A storefront with a black awning labeled "BOOKMAN'S ALLEY."

Downtown Evanston Holidays from £891

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to £750 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
Packages with flights are ATOL protected

The Latest Downtown Evanston Holiday Packages

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

19 Jan - 23 Jan
Kimpton Gray Hotel by IHG + Flight
Downtown Chicago
4 nights
4.5 star property
9.4/10 - Exceptional (1,002 reviews)
Return • London (LON) - Chicago (ORD)
LHR - ORD • Direct ORD - LHR • 1 stop
~~£1,036~~
£891
per traveller
found 1 hour ago
Kimpton Gray Hotel by IHG
19 Jan - 23 Jan
The Peninsula Chicago + Flight
Downtown Chicago
4 nights
5.0 star property
9.8/10 - Exceptional (1,000 reviews)
Return • London (LON) - Chicago (ORD)
LHR - ORD • Direct ORD - LHR • 1 stop
~~£1,665~~
£1,367
per traveller
found 1 hour ago
The Peninsula Chicago
19 Jan - 23 Jan
Trump International Hotel & Tower Chicago + Flight
Downtown Chicago
4 nights
5.0 star property
9.6/10 - Exceptional (2,073 reviews)
"i love it"
Reviewed November 10, 2026
Return • London (LON) - Chicago (ORD)
LHR - ORD • Direct ORD - LHR • 1 stop
~~£1,366~~
£1,131
per traveller
found 1 hour ago
Trump International Hotel & Tower Chicago
19 Jan - 23 Jan
Pendry Chicago + Flight
Downtown Chicago
4 nights
4.5 star property
9.2/10 - Wonderful (1,164 reviews)
"The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
Reviewed November 8, 2026
Return • London (LON) - Chicago (ORD)
LHR - ORD • Direct ORD - LHR • 1 stop
~~£1,087~~
£914
per traveller
found 1 hour ago
Pendry Chicago
19 Jan - 23 Jan
Sofitel Chicago Magnificent Mile + Flight
Downtown Chicago
4 nights
4.5 star property
9.4/10 - Exceptional (2,689 reviews)
Return • London (LON) - Chicago (ORD)
LHR - ORD • Direct ORD - LHR • 1 stop
~~£1,054~~
£928
per traveller
found 1 hour ago
Sofitel Chicago Magnificent Mile

Where to stay in Downtown Evanston

Find the best Downtown Evanston areas for the activities you enjoy most.

A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

See properties

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

See properties

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

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

See properties

A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

See properties

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

See properties