Book Exclusive Chicago Vacation Packages

Choose one or more items to build your trip:

Chicago flight + hotel packages

Sheraton Grand Chicago

Sheraton Grand Chicago

4 out of 5
Streeterville
Price was C$945, price is now C$777 per person
per person
Dec 4 - Dec 8
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Located in Near North Side, this hotel is within a 15-minute walk of Michigan Avenue and Navy Pier. Millennium Park and John Hancock Center are also within 1 mi (2 km). Grand Station (Red Line) is 11 minutes by foot and Randolph-Wabash Station is 13 minutes.
Residence Inn Chicago Downtown/Loop

Residence Inn Chicago Downtown/Loop

3.5 out of 5
Theatre District
Price was C$733, price is now C$604 per person
per person
Nov 20 - Nov 23
Roundtrip non-stop flight included
Toronto (YYZ) 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 McCormick Place

Hyatt Regency McCormick Place

4 out of 5
Near South Side
Price was C$1,519, price is now C$1,259 per person
per person
Dec 4 - Dec 8
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Located in South Loop, this eco-friendly hotel is within a 5-minute walk of McCormick Place and Wintrust Arena. Lakefront Trail and Soldier Field are also within 1 mi (2 km). Chicago McCormick Place Station is only a 4-minute walk and Cermak-McCormick Place Station is 9 minutes.
The Langham, Chicago

The Langham, Chicago

5 out of 5
River North
Price was C$1,775, price is now C$1,473 per person
per person
Dec 4 - Dec 8
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
This family-friendly Chicago hotel is located in the entertainment district, within a 15-minute walk of Michigan Avenue, Millennium Park, and Art Institute of Chicago. John Hancock Center and Navy Pier are also within 1 mi (2 km). State Station is 5 minutes by foot and Randolph-Wabash Station is 6 minutes.
Hotel Lincoln, part of JdV by Hyatt

Hotel Lincoln, part of JdV by Hyatt

4 out of 5
Old Town Triangle
Price was C$660, price is now C$552 per person
per person
Nov 20 - Nov 23
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
Located in Lincoln Park, this boutique hotel is within a 10-minute walk of Chicago History Museum, Second City, and Park West. Lincoln Park Zoo and North Avenue Beach are also within 15 minutes. Sedgwick Station is 11 minutes by foot and Clark-Division Station is 16 minutes.

Top Chicago hotels deals

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$183 per night
Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Northwestern Memorial Hospital, and Chicago Riverwalk. 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$124 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.
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$111 per night
Located in Near North Side, this romantic hotel is steps from Michigan Avenue, 900 North Michigan Shops, and State Street. John Hancock Center and Water Tower Place are also within 5 minutes. Chicago Station (Red Line) is 6 minutes by foot and Clark-Division Station is 11 minutes.
The St. Clair Hotel – Magnificent Mile

The St. Clair Hotel – Magnificent Mile

2.5 out of 5
162 East Ontario Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$142 per night
Located in Near North Side, this hotel is within 1 mi (2 km) of Grant Park, Millennium Park, and Cloud Gate. Art Institute of Chicago and Navy Pier are also within 1 mi (2 km). Grand Station (Red Line) is 7 minutes by foot and Chicago Station (Red Line) is 10 minutes.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
85 East Wacker Drive, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$235 per night
Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Theatre and Wrigley Building. Michigan Avenue and Chicago Riverwalk are also within 10 minutes. State Station is only a 5-minute walk and Randolph-Wabash Station is 5 minutes.
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
221 N Columbus Dr, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is C$258 per night
Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Grant Park, and Aon Center. Harris Theater and Michigan Avenue are also within 10 minutes. Randolph-Wabash Station is 8 minutes by foot and State Station is 8 minutes.
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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