South Side Vacations from $503

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The Latest South Side Vacation Packages

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

Congress Plaza Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
7.6/10 Good! (6,733 reviews)
Its close to manny atractions manny food places near and it is clean.

Reviewed on May 17, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Had an amazing time! Room cleaners were very sweet and

Reviewed on May 6, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 17 - Jul 23
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
9.2/10 Wonderful! (96 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Location was fantastic and the property is beautiful!

Reviewed on May 15, 2024

W Chicago - Lakeshore

W Chicago - Lakeshore

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 8 - Aug 13
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (1,009 reviews)
Staff very friendly and helpful. Rooms were good. No coffee makers in rooms which is a bit different but each morning complimemtary coffee was available in the lobby. Really good location for us and we would highly reccommend.

Reviewed on May 14, 2024

Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. Learn more about South Side
South Loop featuring a skyscraper and a city

South Loop

4.5/5(607 area reviews)

South of downtown Chicago, this neighborhood features cultural activities, sports and convention centers and a great dining and nightlife scene.

Find hotel + flight trips in South Loop

South Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

South Side 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
The price is $167 per night from May 27 to May 28
$167
$196 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (6,728 reviews)
"I really liked how clean the room was."

Reviewed on May 14, 2024

Congress Plaza Hotel
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $100 per night from May 27 to May 28
$100
$132 total
includes taxes & fees
May 27 - May 28
7.6/10 Good! (2,584 reviews)
"Large, super clean, convenient hotel. Staff was excellent and friedly. Bar staff was great. Would definitely stay again."

Reviewed on May 16, 2024

Warwick Allerton - Chicago
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $179 per night from May 27 to May 28
$179
$210 total
includes taxes & fees
May 27 - May 28
8.6/10 Excellent! (2,869 reviews)
"I enjoyed staying in this hotel. Very convenient and nearby to tourist attractions. The staff are very accommodating. I will definitely book this hotel if I’m in Chicago."

Reviewed on May 15, 2024

River Hotel
See all 4,832 properties in South Side
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a South Side vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in South Side from just $503. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
How do I get a cheap travel package to South Side?
Book everything in the one place with our South Side vacation packages. You’ll find deals on flights, hotels and more that’ll keep your pocket happy and your adventurous side busy. And, with more than 550 air carriers and 1,000,000 hotels throughout the world to pick from, you’ll have the flexibility to mix and match all you want.
What are the top hotels in South Side?
When it comes to properties in Carville, Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton are a couple of favorites. If you’re considering heading to Chatham Fields, The Whitehall Hotel and Hyatt Regency Chicago are waiting to welcome you.
How far in advance should I book my South Side vacation?
While not all airlines advertise ticket prices early, it’s usually possible to look up international flights on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you’re purchasing tickets last minute, there’s a chance you could get lucky. Sometimes the lowest prices become available a few weeks prior to departure.
What does an Expedia South Side travel package include?
Expedia has everything you need to book your South Side escape, but what your package looks like is up to you. Choose from a combination of rental cars, hotels and flights. Searching for some activities to keep you busy? Once you’ve made your booking, you can add them on too. Whatever your style or budget, there’s a package deal to suit your needs.
What should I know before booking a South Side travel package?
Discover deals that suit your budget with an Expedia package. Flights, hotels, rental cars — we’re a one-stop shop for all of them. You’ll save precious cash just for combining your bookings. Whether you’re embarking on a ski trip or relaxing on a sunny beach, your perfect getaway is only clicks away.
Can I choose my airline with a South Side Expedia vacation package?
Most definitely. Expedia has over 550 partner airlines to choose from all over the world. With so many choices, finding the right carrier to bring you to South Side will be a snap.
If I'm not able to travel, can I cancel my South Side vacation package?
You can. We get that even the best-laid plans can go awry, so we’re here to help if you have to make changes to your South Side vacation package. It may be possible to amend or cancel your itinerary for free if you’ve booked within 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in South Side

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

What to do in South Side

Image for Chicago Shoreline Adventure Boat Tour

Chicago Shoreline Adventure Boat Tour

$90
Per adult
Chicago Shoreline Adventure Boat Tour
Image for Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour

$7
Per adult
Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour
Image for Chicago's Ultimate City Bike Tour

Chicago's Ultimate City Bike Tour

$55
Per adult
Chicago's Ultimate City Bike Tour
See all activities in South Side

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.