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,519 reviews)
    "Beautiful place and at a breath taking spot. Staff in the front were very helpful. Good, clean and the most important thing is that its private for the guests. There is a security at the entrance of the pier so nobody can come in. Guests can take walks at the pier, but not the whole pier but some areas. Security was very helpful and understanding. 2 things that need work are: 1. Pillows: the pillows were a pain in the neck. 2. The body wash: our room had an empty bottle of body wash and wasn't..."
    Reviewed May 31, 2026
    Roundtrip Toronto (YTZ) - Chicago (MDW)
    YTZ - MDWNonstop MDW - YTZNonstop
    CA $1,936
    CA $1,288
    per traveller
    found 2 days ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Aug 10 - Aug 14

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,362 reviews)
    "The gym is on 43 floor.. amazing"
    Reviewed May 31, 2026
    Roundtrip Montreal (YUL) - Chicago (ORD)
    YUL - ORD1 stop ORD - YUL1 stop
    CA $1,657
    CA $1,166
    per traveller
    found 2 days ago
    Swissotel - Chicago
  • Aug 10 - Aug 14

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (491 reviews)
    "Amazing place"
    Reviewed May 26, 2026
    Roundtrip Montreal (YUL) - Chicago (ORD)
    YUL - ORD1 stop ORD - YUL1 stop
    CA $1,983
    CA $1,403
    per traveller
    found 2 days ago
    Level Chicago Fulton Market
  • Jun 30 - Jul 4

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (117 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Roundtrip Montreal (YUL) - Chicago (ORD)
    YUL - ORDNonstop ORD - YULNonstop
    CA $1,466
    CA $1,064
    per traveller
    found 14 hours ago
    The Talbott, Autograph Collection

Where to stay in Clearing

Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing

Clearing Hotel Deals

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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"No heat, toilet was broken, no hot water. I left. Front staff was very rude. The staff who came to fix the toilet and bring me more blankets and a portable heater were very nice."

Reviewed on May 31, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 28 to Jun 29
CA $210
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,498 reviews)
"Everything was great"

Reviewed on May 31, 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Jun 30 to Jul 1
CA $261
CA $349 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,309 reviews)
"I loved everything about this hotel. Great staff, great location and amazing rooftop."

Reviewed on Jun 1, 2026

Hotel Riu Plaza Chicago
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.

Frequently asked questions

How much does a Clearing vacation package cost?
Handcraft your Clearing vacation package from an affordable . 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

Things to do

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.