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Book Exclusive Chicago Vacation Packages

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Chicago flight + hotel packages

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Lakeshore East
Price was C$1,140, price is now C$852 per person
per person
Oct 10 - Oct 13
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Aon Center are also within 10 minutes. Millennium Station is 10 minutes by foot and State Station is 11 minutes.
Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop

3.5 out of 5
Theatre District
Price was C$1,331, price is now C$996 per person
per person
Oct 10 - Oct 13
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Located in The Loop, this hotel is within a 5-minute walk of Chicago City Hall and Cadillac Palace Theatre. Willis Tower and Millennium Park are also within 10 minutes. Washington-Wells Station and Monroe Station (Blue Line) are within a 5-minute walk.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
The Loop
Price was C$1,228, price is now C$949 per person
per person
Oct 10 - Oct 13
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within 10 minutes. State Station is 9 minutes by foot and Randolph-Wabash Station is 9 minutes.
Renaissance Chicago Downtown Hotel

Renaissance Chicago Downtown Hotel

4 out of 5
The Loop
Price was C$1,300, price is now C$1,033 per person
per person
Aug 26 - Aug 30
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Located in The Loop, this hotel is steps from Chicago Theatre, House of Blues Chicago, and State Street. Chicago Riverwalk and Michigan Avenue are also within 5 minutes. Clark-Lake Station is only a 4-minute walk and State Station is 6 minutes.
Lincolnshire Marriott Resort

Lincolnshire Marriott Resort

4 out of 5
Price was C$1,264, price is now C$1,013 per person
per person
Oct 10 - Oct 14
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
Situated in Lincolnshire, this golf resort is 2.8 mi (4.6 km) from Chevy Chase Country Club and 2.9 mi (4.6 km) from Trinity International University. Northwestern Medicine and Cuneo Mansion and Gardens are also within 6 mi (10 km).

Top Chicago hotels deals

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

3.5 out of 5
300 E Ohio St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$191 per night
Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Northwestern Memorial Hospital. Ann and Robert H. Lurie Children's Hospital and State Street are also within 10 minutes. Grand Station (Red Line) is 9 minutes by foot and Chicago Station (Red Line) is 13 minutes.
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 C$153 per night
Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building and Buckingham Fountain are also within 5 minutes. Harrison Station and Chicago Van Buren Street Station are within a 5-minute walk.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
The price is C$245 per night
Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Grant Park and Chicago Theatre are also within 10 minutes. State Station is 9 minutes by foot and Randolph-Wabash Station is 9 minutes.
Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

2.5 out of 5
216 East Ontario Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$178 per night
Located in Near North Side, this hotel is within a 10-minute walk of Northwestern Memorial Hospital, Tribune Tower, and Ann and Robert H. Lurie Children's Hospital. Water Tower Place and John Hancock Center are also within 10 minutes. Grand Station (Red Line) is 8 minutes by foot and Chicago Station (Red Line) is 11 minutes.
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$122 per night
Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, Water Tower Place, and Michigan Avenue. John Hancock Center and State Street are also within 5 minutes. Chicago Station (Red Line) is 6 minutes by foot and Clark-Division Station is 11 minutes.
Loews Chicago Hotel

Loews Chicago Hotel

4.5 out of 5
455 North Park Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$237 per night
Located in Near North Side, this luxury hotel is within a 10-minute walk of Chicago Riverwalk, Michigan Avenue, and Northwestern Memorial Hospital. Grant Park and Navy Pier are also within 15 minutes. Grand Station (Red Line) is 11 minutes by foot and Randolph-Wabash Station is 14 minutes.
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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.

Chicago Vacations

If you were away the day your geography teacher told your class where Chicago is situated, you don't have to stress. With some help from us, you'll be able to find it easily!

Chicago sits 80 miles (129 kilometers) south of Milwaukee, a significant city.

At last count, the population of this area of Illinois was 2,700,000.

Places to visit in Chicago

With a multitude of famous sights in Chicago, it'd be wise to take a pair of comfortable shoes. Number one on your bucket list should be an outing to the Art Institute of Chicago and Willis Tower. After that, you might need to crank up the pace a bit as you shouldn't go home without swinging by the McCormick Place and the University of Illinois Chicago.

Experience the true essence of this bustling metropolis by exploring attractions like Navy Pier and the Lincoln Park Zoo. If you want more options, Lincoln Park and the Chicago Cultural Center are well worth visiting too.

Millennium Park is a lush haven that's easily accessible from the main central area. After a busy morning of exploring, wind down in one of its shady spots. Like some more ideas? Crane your neck back and look up — way up! John Hancock Center is among the most eye-catching structures in the local skyline and one that's tough to miss. And there's more. Skydeck Ledge offers awe-inspiring vistas as well as some unmissable photo opportunities.

Where do you fly into for Chicago?

While you're planning your Chicago getaway, keep in mind that the closest airport, Midway International Airport (MDW), is approximately 9 miles (14 kilometers) to the southwest of the city center. Book your airfares, fill up your luggage and get set for some exciting new adventures!

Frequently asked questions

^Savings based on all package bookings with Flight + Hotel made on Travelocity.ca from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.