Sheffield Neighbors Vacations from $336

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Your Sheffield Neighbors Vacation

Let our Sheffield Neighbors vacation packages transport you to a destination where unforgettable memories are waiting to be made. While it's especially noted for its history, there's loads to love about this neighborhood. Not sure what to see and do during your trip to Sheffield Neighbors? Nearby attractions like Wrigley Field, John Hancock Center and United Center are great places to start. No matter your travel goals or budget, booking a perfect Sheffield Neighbors vacation is simple with Expedia.

The Latest Sheffield Neighbors Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $601, price is now $336 per person
$336
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
It felt very safe and was very clean. The stuff was all ver nice and helpful. The area was nice to walk on the pier but if wanting to do anything downtown it required a lot of uber using.

Reviewed on Oct 12, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,473, price is now $537 per person
$537
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $759, price is now $415 per person
$415
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Healthy breakfast and very clean hotel with friendly staff.

Reviewed on Oct 10, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $853, price is now $478 per person
$478
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on Oct 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $656 per person
$656
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Very clean very nice hotel. Easy accesss to restaurants and shopping.

Reviewed on Oct 11, 2025

Where to stay in Sheffield Neighbors

Find the best Sheffield Neighbors areas and neighborhoods for the activities you enjoy most. Learn more about Sheffield Neighbors
Downtown Chicago showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Sheffield Neighbors Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (9,366 reviews)
"Shockingly updated interior of the rooms based on the historic feel of the common areas- I was so pleasantly surprised!"

Reviewed on Oct 10, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $103 total per night from Nov 12 to Nov 13
$103 total
Nov 12 - Nov 13
Total with taxes and fees
7.8/10 Good! (2,456 reviews)
Great hostel, will book again
"All the staff had great energy and were very helpful. Nice bar/lounge area and cozy space. I had a private room and though it wasn’t huge, it was exactly what we needed for our staycation."

Reviewed on Oct 12, 2025

Freehand Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $169 total per night from Nov 9 to Nov 10
$169 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (3,062 reviews)
"My stay at this hotel was overall pleasant. The staff were professional and welcoming, and the location was convenient for everything I needed. The room was clean, comfortable, and well-maintained, with nice amenities that made the stay enjoyable."

Reviewed on Oct 10, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,561 properties in Sheffield Neighbors
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Sheffield Neighbors

DePaul Art Museum

You can spend an afternoon studying the exhibits at DePaul Art Museum in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.

DePaul Art Museum

St. Josaphat Church

St. Josaphat Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its acclaimed art scene.

St. Josaphat Church

Things to do

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel 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.