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Chicago flight + hotel packages

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Magnificent Mile
Price was CA $972, price is now CA $759 per person
per person
Apr 2 - Apr 6
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Located in Near North Side, this hotel is steps from Michigan Avenue and Shops at North Bridge. Chicago Water Tower and Navy Pier are also within 1 mi (2 km). Grand Station (Red Line) is only a 4-minute walk and Chicago Station (Red Line) is 10 minutes.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Lakeshore East
Price was CA $736, price is now CA $580 per person
per person
Mar 6 - Mar 9
Roundtrip non-stop flight included
Toronto (YTO) 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 Chicago Theatre are also within 15 minutes. Millennium Station is 10 minutes by foot and State Station is 11 minutes.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
The Loop
Price was CA $835, price is now CA $659 per person
per person
Apr 2 - Apr 6
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
Located in The Loop, this hotel is steps from Lakefront Trail and Grant Park. State Street and Columbia College Chicago are also within 5 minutes. Harrison Station is 7 minutes by foot and Roosevelt Station is 8 minutes.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
River North
Price was CA $1,373, price is now CA $1,088 per person
per person
Apr 5 - Apr 8
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
This family-friendly Chicago hotel is located near the beach, within a 10-minute walk of State Street, Chicago Theatre, and Chicago Riverwalk. Grant Park and House of Blues Chicago are also within 10 minutes. Grand Station (Red Line) is only a 4-minute walk and State Station is 6 minutes.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
River North
Price was CA $1,765, price is now CA $1,402 per person
per person
Mar 10 - Mar 17
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
Located in River North, this luxury hotel is within a 5-minute walk of Michigan Avenue and State Street. Chicago Riverwalk and Northwestern Memorial Hospital are also within 10 minutes. Grand Station (Red Line) is only a 3-minute walk and Chicago Station (Red Line) is 10 minutes.

Top Chicago hotels deals

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 CA $128 per night
Located in The Loop, this luxury hotel is within a 10-minute walk of Chicago Theatre, Michigan Avenue, and Chicago Riverwalk. Grant Park and Millennium Park are also within 10 minutes. State Station is only a 5-minute walk and Randolph-Wabash Station is 5 minutes.
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
The price is CA $126 per night
Located in River North, this romantic hotel is steps from Chinese Consulate and State Street. Michigan Avenue and Northwestern Memorial Hospital are also within 10 minutes. Chicago Station (Red Line) and Grand Station (Red Line) are within a 5-minute walk.
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 CA $124 per night
Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Northwestern Memorial Hospital. Grant Park and State Street are also within 15 minutes. Grand Station (Red Line) is 9 minutes by foot and Chicago Station (Red Line) is 13 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 CA $150 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.
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 CA $91 per night
Located in Near North Side, this romantic hotel is steps from Water Tower Place, Michigan Avenue, and State Street. John Hancock Center and Lake Michigan are also within 10 minutes. Chicago Station (Red Line) is 6 minutes by foot and Clark-Division Station is 11 minutes.
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr, Chicago, IL
Free cancellation
The price is CA $160 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.
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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