A coastal cityscape with a prominent skyscraper and a peninsula extending into the water.

Grand Boulevard Vacations from $340

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Your Grand Boulevard Vacation

Experience all the fabulous things this neighborhood has to offer with a customized Grand Boulevard vacation package. However you imagine spending your days here, you'll find endless opportunities for adventure, relaxation and fun. Not sure what to do during your trip to Grand Boulevard? Nearby attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field are good places to start. Whatever your travel plans or the size of your budget, booking your ideal Grand Boulevard vacation is a cinch with Expedia.

The Latest Grand Boulevard Vacation Packages

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

Jan 15 - Jan 19
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight
Downtown Chicago
4 nights
4.0 star property
8.6/10 - Excellent (1,002 reviews)
"Nice environment and very reasonable prices..right downtown so great location!"
Reviewed November 5, 2026
Roundtrip • Atlanta (ATL) - Chicago (ORD)
ATL - ORD • Nonstop ORD - ATL • Nonstop
~~$534~~
$340
per traveler
found 1 day ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Dec 20 - Dec 23
Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago
3 nights
4.0 star property
8.6/10 - Excellent (1,874 reviews)
Roundtrip • Atlanta (ATL) - Chicago (ORD)
ATL - ORD • Nonstop ORD - ATL • Nonstop
~~$1,483~~
$471
per traveler
found 1 day ago
Sheraton Grand Chicago Riverwalk
Dec 8 - Dec 13
Hotel Riu Plaza Chicago + Flight
Downtown Chicago
5 nights
4.0 star property
9.4/10 - Exceptional (5,645 reviews)
"El mejor lugar para quedarte en Chicago⭐️"
Reviewed November 4, 2026
Roundtrip • Atlanta (ATL) - Chicago (ORD)
ATL - ORD • Nonstop ORD - ATL • Nonstop
~~$1,020~~
$637
per traveler
found 1 day ago
Hotel Riu Plaza Chicago
Jan 15 - Jan 19
Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago
4 nights
4.0 star property
8.6/10 - Excellent (2,377 reviews)
"Elevator was slow but everything else was great!"
Reviewed November 4, 2026
Roundtrip • Atlanta (ATL) - Chicago (ORD)
ATL - ORD • Nonstop ORD - ATL • Nonstop
~~$542~~
$350
per traveler
found 1 day ago
Hotel Saint Clair- Magnificent Mile
Dec 24 - Dec 29
Pendry Chicago + Flight
Downtown Chicago
5 nights
4.5 star property
9.2/10 - Wonderful (1,161 reviews)
Roundtrip • Atlanta (ATL) - Chicago (ORD)
ATL - ORD • Nonstop ORD - ATL • Nonstop
Save 100% on your flight
~~$1,023~~
$662
per traveler
found 1 day ago
Pendry Chicago

Where to stay in Grand Boulevard

Find the best Grand Boulevard areas and neighborhoods for the activities you enjoy most. Learn more about Grand Boulevard

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.

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A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.

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 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 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.

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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.

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Discover the most popular places to visit in Grand Boulevard

Harold Washington Cultural Center

Enjoy an outing to Harold Washington Cultural Center during your stay in Chicago. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.

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