Clearing Vacation Packages
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- JW Marriott Chicago
Aug 6 - Aug 9JW Marriott Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,003 reviews)Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,405CA $950found 1 day agoper traveller - Level Chicago Fulton Market
Aug 2 - Aug 8Level Chicago Fulton Market + Flight
Downtown Chicago6 nights9.2/10 - Wonderful (488 reviews)"Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."Reviewed May 22, 2026Roundtrip • Toronto (YTZ) - Chicago (MDW)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $2,919CA $1,699found 1 day agoper traveller - Level Chicago – Old Town
Aug 2 - Aug 8Level Chicago – Old Town + Flight
Downtown Chicago6 nights9.0/10 - Wonderful (481 reviews)"Nice and big"Reviewed May 24, 2026Roundtrip • Toronto (YTZ) - Chicago (MDW)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $2,741CA $1,702found 1 day agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Aug 6 - Aug 9Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago3 nights9.4/10 - Exceptional (2,515 reviews)"Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"Reviewed May 26, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,495CA $1,049found 1 day agoper traveller - Pendry Chicago
Aug 6 - Aug 9Pendry Chicago + Flight
Downtown Chicago3 nights9.2/10 - Wonderful (1,120 reviews)"The staff were extremely accommodating and friendly."Reviewed May 25, 2026Roundtrip • Toronto (YTZ) - Chicago (ORD)YTZ - ORD • Nonstop ORD - YYZ • NonstopCA $1,516CA $1,072found 1 day agoper traveller
Where to stay in Clearing
Find the best Clearing areas and neighborhoods for the activities you enjoy most. Learn more about Clearing
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.
Clearing Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CA $184 per night from May 27 to May 28
CA $184
CA $219 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."
Reviewed on May 25, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is CA $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,249 reviews)
"This is an amazing hotel at this price. The complimentary buffet breakfast each morning is unbelievable. That alone is great, add to that great service. Gerardo at the front desk was great, got us checked in right away and always made sure to ask if there was anything we needed. The room was modern ..."
Reviewed on May 25, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
The price is CA $263 per night from Jun 3 to Jun 4
CA $263
CA $312 total
Jun 3 - Jun 4
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"The room was clean and staffs were approachable. Hotel is close to nearby restaurants and shops."
Reviewed on May 25, 2026
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
Discover the most popular places to visit in Clearing
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
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- Flights to Chicago
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- Art Institute of Chicago
- Blue Island Vacations
- Broadview Vacations
- Buckingham Fountain
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- Cibc Theatre
- Chatham Fields Vacations
- Chicago Museum of Science and Industry
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- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Grant Park
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- Millennium Park
- Obama's House
- Richard J. Daley Center
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- Robie House
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- The East Bank Club
- The Loop Vacations
- United Center
- Unity Temple
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.