Clearing Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
- Fairmont Chicago at Millennium Park
Jul 8 - Jul 12Fairmont Chicago at Millennium Park + Flight
Downtown Chicago4 nights8.8/10 - Excellent (2,174 reviews)"Beautiful hotel. Was surprised they didn’t have any usb ports. I forgot a square"Reviewed May 31, 2026Roundtrip • Toronto (YTZ) - Chicago (MDW)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,431CA $1,028found 2 days agoper traveller - Sable at Navy Pier Chicago, Curio Collection by Hilton
Jul 8 - Jul 12Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights9.4/10 - 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, 2026Roundtrip • Toronto (YTZ) - Chicago (MDW)YTZ - MDW • Nonstop MDW - YTZ • NonstopCA $1,936CA $1,288found 2 days agoper traveller - Swissotel - Chicago
Aug 10 - Aug 14Swissotel - Chicago + Flight
Downtown Chicago4 nights9.0/10 - Wonderful (3,362 reviews)"The gym is on 43 floor.. amazing"Reviewed May 31, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,657CA $1,166found 2 days agoper traveller - Level Chicago Fulton Market
Aug 10 - Aug 14Level Chicago Fulton Market + Flight
Downtown Chicago4 nights9.2/10 - Wonderful (491 reviews)"Amazing place"Reviewed May 26, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • 1 stop ORD - YUL • 1 stopCA $1,983CA $1,403found 2 days agoper traveller - The Talbott, Autograph Collection
Jun 30 - Jul 4The Talbott, Autograph Collection + Flight
Downtown Chicago4 nights9.4/10 - 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, 2026Roundtrip • Montreal (YUL) - Chicago (ORD)YUL - ORD • Nonstop ORD - YUL • NonstopCA $1,466CA $1,064found 14 hours 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
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
The Chicago Hotel Collection - Magnificent Mile
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
Hotel Riu Plaza Chicago
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
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.
Michigan Avenue
4.5/5(20 reviews)
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.
Things to do
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- Adults Only Resorts & in Bedford Park
- Cheap Hotels in Bedford Park
- Hotels with Childcare in Bedford Park
- Hotels with Free Airport Shuttle in Bedford Park
- Hotels with Free Breakfast in Bedford Park
- Luxury Hotels in Bedford Park
- Bedford Park Hotels
- Burbank Hotels
- Chicago Hotels
- Downtown Chicago Hotels
- Aparthotels in Forest View
- B&B in Forest View
- Chalets in Forest View
- Guest Houses in Forest View
- Luxury Hotels in Forest View
- Forest View Hotels
- Resorts in Forest View
- Townhomes in Forest View
- Cheap Hotels in Garfield Ridge
- Hotels with Free Parking in Garfield Ridge
- Romantic Hotels in Garfield Ridge
- Farmstay in Lyons
- B&B in Lyons
- Chalets in Lyons
- Guest Houses in Lyons
- Lyons Hotels
- Inns in Lyons
- Motels in Lyons
- Mccook Hotels
- Hotels near Midway Intl.
- Hotels near SeatGeek Stadium
- Farmstay in Summit
- Aparthotels in Summit
- B&B in Summit
- Chalets in Summit
- Guest Houses in Summit
- Hostels in Summit
- Lgbt Friendly Hotels in Summit
- Hotel Wedding Venues Hotels in Summit
- Summit Hotels
- Resorts in Summit
- Townhomes in Summit
- Flights to Chicago
- Flights to Lyons
- Flights to McCook
- Flights from Midway Intl.
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Porter Airlines Ottawa (YOW) to Chicago (MDW) flights
- Flights from Buffalo (BUF) to Chicago (MDW)
- Flights from Detroit (DTW) to Chicago (MDW)
- Flights from South Bend (SBN) to Chicago (MDW)
- Flights from Edmonton (YEG) to Chicago (MDW)
- Flights from Hamilton (YHM) to Chicago (MDW)
- Flights from Halifax (YHZ) to Chicago (MDW)
- Flights from Kelowna (YLW) to Chicago (MDW)
- Flights from Ottawa (YOW) to Chicago (MDW)
- Flights from Windsor (YQG) to Chicago (MDW)
- Flights from Thunder Bay (YQT) to Chicago (MDW)
- Flights from Sudbury (YSB) to Chicago (MDW)
- Flights from Timmins (YTS) to Chicago (MDW)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Montreal (YUL) to Chicago (MDW)
- Flights from Vancouver (YVR) to Chicago (MDW)
- Flights from Winnipeg (YWG) to Chicago (MDW)
- Flights from Saskatoon (YXE) to Chicago (MDW)
- Flights from North Bay (YYB) to Chicago (MDW)
- Flights from Calgary (YYC) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Art Institute of Chicago
- Blue Island Vacations
- Broadview Vacations
- Buckingham Fountain
- Burbank Vacations
- Cibc Theatre
- Chatham Fields Vacations
- Chicago Museum of Science and Industry
- Chicago Vacations
- Elmhurst Vacations
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- Garfield Park Conservatory
- Grant Park
- Hillside Vacations
- Hometown Vacations
- Loretto Hospital
- Melrose Park Vacations
- Millennium Park
- Obama's House
- Richard J. Daley Center
- River Forest Vacations
- Robie House
- Sleepy Hollow Vacations
- South Loop Vacations
- 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.