Downtown Evanston Vacation Packages

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Top Holiday Package Deals in Downtown Evanston

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

The Talbott, Autograph Collection

Downtown Chicago

CA $845

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (179 reviews)

Clean room. Valet service slow.

Reviewed on Oct 18, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

CA $1,152

per person

Jan 3 - Jan 9

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

8.6/10 Excellent! (1,015 reviews)

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

CA $1,336

per person

Nov 27 - Dec 2

found 10 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

CA $1,754

per person

Dec 5 - Dec 8

found 18 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Pendry Chicago

Downtown Chicago

CA $1,039

per person

Nov 26 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (1,163 reviews)

Staff was friendly and polite. In-room dining set a high bar both in quality and service.

Reviewed on Oct 19, 2026

Where to stay in Downtown Evanston

Find the best Downtown Evanston areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Evanston

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 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 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 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 wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Downtown Evanston Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

CA $148

CA $176 total

Nov 10 - Nov 11

includes taxes & fees

River Hotel

75 East Wacker Drive Chicago IL

CA $215

CA $256 total

Nov 1 - Nov 2

includes taxes & fees

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Fully refundableReserve now, pay when you stay

CA $182

CA $216 total

Nov 2 - Nov 3

includes taxes & fees

See all 4,459 properties in Downtown Evanston

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.