Lakeshore Historic District Vacations from ¥279,799

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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

The Latest Lakeshore Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥279,799
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Hotel, accommodations, amenities, and staff were all amazing!

Reviewed on Oct 4, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥368,160
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥304,194
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥296,436
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.8/10 Excellent! (2,309 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥313,520
per person
Nov 9 - Nov 13
found 19 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (3,324 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.

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 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 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.

Lakeshore Historic District Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
¥20,126
¥23,928 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very Good! (10,167 reviews)
"Cool old hotel, that shows its age a bit. Lots of remodeling over the years, that shows a bit of wear and tear. The room was clean and comfortable. Excellent location for walking to all the great sights and experiences in Chicago. Staff was great, very helpful, especially the doorman."

Reviewed on Oct 4, 2026

Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
¥26,361
¥31,342 total
Nov 1 - Nov 2
includes taxes & fees
River 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
¥22,568
¥26,830 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very Good! (2,414 reviews)
"Beautiful hotel in a perfect location. Big rooms w/big bathrooms and a super helpful staff. The hotel bar is beautiful and is the perfect place to end your evening. Lively place to stay!"

Reviewed on Oct 4, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,438 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.
See properties

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.
See properties

Evanston Space

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

Space

You can enjoy a show at Space during your stay in Evanston. Take in the festivals and sunsets in the area.
See properties

Dog Beach

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

Greenwood Street Beach

Why not spend a lazy afternoon at Greenwood Street Beach during your trip to Evanston?
See properties

Prairie Moon

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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.