South Shore Vacations from $641

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Your South Shore Vacation

Your next great escape is just around the corner with a vacation package to South Shore. Entertainment, relaxation and nonstop great times — you're bound to find it in this neighborhood. When it's time to see the sights, you'll find a lot of awesome attractions nearby including University of Chicago, Chicago Museum of Science and Industry and Robie House. Visit one, two or all during your trip to South Shore. Stop dreaming and start doing. When it's time to book your next vacation to South Shore, Expedia will help you get there.

The Latest South Shore Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,029, price is now $641 per person
$641
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,950 reviews)
The staff at the front desk was fabulous and the the room was clean

Reviewed on Jun 17, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,361, price is now $791 per person
$791
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
Beautiful hotel, perfect location! Loved everything about this hotel. Breakfast was great. But they really want you out of the restaurant right at the closing time so give yourself time in the morning for breakfast

Reviewed on Jun 21, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,327, price is now $787 per person
$787
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on Jun 20, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,429, price is now $877 per person
$877
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,054, price is now $674 per person
$674
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
very clean and friendly staff

Reviewed on Jun 18, 2026

Where to stay in South Shore

Find the best South Shore areas and neighborhoods for the activities you enjoy most. Learn more about South Shore
Downtown Chicago

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

South Shore 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
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,158 reviews)
"It was a beautiful hotel, perfect location, parking was ok. Would definitely recommend staying again"

Reviewed on Jun 22, 2026

Congress Plaza Hotel
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
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (4,457 reviews)
"Nice property right near everything"

Reviewed on Jun 22, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $146 total per night from Jul 1 to Jul 2
$146 total
Jul 1 - Jul 2
Total with taxes and fees
7.8/10 Good! (1,607 reviews)
"The hotel was in a great location, and the staff were friendly and welcoming. My only complaint was that the hallway smelled like cigarettes and damp carpet. Overall, it was a pleasant stay, but the hallway and elevator odor could definitely be improved."

Reviewed on Jun 21, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,485 properties in South Shore
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 South Shore

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% 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.