Lakeshore Historic District Vacations from ￥279,254

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The Latest Lakeshore Historic District Vacation Packages

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

Freehand Chicago

Downtown Chicago
￥279,254
per person
Sep 17 - Sep 20
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
7.8/10 Good! (3,233 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
￥292,022
per person
Nov 2 - Nov 7
found 21 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (149 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
￥361,801
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
The hotel itself is nice! But I want to write a review about the STAFF! I have never stayed in a hotel where the staff is so well trained, professional, respectful, serving with positive attitude and smile, make you feel at home, spoil you and so much more! I absolutely wanted to stay longer because of the TOP NOTCH SERVICE! We need to give credits where credit is due and THIS is one of them! Another positive point was our room had a kitchenette with stove, utensils, a FULL BAR WITH AFFORDABLE PRICES!!! The room service is open 24/7 and that’s something rare that a lot of hotels don’t have! The bathtub was huge 🥰😍 Probablt my favorite amenities! Loved how the rooms were cleaned by the staff! We didn’t even have to ask! I have so many positive things to say! ABSOLUTELY RECOMMEND THIS HOTEL! You won’t regret it! ❤️❤️❤️

Reviewed on Aug 10, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
￥285,690
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
￥300,438
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,631 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

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.

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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.

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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.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

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Lakeshore Historic District Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,655
￥19,801 total
Sep 8 - Sep 9
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
￥22,555
￥26,816 total
Aug 11 - Aug 12
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
￥33,153
￥38,918 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,368 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.

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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Space

You can enjoy a show at Space during your stay in 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 studying the exhibits at Evanston History Center during your travels in Evanston. Wander the lakeside and beautiful beaches in this vibrant area.
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Evanston Space

You can get tickets for a performance at Evanston Space during your stay in Evanston. Discover the area's festivals and shops.
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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

￥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.