Grand Boulevard Vacations from $351

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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.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago
Save 100% on your flight
$351
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,011 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
$972
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
Save 100% on your flight
$427
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$446
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$738
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
Amazing stay. Love the balcony view. Parking was easy and accessible. Will be back!

Reviewed on Sep 19, 2026

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 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.

Grand Boulevard Hotel Deals

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$239 nightly
$284 total
Oct 1 - Oct 2
Total with taxes and fees
8.8/10 Excellent! (5,448 reviews)
"The elevator system needs to be updated."

Reviewed on Sep 19, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$159 nightly
$189 total
Sep 27 - Sep 28
Total with taxes and 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
$152 nightly
$181 total
Sep 30 - Oct 1
Total with taxes and fees
8/10 Very Good! (2,283 reviews)
"Dear Hotel Management, I am writing regarding a very frustrating incident involving your valet service following my stay at your hotel on Friday night. This morning, the valet retrieved my vehicle, but the key was never returned to me. I drove from Chicago to South Bend and only discovered the problem ..."

Reviewed on Sep 20, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,536 properties in Grand Boulevard
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 Grand Boulevard attractions

Robert S. Abbott Residence

Learn about the local history of Chicago when you spend time at Robert S. Abbott Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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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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Elam House

You can learn about the history of Chicago when you stop by Elam House. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Dr. Daniel Hale Williams Residence

You can learn about the history of Chicago with a trip to Dr. Daniel Hale Williams Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Nat King Cole Residence

Find out about the history of Chicago when you take a trip to Nat King Cole Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Chicago Defender Original Site

You can learn about the history of Chicago with a trip to Chicago Defender Original Site. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Oscar S. De Priest Residence

Find out about the history of Chicago with a stop at Oscar S. De Priest Residence. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Savoy Ballroom Site

Learn about the local history of Chicago with a stop at Savoy Ballroom Site. Wander the area's Chinatown or simply enjoy one of its top-notch restaurants.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

$28
per adult
96% of travellers recommend
Flyover in Chicago
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.