West Dempster Vacation Packages

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Top Holiday Package Deals in West Dempster

Price found within the past 48 hours. Click for updated prices.

Swissotel - Chicago

Downtown Chicago

CA $786

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (3,512 reviews)

Holiday Inn Chicago O'Hare – Rosemont by IHG

CA $1,063

per person

Oct 2 - Oct 6

found 7 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (3,097 reviews)

Level Chicago – Old Town

Downtown Chicago

CA $1,686

per person

Sep 14 - Sep 17

found 13 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (512 reviews)

Fairmont Chicago at Millennium Park

Downtown Chicago

CA $808

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.8/10 Excellent! (2,293 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,915

per person

Sep 14 - Sep 17

found 13 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,631 reviews)

Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.

Reviewed on Aug 8, 2026

Where to stay in West Dempster

Find the best West Dempster areas and neighborhoods for the activities you enjoy most. Learn more about West Dempster

A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

West Dempster Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $146

CA $174 total

Sep 8 - Sep 9

includes taxes & fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $200

CA $238 total

Aug 11 - Aug 12

includes taxes & fees

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Fully refundableReserve now, pay when you stay

CA $303

CA $356 total

Aug 30 - Aug 31

includes taxes & fees

See all 4,451 properties in West Dempster

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.