A stone building with a red roof, a lighthouse, and a white fence.

Lakeshore Historic District Vacation Packages

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The Latest Lakeshore Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.
    Jan 7 - Jan 11

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,566 reviews)
    "Breakfast was good"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,051
    CA $758
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,874 reviews)
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $2,739
    CA $1,191
    per traveller
    found 12 hours ago
    Sheraton Grand Chicago Riverwalk
  • A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
    Dec 27 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $3,612
    CA $2,536
    per traveller
    found 14 hours ago
    Park Hyatt Chicago
  • A modern lobby with a sofa, coffee table, and potted plants.
    Jan 7 - Jan 11

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,357 reviews)
    "Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,190
    CA $853
    per traveller
    found 1 day ago
    The Emily Hotel
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 7 - Jan 11

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,044
    CA $760
    per traveller
    found 1 day ago
    Level Chicago Fulton Market

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
Learn more about Lakeshore Historic District
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.
A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

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

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

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.

Discover the most popular places to visit in Lakeshore Historic District

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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Lakeshore Historic District Hotel Deals

A grand lobby with a chandelier, a check-in counter, a sofa, and a coffee table.

Graduate by Hilton Evanston

Graduate by Hilton Evanston
4.0 star property
Lakeshore Historic District
9.0 out of 10, Wonderful, (1,000 reviews)
The price is CA $187
CA $214 total
includes taxes & fees
Dec 6 - Dec 7
Graduate by Hilton Evanston
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.
See all properties in Lakeshore Historic District
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.