Downtown Evanston Vacation Packages

Photo by Tara Jabbari

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Downtown Evanston

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

Hotel Riu Plaza Chicago

Downtown Chicago

CA $1,114

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (5,106 reviews)

Freehand Chicago

Downtown Chicago

CA $1,759

per person

Oct 8 - Oct 12

found 3 hours ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

7.8/10 Good! (3,367 reviews)

Clean, freindly Staff, good location- the+'s. Should of known to bring towels and parking was kidde korner from entrance not next to it. 4.75 stars

Reviewed on Sep 4, 2026

The Talbott, Autograph Collection

Downtown Chicago

CA $1,153

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (159 reviews)

The room was spacious for two. The location was easy to reach from the bus line. We were able to check in early! The only problems were that the phone would ring randomly throughout the morning. We didn't ask for any wake-up calls, and you could hear through the walls into the next room. All in all, the hotel location was a good choice for this trip.

Reviewed on Sep 2, 2026

The Emily Hotel

Downtown Chicago

CA $1,304

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (1,351 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,195

per person

Oct 21 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

9.4/10 Exceptional! (2,685 reviews)

My family (of 4) stayed 5 days/4 nights. The room had a beautiful view. The room itself was very nice too! Front desk staff were nice and helpful. The only thing we didn't like was the housekeeping. We requested more towels because only 3 towels were in the bathroom, and we needed one more. It took a long time for it to be sent to our room. We had to request 4 towels every time, which was annoying. Also, there were 2 days our room was not cleaned, even after we requested housekeeping. Other than that, the hotel itself was great. We ate at the restaurant downstairs for breakfast and dinner on occasion. The surrounding area was beautiful and picturesque. We would stay at Sable Hotel again!

Reviewed on Sep 3, 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 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 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

CA $143

CA $170 total

Sep 8 - Sep 9

includes taxes & fees

8/10 Very good! (10,269 reviews)

"Nice"

Reviewed on Sep 4, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

CA $179

CA $213 total

Sep 30 - Oct 1

includes taxes & fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (888 reviews)

"We thoroughly enjoyed our stay at Kasa- check in instructions were clear and hassle free. The unit was spacious and clean, with a terrific view. Highly recommended!"

Reviewed on Sep 4, 2026

Get rates

See all 4,306 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.