Lakeshore Historic District Holidays from £773

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Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£773
per person
7 Nov - 12 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Great location. Nice hotel

Reviewed on 18 Aug 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
£1,159
per person
7 Nov - 12 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,104
per person
20 Oct - 25 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.

Reviewed on 17 Aug 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
Save 100% on your flight
£931
per person
7 Nov - 12 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is in a great location & does offer various amenities but unfortunately we were not able to take advantage of them. Room was clean but a little outdated. Staff were very helpful. Major con was the valet parking fee daily. It’s a lot per day.

Reviewed on 18 Aug 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
£940
per person
7 Nov - 12 Nov
found 2 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)

Where to stay in Lakeshore Historic District

Find the best Lakeshore Historic District areas and neighborhoods for the activities you enjoy most. Learn more about Lakeshore Historic District
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.

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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.

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

Magnificent Mile

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

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

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.

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

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.

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Top hotels in Lakeshore Historic District

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£95
8 Sept - 9 Sept
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
24 Aug - 25 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£209
12 Sept - 13 Sept
includes taxes & fees
8.4/10 Very good! (2,420 reviews)
"The bed was hard and the air conditioner was so loud that it kept waking us up throughout the night. Not a good nights sleep at all."

Reviewed on 18 Aug 2026

Hilton Chicago O'Hare Airport
See all 4,363 properties in Lakeshore Historic District
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.
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Where to go when
Where to go when

Stay near popular Lakeshore Historic District attractions

Dawes Park

9.2/10 (40 reviews)
Explore the great outdoors at Dawes Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Evanston Space

You can get tickets for a performance at Evanston Space on your trip to Evanston. Discover the area's festivals and shops.
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Space

You can make plans for a show at Space during your trip to Evanston. Take in the festivals and sunsets in the area.
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Greenwood Street Beach

Why not spend a lazy afternoon at Greenwood Street Beach during your trip to Chicago?
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Dog Beach

9.6/10 (20 reviews)
Why not spend a lazy afternoon at Dog Beach during your trip to Evanston?
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Evanston History Center

8.8/10 (39 reviews)
You can spend an afternoon browsing the exhibits at Evanston History Center during your travels in Evanston. Wander through the lakeside and beautiful beaches in this vibrant area.
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Prairie Moon

After visiting Prairie Moon, make a plan to see the other sights and activities in Evanston.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.