Lakeshore Historic District Holidays
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Price found within the past 48 hours. Click for updated prices.
Cambridge Inn on Main
€2,708
per person
17 Dec - 21 Dec
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (74 reviews)
Everything about this hotel was great! A very historic Boutique Hotel that takes you back in time! Each room has a theme of its own which is unique to the period. The owner was very friendly and made sure that I had everything that I needed to make my stay excellent! If you're ever in that area or even doing business in the Madison Wisconsin area you may consider taking an extra half hour to drive to this hotel and stay there. I don't think you'll be disappointed at all as a matter of fact I would be surprised if you didn't like it. I've been in hotels halfway around the world and I must say that next time I'm back in that area I will be staying here!
Reviewed on 4 Oct 2026
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
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.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
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.
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.
Top hotels in Lakeshore Historic District
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€135
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (10,192 reviews)
"Old hotel! Front desk wasn’t helpful l, ask for several things and they never showed up. No A.C., coffee pot broken, ran out of toilet paper and towels. No ice in machine, vending machine served hot beverages. Maintenance men were very nice, Christian at the bar was excellent! I’ll never stay there ..."
Reviewed on 6 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
€170
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,494 reviews)
"Wonderful experience. So close to the river walk and activities. Staff was so helpful and attentive and property was clean and comfy! Highly recommend!"
Reviewed on 6 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€151
1 Nov - 2 Nov
includes taxes & fees
8/10 Very good! (2,427 reviews)
"The room and lobby was dirty"
Reviewed on 6 Oct 2026
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.
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.
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.
Evanston Space
You can get tickets for a performance at Evanston Space on your trip to Evanston. Discover the area's festivals and shops.
Space
You can make plans for a show at Space during your trip to Evanston. Take in the festivals and sunsets in the area.
Dog Beach
9.6/10 (20 reviews)
Why not spend a lazy afternoon at Dog Beach during your trip to Evanston?
Greenwood Street Beach
Why not spend a lazy afternoon at Greenwood Street Beach during your trip to Evanston?
Prairie Moon
After visiting Prairie Moon, make a plan to see the other sights and activities in Evanston.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.